4 must-have boot styles for men and how to wear them
To prepare yourself for the cold months ahead, check out these four stylish men’s winter boot styles to keep your feet warm and your style on point for Fall/Winter 2023. We browsed through the street style catalogs and some of the coolest IG accounts to bring some of the hottest trends for men’s boots this year. And not only that, we’ll also show you how to style these men’s boots trends so you’ll feel confident and comfortable stepping into the winter season.
1. Work boots
Whether your work boots are destined for a construction site or a walk around the park, there’s more to the style than its steel toe and safety obligations. For men’s work boots that can be seamlessly worn in everyday life, one can’t go wrong with a classic Timberland or Dr. Martens pair.
How to wear work boots: Styling work boots is pretty straightforward – because of their more rustic and casual roots, you can’t go wrong with wearing a nice pair of bootcut or straight-fit jeans. Just be careful that the jeans are not too tight in the ankle. They should also be long enough to cover the top of the boot, but too long that you have to cuff them more than once. A really cool menswear trend we’ve seen lately has been work coveralls, which fit perfectly with this boot trend!
-17%
Diesel
1993 D Vyl Jeans Grey
$308.00
$369.00
Balardi
-76%
Richard James Brown
Jeans Blue
$91.00
$387.00
Yoox
-4%
Diesel
Jeans Grey
$347.00
$361.00
Balardi
-62%
Dirk Bikkembergs
Jeans Blue
$94.00
$248.00
Yoox
-17%
Carhartt Work in Progress
Carhartt Wip Stratus Beanie Green
$35.00
$42.00
Balardi
Rick Owens
Mens Quad sole sT-Shirtl toe boots Men Black
$595.00
Simons
-24%
Red Wing Shoes
Classic Moc Mohave Suede Lace Up Boot Brown
$548.00
$720.00
Balardi
Bogs
Mens Arcata Urban laced winter boots Men Black
$180.00
Simons
2. Chelsea boots
One of the most versatile boot styles anyone can include in their wardrobe, Chelsea boots are always an investment worth making. What are Chelsea boots? They are ankle boots with elastic panels on the side, allowing them to be pulled easily on or off. There are a wide variety of different styles, and can have either a pointed toe or a more rounded toe. See this season’s latest from Magnanni, Blundstone, and Frye for stylish and wearable Chelsea boots.
How to wear Chelsea boots: One of the reasons why Chelsea boots have become such a closet staple is because of their versatility. They go with pretty much everything and can also easily elevate your look. Wear them with jeans or slacks – just avoid tucking your pants into the boots as this can make your legs look shorter. Our favorite way to style Chelsea boots? A cool, chunky knit sweater, jeans and a workwear-inspired jacket.
-3%
Carhartt Work in Progress
Carhartt Wip Michigan Black Jacket
$308.00
$319.00
Balardi
-12%
Carhartt Work in Progress
Carhartt Wip Michigan Artificial Suede Hamilton Brown Coat
$438.00
$500.00
Balardi
Durable and tough, combat boots deserve a place in the fashion hall of fame. The first true boot made for U.S. military service, the combat boot has been adapted over time to meet all of life’s challenges. Check out military styles from Etro and Marsèll for high-end combat wear.
How to wear combat boots: One of the easiest ways to style combat boots is to wear them with a pair of loose-fitting pants, a flannel or corduroy button-up and an aviator jacket.
-31%
Ami
Worker Jacket Blue
$787.00
$1,133.00
Balardi
Le 31
Mens Corduroy bib black shirt Modern fit
$150.00
Simons
-41%
Barbour
Tracker Casual Jacket Blue
$329.00
$561.00
Balardi
-23%
Le 31
Mens Corduroy work jacket Brown
$149.95
$195.00
Simons
-47%
Dr. Martens
1460 Vintage combat boots - men - Leather/Leather/Rubber - 9.5 - Black
$260.00
$488.00
FARFETCH
-69%
Moschino
Ankle boots Black
$312.00
$995.00
Yoox
-31%
Guess
Ankle boots Black
$154.00
$222.00
Yoox
-61%
Ducanero
Ankle boots Brown
$195.00
$498.00
Yoox
4. Cowboy boots
You know it’s a strong trend when it overlaps into both men’s and women’s fashion. The cowboy boot has been making its rounds for several months and it doesn’t look like its going away anytime soon. Go with a full-on cowboy boot, or try a more sublte look with a cowboy-inspired ankle boot.
How to wear cowboy boots: Fully embrace the cowboy look and go with a head-to-toe denim look like this fashion week guest in the picture above. But if you’re not quite ready to fully commit, then you can always go with just a T-shirt and a dark-wash jean, for a more laid back rocker look.
Levi's
Mens Dark denim Western shirt Modern fit Black
$79.00
Simons
-27%
Levi's
Western Barstow Blue
$125.00
$171.00
Balardi
Levi's
Mens Western denim shirt Modern fit Blue
$79.00
Simons
-39%
Emporio Armani
Denim Cotton Shirt Blue
$271.00
$444.00
Balardi
Durango
DB510 Cowboy Boots Black : 10.5 EE - Wide, Leather
$175.50
Zappos
-71%
Undercover
Check Shirt Brown
$409.00
$1,395.00
Balardi
-53%
Human Made
Jeans Blue
$329.00
$701.00
Balardi
-28%
A.P.C.
Aaron Jeans Blue
$295.00
$411.00
Balardi
-47%
Dr. Martens
1460 Vintage combat boots - men - Leather/Leather/Rubber - 9.5 - Black
$260.00
$488.00
FARFETCH
-14%
Timberland
Premium 6 Inch Leather Boots With Logo Brown
$338.00
$394.00
Balardi
Dr. Martens
Mens Leather 1460 Pascal boots Men Black
$215.00
Simons
-10%
UGG
Classic Ultra Mini Sheepskin Boot Brown
$308.00
$341.00
Balardi
Blundstone
Mens 2429 nubuck leather boots Men Grey
$275.00
Simons
-48%
Sebago
Tala Mid Suede Dk Brown
$248.00
$481.00
Balardi
-75%
Dsquared2
Ankle boots Brown
$246.00
$1,000.00
Yoox
Barbour
Boot Wilton Green
$172.00
Balardi
-81%
Moschino
Ankle boots Black
$133.00
$692.00
Yoox
-3%
Timberland
Waterproof Lace Up Boot Yellow
$314.00
$324.00
Balardi
Pajar
Torsion Ice Gripper winter boots Men Black
$350.00
Simons
Original text: Kayla Kuefler
Updated text and content: Rebekah Ortquist
