Chelsea Boots With Flannel? The 146 Top Answers

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Trends come and go in fashion, but there are garments that will always stand the test of time. You know – the white sneaker, the black leggings, the perfect pair of jeans – the list goes on. However, there is another important element that we must add to this list of fashions that never go out of style: the Chelsea boot.

Yes, Chelsea boots have been around for quite some time and they’re not necessarily something new, but in recent months designers have updated them to make them feel fresh and trendy.

“Chelsea boots are a footwear staple,” NYC-based personal stylist Gloria Cospito tells us. “This season, Chelsea boots get a streetwear upgrade with higher shafts and chunky soles.”

We’ve seen the cleated sole trend come into play in almost every type of shoe this season, so we’re thrilled that the upgraded Chelsea boot is a classic option that you can wear almost anywhere.

Are Chelsea Boots going out of style?

Carrie Cramer, a Los Angeles-based celebrity, wardrobe and personal stylist, says that Chelsea boots “have been a consistent, comfortable and stylish boot option for decades,” making them a timeless companion. However, Cramer believes that in the future “we’ll see a return to the classic, lower-heeled Chelsea boot in a few years. For now, enjoy the added height and rugged, chic styling.”

The classic Chelsea boot probably comes to mind as a sleek black boot with an elasticated gusset, but some of the more upscale styles now include other colors, textures and materials. Cospito says white Chelsea boots are a “trendy graphic statement” right now.

If you don’t already own a pair of Chelsea boots, Cramer recommends opting for a classic black style first. However, a fresh green color may be a more “fashionable” choice for the more experienced Chelsea boot wearer, as it “can coordinate with everything in your wardrobe”.

“Chelsea boots look very chic and modern with cropped jeans or black pants any time of the year,” said Cramer. “This winter I can’t wait to style Chelsea boots with joggers and a chunky sweater or cropped jacket.”

Are Chelsea Boots Comfortable for Walking?

Apart from their fashionable look, Chelsea boots are also surprisingly comfortable and can be worn on any occasion.

“Because most Chelsea boots are flat, they’re a great option if you have to be on your feet all day or if you’re traveling,” Cramer said. “They are also a perfect choice for city living. Living in Los Angeles, I wear Chelsea boots to work and roll them out at night with my husband.”

Cospito also says that cleated Chelsea boots are good for winter, as they offer a bit more traction when it comes to braving the elements. And as the warmer months roll around, opting for a sleek Chelsea boot in a lighter color like brown or beige will keep your look fresh.

According to stylists, the best Chelsea boots

We asked Cramer and Cospito about the best Chelsea boots they either own or have their eye on – and their choices didn’t disappoint. Read on for the boots made for hiking this season.

Cramer says she loves these boots from the Journee Collection, mostly because they come in a variety of fun color options. “This style looks great any day of the year but is also the perfect choice for those days when you don’t know what the weather will be like,” she added.

These affordable Chelsea boots touch on all the classic features of the boot, but the 2-inch block heel and memory foam footbed give them an elevated edge.

These stylish and waterproof boots will take you from autumn to spring. They are available in many different colors and have a rubber profile sole. Cramer says they’re a “perfect choice for those days when you don’t know what the weather is going to be like.”

Cospito chose this white cleated boot as a stylish footwear option for this season. Not only are they trendy, but they also keep your feet comfortable and dry thanks to a “synthetic” insole and waterproof leather material.

You can’t go wrong with a leather Chelsea boot. Another of Cospito’s picks, this platform style from Coach features a rounded toe and pull-up loops for easy carrying.

Need a wider style? These boots feature a wide-fit design and a slim toe silhouette. Reviewers love the faux leather and comfortable fit.

Cramer likes that these boots add some height and a whole lot of edge to any look. In addition, the platform sole is made with “high technology”, which gives them a super comfortable feel.

Cospito says these Chelsea boots show off the classic style. From the smooth leather finish to the almond-shaped toe, there’s so much to love about these boots.

These boots combine a bit of edge with a lot of style. The cleated sole gives them an on-trend look, while the classic black and white designs make them a versatile piece in any wardrobe.

Bestselling Chelsea Boots

For boot lovers, Dr. Martens are a classic, and these Chelsea boots are a super stylish option. The upper and sole of these boots are heat sealed and sewn together for added comfort and durability.

Featuring a bright color and cleated sole, this boot is perfect for those looking to stay on trend this season. This quirky option features classic side panels and back pull tabs, making it the perfect addition to your current wardrobe.

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Chelsea boots have quickly become a must-have in every discerning gentleman’s casual wardrobe. Whether it’s for a wintry weekend or a casual dinner, they’re the ultimate shoe when it comes to style and versatility. And with an illustrious lineage stretching back to the British monarchy, it’s no surprise they’re so popular today.

