The Busy Gentleman’s Guide: 5 Leather Shoes For Work and Play

BY RALPH DESIDERIO

Making a sartorial statement with every step.


The modern working man’s dilemma has less to do with being productive and more to do with looking effortlessly stylish while doing so. With their ever-busy schedules- filled of course with work meetings, dinner invites, and after work drinking sessions- a desk to dinner look proves to be simpler than having to change in-between events.

5 Leather Shoes For Men
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Whether they’re soft suede, faux, or simple cowhide, these leather shoe options will keep you on top of the game for both work and play.

The Sophisticated Oxford

The Sophisticated Oxford
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Often considered as the player one of footwear, the classic oxfords are everyone’s go-to for a more formal take on things, from corporate meetings to a fancy dinner date.

The Breezy Brogue

The Breezy Brogue
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Known for the decorative perforations (in translation: the patterned cutouts) on the cap and sides, brogues are a less dressy yet more stylish substitute for plain oxfords.

The Chic Chelsea

The Chic Chelsea
Photo retrieved from The Idle Man

As timeless and iconic as a pair of shoes come, Chelsea boots are perfect for those who work in offices that have a more fluid dress code. From casual blue jeans to crisp slacks, these easy to wear boots will serve you well on almost any occasion.

The Friday Chukka

The Friday Chukka
Photo retrieved from The Idle Man

Often used as a more casual alternative to the other dress shoes, the chukkas have moved on from their humble desert beginnings into a staple weekend silhouette. Paired perfectly with jeans and chinos, your casual Friday’s just got an upgrade.

The Casual Sneaker

The Casual Sneaker for men
Photo retrieved from Beckett Simonon

Not every office has a strict dress code that requires you to resemble a sartorial gladiator (i.e. a suit and tie ft. dress shoes). In some instances, crisp leather trainers will do the job just fine while still remaining a smart edge to your look.

A well-curated wardrobe is never complete without the right shoes — the piece that pulls your entire look together. While the rules aren’t set in stone, classic guidelines suggest pairing black shoes with black outfits, while brown shoes offer more versatility, working seamlessly with both office attire and weekend looks.

Explore more shoe options that match your everyday outfits here.