Review 12: The 3 Best Sock Options a boot enthusiast should try

by | February 18, 2021 | Buying Experiences, Reviews

Chris Clark Thicker Socks

Ask just about any boot enthusiast what their preferred sock brand is, and you get as many answers as you have people to poll. That said, three brands emerge in trend more than the others: CHUP, Smartwool, and Darn Tough.

A few months back, Grant, the Editor at The Arcuate, wrote a guest piece for Stridewise comparing three leading sock brands against his staple athletic sock and their performance in his boots. While well researched, tested, and written, the article hit a snag with readers as they missed the fact that Grant wasn’t comparing the socks against each other but rather their performance against his baseline athletic sock in his boots.

Grant decided to give me, a hardcore boot enthusiast, a platform to write the review readers thought they were getting at Stridewise. The timing for this was perfect, as CHUP releases its wool variants every fall, making for a more fair and balanced review when comparing them against Darn Tough and Smartwool, brands known for their wool socks. 

I’m on my feet all day and put these socks through the wringer. When I say I did my due diligence, take my word for it. I spent about 18 hours a day in these socks, 10 of which were spent on my feet. I work my ass off, trodding around in work boots for my entire shift, and I abuse the shit out of socks. Here’s what I learned from my field testing.

Review 12: The 3 Best Sock Options a boot enthusiast should try 1

CHUP Wool Edition:

CHUP is well known for high-end, high-quality cotton socks. What initially catches the eye of all who encounter CHUP socks are their elaborate patterns and colorways. What is unrealized about CHUP socks is just how well-made they are and their toebox’s unique construction.

The CHUP toebox is hand-linked. Hand-linking begins with the fabric being milled on a circular knitting machine, as all socks are. Once the tubular fabric is knitted, the two sides of the toe seam are linked by a single yarn of thread. This process produces a sock without that pain-in-the-ass toe seam.

One drawback to the CHUP, they can be a bastard to don. If you think the cotton versions are hard to get on, these suckers are straight-up almost impossible. That said, once you do have them on, they quickly conform to your foot. They are incredibly comfortable. The fit is ideal and fills up a boot very nicely, and don’t slip up or bunch at all.

Of the three socks I tested for this review, they are the thickest of the bunch. Their composition boasts an impressive 87% merino wool. Merino wool, if you don’t know, is a killer material. It’s thinner and softer than standard wool, which makes it comfortable right away, plus it self-regulates temperature. If you’re hot, it helps wick sweat away to cool you off and effectively traps body heat to keep you warm.

CHUP Wool Sock

Chup socks may be a little challenging to get on, but they’re made to match the contours of your foot. After a few minutes, they stretch out where they are snug and conform to the right fit. They don’t bunch up or sag, offering all-day comfort, no matter what footwear you choose to wear them with. I prefer to wear Chup socks with my White’s MP boots. Chup provides an experience like no other sock, and I pair them accordingly with some go the best boots available.

The only downside is the price. They clock in at $35 a pair. The only way you’re going to get them cheaper is eBay for $32 or using Okayama Denim loyalty rewards. Additionally, while CHUP does offer some socks with a lifetime warranty, these socks do not fall in this category. 

I will say, though, I have been wearing this specific pair of CHUP socks since July, at least once a week, and they show little to no signs of wear. I could easily see these socks lasting a few years before needing to be replaced. You should be able to get your money’s worth out of them. 

Who Should Buy CHUP Socks

  • Those looking for the highest quality a pair of socks has offer while still being aesthetically pleasing with new bold designs being offered every year.

Who Shouldn’t Buy CHUP Socks

  • Those who may not enjoy any sort of texture in their socks. I know this may sound weird, but Chup socks took me quite a while to get used to. You will indeed feel every stitch, seam, and variation of yarn inside a pair of Chup Socks, no matter what they’re made of.

CHUP Bottom Line:

Chup wool socks are a work of art. They’re bold and daring while still being functional. From a night out at the pub to hiking in the mountains, these socks will not let you down.


Darn Tough Men’s Micro Crew Midweight Hiking Sock:

The name is a fucking mouthful; don’t hold it against the sock or any of Darn Tough’s socks. All their names are literal descriptions of the garments—no points for creativity.

Compared to the CHUP wool socks and their cotton brothers, these socks are easy to don. There’s lots of stretch but do an outstanding job of staying put all day long. Killer warranty, comfy and cozy, the Midweight Hiker from Darn Tough is built for the trail, the hunt, or the log cabin in front of a roaring fire. These are working socks and should be used accordingly.

I prefer to wear my Darn Tough socks at work, where fashion is out the window, and comfort is the only thing on my mind. These socks perform at a level where the others can’t compete. I’ve worn many boots over the years. I still have one pair of 511 boots from my tour in Iraq in 2008 that are doing just fine. I prefer to wear Darn Tough socks with my Thorogood Moctoe work boots. I’m not afraid to fuck these boots up; the same goes for Darn Tough Socks!

