When thinking about essential footwear for men, boots are a wardrobe staple worth investing in. Men’s boots can be comfortable, stylish and versatile, offering a functional style every man can pull off. From Chelsea boots to Chukkas, dress boots, work boots, and beyond, there are many types of boots to wear with different outfits. Guys can pair casual boots with jeans and a shirt, Chukkas or Chelsea boots with trendy pants and a blazer for a smart casual look, or dress boots with slacks for a business professional style. Some guys have even started dressing dark brown or black leather boots with suits for a bold fashionable look that stands out. With so many different types and colors, it can be a challenge figuring out the best ways to style boots. To inspire your fashion with outfit ideas, we’ve compiled a guide on how to wear boots for a good look.
- 1 Types of Boots For Men
- 2 Men’s Boots Outfits
- 3 How To Wear Ankle Boots
- 4 How To Wear Combat Boots
- 5 How To Wear Work Boots
- 6 How To Wear Timberland Boots
- 7 How To Wear Biker Boots
- 8 How To Wear Lace-Up Boots
- 9 How To Wear Chelsea Boots
- 10 How To Wear Leather Boots
- 11 How To Wear Brown Boots
- 12 How To Wear Black Boots
- 13 How To Wear High Top Boots
- 14 How To Wear Dress Boots
- 15 How Boots Should Fit
- 16 How To Clean Leather Boots
- 17 How To Clean Suede Boots
- 18 What To Wear With Boots
Types of Boots For Men
Chelsea boots are ankle-high boots made with an elastic side panel that allows you to slip on this footwear. This laceless boot style is exceptionally trendy right now and comes in a variety of colors, including black, light and dark brown, grey, and dark red. While the Chelsea boot is generally made with leather, it also comes in suede for a unique textured look. The pull-on design makes these boots easy to wear, comfortable, and low-maintenance. From casual to smart casual looks, the sleek cut works well with many outfits and can add an edgy or classy look depending on how you style them.
Chukka boots are ankle-style boots that come in leather or suede uppers, rubber or leather soles, and open laces that feature two or three eyelets. Also known as desert boots, Chukkas are comfortable, dapper and elegantly relaxed, making them a popular choice for modern men. The Chukka boot can be great for casual and smart casual outfits, but you’ll need to find the right brand and style to fit your clothing. Once you’ve picked a good pair, you can wear them with jeans or chino pants and a t-shirt, button-up, or sweater. You can take the outfit to the next level with a denim or bomber jacket on top.
Work boots are a type of footwear worn by construction workers and tradesmen, and tend to be made with durable materials for maximum protection. While work boots are comfortable and functional in nature, this boot style can be worn with casual outfits for a rugged, cool look. The most popular work boots are Timberlands, and most guys like to wear these boots with jeans. To dress work boots casually, you’ll want to pair skinny black, grey or dark blue jeans with a t-shirt, jacket and light or dark brown work boots. Simple and trendy, guys can experiment with brands like Red Wing, Timberland, Dr Martens, Golden Fox, and Wolverine.
Dress boots are lace-up boots that look and feel like dress shoes. Made with high-end materials like leather, the dress boot is generally an alternative to a dressy shoe when the weather is bad. Also known as formal boots, these men’s boots can be styled with smart casual, business professional, and formal outfits to create the perfect ensemble. Plain toe boots are good for an understated look, while brogue and Oxford boots are elegant and dressy thanks to their quality craftsmanship. Whether you wear your dress boots with jeans and a shirt, chinos and a button-down, or dress pants and a suit will determine the style you pick.
Men’s Boots Outfits
Casual Boots Outfits
Casual boots look best when paired with jeans or chino pants, but there are many ways to style casual outfits. For starters, you’ll want to have the right men’s boots for your desired look. Work boots like Timberlands or all-around versatile Chukka, Chelsea, or Cap-Toe boots will go with a relaxed attire. While black boots work well with everything, you can also mix and match the color of your boots with your clothes.
The classic casual fashion with boots is t-shirt and jeans, but some guys may want to elevate the look with slim-fit jeans, a flannel over a fitted black shirt, and suede boots. Alternatively, you can wear chinos or black jeans with a sweater under a jacket, and leather combat boots.
If you’re interested in a unique aesthetic during the summer, you can even combine boots and shorts for a very relaxed option. Simple and handsome, casual outfits with boots are effortlessly cool to rock around town.
