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!
-40%
Pantaloni Torino
Cotton Jeans Male 32 Blue
$162.00
$271.00
Base Blu
-55%
ERL
Men s Breakwater Wash Jeans Indigo Blue
$208.00
$463.00
Slam Jam
-36%
Sunflower
Loose
$288.00
$447.00
Balardi
-39%
Incotex
Jeans Blue
$189.00
$309.00
Yoox
Timberland
Mens Black Premium 6-inch waterproof boots Men
$230.00
Simons
-45%
adidas
Superstar Lux Made in Italy Sneakers Preloved Brown
$224.00
$407.00
Slam Jam
Bally
Mens Elios chocolate brown suede loafers Men Black
$995.00
Simons
-50%
Roa
Our Legacy WORK SHOP Andreas Boots Slate Black
$301.00
$601.00
Slam Jam
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.
Carhartt Work in Progress
Logo-patch Button-down Jacket Blue
$220.00
Eraldo
Carhartt Work in Progress
Men s Quentin Jacket Tobacco / Black Brown
$274.00
Slam Jam
Carhartt Work in Progress
Curtis Sweater Jacket Grey
$173.00
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.
Ralph Lauren
Corduroy-trimmed denim jacket Beige
$1,081.00
Mytheresa
A.P.C.
Mens Basile blue-grey corduroy overshirt
$450.00
Simons
Rubinacci
Cotton corduroy overshirt Green
$1,375.00
Mytheresa
Rubinacci
Cotton corduroy jacket White
$1,375.00
Mytheresa
-70%
Dr. Martens
1460 Vintage combat boots - men - Leather/Leather/Rubber - 6.5 - Black
$154.00
$514.00
FARFETCH
-61%
Palm Angels
Ankle boots Brown
$555.00
$1,427.00
Yoox
-40%
Bally
Ankle boots Black
$534.00
$890.00
Yoox
Dr. Martens
Ankle boots Brown
$210.00
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
Buffalo West denim shirt Blue
$396.00
Mytheresa
Eleventy
Denim Western shirt Blue
$695.00
Mytheresa
Saint Laurent
Cassandre denim shirt Blue
$1,885.00
Mytheresa
Fendi
Cotton-blend denim shirt Blue
$2,350.00
Mytheresa
Durango
DB510 Cowboy Boots Black : 10.5 EE - Wide, Leather
$175.50
Zappos
Eraldo
Western-style Embroidered Boots Black
$718.00
Eraldo
-27%
Sunflower
Jeans Gold
$364.00
$499.00
Balardi
Eraldo
Floral-embossed Boots Brown
$874.00
Eraldo
-70%
Dr. Martens
1460 Vintage combat boots - men - Leather/Leather/Rubber - 6.5 - Black
$154.00
$514.00
FARFETCH
-50%
Clarks
x Undercover Wallabee suede boots Black
$294.00
$588.00
Mytheresa
Steve Madden
Mens Decanto lace-up boots Men Brown
$220.00
Simons
-60%
Slam Jam
Vibram Rubber Core Boots Chocolate Multi
$118.00
$295.00
Slam Jam
Steve Madden
Mens Decanto lace-up boots Men Black
$220.00
Simons
UGG
Men s Classic Mini Boots Chestnut Brown
$193.00
Slam Jam
Steve Madden
Mens Stergis Western boots Men Brown
$325.00
Simons
-50%
Dr. Martens
Qubist Rigger Boots Black
$133.00
$265.00
Slam Jam
Blundstone
Mens 2429 nubuck leather boots Men Grey
$280.00
Simons
-29%
Diemme
Ankle boots Brown
$325.00
$459.00
Yoox
HUGO BOSS
Mens Thorton zipped boots Men Black
$349.00
Simons
Original text: Kayla Kuefler
Updated text and content: Rebekah Ortquist
