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!
-77%
Dsquared2
Jeans Blue
$190.00
$837.00
Yoox.com
-35%
A|X Armani Exchange
Jeans Black
$133.00
$206.00
Yoox.com
-90%
Yan Simmon
Jeans Blue
$21.00
$214.00
Yoox.com
Georgia Boot
Work Wellington in Dark Brown at Nordstrom, Size 11
$38.00
Nordstrom
Karl Lagerfeld
Mens Tumbled Leather Lug Sole Work Boots Black
$395.00
Neiman Marcus
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.
-15%
Tommy Hilfiger
leather ankle boots - men - Calf Leather/Rubber/Calf Leather - 44 - Black
$392.00
$461.00
FARFETCH
AllSaints
Skiff Chelsea Boots Gray
$319.00
AllSaints
-53%
Giovanni Conti
Ankle boots Brown
$329.00
$699.00
Yoox.com
AllSaints
Bloom Chelsea Boots Black
$319.00
AllSaints
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.
-40%
Stio
| Mens Saratoga Cord Shirt, Size Extra Small in Blue Heron | Cotton
$83.40
$139.00
STIO
Tailorbyrd
Corduroy Sport Shirt Green
$39.99
Rue La La
-40%
Stio
| Mens Saratoga Cord Shirt, Size Extra Small in Lodge Beam | Cotton
$83.40
$139.00
STIO
Moncler
Moncler Gelt Corduroy Down Shirt Jacket, Men, Green, Size: 2
$1,995.00
Moncler
-47%
Dr. Martens
1460 Vintage combat boots - men - Leather/Leather/Rubber - 9.5 - Black
$260.00
$488.00
FARFETCH
-66%
Bally
Ankle boots Green
$329.00
$955.00
Yoox.com
Valentino
Rockstud Leather Combat Boot Brown
$386.99
Rue La La
John Varvatos
Lex Combat Boot in Black at Nordstrom, Size 11.5
$598.00
Nordstrom
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.
-16%
Ferragamo
Mens Shirts Blue
$985.00
$1,179.00
LUX LAIR
Durango
DB510 Cowboy Boots Black : 10.5 EE - Wide, Leather
$175.50
Zappos
-50%
AllSaints
Skiff Ankle Boots Black
$159.00
$319.00
AllSaints
Christian Louboutin
Mens Ziggissimo Forever Leather Ankle Boots Black
$1,395.00
Neiman Marcus
Dingo
Banner Western Boot in Plantain at Nordstrom, Size 10.5
$169.95
Nordstrom
-47%
Dr. Martens
1460 Vintage combat boots - men - Leather/Leather/Rubber - 9.5 - Black
$260.00
$488.00
FARFETCH
-60%
AllSaints
Vaughan Chunky Leather Boots Black
$127.00
$319.00
AllSaints
-50%
AllSaints
Skiff Ankle Boots Black
$159.00
$319.00
AllSaints
-50%
AllSaints
Skiff Boots Black
$159.00
$319.00
AllSaints
Florsheim
Lodge Plain Toe Boot in Brown Ch at Nordstrom, Size 8.5
$145.00
Nordstrom
AllSaints
Bloom Lace Leather Boots Gray
$319.00
AllSaints
-33%
AllSaints
Milton Harness Boot Black
$318.00
$475.00
AllSaints
Original text: Kayla Kuefler
Updated text and content: Rebekah Ortquist