Originally invented as a riding boot, the style was later popularized by the Beatles and became a mainstay of the British Mod movement in the 1960s. Since then, the boot’s appeal has expanded even further with a wide variety of manufacturing and price points. Here we explain how to wear Chelsea boots and how to choose the perfect pair that will take you from a weekend getaway to a night on the town and back again.

How To Wear Chelsea Boots With Jeans

Chelsea boots and jeans are a recipe for a classic, relaxed look. Easy to slip on for an after work drink or dinner, a pair of these dark brown or black boots will instantly complement indigo jeans and a casual shirt. For best effect, make sure the jeans are cut slim (not skinny) as this allows the top of the boot to sit comfortably under the hem without being pinched. Pair this with a white chambray button-down shirt from Brooks Brothers or Ralph Lauren and a matching belt for a simple yet elegant outfit.

If your style leans a little more Yeezy, suede Chelsea boots can add a touch of shine to distressed denim like nothing else. Pair this with a fitted khaki plain tee and a black bomber jacket for a more sophisticated street style.

How to wear chelsea boots with a suit

A nod to the tailored suits and pointy boots of the ’60s, Chelsea boots aren’t just for weekend larks and after-hours wear. Indeed, choose your pair well and this shoe can take you from the office to the bar and then some. However, there are two important points to remember when pairing boots with a suit.

First, if you plan on pairing a suit with boots, bring them with you when you get your pants hemmed. Since Chelseas sit higher on the foot than a regular derby or brogue, the hem needs to be shorter to avoid multiple disruptions down the front of your pants.

Second, not all Chelsea boots are dress-worthy. Look for models with textured uppers. These look more appropriate to the suit and also keep you from looking like you were dragged into the office in last night’s kicks. People like Loakes and R.M. Williams are great places to start and if taken care of they are worth the investment.

How To Wear Chelsea Boots With Chinos

Dressier than jeans but less formal than a suit, chinos and Chelsea boots exude sophistication. The trick is understanding the fit and pairing it with the right pieces. In particular, avoid chinos that grab the calves. This has the unfortunate effect of making you look like you’ve skipped leg day all the time. Instead, opt for a pair of slim-fitting chinos that fit comfortably over the upper of the boot. Beige, navy and khaki styles are great basics for any casual wardrobe and you can wear them all year round.

When it comes to choosing your top half, casual shirts are a great choice. To add some personal flair, look for bold colors in checks and stripes that add an interesting point to the outfit. Team it with a half-zip sweater or quilted jacket in the cooler months for an effortless look.

How to combine Chelsea boots with a winter coat

Chelsea boots are perfect for winter, adding that extra layer of warmth and keeping the wet weather off your socks. If so, you’ll probably pair them with a winter coat at some point. When wearing a collared shirt, I usually opt for a more structured wool coat in navy or camel. Suitsupply has a wide range, as do retailers like Harrolds or Mr. Porter. Look for either mid-rise, single-breasted styles or pea coats if you’re vertically challenged.

Alternatively, if you prefer a more casual look – with jeans and a t-shirt, for example – you can wear a light wash denim jacket or vest over a chunky knit sweater. This has the appeal of being both rustic and supremely comfortable.

How to care for and store Chelsea boots

Chelsea boots can come at a steep price – especially when you’re choosing an iconic label like Australia’s own R.M. Williams. For this reason, knowing how to take care of your boots is a must. Above all, leather Chelsea boots need to stay hydrated. As with any leather product, it is more prone to cracking as it dries out. We recommend using a moisturizer a few times throughout the year to keep it supple and give a good shine. If you have a suede pair, a good shoe brush will keep them looking fresh and will also help remove stubborn stains.

Finally, we cannot stress enough the importance of resoling. If you’re buying a leather-soled pair, it’s highly recommended that you go to the local cobbler and have a topy sole put on. This is a thin piece of rubber that goes over the ball of the shoe and greatly increases its lifespan.

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Chelsea boots are a great all-season boot that not only suits any weather, but any occasion, be it casual or dressy. Not just the black, pointed-toe style typically associated with this type of shoe, Chelsea boots actually come in a wide variety of colors and shapes, including casual, rounded-toe designs for those seeking a less sharp, suave style.

Slim fit

Slim fit jeans are without a doubt the most stylish way to wear with Chelsea boots. They hug the leg without making the lower body appear narrow, and the slimmer leg tapers down so your jeans sit perfectly over your boots.

tapered

Tapered jeans are great for the same reason as above: they taper towards the bottom of the leg and sit comfortably and stylishly on your boots. Tapered jeans are not as tight on your leg as slim fit and offer more room around the thighs, making them ideal for the taller man who still wants to look stylish.

