Modello Momento Style: 4 Go-To Ways To Wear Boots In Winter

You already own boots. Hell, you’ve probably got a few pairs gathering dust on your shoe rack right now. But are you exploiting them to their full, weather-defying potential? Possibly not. And that’s understandable; boots’ higher profile and reasonable heft can sometimes make them seem more appropriate for a building site, rather than a bar.

Here, we equip you with four foolproof ways to wear boots this winter and put a few different outfit combinations on your radar – all of which will ensure you style out the season’s coldest months well-clad.

1. Chelsea Boots + Tailoring

Not only does the Chelsea boot play a crucial role in your year-round smart-casual wardrobe, it also leads the charge in winterising your formalwear for the snowy season. Unlike Derbies or Oxfords, a quality pair of Chelsea boots offers better grip and warmth than a traditional dress shoe – plus, pulling them on with your tailoring just so happens to look progressively stylish.

Yet whether you’re looking to kick out Saint Laurent-inspired rocker vibes for a night out or simply for ways to make your work attire more seasonally-appropriate, there are a couple of things worth bearing in mind before teaming your tailoring with Chelsea boots.

Firstly, Chelsea boots really only work with similarly slim or skinny suits. This is because boxier tailoring and trousers tend to jar when put against such a sleek and refined silhouette. Secondly, you’ll want to mind your toes. Pointed-toe Chelsea boots, when worn with a suit at least, look a little off, so keep your sights firmly set on round-toed styles instead.

Finally, as with all things made of leather, the price you pay is often directly proportional to the quality of the product – so consider upping your outlay for a pair that looks the part with a sharp suit. And that won’t be in pieces in a year’s time.

Men's Chelsea Boots Paired With Tailoring Outfit Inspiration Lookbook

Key Styles

Reiss Tenor Chelsea Boots Black
Jack & Jones Radnor Leather Chelsea Boots
Topman Selected Homme Brown Leather Chelsea Boots
Sandro Leather Chelsea Boots
Office Cage Chelsea Boots
Polo Ralph Lauren Dilian Leather Chelsea Boots
Churchs Houston Leather Chelsea Boots
Tods Leather Chelsea Boots
Edward Green Newmarket Grained-leather Chelsea Boots

2. Hiking Boots + Denim

Unless you spend your weekends hauling ass up the nearest mountain, chances are you don’t have much need for this style’s durable laces, lugs and lining. That said, few items have made the transition from outdoors essential to off-duty wardrobe staple as seamlessly as a pair of robust hiking boots.

Whether or not you’d consciously label yourself a lumbersexual, buffalo checks, facial hair and hikers is a combination that’s inarguably still au courant. And, conveniently enough, it’s dead comfy, too. To nail the look for winter, pull on a pair of tan, dark brown or black hiking boots with some over-dyed denim, a flannel shirt and a heavy-gauge cable knit jumper or shawl neck cardigan.

If you’re anything like us, you’ll be more likely to break this look out for a weekend roast than a full-on trek, so steer clear of traditional hiking styles’ more obviously ‘performance’ features like neon laces and multi-coloured mesh panels.

When it comes to finishing touches, ensure you’ve got your pin-roll game on lock down, so you can turn your hems up and let your fellow man marvel at your expert boot sock coordination.

Men's Hiking Boots With Heavyweight Denim Jeans and Outdoors Pieces. Outfit Inspiration Lookbook

Key Styles

He By Mango Leather Hiker Boots
River Island Lace Up Hiker Boots In Leather
Asos Boots In Black Leather With Borg Lining
Timberland Premium Six Inch Leather Boots
Okeeffe Austin Leather Boots
Viberg Hiker Whole-cut Leather Boots
Tods Leather Hiking Boots
Diemme Roccia Vet Boot
Fracap M120 Cristy Vibram Sole Scarponcino Boot

3. Chukka/Desert Boots + Smart-Casual Separates

As far as we’re concerned, there are few instances in which wearing a pair of chukka or desert boots isn’t a good idea. While their mid-weight construction marks them out as a clear choice for spring and summer, they’re actually a killer option for the winter months, too.

Their in-between profile means they’re smart enough to style with a roll neck, blazer and smart wool trousers, but also not so fussy that they can’t be coupled with chinos and a crew neck jumper. Perfect for navigating the festive season’s dress codes quandaries.

Leather pairs are a no-brainer for winter’s harsher conditions, offering resilience and an enduring elegance, while suede pairs can also work if you take the time to regularly treat them with a protector spray and always check the forecast before you leave the house.

Treat your chukka or desert boots as a smarter, more hard-wearing alternative to trainers – team them with chinos, button-down shirts and crew neck jumpers to create sharp, warm getups that will pass the pub-safe test no problem.

As with most footwear, shades of brown and black promise the best bang for your buck (readily teaming with most colours in your wardrobe), while burgundy, navy and stone (especially in suede) will help breathe life into your current go-to looks.

Men's Chukka and Desert Boots With Smart-casual Separates. Outfit Inspiration Lookbook

Key Styles

Reiss Dundee Allen Edmonds Cordovan Chukka Boots Ox Blood
Topman Tan Leather Chukka Boots
Asos Desert Boots In Leather
Santoni Burnished Suede Desert Boots
John Lobb Grove Suede Chukka Boots
Ted Baker Torsdi 2 Desert Leather Chukka Boots
Tods Chukka Shoes
Clarks Brown Tumbled Leather Desert Boots
He By Mango Lace-up Suede Ankle Boots

4. Brogue Boots + Heritage Wear

If you’re not ready to go full Bear Grylls with a pair of hiking boots just yet, there are other, subtler ways to infuse your winter look with some outdoorsy influences. A sartorial hybrid, the brogue boot comes with the same reassuring weight and solid construction of hiking boots, but with all the wing-tipped, country-manor smartness of brogues.

As a general rule of thumb, you can wear your brogue boots with any outfit you might normally wear with traditional brogues, so lace up a dark brown or black leather pair with heavier wool suiting, and smart trouser and shirt/cardigan combinations.

However, owing to their winter-readiness, brogue boots also play well with pieces that straddle the rugged-refined divide, such as heavy-gauge knitwear, gilets, quilted and waxed jackets, as well as heritage fabrics such as corduroy and tweed.

While sock-flashing isn’t necessarily frowned upon when wearing a pair of these, it’s not an entirely natural fit with the brogue boot’s finesse either, so stick instead with trousers with a neat break (i.e. that finish around the top set of lace eyelets), or roll more casual trousers and jeans up to the same point for a smart finish.