I’ve always considered socks to be deeply important. When I was a kid, my favorite shopping trip with my mother was to the perfectly named Sock Exchange, which saw socks and underwear climb probably 30 feet high in a massive footprint of a space. Eh, maybe it was 20 feet high; I was a lot shorter then. But you often had to call over an employee to use one of those grabbing sticks to get what you wanted. If I didn’t tag along, she’d consistently get the wrong socks, and I’d get upset. So I went. And often came home with, say, six-packs of Thorlos, amped to try slip on.

If you can’t tell, I think a lot about socks. Proper thickness depending on your shoes of the day, for sure. General comfort, of course. But also things like whether or not they slide down constantly, or how the toe is stitched—if you get those socks where it’s not a hyper-clean stitch, they end up rubbing on your toes or the balls of your feet all day, and you’re taking your shoes off to adjust, and then it starts again…you know this horror story.

So long ago, I decided I just wouldn’t deal with that, under any circumstances. No cheap or faulty socks, no sir. No socks you have to make excuses for. Socks that fit your feet, and fit your shoes, and feel great. This is an actual lifestyle I’ve developed. And I love it.

Below, I’ve gotten into pretty great detail about all the socks I wear with regularity. I have others, but they’ve been pushed aside by something better. I also have doubles in my rotation, or backups waiting to be unleashed, of many of these.

Most of these socks are not cheap. I’m pretty sure the most affordable ones are $15 a pair, and they range up to about $30—yes, for one pair of socks. But I think like so many things in the quality footwear world, the investment is incredibly worth it, especially if you find the right socks, for you, specifically. And they last. All of these do—they’ve pretty much all proven to me that with proper rotation, they can stay in top shape for 3-5 years, at least. Hopefully this guide helps get you to that same place.

A caveat: while I’ve basically found my golden ideals in terms of socks for boots and other casual shoes, my next phase is finding dress socks I love every bit as much as those. I know some reportedly great brands; I just haven’t gotten to them yet. That will change—as will this story, as it happens.

So here they are: my socks. listed in order of amount of wear they get. Enjoy, and leave a comment or DM me at @stitchdown with any questions. In case you can’t tell, I like to talk about socks.


Socks-Chup x SmartwoolChup x Smartwool Merino Wool Socks

I wear these socks more than any others in my embarrassingly large arsenal—even in the summer. That’s largely because they use Smartwool’s merino wool, which does a tremendous job of wicking that sweat away, and also not becoming smelly and disgusting throughout the course of the day. Japanese brand Chup is perhaps most known in the Instagram cuff-check game, because of its remarkably appealing patterns. These are true to everything great I feel about my other Chups below, in terms of comfort and everything just being finished really, really nicely. They’re an investment, but they seem like they’re going to last forever, and are honestly unmatched style-wise if this is the look you’re going for.

Worn with: Everything from my range of Alden boots (they’re pretty much on 80% of the time when I wear those now) to my Tricker’s Bourtons and Paraboots (which are not, in fact, boots). Sometimes my Iron Rangers, although they tend to slip down a bit in those for some reason.

Best Socks-PendeltonPendleton National Park Merino Wool Jacquard Crew Socks

More Merino! I first found the other Pendleton socks below browsing their website for something else, fell in love, then graduated to these. These also aren’t the cheapest socks—about $25 a pair—but man have they been worth it. After dozens if not a hundred wears, they honestly feel and look as good as new (important when you’re photographing worn socks for a major socks story in a shoe publication). These are the first socks I grab when the laundry is done—I know you have those socks too.

Worn with: Again, a ton of different shoes and boots. Not my true dress shoes, and not my Red Wings or Thorogoods. But pretty much everything else: Alden boots, Danner Lights, plenty more.

Socks Chup x J. CrewChup x J. Crew Socks

I got a couple pairs of these maybe three or four years ago (can’t you tell??), and they’re not available anymore, so I don’t have a ton of hard info on them. They may also have been done with Smartwool and be Merino but I can’t say for sure. What I can say is that they’re the softer kind of Chup socks—I also have some semi-retired ones that are made with a thicker thread, which makes you able to kinda feel the knitting at first when you put them on, which I don’t love quite as much.

Worn with: Alden boots, Paraboots, Tricker’s Bourtons. Almost never with Red Wing boots. For whatever reason they do that sliding and bunching in those—and only those!—a bit more than the Smartwool Chups.


Socks—WigwamWigwam Bear Ears Socks

No Merino here—these are nylon/polyester/spandex/etc. But damn if they’re not comfortable and really breathable. These are also thinner than all of the above socks—especially on everywhere except the bottom of the foot and behind the heel, where they’re nicely padded without being thick-thick. They’re the closest thing to high-performance athletic socks in my lineup, but I like how they have that thicker cushion and the funky designs.

Worn with: 100% of the time with my Viberg Scout boots, which fit perfectly with these, and a little snugger with everything else above. Definitely my Danner Lights. Sometimes with the Paraboots, sometimes with the Tricker’s. If I’m at the end of a wash cycle, I’ll do them with the Alden boots too.