Slim

Another great option, especially for those with a more alternative fashion sense, skinny jeans can look great with Chelsea boots. Colors go a long way in creating a specific look with this combination; For example, wearing black skinnies with black Chelsea boots will give you the rock-hard, Russell Brand-esque look, while light blue jeans and tan suede boots will likely look much more casual.

Above are the three best styles of jeans to wear with your Chelsea boots. Of course, there are other styles like boot cut and loose fit, but these really aren’t in fashion and don’t look great no matter what shoes you style them with. However, if you are not at all interested in looking a certain way, then you can wear such cuts, and Chelsea boots will still add a fashionable flair to your image.

Written by Aaron Thompson

Today’s question comes from Markus:

“Hey Peter, what do you think of duck boots or galoshes? Would like to know what winter boots you recommend for the office.”

While galoshes are practical, they always look to me like your shoes have condoms on them.

And while duck boots can be a stylish look, I still find them a bit clunky and not as functional as I’d like. The classic chain profile seems better suited to mud than slippery city streets.

The good news is that shoe technology has advanced so much that you can find stylish, office-ready shoes that can handle the worst of the weather that winter can throw at you.

Here are my personal favourites.

Warning: For tips on caring for your boots, download my guide to caring for winter boots below!

WHAT MAKES A GOOD WINTER BOOT FOR MEN

Water repellency, durability or proof:

You want your feet to stay dry, especially if you have the unfortunate accident of stepping in a deep puddle.

While these may all like the same thing, they’re not. It’s like saying “hot” and “you must sign a waiver, hot” are the same thing.

It’s good to know what level of protection you’re getting yourself into.

Repellence offers the lightest protection where light water and elements bead up. This is often the most breathable but struggles in heavy rain or submersion due to the lack of a mid layer repellent and exposed seams.

Resistance offers a deeper level of protection, often with a middle layer underneath the outer repellent layer.

This extra layer acts as a barrier, repelling water that might seep through to penetrate deeper into your socks and feet. Because of this extra layer, these are less breathable. Prolonged submersion or unsealed seams still allow water to seep through.

Shoes that are fully waterproof offer the best protection, but are often the least breathable. Along with the same repellency and resilience, an extra step of sealing gaps like the boot tongue, seams and laces gives these shoes the ability to withstand deep puddles.

When wearing fully waterproof boots, it is important that you have a sock that wicks well. Because waterproof boots are the least breathable, your feet can sometimes sweat. A non-wicking sock keeps sweat in and keeps your feet cold.

Although many of these boots come ready to wear out of the box, I always recommend adding an extra layer of water repellent spray. Also note that the effectiveness of your water repellent boots will decrease over time due to use. So I also recommend giving your boots a good spray every year.

For more tips on caring for your boots, download my guide to winter boot care by entering your details below.

GOOD GRIP RUBBER SOLE

While leather-soled shoes look great, this is a time when you want to go rubber with your sole. A good winter boot has good traction, along with treads and baffles that disperse water or snow and prevent slipping.

Look out for boots with Vibram soles, one of the leading providers of high-quality, functional shoe soles.

ANKLE SUPPORT

A boot with good ankle support does two things. First, it helps stabilize you when walking on slippery surfaces. Second, it keeps your socks from getting wet when you step in a deep puddle.

MY 4 FAVORITE WINTER BOOTS FOR MEN

I realize that not all of my readers live in areas that are plagued with snow every year. Below I’ve rounded up my favorite men’s winter boots to wear for all office climates. Whether you live somewhere that doesn’t fall below 70 or are knee deep in snow, I’ve got you covered.

FOR WARM WINTERS AND LIGHT RAIN: THE CLASSIC LACE-UP BOOTS

There’s a reason I put a lace-up boot in almost every closet of my private clients. They’re a wardrobe essential that’s incredibly versatile. You can wear them with jeans and a t-shirt, or with a suit in a pinch.

These are perfect for climates without snowfall and occasional rain in winter. They offer some natural water repellency, but I recommend spraying them with water repellent spray just as an extra measure.

They are not thick or lined, which makes them comfortable to wear even in almost summery temperatures.

BUY: THE PRESIDENT LACE-UP BOOTS AT THURSDAY BOOT. CO, $199

FOR LIGHT RAIN OR SNOW: WATERPROOF CHELSEA BOOTS

These were introduced to me by one of my styling clients and I love them as an alternative to chunky Duck or Hunter boots for rain.

What I love about these shoes: They are extremely easy to put on. The classic looking Chelsea boot design is elegant enough to wear to your most important business meetings, yet totally wearable with something like a pair of sturdy jeans.

This Cole Haan model features a leather upper that has been treated to be 100% waterproof. The Grand midsole technology developed by Nike makes this special boot as comfortable and light as a sneaker.

Best in light rain or snow. Note that the Chelsea boot’s elasticated insert is water-resistant and not durable, and the sole will not give you enough grip and traction on firm, icy snow.

