Stylish Outfits to Show You How to Wear Boots for Men

mens casual boots to wear with jeans

When we think of men’s shoes, sometimes it just doesn’t seem like there is much choice out there. For casual outfits, sneakers may seem like the best choice for footwear, and when we think of suits and formal attire, most men reach for some sort of dress shoe. However, there is a third choice that can be an adventurous option that works well with formal and casual attire, and that is the boot.

Boots come in a variety of color and style options. Men who are new to the booted look may find it a daunting task to come up with the right boot to suit their casual and formal look. Well, never fear, here are some great ideas for creating a complete look for your boots.

How To Wear Your Boots

There really is no set way to wear your boots as this will depend on the type of boot you are wearing and the look you are going for. However, here, we will look at some basic styles of boots to give you the fundamentals of styling advice.

Ankle Boots

Ankle boots rose to popularity in the 60’s. These slim fitting, typically solid colored, non adorned boots are also known as the Chelsea Boot, Beatle Boot or Dealer Boot. They can be found in a variety of materials.

Because these boots have a streamlined look, but are also kind of funky and stylish, they can go with a variety of looks from casual to formal. The trick is not to create too much bunching in the pants where the boot ends. That’s why they will make a great look with skinny or slim cut jeans or chinos. If the boots are causing the fabric to bunch, it may be necessary to cuff the pants a bit.

If you are wearing your ankle boots with a suit, they will look great with a skinny leg although a wider leg will also allow the cuff to fall nicely over the boot giving it more of a dress shoe look. Avoid rolling up legs of suits, as this will break the line of the pants in an unflattering way.

For styling ideas, think of wearing Chelsea boots with an all black suit. For a casual look, pair the boots with jeans while keeping colors light and the shape of the pieces less fitted.

Timberland Brown Work Boot

The Work Boot

The work boot can include anything from construction and motorcycle boots to hiking and combat boots. Simply, they include any boot which is practical for working, typically featuring a sturdy body and thick sole.

Because these boots tend to have a clunky look, they are best for causal occasions and will always go well with jeans, particularly ones that have a slim or skinny cut. To complete this look, add a tee shirt and flannel or leather jacket for a street chic vibe.

The Desert Boot

The desert boot design originated from a traditional bazaar in Cairo and was reworked by Nathan Clark of Clarks’ footwear. It’s soft, flexible material and handmade designs make it ideal for warmer weather, hence the name, desert boot.

Style wise, the desert boot falls somewhere between the work boot and the ankle boot. It is a bit less clunky than the work boot but is slightly more rugged in appearance than the ankle boot. It also ties up the front, making it appear a bit more utilitarian.

Because of the boot’s versatility, it can be worn with suits for less formal social occasions as well as a pair of jeans. Also, the boot is not strictly for summer and spring. Their rugged appearance makes them perfect for fall and winter looks as well.

Outfits to Match Men’s Boots

Now that we are familiar with some basic boot types, its time to think about creating complete outfits starting with the boot and working our way up. That being said, let’s think of some great looks to go with your Chelsea boots.

Black Chelsea Boots

Chelsea boots can complete both formal and casual looks well. If you are creating a more formal look for a black Chelsea, you want to start with some sort of trousers. While a slim or skinny leg will work well, a looser leg can drape over the boot nicely. Colors to consider wearing with black boots include blacks, grays, lighter browns and purple. These can all make great looks for the fall and winter.

Working our way up, you must consider the formality of the event. This will help determine whether you are wearing a dress shirt , jacket, sweater or tie. However, considering you are creating a darker look for the bottom , you will want to bring this up top somehow, whether it be in the jacket color, the print or the shirt or the color of the tie.

For a great complete look with your black Chelsea boot, go for a black, skinny trouser and jacket. Add color interest with a purple dress shirt that really pops. Complete the look with a black or purple tie.

When it comes to casual looks, opt for a skinny jean to go with your black Chelsea boots. This will keep with the sleek look of the boot without appearing too sloppy. Jean colors can include black, blue or gray.

Working our way up, a casual tee will work well. To add interest to the look, throw on a flannel, dress shirt or leather jacket for the right amount of street chic. It’s a good idea to try and incorporate black into your top half to bring up the color of the boots.

Light blue jeans and a camel overcoat look

Brown Chelsea Boots

Here again, either a slim or fuller legged trouser will work well to complement the boots. When it comes to color, grays , blues and other browns will go well with a darker brown shoe. A lighter brown or tan will be great for summery looks which might feature lighter grays, blues and even pastels.

