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!
-24%
Dondup
BOTTOMWEAR - Jeans on YOOX.COM Blue
£116.00
£153.00
Yoox.com
-45%
Levi's
Mens Levis 527 Slim Bootc in New Lake - Blue - Size 36W/34L
£55.00
£100.00
Secret Sales
-20%
Paul Smith
PS TAPERED WASHED JEANS Size: 38-32, colour: BLUE
£116.00
£145.00
Circle Fashion
-19%
Red Wing Shoes
Shoes Heritage Work 6Inch Moc Toe Hawthorne Abilene Mens Chesnut Boots - Brown Leather - Size UK 10
£250.00
£309.00
Secret Sales
Red Wing Shoes
6 Moc Leather Mens Ankle Boots - Oxblood - Size:UK 8.5
£207.12
Legend Footwear
-33%
Skechers
Mens Workshire Relaxed Fit Laced Safety Ankle Boots - Black Leather - Size UK 13
£59.99
£90.00
Secret Sales
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
corduroy-collar patch-pocket jacket - Grey
£225.00
FARFETCH
-30%
Tommy Hilfiger
Lightweight Leather Chelsea Boots Brown
£105.00
£150.00
Tommy Hilfiger
-10%
Blundstone
Chelsea Boots, male, Green, 10 UK, Olive Leather Weatherproof Boots
£176.18
£195.75
Miinto
Pikolinos
Pirineos M6S-8020C1 Leather Mens Ankle Boots - Olmo - Size:UK 10.5-11
£115.77
Legend Footwear
-55%
Diesel
Chelsea Boots, male, Brown, 10 UK, Chelsea Boot
£135.72
£302.76
Miinto
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.
MR MARVIS
Reserves * The Cord Shirt Red
£89.00
MR MARVIS
-50%
GANT
Mens Evening Blue Regular Fit Corduroy Overshirt - Navy - Size X-Large
£87.80
£175.00
Secret Sales
MR MARVIS
Oysters * The Cord Shirt Grey
£89.00
MR MARVIS
-20%
Stone Island
S01144 COMPASS SHIRT Size: L, colour: BLACK
£320.00
£400.00
Circle Fashion
Dr. Martens
1460 Nubuck Lamper Unisex Ankle Boots - Black - Size:UK 6.5
£34.57
Legend Footwear
Panama Jack
Mens P03 Aviator Combat Boot, Castaño, 12.5 UK
£169.49
Amazon
Loake
Bedale Leather Mens Ankle Boots - Black - 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
-46%
HUGO BOSS
Mens H-liam-kent-e-c1-243 Navy - Blue - Size X-Large
£70.00
£129.00
Secret Sales
-28%
Dsquared2
Denim Shirt Blue
£335.91
£469.80
Miinto
Fat Face
FatFace Blue Denim Long Sleeve Chambray Shirt
£55.00
FatFace
Timberland
Euro Sprint Mid Lace Full Grain Leather Mens Ankle Boots - Brown - Size:UK 11.5
£54.87
Legend Footwear
Vivobarefoot
Tracker Leather AT Leather Mens Ankle Boots - Bracken - Size:UK 12
£34.57
Legend Footwear
Harley-Davidson
Harley Davidson Stealth Carbon LAC Leather Mens Ankle Boots - Black - Size:UK 10
£105.62
Legend Footwear
Clarks
Original Desert Boot (Cola Suede, Numeric_8) Brown
£126.45
Amazon
Dr. Martens
101 YS Smooth Leather Unisex Ankle Boots - Black - Size:UK 6.5
£65.02
Legend Footwear
Original text: Kayla Kuefler
Updated text and content: Rebekah Ortquist
