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Style 5 Days 5 Ways

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 Updated: June 26, 2022

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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.

THE DERBY SHOE: H BY HUDSON, $160

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.
MONDAY

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

Shirt: Charles Tyrwhitt, $110 | Suit: Suit 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.

TUESDAY

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.

WEDNESDAY

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. 

THURSDAY

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.

FRIDAY

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.

TELL ME:

WHERE DO YOU WEAR YOUR DERBY SHOES?

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.

Gabi Meyers

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.

More articles by Gabi Meyers

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