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!
-20%
Dondup
BOTTOMWEAR - Jeans on YOOX.COM Blue
£123.00
£153.00
Yoox.com
AllSaints
Cotton Flint Bootcut Denim Jeans, Size: 28 Blue
£139.00
AllSaints
-10%
Levi's
Slim Fit Jeans, male, Black, W32, 501 Original Jeans
£86.13
£95.71
Miinto
-40%
Our Legacy
Mid-rise bootcut jeans Blue
£234.00
£390.00
Mytheresa
-16%
Red Wing Shoes
Mens Red Wing 6 Inch Moc Toe Mens Boot - Oro Legacy - Brown - Size: UK8.5 eu42.5 us9.5/11
£259.56
£309.00
lovethesales
Red Wing Shoes
Iron Ranger Leather Mens Ankle Boots - Amber - Size:UK 10.5
£156.37
Legend Footwear
-25%
CAT
Mens Sire WaterProof P720692 Brown Sugar Mens Boots - Size: 13
£104.50
£140.00
lovethesales
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.
-21%
Carhartt Work in Progress
Light Jackets, male, Brown, S, Jacket with corduroy collar
£138.33
£176.00
Miinto
-23%
Carhartt Work in Progress
Detroit Jacket Brown
£174.00
Miinto
AllSaints
Leather Skiff Chelsea Boots, Size: UK 10/US 11/EU 44 Grey
£199.00
AllSaints
-74%
Woolrich
Suede Chelsea Boots with Lug Sole size 40
£61.89
£241.76
GLAMOOD
-55%
Diesel
Chelsea Boots, male, Brown, 10 UK, Chelsea Boot
£135.72
£302.76
Miinto
Ecco
Ecco Mens MILAN CHELSEA 523384 MENS BOOT - Black - Size: 13
£140.00
lovethesales
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.
AllSaints
Castleford Corduroy Relaxed Overshirt Grey
£159.00
AllSaints
AllSaints
Eastburn Checked Corduroy Ramskull Shirt Black
£99.00
AllSaints
John Elliott + Co
Cloak cotton-corduroy shirt - Neutral - 0
£299.00
The Outnet
-74%
Diesel
Lace-up Leather Combat Boots HAMMER with Lug Sole size 40
£82.89
£323.78
GLAMOOD
Dr. Martens
1460 Nubuck Lamper Unisex Ankle Boots - Black - Size:UK 6.5
£34.57
Legend Footwear
-32%
Diesel
D-HAMMER BT Black
£255.00
£375.00
Yoox.com
Loake
Burnished Calf Bedale Leather Mens Ankle Boots - Brown - Size:UK 10.5
£156.37
Legend Footwear
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.
-29%
Ralph Lauren
Casual Shirts, male, White, XL, Cotton Blend Chemise
£101.59
£144.00
Miinto
Yohji Yamamoto
M Lt Wov Shirt Black
£180.00
Labels
-35%
Dsquared2
Denim Shirt Blue
£294.05
£452.40
Miinto
Luca Faloni
Blue Fine Stripe Shirt Size M
£75.00
HEWI
-50%
AllSaints
Leather Skiff Ankle Boots, Size: UK 10/US 11/EU 44 Black
£94.00
£189.00
AllSaints
-30%
Woodland
Nebraska Ankle Boots Mens - Black Leather - Size UK 6
£55.99
£79.99
Secret Sales
Clarks
Desert Boot Standard Fit Brown
£130.00
Clarks
Clarks
Original Desert Boot (Cola Suede, Numeric_8) Brown
£126.45
Amazon
-11%
Timberland
Lace-up Boots, male, Black, 13 1/2 UK, Euro Sprint Hiker Boot
£119.99
£135.00
Miinto
-74%
Diesel
Lace-up Leather Combat Boots HAMMER with Lug Sole size 40
£82.89
£323.78
GLAMOOD
Vivobarefoot
Tracker Leather AT Leather Mens Ankle Boots - Bracken - Size:UK 12
£34.57
Legend Footwear
-30%
Tommy Hilfiger
Leather Cleat Lace-Up Boots Black
£105.00
£150.00
Tommy Hilfiger
Dr. Martens
1460 Nubuck Lamper Unisex Ankle Boots - Black - Size:UK 6.5
£34.57
Legend Footwear
Original text: Kayla Kuefler
Updated text and content: Rebekah Ortquist