UPDATE: Cole Haan has discontinued this model. I recommend trying the rough Chelsea on Thursday as an alternative.

THE ALL-PURPOSE RAIN AND SNOWSHOE: THE HIKING SHOE

Wearing big snow boots over pants in moderate snowfall is a bit like driving a Hummer in the suburbs. It gets the job done, but it’s also a bit overkill.

A hiking boot, like the Commander from Thursday Boot Co., offers the best of a lace-up boot and a snow boot. It’s light and slim enough to look great in the office, yet gives you the protection you need when the weather gets a little harsher.

Inspired by classic hiking boots (you know, the kind people wore to scale snowy mountains), the Thursday version has everything I love about winter boots: padded ankle support, a thick, grippy Carrarmato outsole (meaning “armoured tread”). . Vibram, ultra-comfortable leather lining, and it looks damn good.

There’s a reason I picked it for my fall 2018 style guide. If you had to buy a boot from this post, make it this one.

BUY: THE COMMANDER BOAT FROM THURSDAY BOAT CO., $249

FOR APOCALYPSE LEVEL BLIZZARDS: THE SOREL CARIBOU

When you need to battle a blizzard worthy of a disaster movie starring The Rock, this is the boot you need.

Sorel’s AeroTracs give me tons of grip confidence on the icy New York streets. The removable lining (felt in the original, wool in this model I own) provides much-needed warmth, along with a comfortable barrier between you and the lower rubber shell.

These things can take a beating. Sorel owners have shared stories of owning the same pair for over 20 years.

It was the Code Red Blizzard snowshoe that I’ve recommended for the last 3 years and I suspect it will remain my recommendation for the next 20 years.

And in case you’re wondering if these are okay at the office, once you have to get those bad guys out, it’s safe to say the formalities go out the window.

Your boss, coworkers, and all important business contacts will be dressing for survival at this point. You will understand.

BUY: THE SOREL WOOL CARIBO BOOT, $180

KEEP YOUR WINTER BOOTS IN GOOD CONDITION

It is always important to practice proper boot care, especially with those tough winter boots.

I’ve put together a free winter boot care guide so you can make sure your boots will serve you well for many years to come.

Just fill in your details below and let me know where to send it to!

Chelsea boots are a must-have in your wardrobe because they are versatile and timeless. You can dress them up or down.

We receive a commission if you purchase through affiliate links on this site.

Photo by David Em/Next Level Gents.

Few shoe models look as good or are as versatile as the Chelsea boot.

Regardless of your age or style preferences, Chelsea boots will make you look fashionable.

Related Article: The Best Turtlenecks for Men

They thrive almost every season except summer. Boots don’t offer much breathability.

In addition, Chelsea boots can be combined with casual or elegant outfits.

Below we will cover many ways to wear Chelsea boots. You will also learn about the different materials, features and best options.

What is a Chelsea boot?

Chelsea boots are ankle boots that have an elasticated side panel and a tab at the back, making them easy to slip on.

Because they are timeless, these sophisticated boots will look great on you regardless of age or personal style.

Related: 15 Best Suede Chelsea Boots

If you are looking for shoes that go well with jeans and a t-shirt and at the same time go well with a suit, Chelsea boots are the right choice.

They are popular because they can be worn with many different outfits and in different seasons.

These boots date from the Victorian era, which was between the mid 19th century and early 20th century.

J. Sparkes-Hall first designed and patented the elasticated ankle boot now known as the Chelsea boot.

The word “Chelsea” comes from south-west London, an area called Chelsea.

In addition to its origins in London, the Rolling Stones and the Beatles also made the Chelsea boot very popular.

The Beatles

Stormtroopers from Star Wars also wore white Chelsea boots.

Han Solo in a Stormtrooper uniform with white Chelsea boots. Photo courtesy of Star Wars.

They are great for numerous occasions such as work, weddings, parties or business meetings. You don’t have to worry about being out of place.

Due to their timeless design, Chelsea boots are very trendy today and in the future.

Chelsea boot outfits

The following are various outfits with black leather chelsea boots.

Use the outfit examples as a basis. You can mix and match different pieces with different Chelsea boot materials and colors.

Chelsea boots with jeans

If you wear jeans, swap your sneakers for Chelsea boots. They are an excellent and stylish alternative.

You can wear leather or suede as both look incredible.

Wear them with jeans and a t-shirt, casual button-up or sweater. They enhance every casual outfit.

A blue corduroy jacket brings back a classic piece in men’s outerwear. The jacket goes well with gray jeans and looks great when paired with Chelsea boots. This look is perfect for a day out or in fall and winter.

Wearing black jeans, a black shirt and a denim jacket creates a pop of color that makes the outfit more interesting.