Darn Tough Sock

The Darn Tough does a fantastic job of wicking away moisture compared to the other 2. My feet stay dry all day long. The CHUP wool socks do a pretty good job of moisture control, but the Darn Tough does it better. 

Price-wise, the Darn Tough is excellent at $23 a pair. They occasionally have sales, but they offer a 20% discount on all their products if you are a veteran like me. Not many of us are vets, but getting these socks for only $18.40 a pair is nice. Darn Tough also offers a lifetime warranty across the board to almost all of their socks, except some of their cotton socks you can pick up in 2 packs from TJ Maxx do not have this warranty. 

Who Should Buy Darn Tough Socks

  • If you’re looking for a performance sock that’s rough and “Darn Tough!” These socks will undoubtedly last a lifetime, and they have the warranty to back them up. 

Who Shouldn’t Buy Darn Tough Socks

  • This is actually quite difficult. These socks will eventually pay for themselves with their lifetime warranty. I would steer anyone away from buying a pair of Darn Tough socks if you cannot justify paying more for one pair of socks than you do on a multipack of sports socks.

Darn Tough Bottom Line:

In the long term, these socks are tough to beat. They’re sustainable and economical. Darn Tough surpass all my expectations while still remaining one of the best on the market today! That warranty, though!


Chup X Smartwool:

The CHUP X Smartwool collaboration feels like it misses the mark. Yes, the socks have all the aesthetics CHUP fans know and love. They are reasonably easy to put on, similar to putting on a pair of cotton CHUP socks. However, just because it looks like a CHUP doesn’t mean it performs like a CHUP. 

As a boot enthusiast, my first pair of “Heritage Style” boots were the Thursday Captains. They offer a classic look while being wallet-friendly. I prefer to wear my Chup x Smartwool socks with my Thursdays. They’re a fashion sock that provides all-day comfort but slightly misses the mark in what they were trying to achieve. 

My biggest issue with the CHUP x Smartwool collabs is that they fall non-stop. It can get a little aggravating. I’ve had little to no problem with either of the other two pairs of socks I tested falling. After wearing these socks for long days, I feel they stretch out to the point that they don’t fit anymore. They start to bunch up in my boots eventually, and I take my boots off to readjust them. 

Chup x Smartwool Sock

Another disappointing issue with these socks is that they don’t do an outstanding job of wicking moisture despite being made with merino wool, especially compared to the other two. These socks still do better than sports socks, but I’ve noticed my feet smell pretty bad after wearing them for an entire day. 

As far as price goes, $31 is their full-blown retail price, and I think that is steep considering the problems I encountered. A little deep Googling, and you can easily find them for much cheaper. My first four pairs of Smartwool x CHUP socks I scored for $10 a pair on backcountry.com. I’ve seen them for sale as low as $6. The moral of the story, don’t pay full whack on these socks, not if you can spend a few extra minutes searching the web for a better deal. 

Who Should Buy CHUP x Smartwool Socks

  • If you’re looking for a sock that stands out from the typical black or white while still being comfortable all day long. If the price-tag of CHUP socks seems a bit steep, these could be a good alternative.

Who Shouldn’t Buy CHUP x Smartwool Socks

  • If you’re picky like I am and want a sock that fits well all day long.

CHUP x Smartwool Bottom Line:

CHUP x Smartwool is a bargain if you’re willing to look for the best deal available and set aside that the particular pattern may not be the latest and greatest, but there is still “CHUP” in their name. Their designs are fantastic, but they fall short where other socks thrive.


Final thoughts:

Compared to my sports socks, all three brands are excellent if you’re going to be spending long periods on your feet. At the end of my 10-hour shift, my feet don’t hurt at all wearing any of these. For me, though, each of these socks had its pros and cons, making it an over-all tie. 

The Darn Tough products are more readily available for almost half the price of the CHUP. I like the CHUP designs better, though, and the CHUPS are more comfortable over-all. I’ll probably never buy another pair of Smartwool socks, to be honest. They’re just not for me, and I feel if you’re going to spend that kind of money, you’re better off going for the full CHUP offering.

If I had to come out for it one way or another, I’d say comfort-wise, CHUP wool fills out my boots better. They are more aesthetically pleasing and are a great boot sock for casual or style wear. However, at work, because of how well the Darn Tough wick away the moisture, I think the Darn Tough socks are best for work.  


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About the Author

Chris Clark

Chris Clark

My name is Chris. I'm a denimhead, bourbon connoisseur, motorcyclist, and a purveyor of clothing that's made to last and stands the test of time. I work as a machinist and a welder. I strive to push the limits of workwear to find what works best, lasts the longest, and survives the brutal environment of shop life.