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!
-81%
Dsquared2
Jeans Blue
$161.00
$837.00
Yoox
Levi's
Jeans Grey
$268.00
Balardi
-25%
A|X Armani Exchange
Jeans Black
$154.00
$206.00
Yoox
Nine In The Morning
Pocket Cottton Jeans Blue
$320.00
Eraldo
Roa
Our Legacy WORK SHOP Andreas Boots Slate Black
$601.00
Slam Jam
Timberland
Mens Black Premium 6-inch waterproof boots Men
$230.00
Simons
-24%
Red Wing Shoes
Classic Moc Mohave Suede Lace Up Boot Brown
$548.00
$720.00
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.
-31%
Carhartt Work in Progress
Shirts Black
$183.00
$266.00
Yoox
Carhartt Work in Progress
Men s Aden Chore Coat Blue (Grind Washed)
$192.00
Slam Jam
Carhartt Work in Progress
Courdoroy-collar Jacket Brown
$232.00
Eraldo
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.
C.P. Company
Cotton-blend corduroy overshirt Blue
$515.00
Mytheresa
Prada
Cotton corduroy overshirt Black
$2,800.00
Mytheresa
Moncler
Ambroisie cotton corduroy down jacket Brown
$2,645.00
Mytheresa
-20%
Rubinacci
Cotton corduroy Western shirt Blue
$1,240.00
$1,550.00
Mytheresa
-47%
Dr. Martens
1460 Vintage combat boots - men - Leather/Leather/Rubber - 9.5 - Black
$260.00
$488.00
FARFETCH
-76%
Giovanni Conti
Ankle boots Black
$193.00
$815.00
Yoox
-77%
Lardini
Ankle boots Black
$243.00
$1,059.00
Yoox
-30%
Alessandro Gilles
Ankle boots Black
$150.00
$213.00
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
Levi's
Mens Western denim shirt Modern fit Blue
$79.00
Simons
-30%
Canali
Suede overshirt Brown
$2,447.00
$3,495.00
Mytheresa
-30%
Dolce & Gabbana
Denim shirt Black
$1,383.00
$1,975.00
Mytheresa
Durango
DB510 Cowboy Boots Black : 10.5 EE - Wide, Leather
$175.50
Zappos
-36%
A.P.C.
Aaron Jeans Blue
$264.00
$411.00
Balardi
-8%
Sunflower
Jeans Gold
$451.00
$492.00
Balardi
-60%
Miharayasuhiro
Padded Check Overshirt Grey
$547.00
$1,379.00
Balardi
-47%
Dr. Martens
1460 Vintage combat boots - men - Leather/Leather/Rubber - 9.5 - Black
$260.00
$488.00
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
-75%
Dsquared2
Ankle boots Brown
$246.00
$1,000.00
Yoox
-32%
Timberland
Premium 6 Inch Leather Ankle Boots With Logo Brown
$269.00
$394.00
Balardi
-76%
Emporio Armani
Boots Black
$310.00
$1,295.00
Yoox
-73%
ATTIMONELLIS
Ankle boots Black
$195.00
$711.00
Yoox
Timberland
Mens Black Premium 6-inch waterproof boots Men
$230.00
Simons
-35%
Diemme
Ankle boots Black
$329.00
$505.00
Yoox
Blundstone
Mens 2429 nubuck leather boots Men Grey
$275.00
Simons
Original text: Kayla Kuefler
Updated text and content: Rebekah Ortquist