No matter what the weather, these boots look great. Combine the boots with a classic rain jacket for the perfect rainy day look

One of the essential rules for matching clothes is to create contrasts. Wearing a light-colored shirt with dark pants and shoes will do the trick.

For a casual but sophisticated look, wear jeans and a checked button placket. It’s perfect for a date or meeting up with a friend. When it’s warm you can roll up your sleeves.

Contrasts are a great place to start when putting together an outfit. A dark top, light trousers and dark shoes make for an eye-catching outfit.

Black jeans pair well with black leather chelsea boots. The bottom of your jeans wraps nicely around the top of the boots without looking weird or feeling uncomfortable.

When it’s cold, the goal is to stay warm and stylish. Wearing a military jacket, light sweater and dark jeans looks great in colder weather.

Chelsea boots with trousers

Chelsea boots also go well with trousers.

Wear them with trousers, a button down shirt or turtleneck and a blazer. You can also exchange the jacket for a coat.

With the business-casual look, a suit without a tie, you can wear it to business meetings or to work.

Black leather chelsea boots go well with this outfit as they resemble dress shoes. Although there are no laces, they are simple and classy.

Chelsea boots with a suit

Chelsea boots are great for formal and business dress codes. Aside from occasions that call for a tuxedo, you can pair these boots with a suit and tie.

Materials and Designs of Chelsea Boots

The main features of Chelsea boots are the pull tab on the back and the elastic side panel.

There are various options in terms of material and style. Leather and suede are the two materials.

While both materials are excellent, your first pair has to be leather.

They are traditional, elegant and allow you to dress semi-formally or casually.

As for the design, they differ in the tip of the boot. The toe can be smooth or have a wingtip or cap toe.

Chelsea boots with a smooth toe are the most versatile, as wingtip and cap-toe styles are more casual.

Best Colors for Chelsea Boots

Photo by David Em/Next Level Gents.

There are many colors for Chelsea boots. Black and brown are the most common.

If you’re looking to buy your first pair, choose brown because it’s more versatile.

You can easily dress brown chelsea boots up or down.

Black is also an excellent color. But it is best with formal outfits.

After a brown pair, add black to your collection and experiment with other colors.

Burgundy is a stylish and versatile colour, while tan and gray are ideal for casual outfits.

Again, brown is the most versatile boot color, so start with that.

How to style Chelsea Boots

Chelsea boots are versatile. So you can wear them with many outfits.

To look good, learn how to style them. A key consideration is your pants.

Whether you’re wearing pants, chinos, or jeans, make sure the pants sit over your boots.

Your pants should have a slight break or no break at all.

If you’re wearing jeans, don’t tuck them into your Chelsea boots. Instead, tie your jeans.

After the pants, you can wear any top that suits the occasion and style of pants.

Chelsea boots have a clean silhouette. They are perfect for adding value to most outfits.

Wear them casually as a sneaker replacement.

Wear Chelsea boots with chinos, a turtleneck and coat for a smart off-duty outfit.

Wear them in a business-casual style with trousers, a button-down shirt and a blazer.

Wear black leather chelsea boots with a suit for a semi-formal look.

Can you wear Chelsea boots all year round?

You can wear Chelsea boots all year round.

However, they are not breathable, so in hot temperatures your feet may feel too hot and sweaty.

As boots, they are ideal for mild and cold weather. In winter, wear thick socks or wool socks to keep your feet warm.

Chelsea boot buying guide

Photo by David Em/Next Level Gents.

Chelsea boots deserve a place in your footwear collection. They are stylish, functional and comfortable.

Before you buy a pair, remember to invest in quality. Many high-quality Chelsea boots cost more than $200.

The following brands sell the best and highest quality Chelsea boots:

When shopping for Chelsea boots, the main things to look for are fit, leather, soles and elastic.

Because Chelsea boots are snug, getting the right size is essential.

Avoid relying on standard shoe sizes as they may not be accurate for Chelsea boots.

Because there are no laces, you need a precise fit.

The only flexibility is in the elastic side panel, which comes into play when putting the boots on and taking them off.

So try them on and walk around. Make sure your toes have some freedom of movement.

Often you will not increase or decrease the size. Instead, you’ll have to change the width, which may mean trying a different brand.

A snug fit without too much restriction is what you want.

The soles are another essential feature.

Traditional Chelsea boots have leather soles. There are now boots with wooden or rubber soles.

The sole thickness also plays a role. A thin sole is excellent when wearing formal attire.

A thick or commando sole looks casual and provides grip in slippery situations.

When shopping for Chelsea boots, you may find some with a zipper instead of the elasticated side panel.

A brand may call it a Chelsea boot, but it’s not. The elastic side panel is a feature that defines a Chelsea boot.

Conclusion

Chelsea boots deserve a place in your footwear collection. They enhance every outfit and work with many combinations.

