The Best Boot Socks You Can Buy (CHUP vs Smartwool vs Darn Tough)

In the community of heritage wear, workwear, rugged wear, whichever name you would like to call it, socks appear almost as critical a garment as the boots into which they slide. So what are the best boot socks?

I tested my socks based on fit, function, and feel for this post to establish which, if any, really make an impactful difference in the boot-wearing experience.

Yes, channeling my best Daniel Day-Lewis voice, there will be CHUPs. As well as Darn Tough and Smartwool.

Our Top Picks for Men’s Boot Socks

• Best Value: Hylete Mid Calf Athletic Sock ($14/pair)
• Best Looking: CHUP Socks ($40/pair)
• Most Comfortable: Darn Tough Boot Socks ($30/pair)
• Best Fitting: Smartwool Crew Socks ($22/pair)

How I Choose the Best Socks

Yes, channeling my best Daniel Day-Lewis voice, there will be CHUPs. As well as Darn Tough and Smartwool.  

To clarify the terms I’ll be using: 

• Feel: I mean both how I think the socks feel on my body and how they feel in the boot.
• Function: I’ll discuss any “tech” that should make a difference. 
• Aesthetics: I’ll mention aesthetics, but I think that’s mostly subjective. 
• Value: This will also be part of the discussion, considering the price, unique features, quality, and overall impact on comfort and feel while wearing boots. 

In the end, I’ll give a verdict on each pair and also compare them against my standard choice, Hylete Mid Calf Athletic support socks. 

For the sake of control, each pair of socks got the following control variables imposed upon it. 

1. They all got two wears before complete evaluation: one pre-wash and one post-wash. 
2. I used the same boots throughout the assessment: US size 9.5 Red Wing Iron Rangers (8085). I went about everyday life activities, including work, playing with my children, and doing outdoor chores. 

I went to the source: Facebook boot groups, denimhead circles, and, of course, Reddit. (Lord, did I hit Reddit). A quick poll surfaced the clear favorites: CHUP, Smartwool, and Darn Tough. A handful of other brands popped up too — names I’d never even come across before.

Why I Love the Hylete Mid Calf Athletic Sock

My baseline, as mentioned, is the Hylete Mid Calf Athletic sock. Why?

Hylete Mid Calf Athletic Sock Highlights

At $14 a pair, it’s on the low end of what I tested for this piece, but still more expensive than the average mass-produced athletic sock.

Looks-wise, there’s nothing flashy — just grey, black, or olive with minimal branding. Pretty plain. But at the end of the day, they’re athletic socks.

So why do they matter? Because they’ve been my baseline for quality and comfort ever since I bought my first real boots.

Originally, I wore them as base layers for hockey. They were thin enough to disappear in my skates, cushioned enough to protect against lace bite, and supportive enough through the arch. I’m flat-footed, and paired with Superfeet pro-carbon insoles, they actually relieved arch pain.

On top of that, they wick moisture, keep their shape, and — this is key — don’t slip around, even during intense activity. They’re also right- and left-footed, with contoured toe boxes that help them stay put and hold their form through heavy use.

All that for about ten bucks a sock: that’s why I use them as the control in this experiment.

What I liked

• Much better quality than your average Costco Athletic Bag-o-Socks for something actually worthy of the “performance” accolade
• Moisture wicking
• Kept their shape
• Don’t slip during intense activity (I wear them while playing hockey)

Downsides, not dealbreakers

• These are simple socks
• Only grey and black avaliable

As mentioned above, you get a hell of a lot of socks for the price point, and even if they don’t make your daily boot rotation, they are exceptionally nice in the gym, even if they don’t win any beauty pageants.

CHUP Socks ($39)

Man, these socks are stunning. They outdo the ugly grey sacks from Hylete in that regard. However, pretty doesn’t mean awesome. Let’s discuss these a little. 

CHUP Socks Highlights

Their composition is the only non-wool option in this article: 43% Cotton / 43% Acrylic / 13% Nylon / 1% Polyurethane.

