How do you get a guy who has everything? A common saying that is pretty overdone (as are gift guides). The answer is you get him the things he’s always wanted but doesn’t ever get around to buying. Maybe that’s why there are tons of pants and shoes on here — no one ever wants to spend hard-earned cash on those but they’re a necessity. Something I’d be stoked to get as a gift.
What it doesn’t include is blazers (for the most part), suits, technical gear — best left to the tailor. There are just too many variables. You’re giving them a job, not a gift.
I have arranged it into sections where I can and imagined I was a girlfriend or mother shopping. As such: send this to your wife, girlfriend, mother, father, dog — whatever. I’ve started to tell folks the Outpost page has 1,000 subscribers so we really gotta get it there lol.
A disclaimer: yes, if you click on some of these and purchase, Outpost will receive a small commission. However, I use the “gravy on top method”™ — Ryan.
Regardless of percentage or fee, I gather products on the website I genuinely believe in — and sure, if ShopMy ends up kicking me a little sumthin’ then so be it. Someone has to pay for the lap dances for the big man (Wedding Crashers reference). All money goes back into Outpost: content, writers, events, and yes, lap dances.
Giver — Giver Gloves
These gloves rock — from chopping wood to skiing slopes, they do it all.
Smythson — Notebook
Treat someone you love to a planner — both chic and a subtle nod to get their life together.
Le Labo — Cologne
This is what I wear.
Hula — Sunglasses
These are the best sunglasses I have ever worn — cheap, durable, and stylish. I have them in multiple colors and restock when they’re lost annually.
Handschue Gentlemen’s Gloves — Gloves
You’ve seen these bad boys before if you’ve followed Outpost for some time.
Persol — Sunglasses
In college I had about 5 or 6 pairs of these stolen. I think I know by who. I also think there’s a chance he may read this.
Manscaped — Grooming Tool
Another subtle nod to clean it up.
Vallon — Glasses
I’ve ordered these and returned them, and then every winter I want to give it another go. Maybe you’ll have better luck.
Sid Mashburn — Canvas/Leather Bag
If you can’t swing the handmade Argentinian bag we’ve spoken about in the past, go with this.
Leatherology — Laptop Bag
I love this item — walking around the streets of New York with a MacBook is asking for trouble. Weirdly, wrapping it in leather makes it more discreet and reasonable.
Alex Mill — Tote
Weekend bang-around bag.
MacKenzie — Golf Bag
Every guy at the club has a Stitch bag at this point — time to up the game. No one will have this.
Octobre — Pant
I want to wear more slacks to the office in 2026. You should too — start here.
Sid Mashburn — Pant
I get asked about these pants once a month — here they are.
Rivay — Pant
Newcomer to the game — Rivay is gonna blow up.
Imperfect — Pant
Another pair of pants I get asked about constantly.
Amundsen — Shorts
These were gifted to me last summer and I lived in them — they get better with age.
Alex Crane — Striped Pants
Hard to think about summer linen pants right now, but get ahead of the game — throw these under the tree.
Belgian Shoes — Belgians
Most guys know them by now, but if you don’t — you’re welcome. While expensive, they are the comfiest shoe in the world.
Sabah — Sabahs
Sabah jumped into the desert boot game and these are incredible.
Crockett & Jones — Derbies
A little higher-end — you can dress these up or down.
Blundstone — Boots
From Australia with love.
Le Chameau — Welly Boots
Every man should own a pair of wellies. I like this brand to Hunter — a bit more masculine and farm-like.
Sid Mashburn — 7 Day Kit Socks
Get this for a man annually — give him the gift of never worrying about socks again. Something that haunts me every morning.
Yeti — Cooler
Land Rover Defender — Defender
Lol — get your boyfriend a Defender.
Sabah — Backgammon Travel Kit
Beretta — 12 Gauge Shotgun
I like to think that a girlfriend visiting someone’s parents for the first time gets their boyfriend a fkn gun — wrapped under the tree and all. Mom thinks you’re strange, Dad thinks you’re awesome, boyfriend starts shopping for rings that night.
Timex Watch Co. — Watch
Something about buying someone you love a really simple watch is charming. Maybe they already have a nice watch — this is number two. Breaks it up a bit. Every time they wear it they think of you — that’d be nice.
Davidoff — Cigars
Box of cigars costs so damn much. If you do get this, take it out of the box, wrap it with a bow, then put it back in the box.
La Parapluie — Umbrella
In talks to do an Outpost edition down the line — stay tuned fam.
Blue Bottle — Coffee Kit
Breville — Espresso Maker
We will do a deeper dive into coffee in the new year — for now, start here.
Shun Japanese — Knife
I’m sure there are better Japanese knives out there, but this is what I use. It’s a great starter.
Peugeot — Pepper Mill
This is the Rolls-Royce of pepper mills. If you see this on a kitchen counter or the smaller version at restaurants, that person knows what’s good. Pro tip: this is the perfect size for a kitchen — don’t go any bigger. If you must compensate, do it elsewhere.
Audio-Technica — Turntable
Someone you know wants to go down the rabbit hole of vinyl — start here. Add a Christmas record.
Staub — Dutch Oven
Kitchen staple.
Hario Japan — Tea Kettle
Another kitchen staple — this model is hard to find. I use it every day.
Permanent Collection — Wooden Spoons
Don’t use plastic.
Vitruvi — Diffuser
Malin + Goetz — Candle
As seen in the scent guide.
Sonic Editions — Print
Get your boyfriend a rock star print or a cheeky girl in a proper matte frame… more ring shopping.
Caffè Panna - Ice Cream Scooper
Available in store only
J.Crew — Oxford Shirt
I’ve explored Oxfords at all price points — I come back to J.Crew.
J. Press — Shaggy Dog Sweater
I once put this in the dryer. It still keeps me up at night… need one in every color.
Rowing Blazers — Rugby Shirt
A classic — this is something you wouldn’t buy for yourself but would be damn happy to wear on occasion.
Amundsen Sports — Sweater
I love this sweater more than most things in my closet. I wear it everywhere — it gets dirtier by the day and I love it.
Buck Mason — White Tee
Buy three of these for your son or boyfriend and thank me in the summer when he pairs these with jeans and a tan.
Holderness & Bourne — Golf Shirt
Someone asked me where to get golf shirts a while back — in truth, I like to wear cotton polos from Sid on the links, but that’s an ambitious look. This is your right-down-the-middle answer.
AYR — Rugby Shirt
Another classic rugby.
Inis — Cable Sweater
Handmade on a Scottish island — someone buy this for me.
Campbell’s — Mens Blazer Heritage Piece
Another gem from Scotland.
This took me all day I hope you enjoy - Ryan