Whether it’s autumn, winter or between seasons, Chelsea boots should be your favorite shoes.

Featured image by David Em/Next Level Gents.

A great pair of boots is a dynamic choice for both dressy and casual occasions. One boot we are particularly eyeing this time of year is the Chelsea boot. This endlessly versatile shoe is as easy to style as it is timeless. And with the sheer variety of materials, colors and finishes available, there’s bound to be a pair to suit every man’s personal style. Here’s everything you need to know about the Chelsea boot.

Read: The essential guide to men’s boots

story

The Chelsea boot was invented in Victorian England by J. Sparkes-Hall, Queen Victoria’s official shoemaker. Using then-reinvented vulcanized rubber (a chemical process that converts natural rubber into more durable materials), the Chelsea boot was designed to be put on and taken off. Now that might not sound like a big deal to you, but in a time when boots were characterized by intrinsic lacing, slip-on boots made things a heck of a lot easier. Although the boots were originally made for the Queen, their popularity grew so much that men of the time eventually adopted the trend as well. Almost a century later, the boot got its iconic name from celebrities in London’s Chelsea, who wore the shoes frequently every day. Its popularity grew even more when the Beatles started wearing them. The rest is history.

Fit

Unlike other boots, which you can just tighten up if they’re a little loose, Chelsea boots need to fit perfectly to be comfortable. Find a boot that is snug around the ankle but still leaves room for your toes. You should also think about your socks. If you often wear thick socks, you should also choose half a size larger. Wear the socks you plan to wear with your boots while trying on the shoe.

materials

As dynamic as they are timeless, Chelsea boots come in a variety of materials to suit your needs. You should choose the material that best suits your lifestyle. If you’re primarily looking for a shoe for casual or indoor wear, look no further than rocking suede. However, if the weather where you live is a bit temperamental, leather might be the right choice.

styles

Rounded vs Pointed

Chelsea boots usually have a rounded or pointed shape. The rounded toe is a great option for everyday wear as it is much more casual and easier to take off. On the other hand, pointed toe Chelsea boots are generally more formal and fancy.

Colours

Black and tan are great classic options, especially if you’re going for a sleek, urban look. Brown suede works best for casual wear, while brown leather could be a great addition for the office. If you’re looking for an office-ready shoe that’s not black or brown, you can’t go wrong with burgundy. Additionally, different colors like indigo, green, and copper are great options to add to your wardrobe if you’re trying to make a statement.

quality

Chelsea boots don’t go out of style anytime soon, so you can rest assured that your investment will be worth it in the long run. If you want to go for a trendier style or non-traditional color, opt for a cheaper pair ($50-$150). However, a more expensive pair that will last longer is a safe bet if you’re looking to expand your shoe clasps. While a $400 pair may seem outrageous right now, these boots will be must-haves for years to come. We’re not saying you should splurge, but we’re not saying it either…

Our selection:

Save on computer

Houston Chelsea Boots, New Republic $99

Sale New Republic | Sonoma Chelsea boot for men with crepe sole suede/leather

All-day comfort

Classic style Get it now

Spend

Liverpool Chelsea Suede Dress Boot, Allen Edmonds $445

Sale Allen Edmonds Liverpool Men’s Chelsea Boot Iconic British Chelsea boot with American attitude. Authentic style of the 60s. Dress up or down, perfectly how you style it. Classic fit, true to size. buy now

The Chelsea boot has been a timeless piece of footwear since the 18th century. Chelsea boots are a great alternative to the typical work boot and offer the added benefit of transitional use. Next time you want to spice up your office outfit or put together a look for a night out, opt for the classic Chelsea boot.

Read Next: The Essential Guide to Men’s Boots

Figuring out which jeans to wear with boots can be a bit tricky, especially when there are so many style tips out there. To address this, I created a guide that answers the question for a whole host of different jean and boot combinations to make sure all the bases are covered.

What jeans do you wear with boots?

Wear skinny jeans with any type of boots and they look great – especially over the knee boots and sock boots. Wear straight-leg jeans over calf-hugging boots, and baggy or mom jeans with heeled ankle boots to elongate your legs and balance your outfit.

Different boot-jeans combinations apply to the change of seasons as well as to day and night outfits:

For daytime outfits, pair tan boots with indigo or light-wash jeans. Alternatively, pair black boots with light wash jeans.

For nighttime outfits, opt for darker wash jeans to pair with black boots.

Combine lighter boots with light-colored jeans in spring/summer.

Combine darker jeans and boots in autumn/winter.

Now you know the basic rules for combining jeans and boots. Let’s break down different styles of boots with different jeans in pictures for style inspiration.

