How to Wear Men's Boots: Men's Boot Style 2022

How to Wear Men's Boots: Men's Boot Style 2022

When it comes to 2022 wardrobes, boots are the ultimate must-have staple. They’re practical, they’re comfortable, and above all else, they’re stylish as heck.


Men’s Boots Fashion

Did you know that men’s boots first showed up in Spanish cave paintings back in 15,000 BC? They’ve been stylish for that long and in today’s fashion world, they’re still kicking just as strong.

Rugged dudes rocked the boot way back when to protect their ankles and legs while they worked. And while this is still true today, they’re also used to add some edge to any outfit — casual or all dressed up.


Boots Outfit Ideas

Since men’s boots are so versatile, it’s hard to know how to style them. Dress ‘em up or dress ‘em down. There’s a time and a place to rough it out. We’ll walk you through every classic boot style so you can show up looking like you know what you’re doing. 



What to Wear With Men’s Boots

We’re organizing this how-to by boot type because that’s the ultimate secret to looking fresh in your favorite pair. So lace up and take the next step towards contemporary coolness with a solid pair of...


Chelsea Boots

They’re classic, they’re stylish, and they’re comfortable as you-know-what. The Chelsea boot is easy to dress up or down and we recommend starting with some light wash, semi-destroyed denim. Then pull it all together with layered jackets, a high-quality tee and call it a day. It’s a look that’s ready for any season and nearly any occasion (dates, the office, hanging with friends, happy hour — you name it).


Ankle Boots

Ideal for all the adventurous guys out there, this boot keeps your ankles protected while you hike and camp. Grab a pair of thick socks to layer underneath. And reach for a pair of jeans that’s got a solid wash. Solid black, solid blue, or even solid yellow — doesn’t matter! It’ll look good, we promise.


Combat Boots

Nothing says edgy quite like a pair of combat boots. Amp up your aesthetic with some dark jeans, a comfortable hoodie, and a deliciously long overcoat. It’ll keep you warm and looking effortlessly stylish. Don’t be afraid to swap out your combat boot laces to match the rest of your outfit.


Work Boots

Ah yes, the classic work boot. If this is your first rodeo, opt for neutral colors and suede materials. Not only are these easier to find, but they’re easier to style. Match them up with some bright colors (like blues and yellows) for a look that truly pops. And remember, just because they’re work boots doesn’t mean you can’t have a little fun.



Dress Boots

Technically any boot can be a dress boot if you style it right. But if you’re not sure, start with some camel-colored, pointed-toe boots that fit you snugly. Go for a tailored fit, both with your boots and your dress pants or denim. Then top it off with a matching camel-colored blazer, overcoat, or jacket. We also recommend dusting off any turtlenecks you have for this ‘fit.


Chukka Boots

The chukka boot should be in every man’s closet, no matter what your aesthetic is. It’s great for work, dates, and even adventures. Plus, they’re easy to style. Grab a denim button-down and pop it over a simple gray crewneck tee. Pull it all together with some dark blue or black jeans, and some leather chukka boots.


Wingtip Boots

If you want to show off your classy side, opt for some wingtip boots — especially in a rich leather material. Wear them with some high-quality selvedge denim and a burgundy sweater or button-down. If you’re open to layering, introduce a gray or blue t-shirt underneath for added dimension.


Biker Boots

This look is great if you want to show off your confidence. Start with a plain white tee and either a black button-down or black vest. Invest in some destroyed, fitted black jeans. The more tattered, the better. Finish the look with some black leather biker boots (yes, studs are a must) and your favorite accessories.


Hiking Boots

Ready for an adventurous outfit? First up, reach for your favorite pair of outdoor or sports shorts. They can be khaki, light brown, or some other neutral color. Introduce a pair of thick socks under your rugged hiking boots (which should also be a neutral or natural color). And depending on the weather, sport a classic tee, or black hoodie, or sweater.


Trench Boots

Trench boots are great at making your legs look fit. So now’s the time to find your favorite pair of skinny jeans that fit you like a glove. You can either roll up the ends or slightly tuck them into your trench boots — do what feels best here. And then lace up those boots and don’t be afraid to get some dust and dirt on them to make your aesthetic more authentic.


How to Wear Men’s Boots With Jeans

Boots and jeans go hand in hand. They’re a timeless pair and if you get it right, you’ll be the freshest dude around. However, we know sometimes it can be difficult determining the right way to pair jeans with shoes. Here are three timeless style tips to keep you looking fly.

  1. Embrace the cuffed jean! Show off your boots by rolling up those denim hems.
  2. Mix and match with contrasting hues. If you’ve got a light wash jean, wear a darker boot — and vice versa.
  3. Highlight your favorite piece. If you’ve got a pair of embellished biker boots, opt for a simple pair of jeans to let those boots be the star of the show.



How to Wear Men’s Boots With Dress Pants

Nothing says “classy but with some edge” like a pair of dress pants and boots. It’s an interesting combination that most guys can pull off… if they know what to do. Follow these steps to style men’s boots with dress pants:

  1. Pick your color palette, and stick to it. Whether you want natural colors or high-contrast hues, identify the ~vibe~ you’re going for.
  2. Find the right cut. If you’re a sleek guy, grab the tailored dress pants and some Chelsea boots. But if you’re more into the rugged look, try chunkier boots and some straight-leg pants.
  3. Pay attention to proportions. If you’ve got a pair of longer slacks, you’ll need to match them with a pair of boots that fit comfortably underneath. If you’ve got dress pants that are shorter and tailored, feel free to rock any pair of ankle boots in reach.


And lastly, rock a smile. It’s the ultimate way to spice up any outfit and radiate confidence — no matter what you’ve got on your feet.

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