Online Shopping Picks: Add to Your Wardrobe with the Best Men’s Socks for Fall and Winter

OK, let’s take stock of what’s on your feet in today’s new Online Shopping Picks entry — no, not your stylish leather boots. Instead, let’s look at … your socks. Yep.  Stylish men’s socks are quite the underrated part of an outfit, it seems; at the very least, they can be an afterthought. But rest assured, no matter whether you’re lacing up classic leather sneakers or classic chukka boots, your socks are just as important as the rest of your outfit. That’s especially true during the chilly fall and winter months, as the right pair of socks can add warmth and comfort — plus serious style points — to your rugged style ensemble. That goes for dressing in casual weekend style just as it does with getting dolled up for a day at the office. And y’know what? We’ve got some excellent pairs on tap for any occasion today, from brands you know (like Anonymousism) and brands that might be a bit newer (take CHUP, for instance).  Either way, you’re going to be stepping out in style this season. If you’ve got feedback or picks of your own, you can hit me up on Twitter. Cheers!

#1. Anonymousism Slub Crew Sock in Brown — $18

Finely crafted socks that are stylish enough to work at the office and laidback enough to wear on the weekend.

Stylish socks can be just as critical as other more essential fall style picks when it comes to adding texture and seasonally appropriate color to your ensemble. Take the Anonymousism Slub Crew Socks. Featuring neat texture and a color that’s very ready for fall and winter, the Slub Crew Socks should fit right in as they peek out from beneath slim blue denim and classic suede lace-up boots. $18 is definitely a fair bit of change to drop on socks, but Anonymousism makes it worth your time & money.

#2. American Trench Fair Isle Socks in Merino and Cashmere — $33

Another pair of socks worth your money, if only for the great pattern and quality.

Let’s keep this list rolling with yet another pair of investment-worthy socks. Yes, investment-worthy is certainly something that applies to well-made American Trench socks like the Fair Isle Socks in Merino and Cashmere. Why the high price tag? Well, American Trench works with family factories to source the materials and produce some of the best men’s socks out there. The fact that the Fair Isle Socks in Merino and Cashmere just so happen to add some cool pattern to any outfit is just a bonus. Wear these with slim charcoal trousers and a navy cardigan for fall-friendly style.

#3. CHUP Vivienda Socks — $35

Japanese-made socks that are the real deal in terms of excellent design and great quality.

You very well might recognize CHUP from our #OOTD series here at The Style Guide — the brand’s reliable socks are unique, carefully made and packed with cool patterns. These Japanese-made socks are made using time-tested methods on stocking frame knitting machines, one of the first types of knitting machines invented. So, the Vivienda Socks have got quite a lot of quality packed in. And when it comes to looks? The CHUP Vivienda Socks blend an intricate pattern with a neutral gray base — the perfect socks to wear when you want to stand out quietly.

#4. Arvin Goods Crew Socks (Three-pack) — $23.98

Simple socks for simple style, particularly on a fall or winter weekend.

There are times you just need a casual pair of socks that look sharp while providing comfort. Nothing fancy — just function with a dash o’ good locks. That’s where the Arvin Goods Crew Socks enter the mix, folks. Equal parts sporty and casual, these Arvin Goods socks are made, like the rest of the brand’s line, with sustainability and style top of mind — good news for us eco-conscious style fans. Wear these with slim sweatpants and stylish leather sneakers, plus a rugged grey crewneck sweater, for your next weekend brunch.

#5. Wigwam Cypress Trail Socks — $26

Functionally minded socks made with outdoor adventure in mind.

We turn once again to simple, understated socks that work in a pinch — especially when you need a durable pair of socks for fall and winter exploration. Thankfully, the Wigwam Cypress Trail Socks come in quite handy in that regard. Namely, if you need a pair of “get-the-job-done” socks to wear alongside rugged leather boots and the Taylor Stitch Chore Pants on your next hike, the Cypress Trail Socks are the way to go. Every guy needs a go-to pair of tough socks in his closet, right?

#6. American Trench Sawtooth Argyle Socks — $29.50

Crisp socks with a dressier look and feel than other options on this list — yet another job well-done from American Trench.

You knew weren’t done recommending American Trench socks, right? Just as with the brand’s Fair Isle socks, the Sawtooth Argyle Socks feature the comfortable and exceptionally well-made blend of merino and cashmere, all the better to keep your feet feeling great. In fact, that fabric blend is engineered to prevent odor and keep your feet dry at the same time — not a bad job from American Trench here. The Sawtooth Argyle Socks are slightly dressier — feel free to punch up your worsted wool navy suit and stylish men’s dress shoes with these American-made socks this fall and winter.

#7. Etiquette Clothiers Sherpa Boot Rib Socks — $24

The perfect wool socks to wear with leather boots in chilly weather this fall and winter.