For top pieces, the same considerations must be made as to whether it is necessary to wear a shirt, tie, jacket, etc. However, because you are wearing brown, when it comes to color schemes almost anything goes including the aforementioned options of grays, blues and pastels and other browns depending on the season.

Suggestions for a complete brown boot formal look may include a tan suit with a white shirt and a deep blue tie. This is a color combination that will really pop for a summer or spring look. In cooler temperatures, substitute your tan suit for a darker brown.

If you are going for a more casual look for your brown Chelsea, you can start with a pair of jeans. Color choices that will work best are blue denim, gray or other shades of brown. For the top, you can add a tee shirt and throw over a dress shirt, flannel or brown leather jacket to create interest. For the over shirt, you want to incorporate colors that complement the browns which will include other neutrals as well as deep reds and army greens.

Brown Chukka (Desert) Boots

Chukka boots are another type of boot that can work well with both formal and casual looks. A brown Chukka look can be the base for a great fall or winter outfit when adding dark brown, grays or navy trousers with either a slim or fuller leg. Complete the look with a smart matching blazer. When thinking of the tie and dress shirt, white is always a safe bet, or you can add color interest with deep reds, army greens, golds and purples.

For a great formal look to wear with your brown chukkas, start with dark brown suit. Add a dress shirt that features a subtle print in tones like whites, browns, reds and navies. Pull the look together with a brown tie that matches the suit.

For a more casual, cold weather look, pair your brown chukkas with dark blue or brown corduroy jeans. A t-shirt will work well with this look, and, to add style interest and keep you warm, throw on a flannel, dress shirt or brown bomber jacket in neutral or complementary colors to keep it street chic.

Tan Chukka Boots

Because of the cooling nature of these boots, and the lighter color, tan chukkas will work well in warmer temperatures. For a more formal look, wear these boots with a stunning blue or navy or light gray pair of trousers. You can also go for other shades of tan or light brown, but be sure to add contrast with a color that doesn’t match the boots too closely as to clash. Complete the look with a matching jacket and cool pastel dress shirt. A print tie will go well with this look, particularly one that incorporates both neutral and pastel tones.

To create a casual look with your tan chukkas, start with a lighter color jean, like a light blue or gray or even a white. Add a tee shirt in a pastel or bright color, although white will work as well.

Brown Captoe Dress Boots

The captoe dress boot is not one we have touched on in great detail. It is a dress boot that laces up to fit tightly around the ankle and has the distinguishing feature of stitching around the toe of the shoe. It is another boot that can work with casual and formal outfits.

For a formal look, wear your captoe boots with trousers that fall naturally over the shoes. To best show off the detail of the shoe, opt for pants that have a cuff or are hemmed slightly higher than some of your other trousers (which will work best with skinny or slim cut pant). This will create a vintage vibe that will work perfectly with your boots.

For your brown captoe, you are best off with shades of trousers that are brown, gray, blue or tan. You can complete this formal look with a jacket that matches your pants, a light blue or white shirt and a stunning, deep blue tie.

To create a casual look with your brown captoes, go for jeans in shades of dark blue or other shades of brown. If jeans are straight leg, you can roll them up to feature the unique design of your shoe. Complete the look with a tee shirt and throw on an over shirt or bomber jacket that brings up the neutral tones.

Black Captoe Dress Boots

When creating a formal look with your black captoe, opt for trousers in colors like black or grays or rich blues. The shirt and tie colors you choose will depend on the color pants you end up going with, but rich jewel tones will work well with black while you may want to opt for more of a neutral to complement gray.

To complete a formal look with your black captoes, start with black trousers. Add a black tie or one that matches the color of shirt without clashing for a great monotone look.  If you start with gray trousers, think of contrasting grays by adding a shirt, jacket and ties in different shades of the color.

For a casual, black captoe boot look, start with a pair of dark blue or black jeans. Add a tee shirt in black, white, or any variety of colors. To create interest, throw on an over shirt or jacket that brings up the color of your shoes and make your casual look that much cooler.

What Are the Best Type of Casual Boots to Wear With Jeans?

