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!
Asket
The Loose Jeans Light Blue Wash
$200.00
ASKET
-40%
A Bathing Ape
Men s Shark Loose Fit 13oz Denim Pants Indigo Blue
$334.00
$557.00
Slam Jam
-72%
Yan Simmon
Jeans Blue
$59.00
$214.00
Yoox.com
-78%
Richard James Brown
Jeans Blue
$86.00
$387.00
Yoox.com
Dr. Martens
939 Sub Fleece Lined Leather Ankle Boots Black
$313.00
Slam Jam
Frye
Hudson Work Boot in Saddle at Nordstrom Rack, Size 10.5
$199.97
Nordstrom Rack
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
Men s Detroit Jacket Black (Rinsed)
$242.00
Slam Jam
-40%
Carhartt Work in Progress
Denim outerwear Blue
$179.00
$296.00
Yoox.com
Carhartt Work in Progress
Black Shepton Jacket
$305.53
TheDoubleF
Carhartt Work in Progress
Men s Aden Chore Coat Blue (Grind Washed)
$256.00
Slam Jam
-15%
Tommy Hilfiger
leather ankle boots - men - Calf Leather/Rubber/Calf Leather - 44 - Black
$392.00
$461.00
FARFETCH
-63%
Emporio Armani
Ankle boots Black
$238.00
$644.00
Yoox.com
-50%
Johnston & Murphy
Jenson Chelsea Leather Boot
$161.99
$325.00
Rue La La
-33%
Diemme
Ankle boots Blue
$356.00
$529.00
Yoox.com
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.
-59%
Tom Ford
Shirts Brown
$376.00
$917.00
Yoox.com
-35%
Stone Island
Military green corduroy shirt
$283.70
$436.47
TheDoubleF
-67%
Tailorbyrd
Tailorbyrd Corduroy Sport Shirt Brown
$33.00
$99.50
Rue La La
-72%
Obey
Shirts Beige
$50.00
$177.00
Yoox.com
-47%
Dr. Martens
1460 Vintage combat boots - men - Leather/Leather/Rubber - 9.5 - Black
$260.00
$488.00
FARFETCH
Roan
Colton II Boot in Tan Greenland Mm at Nordstrom, Size 10.5
$139.00
Nordstrom
-66%
Moschino
Ankle boots Black
$334.00
$995.00
Yoox.com
Allen Edmonds
Dain Combat Boot in Black at Nordstrom Rack, Size 10.5
$179.97
Nordstrom Rack
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.
-49%
Jack & Jones
R. D.D. ROYAL DENIM DIVISION by JACK & JONES Shirts Orange
$46.00
$90.00
Yoox.com
-60%
Alpha Industries
Men s Aloha Safari Shirt Khaki Beige
$44.00
$110.00
Slam Jam
-22%
Durango
DB510 Cowboy Boots Black : 11.5 D - Medium, Leather
$136.13
$175.50
Zappos
-50%
AllSaints
Skiff Ankle Boots Black
$159.00
$319.00
AllSaints
-19%
424
cowboy ankle boots - men - Leather/Leather/Leather - 43 - Green
$454.00
$561.00
FARFETCH
-47%
Dr. Martens
1460 Vintage combat boots - men - Leather/Leather/Rubber - 9.5 - Black
$260.00
$488.00
FARFETCH
-70%
Dsquared2
Boots Brown
$328.00
$1,099.00
Yoox.com
-35%
Johnston & Murphy
XC Flex Connelly Wingtip Boot in Black Full Grain at Nordstrom, Size 10.5
$129.99
$199.00
Nordstrom
-50%
AllSaints
Skiff Boots Black
$159.00
$319.00
AllSaints
-50%
AllSaints
Skiff Ankle Boots Black
$159.00
$319.00
AllSaints
-58%
Dune London
Cayden Leather Boot Brown
$100.00
$240.00
Rue La La
Dr. Martens
Slam Jam 1490 OUTLIER Steel Toe Boots Black
$326.00
Slam Jam
Original text: Kayla Kuefler
Updated text and content: Rebekah Ortquist