Socks DarnTough x JCrewDarn Tough x J. Crew Socks

I’m a huge proponent and recommender of Darn Tough socks (the Vermont company’s lifetime guarantee is a big part of it), but for some reason I enjoy these particular ones they did with J. Crew years back over their stock stuff. They’re a little taller than other Darn Toughs (here’s a pretty close version that’s a touch shorter), have a bit more padding all around, and have the stripes to give them a little pop whereas a lot of Darn Toughs are more straighforward. That lifetime guarantee—they’ll send you a new pair for any sock that gets even the smallest hole in it, no questions asked—seems to just force Darn Tough to make socks that will never get holes in them. Despite that, and the guarantee, for some reason I have three more pairs in the backup box. Oh, sock addiction!

Worn with: Red Wing Iron Rangers, a ton. Also my Thorogood Moc Toes. Sometimes with the Red Wing Moc Toes.

Socks—PendletonPendleton National Park Crew Socks

These are the ones that got me started on Pendleton, which is not all that widely known as a sock-maker. Before switching to the Chup x Smartwools, for a while these were my 100% of the time Alden boot socks, especially with my two pairs of plain toe Alden Roys (for some reason I like a slightly thicker with my Indys). And I found as many other shoes as possible to wear them with. But then, those very very wonderful Merino wool Pendletons came into my life, and jumped the line. Over time they don’t stay quite as soft as a lot of the above socks, but not to an uncomfortable point. Also they’ve gotten a little loose around the ankle and can sometimes sag down, but they’re admittedly a little old at this point. And hey, I guess I cuff check is really a sock check if we’re being honest with ourselves.

Also these amongst the best-priced socks at retail on this list—$12.50 a pair.

Worn with: Paraboots, Tricker’s Bourtons, Viberg Scouts when the Merino Pendletons are in the wash, Alden boots—just…less than they used to be.


Socks—SmartwoolSmartwool Hiking Socks

This seems to be another out-of-production sock (the closest I could find were these Larimers), because everyone who makes socks is apparently crazy. Luckily for me it’s a limited-use model. Largely because these are THICK and hearty all around—they’re the Campbell’s Chunky Soup of socks. Reggie White and his mother would love these socks. And Donovan McNabb and his mother, and…I don’t know who’s making those now, I watch a lot less NFL than I used to.

Worn with: Red Wing Moc Toes (which have some extra room at my Iron Ranger size), my big-dog Zamberlan winter boots, and sometimes the Thorogoods but they’re honestly a little too much in there most days.

Socks—Darn ToughSome Other Darn Toughs

Again, I’m not 100% sure which model these are (and they may not make these exact socks today), but they’re from Vermont sockmaster Darn Tough’s lightweight hiking range. They’re excellent, and well-padded, and 100% bulletproof, but are cut a little lower than I generally like.

Worn with: Danner Lights, Viberg Scouts, some other boots on spot duty.

Socks—Happy SocksHappy Socks—Various Crew Socks That Are Happy

About a decade ago, someone in Sweden said “we are a happier people than you, and also I’m going to take over the sock game, via happiness”. And it worked. Their designs are irresistible if rarely formal (these argyles come close-ish I guess), and the socks are just pretty damn good socks. I used to wear these a lot with sneakers; now I don’t really wear sneakers at all, and they’re strictly on dress-shoe duty. But they hold up great. And are rarely sad.

Worn with: Allen Edmonds Strands, Alden Longwings, the occasional pair of Jordans to run get 1% milk for my cereal.

Socks Boardroom SocksA Range of Boardroom Socks

These are newest to my sock drawer(s). Nathan from family-owned, all-USA-made Boardroom sent me a package, just to wear and get some feedback (full disclosure: he reached out to me, sent them no strings attached, and did not know I was including them in this article).

My feedback: they’re honestly pretty great. However happy my dress socks felt they were previously, I needed a dose of formality with my dress shoes, and these provide that in spades. Their big differentiator is over-the-calf socks, which you can see on the far right here (my other pair that I’ve worn was in the wash). They do what they say: hike up over your calf, like soccer socks, with the express goal of not falling down throughout the course of the day. And guess what: they most certainly do not. There’s also something oddly comforting about having a snug, thin sheath over your legs all day. It’s hard to know what you want when you don’t know you want it. Now I know.

These are basically tied for most affordable—they start around $12 a pair.

Worn with: Alden longwings


Another sock company making big loud moves—you’re probably going to see them on Instagram or Google in…ok by now you’ve definitely seen them. But for one more minute, focus on this story please!

I got these for Christmas. In my stocking. I have to say I do love pulling socks out of much larger socks. The smaller socks (these) are good. Definitely solidly built, and I like the design although I don’t really know what it is. The one thing is, because of how that design is knit (I think?), they’re pretty tight and sometimes tough to get on and off. But, you hopefully don’t do that dozens of times a day, and it makes them nice and snug and not prone to slip down. My advice to Bombas: you’ve made a really nice sock. Now get some cooler designs, and some thematic consistency to them. It’ll get you places.

Worn with: Danner Lights, Alden boots and Tricker’s Bourtons, in a pinch

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