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!
-30%
Sunflower
Loose
$314.00
$447.00
Balardi
-30%
Nine In The Morning
Pocket Cottton Jeans Blue
$225.00
$321.00
Eraldo
Levi's
Jeans Grey
$272.00
Balardi
-40%
Sunflower
Loose jeans Man 30 Black
$180.60
$301.00
rBoutique
Timberland
Mens Black Premium 6-inch waterproof boots Men
$230.00
Simons
-50%
adidas
Superstar Lux Made in Italy Sneakers Core Black
$204.00
$407.00
Slam Jam
Bally
Mens Elios chocolate brown suede loafers Men Black
$995.00
Simons
-24%
Red Wing Shoes
Classic Moc Mohave Suede Lace Up Boot Brown
$556.00
$730.00
Balardi
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.
-35%
Carhartt Work in Progress
Men s Aden Chore Coat Blue (Grind Washed)
$125.00
$192.00
Slam Jam
Carhartt Work in Progress
Helston Denim Jacket Black
$232.00
Eraldo
-35%
Carhartt Work in Progress
Men s Everson Trucker Jacket Black (Garment Dyed) Multi
$132.00
$203.00
Slam Jam
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.
Prada
Cotton corduroy overshirt Black
$2,800.00
Mytheresa
Stone Island
Compass cotton-blend corduroy overshirt Blue
$1,305.00
Mytheresa
-30%
ERL
Checked cotton corduroy shirt Red
$444.00
$634.00
Mytheresa
-20%
Rubinacci
Cotton corduroy Western shirt Blue
$1,240.00
$1,550.00
Mytheresa
-64%
Dr. Martens
1460 Vintage combat boots - men - Leather/Leather/Rubber - 6.5 - Black
$169.00
$475.00
FARFETCH
-55%
Bally
Ankle boots Green
$427.00
$955.00
Yoox
-55%
Bally
Ankle boots Blue
$427.00
$955.00
Yoox
-45%
Geox
Ankle boots Black
$111.00
$200.00
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.
Ralph Lauren
Sawtooth West denim shirt Black
$480.00
Mytheresa
-44%
Valentino
Papier Floral Casual Shirt Black
$1,208.00
$2,164.00
Balardi
-30%
Canali
Suede overshirt Brown
$2,447.00
$3,495.00
Mytheresa
Polo Ralph Lauren
Embroidered linen shirt White
$295.00
Mytheresa
Durango
DB510 Cowboy Boots Black : 10.5 EE - Wide, Leather
$175.50
Zappos
-20%
Sunflower
Jeans Gold
$399.00
$499.00
Balardi
Eraldo
Western-style Embroidered Boots Black
$722.00
Eraldo
-51%
Valentino Garavani
Valentino Garavani Vlogo Ankle Boots Black
$1,290.00
$2,639.00
Balardi
-64%
Dr. Martens
1460 Vintage combat boots - men - Leather/Leather/Rubber - 6.5 - Black
$169.00
$475.00
FARFETCH
-50%
Clarks
x Undercover Wallabee suede boots Black
$294.00
$588.00
Mytheresa
Timberland
Mens Brown Premium 6-inch waterproof boots Men
$230.00
Simons
-60%
Slam Jam
Vibram Rubber Core Boots Chocolate Multi
$118.00
$295.00
Slam Jam
Timberland
Mens Black Premium 6-inch waterproof boots Men
$230.00
Simons
Michael Kors
Boot Mandy Black
$298.00
Balardi
Blundstone
Mens 2429 nubuck leather boots Men Grey
$275.00
Simons
HUGO BOSS
Boot Tayil Brown
$312.00
Balardi
Simons
Mens Sigrid square-toe boots Men Black
$295.00
Simons
Dr. Martens
Slam Jam 1490 OUTLIER Steel Toe Boots Black
$255.00
Slam Jam
Simons
Mens Sigrid square-toe boots Men Brown
$295.00
Simons
Original text: Kayla Kuefler
Updated text and content: Rebekah Ortquist