Cropped Jeans With Chunky Boots:

©[Ursula Madariaga] via Canva.com

Wear cropped or cuffed jeans with Dr. Martens boots to show off the boot and not burden the ankle and calf trying to cover them by pulling the jeans over them. dr Martens or other chunky boots also look great tucked in skinny jeans.

The rule with these types of boots is to show them off, so make sure you either tuck in your jeans or roll up the cuffs to reach the top of the boot rather than trying to wear them under your jeans. You can also wear high-waisted baggy jeans with these types of boots, as long as you roll them up and wear a fitted top or jacket to balance the look, for a modern on-trend style.

Skinny jeans with sock boots:

©[Godisable Jacob] via Canva.com

With sock boots you wear them best with skinny jeans to create a seamless look. Sock boots traditionally look best over skinny jeans, but you can wear them underneath if you wish as they are snug enough not to bulk up your ankles and calves.

All types of sock boots look great with skinny jeans; Velvet (as pictured above), suede or simpler fabrics. You can pair skinny jeans in different washes with your sock boots, although I usually prefer to pair them with black or dark skinny jeans like an indigo wash to elongate the legs.

Heeled sock boots pair best with skinny jeans to create a streamlined silhouette.

The same rules apply to over-the-knee and knee-high boots; Combine them with skinny jeans to create a well-fitted look. Pairing over-the-knee or knee-high boots with any other type of jeans will look odd as the material will baggy and the legs will look bulky.

Mom Jeans and Black Booties:

Mom jeans pair really well with black heeled ankle boots for an on trend 2021 style. I paired my light wash mom jeans with two styles of black ankle boots to show how well the two go together.

With my gold heeled ankle boots I put on the mom jeans along with a floral top and a bag. To keep it more casual, pair mom jeans with black ankle boots with a plain heel for a daytime look.

Mom jeans look great with higher ankle boots as the hem of the jeans tends to meet the shaft of the boot. If your mom jeans are too long, instead of tucking them in, simply roll up the cuffs slightly until they meet the tops of the booties.

Skinny jeans and larger booties:

Wearing tall ankle boots with skinny jeans is a great way to show off the boot and elongate your legs.

I love this pairing as it looks so streamlined and elegant. It also works well for day and night outfits; Just swap out your top and bag for fancier options and you’re ready to hit the town.

Above, I paired tall black ankle boots with black skinny jeans and skinny mom jeans to show off this effect. Pair with black skinny jeans and black tall ankle boots to tuck the jeans into the boot for a seamless finish. Alternatively, you could cuff the jeans if you wish.

Baggy jeans and heeled boots:

Pair baggy jeans with heeled boots for a 2021 style look. The heeled boots lengthen your legs and flatten your figure, while the high-waisted baggy jeans add a touch of on-trend style.

The pairing looks great for both day and night outfits. Just make sure to wear a fitted top for your top half to balance the outfit as I styled it above. Of course, there are no rules when it comes to fashion, so style it however you like, but I think a fitted top looks great with this pair of jeans and boots.

Baggy jeans in light and dark washes pair really well with black heeled boots, so take a look in your closet and try to style the options you have.

Which jeans for women to wear with Chelsea boots?

Wear skinny jeans with Chelsea boots to elongate the legs and show off the boots without spreading your ankles. Chelsea boots also look best with cuffed jeans or slightly cropped jeans for an on-trend style.

Alternatively, choose a pair of jeans with a distressed hem that meets the top of Chelsea boots for an on-trend look. Mom jeans also pair well with Chelsea boots as long as they’re cuffed and don’t protrude past the top of the boots.

Wear a chunky fleece jacket with your mom jeans and Chelsea boots for a cool and trendy look. For summer/fall, pair your mom jeans with a crop top and chelsea boots for relaxed chic style.

Which jeans to pair with ankle boots in 2021?

Wear 2021 skinny jeans with ankle boots for a modern style. Tuck the jeans into the boots to keep the denim from bulking around the ankle. You can also combine ankle boots with distressed hem mom jeans for a trendy look.

Ankle boots and skinny jeans are a classic pair that looks instantly attuned. They can look casual as a couple or dress up for a night out.

For a daytime look, pair tan ankle boots with indigo skinny jeans, a white t-shirt or cream turtleneck and a neutral-toned jacket or cardigan, as pictured below. For a night out look, pair black ankle boots with black skinny jeans and a nice top or bodysuit with a tailored jacket for a smart casual smart look.

©[Snapwire] via Canva.com

Can you wear boots with straight leg jeans?

You can wear boots with straight leg jeans as long as you pair the right type of boots with the jeans. For example, heeled boots that fit under straight-leg jeans look best as they lengthen the leg. Pair with a boot that fits snugly on the calf to avoid bloating.

Choose straight-leg jeans with a shorter hemline so they don’t completely cover the boot, and choose a boot with a higher shaft so no part of your ankle is exposed. This creates a more streamlined look as a slightly exposed ankle can look odd on straight leg jeans.

