Gifts For Cool Guy

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 (but you’ve only met on Zoom). 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 photos of the perfectly seared steak he just pulled off the grill. 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 this hard-to-please fellow.

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Aesop Body Cleansing Slab

You thought that you were a product junkie until you met this guy. He gives you a run for your money when it comes to knowing about — and, uh, spending money on — all the latest in natural deodorant and beard oils. Aesop is his Achilles Heel, so why not surprise him with a slab of soap this year?

Aesop Body Cleansing Slab, $, available at Nordstrom

Omsom East Asian Sampler

Send him on a global culinary adventure without ever leaving his kitchen with this sample box of six East Asian starter sauces — each one offering hard-to-get quality ingredients and complex flavors that are normally pretty tricky to conquer unless you travel to a ton of specialty stores. This pantry shortcut in a box includes: Japanese yuzu misoyaki, Korean spicy bulgogi, and Chinese mala salad sauces. All are vegan and gluten free.

Omsom East Asian Sampler, $, available at Omsom

The Men's Store at Bloomingdale's Cashmere Half-Zip Sweater

He'll love this cozy cashmere half-zip as a champion winter layering piece — and so will you, when you "borrow" it.

The Men's Store at Bloomingdale's Cashmere Half-Zip Sweater, $, available at Bloomingdale's

The Snuk Chili Crisp Gift Box

If he already knows what he wants (chili crisp!) then indulge him a quattro of beloved jars, including Fly by Jing, Blank Slate Sichuan Chili Oil from Brooklyn, Lao Gan Ma, and Don Chilio Habanero chili crisp from Mexico. He'll appreciate getting a gift box from the small global bazaar brand Snuk, which stocks some of the best specialty ingredients from all over the world.

Assorted Brands Chili Crisp Gift Box, $, available at Snuk

“Is This Anything?” by Jerry Seinfeld

The man is a stand-up fiend, and can quote routines from all the greats, from Richard Pryor to Bill Hicks to Mitch Hedberg. Help him add to his encyclopedic knowledge of the comedy canon with the gift of Jerry Seinfeld’s career-spanning retrospective of jokes.

Shop it on Amazon

Jerry Seinfeld Is This Anything?, $, available at Bookshop

Rechargeable Hands-Free LED Book Light

If he's an avid reader or a night runner, this rechargeable, adjustable LED neck light will the affordable, functional gadget he'd be pleased to acquire.

Ledgle Rechargeable Hands-Free LED Book Light, $, available at Amazon

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