Smart Casual Boots Outfits
When designing a smart casual outfit, you should start pulling styles of boots like the Chukka, Chelsea, Wingtip, Brogue and Trench. Generally, darker colors like black and dark brown are better for a classy look, but light brown and grey have been trending lately.
Chukka boots can be dressed up and paired with blue jeans or chinos, an Oxford shirt, and a sweater. For a slimming appearance, you can wear skinny dark jeans, a slim-fit sweater and a blazer with Chelsea boots. Guys can also pair stylish work boots like Timberlands with dark jeans, a v-neck shirt or sweater, and a bomber jacket.
To get a classic look that’s been on-trend in recent years, men can also dress fitted dark denim, a neutral shirt, and leather jacket with black leather boots for a fashionably edgy finish. While the Wingtip and Brogue might seem too much for a smart casual look, these boots can add flair to your style so don’t be afraid to push the boundaries of a dress code.
Formal Boots Outfits
Wearing a suit with boots has become much more common as modern gentlemen experiment with their fashion. A navy or black suit paired with brown or black Brogue boots instead of dress shoes will give you a unique look that is still formal enough for most occasions.
Many dress boots can be polished similar to dress shoes so make sure you clean and polish your footwear for the perfect finish. But you don’t have to go that far if you want to enjoy dress boots with more formal menswear.
Dark brown or black leather boots can be dressed up with slacks and a dress shirt to create business professional or semi-formal attire. With the right fabric, cut, and styling, you can combine several upscale pieces to pull off an upscale outfit.
Men’s Boots To Wear with Jeans
Guys can wear boots with jeans for a classic men’s style that’s rugged and cool. A stylish pair of boots and a good pair of jeans go together naturally, allowing men the ability to dress the look up or down. Whether your boots and jeans with a button-down shirt and blazer, a field jacket and sweater or flannel and hoodie, the combination of denim and leather will always be on-trend.
For starters, you can dress your standard dark tapered denim jeans with Chukkas, Chelsea boots, and other lace-up boots. Similarly, raw denim with its trademark faded look and selvage lining on the cuff naturally styles well with work boots.
Skinny jeans look great with Chelsea boots for a sleek finish or you can try combat boots if you want an edgy, bold look. You can also try dark washes for medium and dark brown boots, while light washes are chic with tan and grey suede.
Pants To Wear with Boots
While you should already know that denim is universal, there are many other pants styles to wear with men’s boots. If you’ve chosen your boots, consider pairing them with joggers, chino pants, trousers, or slacks and a button-up shirt or sweater on top.
The joggers and sweatpants should be reserved for very casual boots like Timbs, and can be matched with an oversized sweater or hoodie.
The chinos, cargo pants and fitted trousers are versatile, and can be dressed up or down with Timberlands, Chukkas, Chelsea, or Bean boots. Chinos, henley pants and slacks are ideal if you want to style a smart casual or business casual outfit with ease.
How To Wear Ankle Boots
Versatile and easy to wear, ankle boots are must-have footwear for fashionable men. Ankle boots are one of the most popular types of boots because they suit many different outfits. From casual to smart casual, you’ll want to decide on the style you want.
Chelsea boots can be made of leather or suede, but the look will always be simple and sleek. Chukkas and other lace-up boots are also amazing styles when crafted with premium materials and designed well.
Your standard smart-casual look of henley pants, fitted chinos or slim denim jeans with a button-down and bomber jacket will always pair nicely with Chukkas or Chelsea boots. You can even consider rolling your jeans for extra styling and flair.
How To Wear Combat Boots
For a dark touch, combat boots represent a casual heavy-duty style of boot that looks good and will protect your feet in all weather. Similar to boots worn by military members, combat boots are no longer limited to the punk and grunge movements.
Guys can wear combat boots with easy casual outfits when an edgy approach is required. Stick with dark clothing with black leather combat boots, and choose rough materials like denim and leather. The best way is to team black jeans with a dark shirt and dark denim or black jacket for a badass all-black outfit.
How To Wear Work Boots
Work boots have become a staple of men’s fashion and are commonly worn in casual outfits with jeans. Work boots made by brands like Timberland, Thorogood, Red Wing, and Chippewa are sturdy and functional as workwear, but can be styled with denim jeans, canvas work pants, or khakis for a classic masculine look.
