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5 Days, 5 Ways: How to Wear a Chukka Boot

the shoe that keeps on giving

By Gabi Meyers | Aug 20 2018

If the quintessential SG Reader were to wear a shoe—just one—it would be a chukka boot. The ankle-high leather boots with suede or leather uppers, leather or rubber soles, and open lacing with two or three pairs of eyelets, 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 (the same way an orange is a type of fruit), and you’ve probably noticed them pop up in quite a few past 5 Days, 5 Ways. Meaning? It was about time for the spotlight to shine their way!

How to wear a chukka boot, 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.


blazer: Topman, $200 | shirt: David Donahue, $155 | trousers: Bonobos, $98

watch: Fossil, $125 | tie: The Tie Bar, $19

Wear it well: Ease into the work week with a slightly more casual shoe than the rest of your office wear.


sweater: Brooks Brothers, $128 | shirt: Charles Tyrwhitt, $110 | glasses: Warby Parker, $95

cords: Patagonia, $89 | socks: Pair of Thieves, $10 | belt: Trask, $95

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


denim jacket: Dstld, $95 | shirt: H&M, $7 | beanie: Tilley, $28

jeans: H&M, $25 | wallet: Fossil, $40 | backpack: State, $115



topcoat: Land’s End, $349  | sweatshirt: Mack Weldon, $68 | pants: Bonobos, $68

shirt: Gap, $42 | watch: Movado, $495 | sunglasses: Vuarnet, $285

Wear it well: When the weather starts to cool, layer the chambray under the sweatshirt under the 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.



See more ways to wear your favorites like a topcoat, colored chinos and felt hat 5 ways.

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