Should Jeans Go Over Boots – Women?

Women’s jeans can be worn over boots or tucked into boots depending on the style of jeans. Wear straight-leg jeans over your boots as long as the boots fit snugly around the calf. Tuck skinny jeans into boots for a comfortable fit.

For chunky boots, wear either cuffed jeans or a cropped length that goes to the top of the boot, or wear skinny jeans and tuck them into the boot. When pairing boots with straight-leg jeans, choose jeans with a slightly shorter hemline, allowing some of the boots to show for a more tailored style.

Do you tuck skinny jeans into ankle boots?

Skinny jeans can be tucked into ankle boots for a streamlined effect that elongates your legs. Skinny jeans look best when tucked into ankle boots so the material doesn’t add bulk when pulled over them.

If you try to wear your booties under your skinny jeans, the material will bunch up and stretch, which can ruin the hems of your jeans. This also doesn’t look very polished and can make the calves or ankles look bulky. When in doubt, pair black ankle boots with a dark wash or black skinny jeans and tuck them in for a smart look.

Alternatively, if you have tan ankle boots, you can pair them with indigo-wash jeans and either turn up the hems for an on-trend look or tuck them in.

What boots do you wear with skinny jeans?

You can wear almost any type of boot with skinny jeans as it is a versatile jean that pairs great with most shoes. Make sure you tuck your skinny jeans into your boots instead of wearing them over them as this will bulk up the material. Alternatively, for an on-trend look, ruffle the hem of your skinny jeans to meet the top of your boots.

Knee-high and over-the-knee boots should always be paired with skinny jeans. Likewise, ankle boots, sock boots, cowboy boots, chelsea boots and chunky boots look fantastic with skinny jeans as this type of jeans elongates the legs and shows off the boots.

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A note

Thanks for reading this boots and jeans style guide and I hope you now feel confident pairing your shoes with your jeans! Remember that there are no rules in fashion, only guidelines, so mix and match your boots and jeans however you like and what feels comfortable to you.

For more fashion tips, check out the related articles below…

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Chelsea boots are one of the biggest shoe trends. If you want to figure out how to wear them with dresses, here are 4 easy looks.

Chelsea boots with dresses

You’ve probably bought yourself a pair of Chelsea boots in the past few years. While these boots are so easy to wear with jeans and leggings, pairing boots with dresses can be a little trickier.

I shared about THESE CHELSEA BOOTS last year (I bought them last January) and they have become a staple in my closet. They are currently sold out but have been restocked several times and then quickly sell out again.

So if you see them in your size, grab a pair! They are true to size, a little stiff at first, but then soften up nicely and become insanely comfortable. Hundreds of you have bought them and love them as much as I do.

Here are 4 looks to try and style tips to make boot and dress outfits work.

1. Try your boots on with a shorter dress and a long coat

A knee-length dress goes great with a pair of Chelsea boots (as long as they’re narrow at the ankle)! The large gap of the bare leg makes the leg look elongated and not squat.

If you need more warmth, you can wear tights. And of course I wear a long, slim-fitting coat over it!

SIMILAR BROWN DRESS HERE, HERE and HERE | SIMILAR WOOL COAT | BLACK CHELSEA BOOTS | MADEWELL PEARL EARRINGS

2. Try your Chelsea boots on with a sweater dress and socks

These boots look great with a shorter sweater dress or a longer sweater dress. The slit helps lengthen the leg, but it’s not necessary (a case in point… CHECK THIS POST).

But with a long dress like this, a piece of sock between the leg and the boot (especially if you have lighter skin like me) helps soften the look so the boot doesn’t ride as hard over your ankle.

LOFT SWEATER DRESS | AMAZON BLACK BELT | AMAZON HIGH SOCKS | BLACK CHELSEA BOOTS

3. Chelsea boots go great with a shirt dress

This isn’t the best example of a shirt dress, but it’s all I have right now, so let’s go with it. Chelsea boots look great with more structured dresses, especially if they have a belt and you have a defined waist.

Again I added a high sock to soften the look of the boot on the leg.

WHBM ZIP-UP SHIRT DRESS | AMAZON HIGH SOCKS | CHELSEA BOOTS

4. Chelsea boots even go with more feminine dresses

These boots even go with more feminine dresses! No these shoes wouldn’t be my first choice with this dress (I wore them last week with sheer tights and heels as seen HERE) but they are slim and smooth enough that they work!

As they are a bit chunky with their cleated soles, I would wear a coat with this look to offset the shoe’s heaviness a bit.

To create a slimmer look as well, I added black tights.

WHITE HOUSE BLACK MARKET FLORAL DRESS | SIMILAR BLACK TURTLE NECK | BLACK TIGHTS | BLACK CHELSEA BOOTS

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