When thinking of casual boots, or work boots, there a number of varieties including motorcycle boots, combat boots, construction pants, hiking boots and more. There are really no hard and fast rules about which work best with a pair of jeans and it may be more up to personal style and preference. However, there are some style associations made with certain casual boots that may help you customize your outfit choices as follows:

  • Combat boots: Typically associated with punk rock music, these can be worn with items like leather jackets, jeans that feature plaids, bold colors and zippers and tee shirts…that feature your favorite punk bands of course! But if you don’t feel like being outrageous, don’t worry. Combat boots will also go well with just about any pair of jeans and a tee shirt.
  • Motorcycle boots: More of a rock in roll look, these boots look best with a tight pair of blue jeans and leather or denim jackets or vests. Complete the look with your favorite AC/DC tee shirt.
  • Combat/Hiking boots: A more rugged and slightly less alternative look, these will work best with a pair of jeans and a flannel shirt.
Cuffed Trousers

What Type of Boots Work Best With Chinos?

Because chinos offer a sleek, tailored and more formal look, they will not work as well with casual work boots. Instead pair them with a pair of chukkas or Chelsea or dress boots. Although chinos come in a variety of colors, they are typically seen in tans, grays and pastel tones. Therefore, think of browns and other tans when considering shoe colors. When wearing tan chinos with brown or tan shoes, complete the look with a shirt in a pastel or bright color. White will work as well. If you are starting with a pastel base, a white or light print shirt can work well.

How To Choose a Color for Your Boots

We’ve talked about building an outfit from the ground up, starting with boots, but say you already have your outfit and are now struggling to find a pair of boots that goes best. Which do you choose? Here are some general guidelines:

  • Black boots: Black boots are great for winter and more formal occasions. They go well with primary colors and deep jewel tones and also work with darker grays.
  • Brown boots: When referring to a darker brown, these boots will also work well for the fall and winter months. They complement other neutrals well and can be paired with shades of brown and navy. More colorful tones that will work well with a darker brown include dark reds and greens. Browns boots make for a great professional look and can be worn for less formal social and casual events.
  • Tan/lighter brown boots: These will work with summer and spring tones including whites, blues, pastels as well as some brighter colors. Like brown, tan boots can also work well for a professional look as well as less formal and casual events.

Caring for Your Boots

Boots are often made of expensive materials like leather and suede. It is important to keep them looking sharp by knowing how to clean and care for them correctly. Keeping that in mind, here are some great care tips for your boots.

Cleaning Leather Boots

Although you may be doing your best to keep your leather boots clean and dry, don’t worry too much; they are more durable than you think! They can soften up without thinning out and handle water without getting damaged more so than some other materials. While they can’t be thrown in the washing machine, there are some products you can use to gently clean them. These include:

  • Shoe protection spray: Before wearing your boots, you should spray them with a protective spray that will keep them safe from water damage.
  • A soft cloth: Use a soft cloth dipped in an oil and vinegar solution to remove dirt from your leather boots.
  • Leather polish: Leather polish can be an effective way to cover up scuffs and other permanent marks that may appear on your boots.

Using Oil to Care for the Leather

Oil can help to give you shoes a shiny, well maintained look while preventing them from cracking. It will also make them softer and more comfortable. However, certain oils can damage your leather, so it is important to research carefully before treating your boots. There are certain essential oils that are safe as well as other options like mink oil.

If you are using mink oil to treat your boots , start by heating the oil with a hair dryer until it is melted. Then use a clean rag or sponge to work the oil into all the seams and surface areas of the boot. Once you have finished coating it, use the hair dyer to melt any remaining bits of the mink oil. Then, let your boots rest for 24 hours, periodically picking up the boot to flex it at the toe and rear, where natural bends are likely to form.

After the initial 24 hour period has passed, take another clean rag and work in the excess of mink oil on your boot. Use small circular motions to work the oil in as much as possible. Then buff the whole boot with a pad or rag to remove the remaining oil. For best results, polish the shoe when complete. This will help to protect it from the elements.

Caring for Suede Boots

Suede is a more sensitive material than leather so caring for your suede boots will be a bit trickier. It is a good idea to use protective spray on your boots before wearing them. This will help them repel water and dirt, making cleaning them an easier process.

However, if you do not spray your boots in advance and they start to look a bit shabby, you can still clean them by stuffing them with newspaper and carefully working the stains out with a soft brush and suede eraser.

Boots are a great alternative to sneakers and dress shoes, working well with formal and casual looks while giving your outfit a stylish edge. Those that aren’t used to making boots a part of their outfit may struggle a bit with finding the perfect shirt, pants and jacket combinations. Hopefully this article has given you a good starting point to creating great looks that work for you!

About the author

Jack Prenter

Jack has been fascinated by fashion for decades and spent huge amounts of time researching it and becoming an expert. He's written for many well-known publications and is in the process of opening an online clothing store for men. Jack studied at the University of Nottingham and is now based out of Toronto, Canada.