Gatsby Shoes

Men's Brogues & Great Gatsby Style Shoes

Brogues are the defining footwear of the 1920s gentleman — and the natural choice for anyone putting together a Great Gatsby outfit, a Peaky Blinders look, or simply want shoes with more character than a plain Oxford. The perforated detailing, wingtip toe, and leather construction make brogues one of the few styles that genuinely improves with age.

What Makes a Gatsby Shoe

A Great Gatsby style shoe is built on 1920s tailoring principles — real leather, decorative brogue detailing, and a silhouette that works with a three-piece suit as naturally as it does with dark jeans. The key styles in our collection:

Wingtip brogues — the most iconic 1920s shoe. The W-shaped toe cap with perforated detailing is immediately recognizable and works with any vintage-inspired outfit.

Leather & tweed brogues — a combination unique to the era. Leather and tweed panels together give the shoe texture and personality that plain leather can't match.

Brogue ankle boots — for a more substantial look. Pairs particularly well with tweed suits and adds height and presence to the full outfit.

Two-tone brogues — tan and navy, tan and black, or brown and grey combinations. The boldest choice in the collection and the closest to authentic 1920s footwear.

Shop Gatsby Style Shoes at Happy Gentleman

All shoes in our collection are real leather — not synthetic alternatives. Fast delivery across the US, free exchanges on all orders, and free delivery over $99.