How to Wear Chukka Boots More Ways this Fall and Winter

An all-time favorite at SG HQ

By Gabi Meyers | Last Updated: Feb 20 2019

If we had to call out one shoe as the unofficial mascot of SG HQ—just one—it would be a chukka boot. Yes, we love a Chelsea boot. And a classic white sneaker, too. But there’s just something about a chukka that tugs at our style heartstrings. And that’s why we’re going to show you how to wear chukka boots in more outfits below. But first, some context…

What are chukka boots?

Ankle-high leather boots with suede or leather uppers, leather or rubber soles, and open lacing with two or three pairs of eyelets. Chukka boots are a timeless piece of footwear that can be worn year round. They work equally well mixed into casual or more elevated outfits, and look great with basically everything you already own.

The beeswax leather pair below are desert boots, a type of chukka boots (sort of how an orange is a type of fruit, but not all fruit is an orange…ya dig?). You’ve probably noticed them pop up in quite a few past 5 Days, 5 Ways features. Meaning? It was about time for the spotlight to shine their way!

Are chukka boots stylish?


The great thing about chukka boots is you can treat them like sneakers in terms of the type of outfits they go with. Meaning? Jeans, chinos, twill pants and cords are all great options. You can also dress them up by trading up to dressier pants, or simply choosing a pair in a more luxe suede or leather.

How to wear chukka boots, five ways below:

The chukka boot: Clarks, $130

SG Says: Easy to dress up or down, you’ll be hard-pressed to find a shoe more universally #SGapproved by the whole team than the chukka boot.


trousers: Bonobos | watch: Fossil | tie: The Tie Bar

Wear it well: You can work a chukka boot into your office workwear, so long as we’re talking suit separates. With a full suit, they’d look just a bit too casual.


sweater: Brooks Brothers | shirt: Charles Tyrwhitt | glasses: Warby Parker

Wear it well: Update your standard shirt + sweater combo with cozy cords for a pre-fall lewk.


shirt: H&M | wallet: Fossil, $40 | backpack: State

Wear it well: A rugged dark indigo jean jacket is an easy way to toughen up any outfit. Just be prepared for it to feel a little stiff for awhile, as this material needs time to naturally break in. As you continue to wear your jacket, it’ll fade and form to your frame (that’s when it’s really shines). As outerwear like this will never stretch, make sure to choose a size that’ll you be comfortable wearing for the long run.



topcoat: Land’s End  | sweatshirt: Mack Weldon | shirt: Gap

Wear it well: When the weather starts to cool, layer a chambray shirt under a crewneck sweatshirt under a topcoat for the most casual-yet-pulled-together combo possible.


cardigan: Brooks Brothers, $448 | shirt: Vince, $145 | chinos: Bonobos, $198

scarf: The Tie Bar, $25 | bag: Frye, $598

Wear it well: Tie on a scarf over a thinner cardigan and henley for an easy to adjust travel outfit.

How to wear chukka boots to look stylish and stay warm

What better shoes to crunch autumn leaves underfoot than chukkas? These classic boots perfectly straddle coastal surf vibes and Ivy League timeless style, making it easy for you to incorporate this footwear into your existing wardrobe.

If you’re ready to jump on board the chukka boot wagon but dread the thought of shopping for them…consider letting Team SG shop for you!

Let us rescue you from shopping fatigue and sartorial apathy. We can promise the kind of personal attention and care that will make you feel like the best version of the awesome guy you already are! We’ll also help you figure out how to wear chukka boots with everything else in your closet you already own. If you’re ready for a shopping plan that’ll save you time, energy, and your sanity, give us a shout.

> See more ways to wear your favorites like a topcoat, colored chinos and felt hat five ways