This holiday season, you’ll be shopping for a lot of people from different parts of your life, and they all have their own special needs. Maybe it’s your sister who made it super clear that she liked your last purchase; or your new boss who has enviably sophisticated taste. No matter the challenging individual in question, the greatest head-scratcher of them all has got to be The Dude. This dude is not necessarily your partner, but he is, without a doubt, the “cool guy” in your life — the one who seems to be on the next thing before everyone else is.
Maybe he’s your older brother who, in high school, shared his extremely well-curated CD collection and continues to maintain a digital archive of the best songs you’ve never heard before. Perhaps it’s your brother-in-law who is always Instagramming from some unknown restaurant that you read about on the Infatuation, like, the next day. Or maybe it is your man, who maintains a wardrobe of perfect T-shirts from a heritage workwear brand — not because they’re trendy, but because they simply are the best and most durable t-shirts.
No matter who this cool guy is, his mile-high standards and sixth sense for gear makes him impossible to shop for. But don’t worry — if you’re determined to defy the odds and knock it out of the park with his gift this year, you’ve come to the right place. We observed some of the coolest guys in our own lives to determine which gifts have the greatest wow potential for their highly exacting tastes. With items that range from a $10 true crime novel to a super-rare bottle of whiskey that tops out at $300, everything on this list should pass muster with your guy.
At Refinery29, we’re here to help you navigate this overwhelming world of stuff. All of our market picks are independently selected and curated by the editorial team. All product details reflect the price and availability at the time of publication. If you buy something we link to on our site, Refinery29 may earn commission.
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