As previously seen in an edition of The List — featuring rugged fall style picks galore — the Etiquette Clothiers Sherpa Boot Rib Socks are quite possibly your new favorite socks to wear with …. your favorite fall boots. If ever there was a pair of thick, durable socks to stand up to harsh weather while still looking great, I’d say it might be the Sherpa Boot Socks. Made in Italy from a wool-acrylic blend and done up in a fall and winter-ready color, the Sherpa Boot Socks  would fit right in with black denim and tan leather boots, and they’d also add a shot of vintage-inspired style to charcoal herringbone trousers and chunky wingtip boots (plus a rugged field jacket for a bit of high-low style).

#8. American Trench Kennedy Luxury Athletic Socks — $19.50

Vintage-inspired socks that add sporty, old school looks to any outfit — particularly white leather sneakers, a classic cardigan and tan chinos.

Our last and final pick comes at you from … welp, American Trench. The brand continues to branch out into new, different directions in terms of products — the Kennedy Luxury Athletic Socks are a prime example of that unique approach, with quality still at the forefront. The Kennedy Athletic Socks play off the same styles seen on icons like JFK, so think of these as more old school-style socks than a pair you’d wear to the gym. At any rate, the American Trench Kennedy Luxury Athletic Socks should serve you just fine, especially when teamed with a stylish field jacket and durable chinos.

OK, my friends. Of the above pairs, which one did you like best? Or did you have more than one pair in your sights? Perhaps the sporty and vintage-inspired American Trench Kennedy Luxury Athletic Socks will work for your weekend style pursuits? Or maybe the tough, rugged Etiquette Clothiers Sherpa Boot Rib Socks are more your speed — especially if you consistently reach for boots like the Wolverine Original 1000 Mile Boots. For straightforward style, casual function and comfort — an oh-so-important mix — the Arvin Goods Crew Socks are a prime pick-up, as are the trail-ready Wigwam Cypress Trail Socks. When it comes to dressy situations, a crisply made pair like the Sawtooth Argyle Socks from American Trench fit the bill nicely, and no list would be complete without essential, versatile socks like the CHUP Vivienda Socks. Oh, and what pair of socks to put on for everyday wear? Easy — the Anonymousism Slub Crew Socks are your go-to move. Have any picks you’d add to this list — or remove? Let me know in the comments or on Twitter.
Thanks for reading!
-Beau

Style Pick of the Week: Anonymousism Wool Herringbone Crew Socks

Well-made, crisply designed socks that’ll work with tailored or casual outfits — just what you need from Anonymousism.

Is this post just about … socks? Only socks? Well, bear with me here, because these certainly are stylish men’s socks. As we often bring up at The Style Guide, the little details make a difference in your ensembles, from fit and comfort to sharp looks. And if you find a stylish accessory that you love and that happens to be well-made — like the Anonymousism Wool Herringbone Crew Socks seen here — I’d urge you to stock up as much as you can. When building outfits from the ground up, sharply designed socks shouldn’t be an afterthought — that much is true. They can add a bit of visual interest to slim charcoal trousers, they can provide some needed insulation when worn with rugged leather boots, and great-looking men’s socks can even blend in seamlessly with dressier ensembles (the Wool Herringbone Crew Socks would work nicely with a navy worsted wool suit). So, we’ve got all that down pat. What’s the upside to buying pricier Anonymousism socks? Read on, because you’re going to like what you see. Anonymousism is stocked at retailers from J. Crew to Bespoke Post, providing the kind of classic yet visually striking patterns that can work as a complement to so many fall outfits. And the kicker (pun intended) when it comes to Anonymousism socks? They’re made with excellent materials, folks.

Need a little more pattern in your life? These Jacquard Crew Socks from Anonymousism ought to do the trick.

And if you like what you see when it comes to the Wool Herringbone Crew Socks, you’ll assuredly like other, more pattern-friendly options from the Anonymousism line, like the Jacquard Crew Socks seen above. Whichever pair you pick, you’re getting Japanese-made quality and the type of durability you’d expect for the price tag — most Anonymousism socks will set you back upwards of $20. Here’s the good news with the stylish Wool Herringbone Crew Socks, though: When you sign up for Bespoke Post, you can pick ’em up at the discounted price of $18. Every buck counts, right? Certainly, the Wool Herringbone Crew Socks are nearly the perfect fall and winter sock. If that sounds silly to say, well, the herringbone pattern is a cold weather staple across everything from shirting to blazers, so these Anonymousism socks are going to look refined and on-trend peeking out from beneath your favorite pair of blue denim and some classic suede chukka boots. What’s more, these Anonymousism socks are going to last you quite a long time — I’ve been mighty pleased with the durability of my pairs, and that’s good news. Plus, they’ll also provide crucial versatility with plenty of outfits. Tan chinos and a white Oxford? Add stylish men’s dress shoes and Anonymousism socks. Black denim and a heather grey crewneck sweatshirt? Yes sir, the Wool Herringbone Crew Socks are a go-to accessory. Again, that’s just the tip of the iceberg. Oh, and don’t forget to sign up for Bespoke Post to get that discount (wink, nudge). Let me know via The Style Guide Facebook page if you plan on investing in a pair  … or two … or three of Anonymousism socks this season.