You can wear your work boots with dark blue or black jeans paired with a t-shirt and flannel for a relaxed vibe. While most work boots come in a light brown color, you can find a variety of colors to fit your wardrobe.
How To Wear Timberland Boots
While Timberlands are technically a work boot, the brand and style are so iconic that many guys specifically search for ways to wear Timberland boots. This popular men’s boot is so well-made, durable, and fashionable that modern gentlemen and celebrities love to pair these shoes with all types of outfits.
If you’re dressing in casual attire, partner your Timbs with jeans and a t-shirt. Your jeans can be light or dark, distressed or ripped, skinny or loose fit and the pairing will work.
You can take your outfit to the next level for a smart casual feel with dark blue or black jeans, a dressy shirt, and a blazer. To show off and accentuate your footwear, pinroll or cuff your pants and you’ll stand out. Put on a parka for cold winter days or strip down to cargo shorts in the summer.
How To Wear Biker Boots
Biker boots were pioneered as functional footwear before their style became popular for the everyday man. Luckily, you don’t have to own a Harley Davidson to add this footwear to your collection.
Often made from thick black leather, these boots come up higher on the leg to offer extra protection for a biker. The boot style also features a buckle or harness with a low heel, which can be great for extra height.
You can wear biker boots with class by choosing bold dark colors such as black jeans, a black shirt, and a moto jacket. To change up your look, you may consider dark slim fit jeans, a white dress shirt with a loose tie, and black biker boots like David Beckham did in his GQ feature. Complete the look with a leather jacket and you’ll have a trendy outfit that will stand out in any crowd.
How To Wear Lace-Up Boots
For fitted comfortable and a clean timeless look, you can’t go wrong with lace-up boots. These types of boots are characterized by the fact that you have to tie the laces, and generally refer to slim, plain-toed boots with a slight heel.
Lace-up boots can be black or brown, made in leather or suede, and are perfect for smart casual or business casual outfits. Their slim profile makes them a great replacement for Derby shoes or loafers.
Thanks to their sophisticated design, lace-up boots look best with fitted pants or jeans, an Oxford shirt, and a cardigan or sweater. Use other fall accessories like scarves to personalize your look.
How To Wear Chelsea Boots
Chelsea boots are a great footwear option for guys who seek a sleek and simple boot style. Brown leather or suede Chelsea boots are ideal for casual wear, especially when combined with jeans, a shirt or sweater, and a jacket.
Experiment with different color combinations to make your outfit more interesting. Chelsea boots are also available in more upscale styles made from fine dark red, dark brown, and black leather.
Complete your look with dark denim, a black shirt and a denim jacket, or take it up a notch with a knitted sweater or button-up. These boots are even sophisticated enough for a business casual look that includes a black or navy suit without a tie.
How To Wear Leather Boots
Leather boots look just as good with a t-shirt and jeans as they do with dress pants, an Oxford shirt, and a blazer. As the epitome of quality footwear, the best leather boots provide style, comfort, and durability.
From relaxed casual looks to stylish smart casual to classy formal attire, the right leather Chukka, Wingtip, Chelsea, Balmoral, work, or combat boots can make all the difference in bringing an outfit together.
Simply put, men can elevate any look by choosing a premium leather boot. After consistent wear, it is also important to properly care for and maintain the leather. When in doubt, dark denim looks good with almost every color of leather boot.
How To Wear Brown Boots
Brown boots are incredibly versatile and can be paired with all kinds of outfits and styles. Guys should combine dark brown with darker shade pieces like charcoal chinos or dark blue denim jeans. Light brown boots feature nicer with navy blue, olive green, or grey trousers.
While counter-intuitive, a popular new trend has been black pants with brown shoes and this can be worn casually or more formally. Whether you want to dress up or down, you’ll want to add a few pairs of brown boots in different styles to your wardrobe for maximum styling options.
How To Wear Black Boots
Black boots are timeless and versatile footwear for men, offering a practical fashion staple if you want a pair of boots you can wear with everything. Guys can style black boots with casual, smart casual, business professional, and even formal outfits to create their desired look. Try matching black jeans and t-shirt with black combat or biker boots to channel a rocker vibe.
For a clean-cut look, dress up black Chelsea or Chukka boots with black, navy, or grey trousers and neutral-colored button-down shirts. If you want to transform your corporate look but stay professional, invest in a pair of Wingtip, Brogue, or Oxford Derby boots for continued elegance.