With so much cotton in the mix, I knew these would be comfortable right out of the gate — and they didn’t disappoint. The cotton breathes well, keeps a steady warmth, and the intricate patterns carry a kind of nostalgic charm.

Some designs lean geometric, borrowing from Fair Isle knits, like the Fiddle model. Others, like the Sedona, draw from Native American motifs, echoing traditional tapestry weaving.

The overall shape isn’t groundbreaking, but the toe box is where things get interesting.

CHUP toe boxes are hand-linked. Here’s what that means: the fabric is first knitted on a circular machine like any other sock. Then, instead of a bulky seam, the two sides of the toe are joined by a single thread.

Translation: no annoying seam digging into the top of your toes. It’s a painstaking process that slows production, but the result is unmatched in comfort and quality.

My one real complaint is that they don’t stay put. By the end of the day, the tops tended to bunch, and inside the boot, some fabric stretched and collected in spots. That said, the fit improved noticeably after a wash and dry. On the second wear, all four pairs shifted far less and showed only minimal bunching by day’s end.

Fit issues aside — and price, which is steep for me — CHUPs are undeniably cozy. They fill out the boot volume well without creating dead space, heel slip, or pressure points (again, credit to that hand-linked toe). They look fantastic, are beautifully constructed, and carry that sense of meticulous craftsmanship we associate with Japanese garments, which probably explains the price tag.

When it comes to staying in place, I still prefer my Hyletes. But in almost every other respect, CHUPs deliver better value.

What I liked

• If cost is little or no object, quality is king, and aesthetics are queen, this is the sock for you
• Visually stunning, comfy as a lounger, functional, and built to last

Downsides, not dealbreakers

• These are fairly expensive socks
• I had some fit issues, meaning they have some dead space in their boots, which can’t be corrected, and don’t want to deal with the repercussions of socks bunching in their boots
• These don’t stretch a ton, and they follow the shape of the foot closely. They need to be pulled over the foot, then over the ankle. It takes a few more seconds to put them on than other socks

These socks are exceptionally beautiful, and the hand-linked toe is something to be experienced. Fit issues notwithstanding, these were a fairly incredible experience and opinion-shifting on what socks can be.

Smartwool Crew Socks ($22)

If CHUP socks set the bar for aesthetics, the Smartwool crew socks win for tacky-as-hell. But I kind of love that.

Smartwool Socks Highlights

The socks are made from a blend of 53% Merino wool, 43% nylon, 3% elastane, and 1% polyester. Merino wool is a natural fiber known for its comfort and performance. It is thinner and softer than traditional wool and helps regulate temperature.

When you’re warm, it wicks moisture away to cool you down, and when you’re cold, the natural crimps in the fibers trap warm air from your body to keep you insulated. Because Merino wool helps keep feet dry and sweat-free, it also helps fight the bacteria that cause odor.

The Everyday collection offers thin, lifestyle socks with bold, eye-catching prints. They feature “shred-shield” technology, which is designed to prevent wear and tear at the toes by reinforcing the toe box while keeping the rest of the sock incredibly thin, like a second skin. Additionally, the socks have a “Virtually Seamless” toe for enhanced comfort and a supportive arch brace.

These socks are highly functional, with a seamless toe, arch support, and a second-skin fit. Having previously disliked itchy wool socks, I was surprised by how comfortable these felt and how well they regulated temperature without making my feet sweaty.

I also appreciate the low profile. When skating or running, I often prefer to go sockless to ensure a direct transfer of power to my shoe or boot, but this can lead to foot odor. These socks provide the same low-profile feel without the negative side effects.

However, the low profile is also the main drawback. The thinness of the socks made my boots feel a bit sloppy with some dead space in the heel. While lacing the boots tighter helped, it adds extra stress to the eyelets and speed hooks. Despite this, the features and comfort make them a great value at $22. They would be the perfect socks if they had a bit more volume.

What I liked:

• I liked the premium quality features in socks at a mid-price point
• If you aren’t into some of the wild patterns, Smartwool offers more conservative looks.
• The best-fitting socks I tried

Downsides, not dealbreakers

• Mine were super low volume, so if you have some room in your boots, these aren’t your socks.
• While reasonable in the category, $22, understandably, may exceed some budgets.