#OOTD: Wear Your New Denim Trucker Jacket This Way for Fall

Now that we’re truly getting into fall — at least, on the calendar — it’s time to break out a rugged denim trucker jacket, I’d wager.  Just as a cotton denim jacket works in the spring and summer, it’s a surprisingly easy-to-wear fall layering essential — as you’ll see today. The right denim trucker jacket is made with quality fabric and the type of construction that’ll break in over time, so it’ll work from September into November when worn properly. And it’s all the better that Flint and Tinder is making the tough denim trucker jacket you need for all your seasonal style scenarios. From a tailgate to a day trip to a brewery tour — gotta love those brewery tours — the deep indigo trucker jacket you see below brings comfort, versatility and style in sapdes.  And I think you’re going to like the way we’ve styled it, from classic suede chukkas all the way through to an investment-worthy watch. Let me know what you think of today’s #OOTD in the comments or over on The Style Guide Facebook page. With no further delay, let’s get ready for fall!

When worn with rich green trousers and a striped shirt, a denim trucker jacket can be a fall layering essential.

The Trucker Jacket: Flint and Tinder Stretch Denim Trucker Jacket, $158 — As seen recently in our See Now, Buy Now series, this Flint and Tinder trucker jacket features a crisp indigo color, comfortable fabric and terrific construction.

The Shirt: Life/After/Denim Academy Shirt in Heather Grey, $138 — Although a bit pricey, this Life/After/Denim shirt features yarn-dyed cotton and a neat, neutral color palette — plus, those stripes are a neat design touch.  I have a feeling you’ll get a lot of wear this season out of the Life/After/Denim Academy Shirt.

The Pants: Bridge and Burn Polk Pants in Deep Forest, $108 –Early fall is a great time to start working dark, rich colors into your wardrobe — the Bridge and Burn Polk Pants are an excellent jumping-off point.

The Boots: Astorflex Greenflex Rough Boots, $134.98 — Want a pair of classic suede chukkas? The well-constructed Astorflex Greenflex Rough Boots feature a sturdy sole, visually interesting texture and a color that nicely offsets the navy striped Life/After/Denim shirt and the deep indigo of the Flint and Tinder trucker jacket.
 
The Socks: Anonymous-ism Tweed Nep Crew Socks, $30Anoynmous-ism is known for its ridiculously well-made, stylish men’s socks — the sharp navy color of these tweed socks is fall style at its best, with comfort thrown in for good measure.

The Belt: Line of Trade Veg-Tanned Leather Belt in Auburn, $55 ($40 When Signing Up for Bespoke Post) — As we always say at The Style Guide, don’t sleep on stylish accessories  — this durable leather belt is a fall-ready way to, well, hold up your pants in style.

The Watch: Huckberry Lum-Tec B31 Bronze Automatic Watch, $899.99— We told you we’d get to an investment-worthy watch, right? The incredibly durable, striking Huckberry Lum-Tec B31 is that very watch.

The Everyday Carry: Billykirk Small Carryall, $238.98— With its blend of remarkable craftsmanship and eye-catching looks, the Billykirk Small Carryall is a stylish everyday bag for fall weekend day trips or bar crawls.

I hope today’s #OOTD gives you a few ideas when it comes to how to wear a denim trucker jacket this fall.  It’s a classic silhouette made all the better by the fact that Flint and Tinder crafts its Stretch Denim Trucker Jacket with quality and versatility in mind — that makes it the ideal outerwear piece atop the Life/After/Denim Academy Shirt.  And in a deep shade of green, the Bridge and Burn Polk Pants  are a unique way to nod toward the start of fall — you can wear the Polk Pants into early winter, too. If you don’t yet have a pair of rugged leather chukka boots in your closet, grab the Astorflex Greenflex Rough Boots — the tread sole and fall-appropriate color make them a seasonal footwear essential, surely.

As I always say, stylish accessories are key; in that regard, Anoynmous-ism is going to be a terrific bet when it comes to stylish men’s socks, while the Line of Trade Veg-Tanned Leather Belt is a richly crafted belt for daily wear. On the watch front, the Huckberry Lum-Tec B31 is absolutely the ideal watch to complement a tough denim trucker jacket — it’s investment-worthy and made with rugged good looks.  Last but not least — what would your daily carry be without  a stylish everyday bag  like the Billykirk Small Carryall? Hopefully, we accounted for all the men’s style essentials you might need in the season ahead.
Happy shopping, enjoy the season and stay stylish!
 -Beau