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!
Our Legacy
Loose Jeans Male 33 Black
$322.00
Base Blu
-40%
Sunflower
Loose jeans Man 30 Black
$180.60
$301.00
rBoutique
-40%
Pantaloni Torino
Cotton Jeans Male 32 Blue
$120.00
$200.00
Base Blu
Dolce & Gabbana
Tattered Skinny Denim Jeans - Black
$423.14
Italist
Red Wing Shoes
Boot - Brown
$356.70
Italist
Dolce & Gabbana
Tattered Skinny Denim Jeans - Black
$423.14
Italist
Red Wing Shoes
Boot - Brown
$356.70
Italist
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
Painter Hoodie - Brown
$202.83
Italist
Carhartt Work in Progress
Painter Hoodie - Brown
$202.83
Italist
-50%
-40%
Tommy Hilfiger
leather ankle boots - men - Calf Leather/Rubber/Calf Leather - 45 - Black
$281.00
$467.00
FARFETCH
-27%
Calvin Klein
Brown Suede Leather Chelsea Mens Boots
$147.00
$202.00
LUX LAIR
Doucal's
Brown suede ankle boots
$490.00
TheDoubleF
Diesel
Ankle Boots D-DONALD BEATLE, Mens, Black
$549.00
Vitkac
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.
Moncler
Moncler Corduroy Shirt, Men, Beige, Size: 3xl
$1,495.00
Moncler
Pantaloni Torino
Flat Trousers - Beige
$249.80
Italist
Dolce & Gabbana
Corduroy Trousers - Brown
$439.38
Italist
Jacob Cohen
Straight-Leg Corduroy Trousers - Brown
$337.29
Italist
-70%
Dr. Martens
1460 Vintage combat boots - men - Leather/Leather/Rubber - 6.5 - Black
$154.00
$514.00
FARFETCH
Valentino
Leather Combat Boot Black
$424.99
Rue La La
Camper
Pix Berlin Zip Boot in Black Black at Nordstrom, Size 42
$265.00
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.
PANICALE
Western-Style Flap-Pocket Shirt - Blue
$413.77
Italist
Eleventy
Denim Shirt - Light Blue
$416.53
Italist
Eleventy
Denim Shirt - Light Blue
$416.53
Italist
Eleventy
Denim Shirt - Light Blue
$416.53
Italist
Durango
DB510 Cowboy Boots Black : 10.5 EE - Wide, Leather
$175.50
Zappos
Dolce & Gabbana
Grey Washed Skinny Denim Jeans - Gray
$364.68
Italist
Christian Louboutin
Men & apos;s Ziggissimo Forever Leather Ankle Boots Black
$1,395.00
Neiman Marcus
Frye
Austin Boot in Latte at Nordstrom, Size 10.5
$388.00
Nordstrom
-70%
Dr. Martens
1460 Vintage combat boots - men - Leather/Leather/Rubber - 6.5 - Black
$154.00
$514.00
FARFETCH
Nike
Mens Manoa Boots in Black | 456975-001
$110.00
Nike
UGG
Ugg Australia Boots - Black
$313.87
Italist
Lee
Rowan Boot
$49.99
Rue La La
Moon Boot
Luna Trek Mid Boot - Black
$252.89
Italist
Eastland
Ethan 1955 Cap Toe Boot in Black at Nordstrom, Size 10.5
$225.00
Nordstrom
Rocky
Ride Roper Western Boot in Trail Brown at Nordstrom, Size 11.5
$88.24
Nordstrom
Swims
Men & apos;s Charles Hybrid Water-Resistant Brogue Boots Gray
$328.00
Neiman Marcus
Durango
Black Harness Boot in Oiled Black at Nordstrom, Size 10.5
$181.50
Nordstrom
Lee
Waylon Boot Black
$49.99
Rue La La
Original text: Kayla Kuefler
Updated text and content: Rebekah Ortquist
