The holiday season can put undue strain on the art of gift-giving. Calendars suddenly fill to the brim with parties and cocktails, shops get crowded, items sell out. But don’t let the pressure of the season influence your purchases. Consider each person on your list and ask yourself what they would genuinely love. It doesn’t need to be expensive or extravagant—the best gifts often aren’t. Something thoughtful and perfectly tailored is the goal. It really is the thought that counts.

The best advice I have when it comes to giving gifts is to buy things that the person would buy for him- or herself. This might seem obvious, but, surprisingly, it happens far less than it should. People tend to give gifts for the wrong reasons, often to signal something about themselves rather than provide enjoyment or even utility to the recipient.

You may at some point find yourself having to buy gifts for men, which can feel deceptively easy, but the men I know and love have discerning tastes and an eye for beauty. They enjoy and delight in the unexpected. They might appreciate the finer things and an NFL RedZone subscription. We men contain multitudes—and, luckily, so does this list of gifts.

Small Rugged Twill Duffle Bag
Free Wheelin’ Early Skateboard Company Logos
Cotton-Blend Jersey Hoodie

We all have a graphic designer or two in our lives, and this book of early skateboard-company logos from Klasse Wrecks sub-label KFAX will inspire and even take them back to their youthful days learning to kickflip.

A cutting board is functional and boring, but Los Angeles’s Spiritual Objects has made a version that would please even a sandwich artist. Crafted from walnut and shaped like a painter’s palette, it will make chopping vegetables a little more fun.

A simple, elegant cashmere sweater in navy, black, or camel is a staple of every closet. But Salie 66 wants you to experiment with color, and so do I. The Dakota cashmere crewneck comes in a shade of mood-lifting Kermit green that will be easy to incorporate into any wardrobe.

A rugged-wearing, logo-free duffle bag from Filson will work for a weekend in Rhinebeck or a residency in Rome. Its sturdy twill ages nicely, and the classic and unfussy design makes it a bag you can take anywhere.

The hooded sweatshirt has had a rough few years, most often seen grossly oversized with a gaudy designer logo emblazoned across the chest. This one from French brand Lemaire is the polar opposite. Made from cotton and yak fleece in the perfect shade of brown, it’s understated and luxurious at the same time.

We all brush our teeth, and the drugstore dental brands were our only hope for decades. Linhart applies the same rigor to their packaging and design as the product itself. This trio consists of Linhart’s Linämel Toothpaste, Nano-Silver Toothbrush, and Lip Balm that will have you smiling bright in no time.

The chore coat can feel a little chimney-sweep if done wrong, but, luckily, Drake’s has made a beautiful one in a Harris-tweed gun-club check that feels more appropriate for dinner at the Odeon than performing your duties as a huckster sometime in the 19th century.

Vintage Santos Watch
The Essential Collection
Houndstooth Check Harris Tweed Donkey Chore Jacket

R.E.M. is America’s best band, and Green is their best album. I don’t make the rules, but you can’t go wrong giving something this specific that just looks cool.

This is the best Cartier watch: masculine without being macho, classic without being boring. The white dial with blue hands complements the steel case, giving it just enough spice.

Eros Torso is a series of one-off vases in up-cycled plastic, individually heated and hand-shaped in Copenhagen by the collective Niko June. Any one of them is the ideal vessel for some white lilies.

Nothing says “I really travel” like a giant Rimowa aluminum trunk. If you’re taking a long haul and need to pack for weeks at a time, this is your suitcase—especially when those patented grooves get a little beat up.

Boat shoes are a men’s wardrobe staple, especially on the East Coast. I found them a bit clunky until I was given this supple black leather pair from The Row. Your grateful recipient will wear these every day and think of you fondly.

Candles are always a good choice. Everyone uses them. Everyone loves them. The key is to go a little deeper and find one your recipient might not have. I discovered Perfumer H some years back at Galerie Half, in Los Angeles, and fell in love. The “Smoke” is masculine and clean, plus they offer a refilling service.

Svenskt Tenn is one of the best stores in the world. A sprawling multi-room space on the water in Stockholm, it’s been serving design-minded people since 1924. These candle holders elevate any table they’re placed on. I have a set, and they bring me great joy.

These are for the amateur athlete in your life who tracks their miles on Strava but wants to look good doing it. District Vision sunglasses are made in Japan and light as a feather, great no matter if you are riding 100 miles with the lads on a Saturday morning or slogging through marathon training in the dead of summer.

Chris Black is the founder of Done to Death Projects and a co-host of the podcast How Long Gone. He lives in Los Angeles and New York