These funky looking socks are comfortable and durable as hell, for a low-profile boot or shoe, these socks work well and look cool in the process.

Darn Tough Boot Socks ($30)

Darn Tough is darn boring in the aesthetics department. That doesn’t mean much, though. Ok, there’s not a lot to write home about in that regard. So what? 

Darn Tough Socks Highlights

The Darn Tough are built for boots. These socks are rocking a 68% Merino Wool 30% Nylon 2% Lycra® Spandex composition and are easily the softest wool sock I have ever worn. This sock is midweight, which is kind of what I was hoping for in a Smartwool CHUP hybrid, so I got what I wanted in that regard. It is a full cushion high-density garment as well. 

As far as function goes, it checks all the same boxes as the Smartwool socks: temp regulating, moisture-wicking, comfortable, and durable. Hell, Darn Tough even puts a lifetime guarantee on their socks. (Like, for LIFE.) That’s insane. I was impressed with the fit as well. I keep coming back to a critical necessity for me, and that is no slipping and no bunching. The Nomads met that need spectacularly.

For me, the downfall of these is that the volume, or “loft” of the sock was so high that it made my boot uncomfortable to wear. This issue did not improve with washing and drying, and by midday on day two, I was changing socks. In my opinion, the Iron Ranger is a forgiving boot for the category, and I didn’t expect this issue.

Alas, it was problematic, and for me, on this vital issue was a deal-breaker. I will happily wear these around the house or in a more spacious boot. Remember, this depends on the boot you’re wearing: while Smartwool is best for slimmer-fitting boots, Darn Tough is better for roomier ones.

While on the drab side, and I didn’t quite have the right mix of products or boots in this part of my experiment, I liked the product composition and reassurance that, in the event of failure, Darn Tough would stand by their products. However, for near $30, I might be finding ways to make my socks fail every twelve months or so. (Kidding. Or am I?)

What I liked:

• Killer warranty, comfy and cozy, the Nomad 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.
• Blustery weather or tough trail, these are your socks.

Downsides, not dealbreakers

• Pushing the $30 envelope, these aren’t exactly budget-friendly.
• Additionally, if you are the casual wearer and not one to hit the trail or one to put their feet through some abuse, these might not be your model from Darn Tough. 

If aesthetics don’t matter and you don’t mind the price tag, these are a great option for those who plan on abusing their socks. Otherwise, it feels like you’re pre-paying for a possible replacement pair you may never need.

The Bottom Line

All three premium sock options in this article brought something great and unique to the table. For me, it is these unique features that help justify the cost of the garments. 

CHUP pushes that line for me the hardest; at $35, I wanted a better fit, one that didn’t slip and bunch. However, the hand-linked seam and old-school manufacturing brought the sock’s overall quality into light, and you can’t fault them for outstanding quality. Ultimately, I liked these socks more than my Hyletes in terms of quality and aesthetics, but I wanted a better overall fit. I want another crack at the brand if I can get my hands on the Smartwool collaboration. I think this would address my biggest complaints.

Smartwool was great for fit and function, but it felt a little sloppy walking around once my feet were inside my boots. I want there to be less play inside the boot; however, it wasn’t a deal-breaker for me. Given the comparable price point, these socks outperformed my Hylete socks. Out of everything I evaluated, I think this is a stellar option. I still want the CHUP x Smartwool hybrid that they actually launched a while back, but it’s currently sold out.

Darn Tough fell shortest on delivery for what I wanted, given the price point. Again, I just might have had the wrong socks for the wrong boots. While that might be the case, I could get what I want out of Smartwool for less money and still get a product with an excellent performance guarantee. Simply put, I didn’t get anything more out of Darn Tough vs. the Hylete socks.

One might argue this evaluation is flawed, in that while each product I compared was, in fact, a premium pair of socks, they weren’t all that comparable. True, but my goal wasn’t to say which product was better than the other; it was to compare them against my baseline and determine if they equaled or enhanced the boot-wearing experience.

