At a drive-in in December 1979, Larry Stewart's private holiday giving began after he had been fired for the second Christmas week in a row. He noticed a carhop without much of a jacket, gave her a bill, and told her to keep the change. That small, observant gesture is where the Kansas City Secret Santa story starts. The Associated Press reports that Stewart went on to give anonymously each December for 26 years.

 

The Swedish julklapp, by contrast, began with a knock. It became common in bourgeois homes during the 19th century, and the older playful handoff could be a piece of wood or a carved doll tossed through the door, with a teasing rhyme attached. I like these two versions of the holiday exchange for opposite reasons. One is a neighborly surprise, the other a quiet act of noticing. Both make a present feel personal before you even know what is inside. For Secret Santa gifts for men, I would borrow the thoughtfulness and leave the theatrics to old julklapp lore.

 

The socks and beanies are the useful starting point here. Smartwool says it was founded in Steamboat Springs in 1994 and was the first outdoor company to make performance Merino wool ski socks. I would pick Barbour's Danforth beanie for a man who already reaches for a cuffed hat, or the Brooks Brothers rib-cuffed cashmere beanie if he likes a chunkier knit. The Polo Ralph Lauren three-pack and BOSS three-pack speak to a dress sock drawer; Mio Marino brings brighter patterns. Smartwool Larimer's full-foot cushioning and Nike's breathable mesh panels give two different everyday directions, while Falke Tiago stays a black dress-sock option. Before wrapping, I would look at whether his usual coat is charcoal, navy, or something louder, then match the knit or socks to colors already in rotation.

Swedish julklapp was once a small performance: a knock, a quick toss, and a teasing rhyme. I would keep that sense of surprise but avoid guessing at a man's exact grooming routine. A boxed set lets him choose what becomes part of the bathroom shelf, especially when it combines familiar categories rather than promising some dramatic transformation.

 

The Jack Black Beard Grooming Set is a straightforward pick if he has a beard; the wash, shave cream, oil, and comb mean he can choose how much of the kit to use. Jack Black Beard Oil is tidier if his beard care is already set, but I would skip it for a clean-shaven man. The Lab Series two-step set pairs a face wash with a treatment, while Clinique's four-piece set has a pouch and several clearly named steps. ATWATER Daily Skin Essentials keeps to a compact group of face-care pieces, and the Exoceuticals EXO MEN Travel Kit keeps the format compact for packing. Those are gifts for someone whose face-care habits you actually know, not a hint that he needs correcting.

 

For scent, the Caswell-Massey Heritage Cologne Discovery Set or Escentric Molecules five-piece sampler leaves the choice with him. The small sprays let him explore a few directions. I would check whether he likes beard care, fragrance, or plain face wash before choosing. What I would skip: a single scent when I do not know his preferences, or beard oil when he has never mentioned wanting it. A gift should feel like a note, not an assignment.

Keep a desk gift compact enough to live beside the laptop rather than take over the room. In Sweden, Christmas Eve remains the main day of celebration, and I like the idea of giving him something that earns its place in the quiet hours around a holiday, then keeps working afterward. The Bellroy Lite Tech Kit is for cables and small electronics; its mesh pockets, elastic loops, and power-bank slot give each item a home. Smythson's Pen Pot with Divider splits pens from smaller accessories, while the Yamazaki Desk Organizer Caddy gives him an open wood-and-steel landing spot for notes and daily bits. I would choose the closed pouch if he travels with cables, the open caddy if he likes seeing everything at a glance.

 

Coffee gear is a little more personal, so I would look at his morning habits before choosing. The Fellow Atmos canister has a vacuum pump and silicone seal; Corkcicle's pour-over set pairs a dripper with a ceramic mug; the Palmpress is a compact brewer for one cup. CILIO's porcelain cone is a simple pick if he already uses #4 filters, and its Latteforte frother comes with a stand for storage. Each option has a different footprint, so a quick look at the counter and the mug he reaches for tells me more than a guess about his ideal coffee setup.

 

What I would skip: another brewing tool if he drinks tea or already has a routine he likes. A gift that fits beside his existing ritual has a better chance of being used than one that asks him to reorganize the kitchen.

Games work best when they invite him into the room instead of requiring a manual. Larry Stewart's giving continued each December, a small ritual repeated over years; I like gifts that can become part of a ritual too, whether that means a quick game after dinner or an instant photo before friends head out. The LEGO Game Boy is a 421-piece build for an adult who likes a weekend project; I would make sure he enjoys building before choosing it. The Polaroid Go Generation 3 Travel Set includes an eight-photo film pack and camera bag, while the Hi·Print 4x6 starter set comes with an 80-sheet cartridge for postcard-size prints. One turns a gathering into a photo moment; the other needs a spot on his desk.

 

For table play, the Bey-Berk Domino Set has a leather case and 55 dominoes. PRINTWORKS Yatzy keeps dice, pencils, and score sheets together; Matr Boomie's 3D Tic Tac Toe gives the familiar game a carved wooden shape, while its 5 Dice Box Set is a smaller tactile alternative. Foster & Rye's poker chips suit a man who hosts cards, if he already has people to play with.

 

What I would skip: a camera kit if he does not enjoy taking or printing photos, or a game that depends on a full group when he prefers a quiet evening. I would check the exact film format and who will play before wrapping, so the surprise is the activity, not an extra errand.

An edible kit should match the way he actually cooks, while bar tools are best for someone who enjoys making a drink for guests. The Swedish julklapp tradition included humorous, teasing gift rhymes, and I would put that spirit into the card rather than choose an object just for the joke. The Spice House Chicago Heritage set gives a spice drawer a clear starting point with eight seasonings; Fly by Jing's four-jar mini sampler makes chili crisp and sauce the point of the gift. Alchemy Spice Co.'s four blends are framed for grilling, while Teaspressa's Raspberry Mixology Cubes bring a sweeter cocktail addition. I would check what kind of heat or flavor he already reaches for and whether anyone at home avoids an ingredient.

 

Caraway's seven-piece bar set keeps its tools on a storage base; Jonathan Adler's Como set displays brass-tone tools on a marbleized stand. Vacu Vin has seven pieces for someone ready to mix, and Printworks' large wine tool set stores six tools in a book-style case. The format matters: I would think about whether he hosts, makes a drink occasionally, or prefers just opening a bottle. If he already owns the core tools, a spice collection or small sauce sampler feels more specific.

 

What I would skip: a full bar kit for a man who never entertains, or an edible set before checking dietary preferences. I would choose one small improvement to a ritual he already has, not a new hobby to maintain.

I would decide in this order: start with the thing he already uses, then choose one detail that makes it feel like his. If he is always in a knit cap, the Barbour beanie is easy to picture; if he makes coffee each morning, the pour-over set has a built-in occasion; if he hosts, a compact game or bar tool can turn an ordinary evening into a small tradition. For skin care and scent, I would rely on what he has said he likes, not my own guess.

 

Secret Santa started with surprise in both the old Swedish julklapp and Larry Stewart's annual gift-giving, but thoughtful is better than mysterious. I would wrap something useful, write one line that explains why I picked it, and let the little reveal do the rest.

 

For more gift ideas: Secret Santa Gift Ideas for Coworkers, Gifts for Male Coworkers, Going Away Gifts for Coworkers and Birthday Gifts for Coworkers.