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.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.Aesop Body Cleansing SlabYou 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“Is This Anything?” by Jerry SeinfeldThe 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 BookshopiPhone 12/12 Pro Leather CaseOf 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.Native Union Clic Classic Leather Case, $, available at MadewellYeti Roadie 24 CoolerThis man WILL be watching the Superbowl with his usual crew this year, pandemic be damned. Prepare him for safe and socially distant outdoor viewing with Yeti’s top-of-the-line, highly-rated cooler, for stashing whatever beverages he prefers to knock back while rooting for his team.YETI Roadie 24 Cooler, $, available at BackcountryCarhartt 100% Cotton HenleyYes, dudes love a T-shirt gift. And yes, dudes love Carhartt. (Actually, ladies love it too.) The heritage workwear brand has been in the throes of a “moment” for several years now, but there’s a reason why — they really do make sturdy, heavy-duty, well-designed basics for guys who abuse their clothing. We love a henley-style long-sleeve shirt as a stylish alternative to the classic tee.Carhartt Workwear Pocket Henley Shirt, $, available at AmazonSmartWool Larimer SockMerino wool is seriously a miracle fiber, and its moisture-wicking properties make it the perfect material for socks. SmartWool’s rugged hiker-style has just the right combination of aesthetics and function for someone who is picky about everything he puts on his body — even socks.Smartwool Larimer Socks, $, available at REIHeston Blumenthal for Everdure Charcoal GrillThe guy loves to cook, and has seared some amazing steaks on his 3-foot square apartment patio with the help of a miniature Smokey Joe. This year, he deserves an upgrade that matches his skill set — something like this sleek, porcelain-enamel charcoal grill co-designed by knighted British chef Heston Blumenthal; complete with an interior food tray, bamboo chopping board, stay-cool handles, and safety latches for easy transport.Everdure Heston Blumenthal Portable Charcoal Grill, $, available at WalmartJean Dubost Laguiole Steak Knives (Set of 6)If the grillmaster in your life is already equipped with enough smoking apparati to start a restaurant, he might appreciate the addition of some new cutlery that will help him enjoy the fruits — er, meats — of his labor. Laguiole’s sturdy stainless-steel steak knives are made in France and come in a foncy wooden storage box.Dubost Laguiole Steak Knives, Set of 6, $, available at Williams-Sonoma“Home Style Cookery” by Matty MathesonLast food thing, we promise! But this is a really good one. Earlier this year, beloved Canadian home chef Matty Matheson served up a (long-awaited) second cookbook, written in his trademark intimate and funny tone and filled with recipes that are just plain good. Whether your dude is a devoted home cook or just starting to tinker with pickling his own vegetables, this book will be a welcome addition to this arsenal.Matty Matheson “Home Style Cookery”, $, available at AmazonMasterClass Subscription (Buy One, Get One Free for a Limited Time)The engaging and beautifully produced online courses taught by a wealth of luminaries and experts (David Sedaris, Bob Iger, Stephen Curry, Timbaland, Aaron Franklin, to name just a few) was already well worth the $180 annual subscription fee — but MasterClass is running a limited-time BOGO deal on subscriptions, so you can nab one for yourself and the cool guy in your life.Masterclass Masterclass Subscription, $, available at MasterClassAir Max 90 SneakerSneaker nerds are very, very, very hard to shop for — especially since the goods they covet the most are usually only available via raffles or hyper-inflated secondary market pricing. If you do decide to go this perilous gift-giving route, it’s best to choose a classic, perennially available style that can go into their backup stash, like the forever cool Nike Air Max.Nike Air Max 90, $, available at NikeApple AirPod ProThis devoted headphone user deserves an upgrade this year, and he’ll really appreciate the sleek designer and supreme sound quality of the “Pro” AirPods.Apple AirPods Pro, $, available at AmazonHibiki Japanese Harmony WhiskeyRecently, he and his boozehound spirit-nerd friends have all been freaking out about Japanese whiskey. A more delicately-flavored alternative to the bolder, sweeter American varieties, these grain-based spirits are selling out everywhere, with prices of available bottles skyrocketing into the thousands. This expertly crafted blend from Hibiki is a delicious and much more reasonably-priced option.Hibiki Japanese Harmony Whisky, $, available at DrizlyDorset Crystal Double Old-Fashioned GlassesIs whiskey that pushes the hundred dollar-mark a little rich for your blood? We don’t blame you. Get him some nice drinking equipment instead. It doesn’t get more classic than a cut-crystal Old Fashioned glasses, and a set of two will only set you back about $40.Dorset Crystal Double Old-Fashioned Glasses, $, available at Williams-SonomaHelinox Chair ZeroThis top-rated camp chair is nothing short of miraculous; measuring no larger than a water bottle when packed up and weighing a pound — but still supports up to 265 lbs. If the man in question is a fan of the outdoors, he’s definitely got his eye on this chair. Helinox Chair Zero, $, available at REIBaboon 60L Go BagWe are kinda evangelical about Baboon’s colorful, super-sturdy luggage and handbags. The company’s website — which is a trip of its own, resembling an acid-tinged graphic-design funhouse — carries durable products that will brighten up any trip with an eye-catching palette of every shade from fluorescent orange to a subtle eggplant. Their signature “big” Go-Bag is a roomy, double-stitched duffle with convertible straps so it can be worn as a backpack.Baboon 60L Go Bag, $, available at BaboonThe North Face Unisex Down Mid LayerWe love the throwback vibes of this color-blocked North Face down shirt. Not only will it remind the cool dude in your life of his grade-school style — we’re sure he was on the verge back then, too — it will keep him seriously warm.The North Face Unisex Down Mid-Layer, $, available at The North Face-PAID-Levi's Sherpa TruckerEvery 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'sLike what you see? 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