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

Levi's Sherpa Trucker

Every cool guy needs a staple denim jacket — double points for this one being vintage-looking and sherpa-lined.

Levi's Sherpa Denim Trucker Jacket, $, available at Macy's

“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.

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

iPhone 12/12 Pro Leather Case

Of course, he ran out and bought the iPhone 12 the moment it came out. Only this minimal leather case will do for his minimal tastes — it will break in beautifully with age and doesn’t detract from the phone’s slim profile.

Bouletta Case Genuine Leather Apple iPhone 12 Case, $, available at Etsy

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