Most of my gift ideas start as a screenshots folder. Things I looked at twice in July, didn’t buy, and kept thinking about through August. These six made the cut.
Laid out together they’re basically a fall outfit with a bottle of wine attached. That wasn’t the plan, but it turns out to be a useful way to shop. If the guy you’re buying for already has a closet full of stuff, the move is to replace one thing he owns badly with one thing he’ll own for a decade.
Prices run from $68 to $319, so there’s room here whether you’re covering a birthday or splitting a big one with a sibling. I’ve flagged where sizes are already thin, because a few of these are small-batch and won’t be sitting around in November.
Bridge & Burn Pointer Overshirt in Camel
Price: $168
Who it’s for: The guy who wears a hoodie to dinner because he doesn’t own a middle layer.
Heavyweight twill cut as a shirt but with enough substance to work as a light jacket from September through whenever it actually gets cold where you live. The fabric is recycled cotton and polyester sorted by color rather than dyed, which is why the camel has that slightly uneven, already-lived-in tone straight out of the box. Small and XXL are gone already, so check his size before you get attached to the idea.
Timex Expedition Sierra Field Watch
Price: $149
Who it’s for: Someone who wants a watch with a little personality and zero interest in charging it.
The camo-print green dial is the whole argument. Under $150 you can find a hundred competent field watches and almost all of them look like each other. This one runs a 40mm brushed steel case that sits right on most wrists, 100m of water resistance so nobody has to baby it, and a slip-thru fabric strap that’s easy to swap once he gets bored. Quartz movement, so it just runs.
Entourage of 7 Beacon 1020 Sunglasses
Price: $319
Who it’s for: The guy who has watched Ford v Ferrari four times and knows exactly which frames those are.
Knockoffs of these are everywhere. These are the real ones, the Beacon 1020s Matt Damon wore as Carroll Shelby, handmade in Japan from translucent Zyl acetate with titanium hinges and G-15 green lenses. Two dice on the temple hinges add up to seven, which is the kind of detail the right person clocks immediately and the wrong person never notices. One thing worth knowing before you spend $319: a few buyers have reported the fit running loose, so this is a better bet for a wider face than a narrow one.
Imogene + Willie The Heart Tee
Price: $68
Who it’s for: The guy whose drawer is nothing but blank tees he can’t tell apart.
Sixty-eight dollars for a t-shirt sounds absurd until you handle a 7 oz one. This is midweight cotton, patterned and sewn in the U.S., with hand-drawn artwork printed in Nashville, and it hangs like a shirt instead of draping like a drop cloth. Sizing note worth passing along: it’s cut unisex, so men should go up one from their usual.
WP Standard Solo Wine Tote
Price: $88
Who it’s for: The friend who always shows up with a good bottle and a grocery-store plastic bag.
A woven full-grain leather sleeve for a single bottle, with a small pouch on the side for the corkscrew. It’s a slightly ridiculous object in the best possible way, and it’s the rare gift that actually gets used by anyone who hosts dinners or brings wine to their in-laws. Tan is the only color, and stock was down to a handful when I checked.
Dr. Martens 2976 Chelsea Boots
Price: From $170
Who it’s for: The one still wearing sneakers to weddings.
No boot solves more problems for less thought than the 2976. Pull-on, no laces, works with jeans and works with wool trousers, and the lugged sole means salt and slush stop being an event. Break-in is real, though, so if he’s never owned Docs, buy them in October and let him suffer through a few weeks before the holidays hit. Black smooth leather is the safe pick and the brown nappa is the more interesting one.
Levi’s 507 Western Slim Bootcut Jeans
Price: $39.99 (regularly $64.95)
Who it’s for: The guy who owns Chelsea boots and no pair of jeans that will go over them.
Bootcut is back and this is the version worth owning. The 18-inch leg opening clears a boot shaft without looking like it’s 2003, the denim is 99% cotton with just enough elastane that you can sit down in it, and the felled seams and reinforced pockets are why a $40 pair of Levi’s tends to outlast jeans costing four times that. Two caveats. The “slim” in the name is doing some work, since a few buyers report it fitting closer to a regular than a 511, so if he likes a tight leg, size down. And this light wash was showing out of stock both online and in stores when I checked, so verify before you commit. The darker Caught In The Rain colorway is the fallback.
If I had to pick one, it’s the overshirt, because it’s the piece he’ll reach for four days a week and would never think to buy himself. That’s the real test for fall gifts for men. Not whether it looks impressive coming out of the box, but whether it’s still in rotation in March. Everything on this list clears that bar, which is more than I can say for most of what I get talked into buying. If you’re still hunting for ideas, my [link to related guide] has a few more worth a look.
