5 Days, 5 Ways: Brown Derby Shoes

5 Days, 5 Ways: Brown Derby Shoes

get you a shoe that can do both
derby shoe, brown, leather, casual shoe, dress shoe, lace up

By Gabi Meyers | Last Updated: Jun 26 2022 | 2 min read

If you could only wear one shoe for the rest of your life, a derby wouldn’t be the worst choice. A pair of derby shoes would be a better choice. Working equally well for work, the weekend or a wedding, derby shoes can be dressed up and down to fit nearly every occasion. What separates a derby from an oxford is the open laces, which can feel a little more casual than the closed laces of an oxford. If you do plan to own a pair of both, your best bet is a black oxford, which means you should opt for a brown derby, so that your two-shoe-wardrobe runs the gamut.


derby shoe, brown, leather, casual shoe, dress shoe, lace up

A brown derby is one of the most versatile shoes a man can have in his closet.

work, office style, work wear, suit, suit supply, jack spade, pocket square, nixon

Shirt: Charles Tyrwhitt, $110 | SuitSuit Supply, $499 Watch: Nixon, $125

Belt: Maximum Henry, $95 Glasses: Warby Parker, $95

Tie: The Tie Bar, $19 | Pocket Square: Jack Spade, $22

Wear it well: Keep it classic for work by pairing your derbies with a navy suit.


business casual, high low styling, souvenir jacket, neppy pants, band collar, fall trend, aw 16, menswear

Shirt: River Island, $40 | Jacket: Vanquish, $275  | Pants: Reiss, $210

Socks: Happy Socks, $20 | Cologne: Doc Elliot, $18 | Belt: Anderson’s, $160

Wear it well: A fun jacket over your work clothes can make any outfit ready for a night out.


casual, elevated casual, white denim, white pants, transitional style, in between weather

Tee: Topman, $35 | Pants: Obey, $69 | Jacket: Publish, $168

Watch: Jack Mason, $185 | Hat: Brixton, $59

Wear it well: Elevate your tee and jeans with a sleek shoe and soft yet structured jacket. 


chino, steven alan, denim shirt, everlane, bright colors

Shirt: Everlane, $55 | Chinos: J.Crew, $75 | Glasses: Steven Alan, $205

Bag: Will Leather Goods, $395 | Belt: Whistles, $45 

Wear it well: Go business casual with colorful chinos and a tailored denim shirt.


bomber, norman porter, retrosuperfuture, derby shoes,

Short Sleeve Shirt: AMBSN, $32 | Jeans: Norman Porter, $250

Jacket: Carhartt WIP, $104 | Sunglasses: RETROSUPERFUTURE, $168

Wallet: First Settlement Goods, $148

Wear it well: Roll up your jeans and skip the socks for a rakish look.



Want to see more ways to wear your favorite pieces for summer? We show you how to style the chambray shirt, colorful chino and souvenir jacket, 5 ways.

Like a phoenix rising from the ashes, Gabi Meyers went from Team SG's first-ever intern to a trusted fashion editor and stylist. She currently lives in Chicago with a very cute dog.