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The Dandy Gift Guide: Groomsmen Gifts That Aren't Flasks

JB

Jordan Blake

2025-08-06 · 5 min read

The Dandy Gift Guide: Groomsmen Gifts That Aren't Flasks

The groomsmen gift industrial complex has convinced every groom that a monogrammed flask, a pair of novelty socks, or a cigar box is the move. Your groomsmen deserve better — they took days off work, rented tuxedos, and dealt with your wedding stress for months. Here are gifts they will actually keep.

Herschel Supply Co. Chapter Travel Kit ($35) is the dopp kit that every groomsman needs and most do not own. The waterproof zipper, internal mesh pocket, and durable polyester shell handle years of travel. Buy them in the same color for a cohesive photo-op, or personalize by choosing each groomsman's preferred colorway.

Carhartt WIP Chase Sweatshirt ($85) is the luxury-adjacent crewneck that looks good on everyone. The heavyweight cotton-polyester blend, ribbed cuffs, and embroidered logo hit the intersection of casual and considered. Order in each groomsman's size and preferred color — the same style creates unity without the matching-outfit cringe.

Ray-Ban Original Wayfarer ($143) is the sunglasses gift that nobody returns. The Classic frame works on every face shape, and the tortoise-with-green-lens colorway is universally flattering. Pair them with a personalized card thanking each groomsman individually at https://www.ray-ban.com.

A bottle of quality spirit, chosen specifically for each groomsman's taste, costs $40 to $80 and shows genuine thought. Woodford Reserve Double Oaked for the bourbon drinker, Roku Gin for the G&T guy, Casamigos Reposado for the tequila fan, and Lagavulin 16 for the Scotch loyalist. Personalization through selection beats monogramming every time.

For the creative groomsman party, Italic.com offers luxury-quality leather goods — wallets, cardholders, and belt bags — at factory-direct prices between $30 and $60. The full-grain Italian leather is sourced from the same tanneries used by brands charging $200-plus for comparable products.

Set a budget of $75 to $150 per groomsman and spend the time to pick something each person would actually want rather than ordering identical gifts in bulk. The personalization does not need to be a monogram — it needs to be evidence that you know who they are and appreciate what they did.