In the summer, some guys like black boots with shorts for an effortlessly cool ensemble, while we recommend tailored pants and a thick wool overcoat in the winter. Introduce a pair of black boots into your wardrobe and you’ll have access to limitless outfits and styles.
How To Wear High Top Boots
When you need a little extra protection around the lower leg or want a rugged outfit with flair, combine your attire with high-top boots. While there are many types of high tops, the most common style is the 6-inch boot. Masculine and edgy, you’ll want to wear pants and shirts that will show off these cool boots.
Whether they are work boots or classic lace-up boots, wear your jeans or chinos short enough to rest just below the top of the boot. Some guys will buy shorter trousers while others will roll up and cuff their jeans and slacks. While 10-inch logger boots finish higher, you can still show off the lower half of your shoes.
How To Wear Dress Boots
Dress boots are a fashionable modern substitute for your usual dress shoes. Keep up with the latest men’s fashion trends by wearing trendy dress boots all season.
Like Oxfords or brogues, a sleek Chelsea or wingtip boot can elevate your look. These options would be inappropriate for black-tie occasions but can be dressed with smart and business casual outfits. You can even pair dark brown wingtip boots with your navy suit this winter for a daring look.
For a universally-flattering style, consider cuffing and rolling your dark denim jeans to draw attention to your classy dress boots. Whether you put on a t-shirt, button-down, or sweater on top, everyone will be staring at your bold footwear.
How Boots Should Fit
Boots should fit snugly without being uncomfortable and your feet need to feel properly supported. Not too tight or too loose, finding boots that offer the right fit for your feet is a process and requires basic research and then trial and error.
Leather boots are often tighter than you would like when you first buy them. Many brands suggest that you buy one-half size smaller to account for the break-in process. To be sure, no pair of boots are completely comfortable at the beginning, and all styles require some time to loosen up.
Nevertheless, you should be able to put on your boots without trouble or pain, and your heels and toes shouldn’t be pressed against the ends. Always check with the manufacturer to see if there is a sizing guide that will help you ensure you choose the correct size.
When in doubt, you can always try on boots in department stores to find the perfect size, and then shop online to get the best deal.
How To Clean Leather Boots
For leather boots, you’ll want to make sure that you clean and condition your boots often. While boots are generally made of durable materials and engineered to last, men’s boots can get dirty, scuffed, and dull.
To clean leather boots, you’ll need to remove your laces, wash them with warm soapy water and let them air dry. Use a horsehair brush to buff out any dirt or grime from your boots. Use a quality saddle soap and a damp rag to give your boots a nice, deep clean, then let them air dry as well.
You should also condition your boots with a leather conditioner to prevent cracking. Use a leather conditioner and apply it to the entire boot, making sure to get the nooks and crannies.
How To Clean Suede Boots
Keeping suede boots clean and in good condition can be a challenge, but the time spent can be worth maintaining this beautiful type of leather. To clean your suede boots, start by removing the laces and simultaneously soaking a soft bristle brush in a suede cleaner product. You’ll want to get products that are specifically made for use with suede and are soft enough to not damage the nap of the suede.
With a hand inside your boots, use the brush to clean away dirt and grime. Run the eraser over any stains or marks to remove these blemishes. You can also try a small amount of white vinegar if the stains won’t come off. When you’re done with the pair of boots, leave them to dry for at least 24 hours. Afterwards, apply a little conditioning product like mink oil to soften your boots again.
What To Wear With Boots
- Research the different styles of boots and choose the right type for your look.
- Dark brown and black boots are the most versatile and work well with most men’s styles.
- Try to match your boots with your clothes for a chic aesthetic, but don’t be afraid to buy bold colors and stand out.
- For a casual look, pair chukkas or work boots like Timberlands with jeans and a t-shirt.
- The best men’s casual boots to wear with jeans are chukka, Chelsea, and combat boots.
- To style a smart-casual outfit, pick trendy boots such as Chelsea boots and combine them with dark denim jeans or chino pants, a button-up shirt, and a blazer.
- Wear suede ankle boots such as chukkas or dress boots for a refined, semi-formal outfit.
- For a ruggedly handsome look, choose biker or combat boots with jeans, an edgy shirt, and a leather jacket.
- Clean, condition and maintain your boots to help them last longer and always look good.