Gifts for him – 12 ideas: watches, leather goods and a trucker jacket

At this level you can give one proper piece instead of several small ones. The list leans toward things he will wear every week, in colors that go with most wardrobes.

Watches

Timex Expedition Scout 40mm, brown. A field-style watch for everyday wear. A 40mm case is a middle size, neither small nor oversized.
Timex Easy Reader, black. A plain, classic watch; the black version suits a man who dresses mostly in dark colors.

Leather

Carhartt brown oil tan leather passcase wallet. Oil-tanned leather generally darkens and softens as it is used, so it looks better after a year than on day one.
Carhartt brown full grain leather belt. Full grain is the outer layer of the hide and generally the most durable kind of leather. Made for jeans and work trousers.

Layers and jackets

Tommy Hilfiger navy cotton quarter-zip sweater. Works over a collared shirt at the office or a tee on the weekend.
Columbia black Steens Mountain fleece. For hikes and yard work, or as a warm layer under a shell.
Tommy Hilfiger navy hooded packable puffer jacket. "Packable" means it compresses into a small bundle, which suits a man who travels or keeps a spare layer in the car.
Levi's mid blue trucker jacket. The classic denim jacket for spring and fall.
Wrangler light blue Rugged Wear denim jacket. A lighter wash; choose this one if he already owns a dark denim jacket, and pick only one of the two.

Shoes, hat and jeans

Cole Haan navy Grand Crosscourt II sneakers. A court-style sneaker in navy, which pairs with jeans and chinos alike.
Calvin Klein black cuff hat. A knit hat with a folded cuff, for anyone who refuses to wear a hood.
Calvin Klein dark blue slim high stretch jeans. A slim cut with stretch, for a man who finds rigid denim uncomfortable.

Getting the size right

The watches, wallet and hat need no size at all, which makes them the safe choices if you are guessing. For jackets, the size on the label of a jacket he wears regularly is the best reference. Jeans need both waist and inseam, so only buy them if you can check a pair he owns. Shoe sizes vary between brands; look inside his sneakers rather than relying on memory.