20+ Gap Gifts That Will Make Guys Grin This Holiday Season (We Promise!)

This Gap Vintage Soft Bomber Sweatshirt ($70) looks like a leather bomber at first glance, but it's made of specially dyed, soft-fleece material instead.

The textured Gap Waffle Henley T-Shirt ($10-$35, originally $35) makes a great layering piece.

This Gap Pocket Flannel Shirt in Standard Fit ($55-$60, originally $60) is a classic no matter the plaid pattern you choose.

Who couldn't use a new winter hat to add to the rotation? This Gap Rib Beanie ($20) comes in 13 colors for him from basic black to bold gold.

Freshen up his sock stash with these Gap Crew Socks (3-Pack) ($18). Yes, some of the combos are rather bright, but there are more neutral picks, too.

If he's not the type to splurge on himself, these Gap Selvedge Skinny Jeans with GapFlex ($129) make a sweet gift of premium Japanese denim made on vintage looms.

Keep his fingers toasty with these Gap Wool Knit Gloves ($40) and he can even text you his thanks . . . thanks to the handy pointer-finger opening.

This Gap Mainstay Sweater ($20-$50, originally $50) can be a mainstay in his wardrobe for years to come, whether he prefers solid or striped looks.

Each Gap Upcycled Puffer Vest ($60) is made of 24 discarded plastic bottles and, if that's not an automatic conversation starter around the tree, we don't know what is.

If he's got more stretched-out tees with holes than you'd like to see, why not pick up a few Gap Classic T-Shirts ($20) to slip into his drawers this season?

A top-rated Gap Casual Classic Blazer in Stretch ($50-$56, originally $90) is exactly what he needs in close reach for any impromptu virtual work meetings.

These Gap Adult Contour Mask with Filter Pocket (3-Pack) ($7-$9, originally $18) make great stocking stuffers all together, or split up between your loved ones.

Upgrade his baggy old sweats to a pair of these Gap Vintage Soft Slim Sweatpants ($45) for a modern look that's still just as comfy.

A Gap Merino Mockneck Sweater ($80) is a more polished pullover to pull even a casual look together.

There are 11 chances that one of these Gap Recycled Cozy Scarves ($30) will complete his winter wardrobe (and keep his neck warm, too).

This Gap Reversible Fleece Jacket ($98) is like two coats in one with a nubby sherpa side and a solid bomber when it's flipped. Bonus!

Gap Print Boxers ($15) make a cheeky gift whether you opt for reindeer, bacon and eggs, or these cute dogs-in-sweaters instead.

This lightweight, 100-percent-cotton Gap Vintage Slub Polo Shirt ($30) is a preppy choice he can wear year-round.

If this marled brown Gap Shaker Cardigan ($80) isn't his speed, there's also the similar Gap Ribbed Shawl Cardigan ($80), coming in solid green, cream, black, or navy instead.

The Gap Vintage Soft Hoodie ($60) is so cozy it feels like he's worn it forever, but still looks — and obviously is — brand-new.

This Gap Leather Belt ($45) in brown or black makes a practical gift, especially if he's returning to an office one day.

A Gap Oxford Shirt in Untucked Fit ($30-$60, originally $60) can be dressed up or down, however he sees fit.

Colder weather practically demands you pick him up some Gap Flannel Pajama Pants ($15, originally $40) for binge-watching nights in.

While it may look like just a basic cotton coat, this water-resistant, windproof Gap ColdControl Filled Mac Jacket ($148) actually has a polyester fill for insulation on chillier days.