Holiday gifts for the best-dressed gent on your list

Holiday shopping gets easier when you know exactly who you’re buying for — and harder when that person happens to be the best dressed in the room. The one who never misses, never underdresses, and somehow always looks put together without trying. Whether you’re shopping for your dad, your brother, your partner, or anyone whose style you genuinely respect, this guide is your shortcut. Thoughtful fashion gifts that feel considered, wearable, and worthy of someone who already has great taste.

See also: Holiday gifts for her

Lacoste Zip-Up Polar Fleece Sweatshirt

There’s something about gifting a sweatshirt that feels risky — until you find one that actually earns its keep. This Lacoste sherpa fleece does exactly that. It’s warm without being bulky, soft in a way you notice immediately, and finished with a high zip neck that makes it feel intentional rather than thrown on. The kind of layer he’ll live in all winter, whether he’s running errands or doing absolutely nothing at all.

Call it Spring Hillman Western Boots

Hillman takes the cowboy boot and edits it for real life. The pointed toe and zip closure give it that Western edge, but the silhouette stays clean and city-ready. Built entirely from vegan materials with B.E.D Foam™ comfort, it’s comfortable enough for all-day wear without losing its shape or attitude. A smart pick for someone who likes their footwear to say something — just not too loudly.

Our Legacy No Time Watch Bracelet

A piece that lives comfortably between jewellery and hardware. This leather bracelet borrows the language of a watch — raised indices, crown detailing, brushed sterling silver — and translates it into something quieter and more personal. The contrast stitching keeps it grounded, the pin-buckle fastening makes it feel intentional, and the weight of the silver gives it presence without trying too hard. The kind of accessory that works every day and still feels considered.

Emporio Armani Tumbled Leather Shoulder Bag

This is the bag for someone who hates carrying too much but still wants everything to look intentional. The shape is boxy and precise, the leather is tumbled and soft, and the hardware keeps things quietly polished without screaming for attention. It sits comfortably on the shoulder, opens easily, and somehow always looks pulled together — whether it’s paired with a coat, a knit, or nothing but confidence. Practical, yes. Boring? Absolutely not.

Spencer Badu Black Knitted Vest

For the fashion guy who’s bored of the obvious, this knit vest hits different. Cropped with a raglan cut that contours the shoulders, it plays with proportion in a way that feels intentional, not trendy. Ribbed, soft-as-butter cotton that works layered or solo — the kind of piece people ask about because they haven’t seen it everywhere yet.

Moose Knuckles Toba Bomber Jacket

This is the jacket for the guy who wants presence without performance art. The kind you throw on when the outfit already works and you just need the final layer to carry it. The leather has weight without feeling stiff, the shearling collar softens the whole thing, and the cut gives you room to move without swallowing your frame. It reads confident, not costume — the type of piece that makes even a plain tee and trousers feel deliberate.

Prada Collapse Re-Nylon & Suede Elasticized Sneakers

One thing you never second-guess when gifting? Prada. These low-top sneakers land right in that sweet spot between sport and polish — lightweight, collapsible, and easy to live in. The mix of nylon and suede keeps them feeling modern without trying too hard, and the elastic sides mean he can slip them on without breaking stride. A smart pick for the dad who travels light, the brother who hates fuss, or the partner whose off-duty wardrobe still needs to look intentional.

Dean Davidson Mini Sol Huggie Hoops

For the one who’s officially over the same tired studs they’ve been wearing since forever. These Sol Huggies take everything people loved about the original — the concave shape, brushed finish, easy hinge closure — and scale it down for a subtler, more considered look. They’re comfortable, lightweight, and quietly versatile, which makes them perfect for stacking or wearing solo when you want something polished without trying too hard. A small switch that makes getting dressed feel new again.

Tom Ford Icon Navigator Sunglasses

There’s something undeniably cinematic about these. The shape is bold without being loud, the acetate glossy but controlled, and the gold T-logo catches the light just enough to feel intentional. They sit comfortably, feel substantial in hand, and instantly sharpen whatever you’re wearing — even if it’s just a coat and a coffee run. Less trend, more presence. The kind of frame you don’t explain — people just clock it.

Snow Goose Echo Pant

Just because it’s winter doesn’t mean his style has to hibernate. The Echo Pant is for the guy who still cares how things look when the temperature drops — lightweight, quilted just enough to feel intentional, and made from recycled ripstop that doesn’t weigh him down. The adjustable tie hems let him change the silhouette depending on the day, while the elastic waistband keeps it effortless. Made in Canada, easy to wear, and the type of piece he probably wouldn’t buy for himself — which is exactly why it works as a holiday gift.

Bulova Super Seville

This is the kind of gift that instantly raises your stock. Inspired by a 1970s Bulova classic, the Super Seville feels nostalgic without feeling dated — gold-tone, TV-shaped case, green dial that catches light in all the right ways. It’s bold enough to stand on its own, but versatile enough to wear every day, which is exactly why it works as a gift. Something he’d never splurge on for himself, but will wear constantly once it’s on his wrist.

This is the layer he’ll appreciate the second the temperature drops but a full coat feels like overkill. Lightweight, packable, and quietly refined, this vest adds warmth without bulk and slips easily over knits or under outerwear. The matte EnduraLuxe finish keeps it clean and modern, while the down fill does exactly what it’s supposed to do. Thoughtful, practical, and easy to live with — which is usually what makes something a good call in the first place.