Gifts for the Coolest Guy You Know

Our Menswear Editor, John Jannuzzi, has some ideas.

With precious little time left before the holidays, we’re back with another gift guide to make your life a little easier. For this round, we’re focusing on gifts for the men in your life, whether they're husbands, boyfriends, brothers, dads, crushes, or something complicated.

Holiday shopping is my personal Olympics. I’ve been told gift-giving is my love language (if you believe in that sort of thing), so I like to think of myself as well-practiced. So let’s get to it. And good luck, you’ve got this.

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Ghiaia Cashmere Half Zip // Loewe Fringe Scarf // Rag & Bone Textured Sweater // Todd Snyder “Dylan Jacket” // 1991 Rolex Datejust // Hanro Boxers // Kaweco Fountain Pen // Polaroid Lab Phone Printer // // Kevlar Scissors // Bottega Veneta Cassette Wallet (Monogrammable)

Worth Noting: The whole half-zip thing is very zeitgeisty. I don’t want to steer you down a one-and-done trend, so I think this Ghiaia one fits the bill. First, it’s Ghiaia. That means it’s sumptuous, perfect, and heavenly at once. Second, it has a beautiful ribbed texture, and in my experience, that adds some life to cashmere while adding a bit of an interesting detail. You won’t look at this in 10 years and think “ew.” And that Todd Snyder jacket is absolute mastery. When I spoke to Todd a few weeks ago, he wouldn’t stop cooing about this jacket — neither would I! I need one in every color.

Billy Reid Chore Coat // Charvet Suede Sleepers // Mallard Duck Tabletop Lighter // Schoolhouse Electric Floor Lamp // Fellow Black Kettle // Chen and Kai Foot Bowl // Bose Ultra Noise Canceling Headphones // Alex Mill Painter Pants // Cinderblock Bookends // Kodak 1080p Portable Projector // Alex Mill Monogram Tote // Paige Jimenez Seater

Worth Noting: Hot tip: if you’re going to order that monogrammed tote, you better do it fast. Shipping cutoffs will get you on custom stuff. And speaking of Alex Mill stuff, I truly live in those Painter Pants, and I have them in those exact colors. From my varied travels, I can confirm that they have a “Brotherhood of the Traveling Pants” mystique. Now, onto the Edie Parker duck lighter. I love a Mallard. There was a duck couple I used to know on the Hudson River — they were definitely an older gay couple, but one of them was a Mallard. This is for him (and Nintendo Duck Hunt fanatics).

NN07 Tweed Coat // Ralph Lauren Down Puffer Vest // Loewe Fleece Gilet // LL Bean Classic Bean Boot // Collection of Vintage Matchbooks // Donegal Cashmere Turtleneck // Canada Goose Touchscreen Gloves // A Custom-Built Rehabbed iPod Classic // Forsyth Mushroom // Blackstock & Weber Loafers // Sterling Silver Signet Ring // Gold Signet Ring // Wonder Valley Hair Kit // Steve Madden Birkenstock Dupes

Worth Noting: There’s a lot to love here, but one of the simplest and most-loved gifts I’ve given is that vintage matchbook collection. It’s simple: you pay a nominal fee and get a random assortment. But it’s a fantastic stocking stuffer or Secret Santa thing. Also, I’ve been using the Wonder Valley hair stuff for a year, and this is how every man on earth should smell. It’s fragrant and gentle, but masculine. (I shan’t elaborate, but my wife is a big fan…)

For the gadget-heads, if you’re going to get an iPod, there are a few things to keep in mind. First, you’ll want to make sure you’ve got wired headphones (or have them upgraded to Bluetooth). More importantly, you cannot use this unless you have a music library, so if you’ve got a Spotify fanatic on your hands, you may be disappointed.

Lastly, the Steve Madden clogs… yes, they are absolutely Birk dupes, but the way the strap works, and the cushioning on the footbed are excellent. They’re the only clogs I can walk miles in without being annoyed.

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With all of these picks, there’s enough to go around for all of those archetypes out there. The roundup includes plenty of fashion-forward items, some general safe bets, and, indeed, a gadget or two. Remember, some of these items — like the Rolex, which was too pretty to resist — are extremely limited in supply, so act sooner rather than later.

If you’d like to shop it all at once, you can visit the whole collection on ShopMy. If you’re still stumped in the coming weeks, keep an eye on the Love List subscriber chat. I’m always around and happy to help if I can.

(And don’t forget to get some of that good good wrapping paper I design.)