I came into this project thinking socks didn’t much matter and that paying anything more than $15 for a pair of socks made you a bit of a label chaser. At 35 dollars a pair, I am still struggling to make the value argument for CHUPs to my wife, but if I got a pair or two for Christmas, I wouldn’t kick them out of bed for eating crackers. For my money, though, my favorite socks I reviewed were the Smartwool.

More Best Men’s Boot Socks

Since writing this, we’ve received a few questions about special-purpose socks like work boot socks, hiking socks, and even military socks. These weren’t in the scope of the original piece, but I’ve done the research and answered a few of the popular questions here.

The Best Dress Boot Socks

I want a dress sock that doesn’t feel like compression socks, my varicose veins aren’t pop’n yet.

Dress boots are often snugger than casual boots, so we’re looking for a thinner sock as well. Arch support isn’t as important because when I wear dress boots, I don’t walk very much. Lastly, I want solid colors like black and gre,y and minimum branding.

Darn Tough hits all of these requirements; they make a great selection of dress socks. While Hylete makes great athletic and casual socks, they aren’t classy enough for dress boots.

[SHOP THE DARN TOUGH DRESS SOCKS HERE]

The Best Work Boot Socks

The best work boot sock is the Fox River Steel Toe Heavyweight Crew sock, developed specifically for steel-toe boots.

They’re under 20 bucks for a pack of 2, come in three sizes, provide arch support with their cushioned sole, and extra cushioning around the back of the heel and over the toe for steel-toe boot protection. The reinforced toe and heel add durability and a longer sock life.

[SHOP THE FOX RIVER STEEL TOE HEAVYWEIGHT CREW SOCKS HERE]

The Best Boot Socks for Winter

If you want a great winter sock, look for cold-weather thermal socks like Smartwool’s Merino Wool is great for winter because it has a high thermal value without being a super thick sock.

Smartwool makes a few great socks for cold fee,t including their Work Extra Cushion Tall Crew Socks and their Hike Classic Edition Extra Cushion Crew Socks.

[SHOP SMARTWOOL’S WINTER SOCKS HERE]

Other Types of Boot Socks

Still haven’t found the boot sock for your needs? Here are a few other types of boot socks.

For a cowboy boot, go for an over-the-calf sock. The taller the better but not too tall. Justin Boot Company makes an over-the-calf sock that has a reinforced heel specifically for a cowboy boot.

Military boots work great with Hyete socks. Some guys will recommend Darn Tough, but at that price point, you don’t get objectively better men’s boot socks. 

Hiking socks are similar to military socks; they used to be cotton, which is not great if they get wet. A cotton sock allows your feet to get cold. It’s much better to get a merino wool sock. They won’t itch or smell and keep your feet warm even when wet. A synthetic fiber like polyester will achieve the same, but they aren’t as durable. A Darn Tough Sock would also work well.

You also want a reinforced heel for longevity.

Best Boot Sock FAQs

Can I wear a hiking sock as a work sock?

Yes you can, they are made very similarly with reinforced heels. A crew work sock can also be used for hiking.

What are the best work socks?

Any sock that is durable, fits well, and is affordable. We like the Fox Steel Toe mid calf boot sock.

What are the best warm socks?

Any thermal sock will do, we recommend a cushioned sock. Anything merino wool socks or synthetic fiber socks.

Is a wool boot sock itchy?

Not if you buy a sock made of merino wool.

Should I wear a thick sock with my work boots?

This depends on the climate where you work and the fit of your boots. A work sock is typically thicker than a regular sock.

How to keep ankle socks dry in work boots?

Keep your work boots dry by buying wicking socks. Regular socks are often cotton, which absorbs moisture. You want to purchase either synthetic materials like polyester and spandex or wool. You can also buy waterproof work boots and use talcum powder.

Which work sock should I wear with my steel toe boots?

You want a work sock with extra cushioning and reinforcement in the toe box.

How do I avoid sweaty feet in my work boots?

The best socks for sweaty feet are wicking socks. Avoid regular socks like a cotton sock. You want something with synthetic fiber or merino wool.