Guest Post: Boot Season Starts with the Right Socks – A Guide to Merino Wool

AI-generated styling illustration supplied by MP Magic; not a product photograph.

The first cool morning brings the boots back out: Brown leather, familiar denim, perhaps a jacket that has spent the summer in the closet. Then comes the detail that is easy to overlook—what goes inside those boots. A sock that feels fine with sneakers can bunch under a boot or leave its collar against bare skin. Here is how to choose merino socks by weight, cushioning and height for everyday fall wear.

Start with the room inside your boots

A close-fitting Chelsea boot and a roomy lace-up do not need the same sock. Start with a lightweight knit for snug boots, mild afternoons or days spent mostly indoors. Consider a medium-weight pair for cooler outings when your boots have room for the extra fabric.

Try the combination on before heading out. Your toes should move comfortably, and the upper should not feel newly tight across your foot. If a thicker sock changes a comfortable boot into a squeeze, choose a lighter pair.

Merino is useful here because its fibers can absorb and release moisture vapor, as Woolmark explains. Still, fiber content alone does not tell you how substantial a sock will feel. Check the knit and cushioning as well as the blend.

Put cushioning where you want it

Sock weight and cushioning are related, but they are not identical. A sock can have a relatively light upper with extra padding underfoot. For everyday walking, consider cushioning around the heel and forefoot without automatically choosing the thickest pair.

Walk around indoors and notice the seams, heel position and space above your toes. The fabric should sit smoothly, without folds beneath your foot. Extra padding should feel comfortable inside the boot; it should not be used to compensate for footwear that fits poorly.

AI-generated styling illustration supplied by MP Magic; not a product photograph.

Choose a height that clears the collar

For many ankle boots, a crew sock is a practical starting point. Check that it extends above the boot collar when you sit down or bend your ankle, rather than relying on the height name alone. Taller shafts call for taller socks.

With cuffed denim, a small glimpse of ribbing adds texture. With chinos, keep the trouser hem clear of bulky folds so the transition into the boot stays tidy.

Build your everyday rotation

Looking to start your search for the best socks for every situation you can imagine? Take a look at MP Magic. Its merino wool socks collection includes options for everyday dressing.

MP Magic Classic Basic crew socks combine 82% merino wool with targeted cushioning, mesh ventilation and stretch, making them an ideal option to consider for commuting, travel and casual boot outfits.

Keep the care label in mind, too. The Classic Basic is machine-washable, but washing instructions vary between socks. Choose a pair whose fit and care routine suit the way you actually dress.

Key Takeaways

Match sock weight to the space in your boots, choose cushioning without crowding your feet, and keep the cuff above the boot collar. Try the whole combination together before committing to a full day in it.

See Now, Buy Now: Get the Job Done With these Rugged Taylor Stitch Good Acre Chore Pants

Knocking out your to-do list, or trekking out far afield for an adventure, demands gear that passes muster and literally gets the job done, ehh? It’s no joke when brisk weather rolls into town and when duty calls — you’d better be outfitted with the best workwear on the market, I’d say.

And that brings us to Taylor Stitch, the NoCal brand best known for its burly flannel shirts, expertly crafted Oxford shirts and dependable outerwear — gear fit for both the work done at the office and work done out in the field.

The Taylor Stitch Good Acre Collection fits the second of those two pursuits, a fan favorite offering that recently returned to the Taylor Stitch menswear lineup by popular demand. Taylor Stitch perhaps said it best, calling these durable chore pants “homegrown workwear for whatever an honest day’s work looks like for you,” which sounds like a mission statement I can get behind.

The key with the Good Acre Chore Pants? The use of hard-wearing 100 percent duck canvas construction, which stands up to wind, rain, abrasions, dust and debris with ease — as I found out testing these pants during a brisk, breezy fall season in my home state of Michigan.

Best workwear for men.

The Coffee Canvas color is particularly appealing when it comes to these handsome yet sturdy work pants, which are built out with details like reinforced knee construction, plus a pen sleeve and reinforced rear pockets to amp up your everyday carry storage space.

The Good Acre Chore Pants are also expertly crafted with a classic medium rise and a leg opening that tapers ever so slightly from the thigh through the knee down to the ankle — wide enough to wear over a pair of leather work boots, clean enough to wear with moc toe chukka boots for an off-duty dive bar beer alongside your trusty Taylor Stitch trucker jacket.

You’ll certainly find that Taylor Stitch took good care of the details, pun intended, with the Good Acre Chore Pants, including an eye-catching leather back hip patch and front slash pockets, all the better to access your EDC at a moment’s notice. And while these durable work pants for men might prove a touch pricey at $208, they’re also crafted in California with plenty of attention to detail and quality craftsmanship in mind.

I myself prefer the Coffee Canvas offering of the Good Acre Chore Pants, but the Olive Canvas colorway should pair easily with everything from a dark blue chambray shirt to a grey waxed cotton trucker jacket and your favorite thermal henley. The possibilities in terms of rugged workwear are limitless with your new favorite pair of outdoor adventure pants this season (and beyond), my friends. Trust Taylor Stitch to — you guesssed it — get the job done.

The Sunday Sale: Now Is the Perfect Time to Stock Up On the Best Men’s Boots (for a Discount) at Huckberry

Let’s talk about entering the fray in matters of fall footwear. The right pair of rugged boots makes all the difference, of course — come across inclement weather,slippery ground, treacherous conditions on the coast or out in the field, and you sense it right away.

Hard-wearing boots that can keep you moving swiftly on your feet, especially when paired properly with a waxed field coat, a thermal henley and canvas work pants — for instance — make all the difference, as you well know if you read this blog on the regular.


And that’s where you’re going to love the wide array of durable men’s boots for sale right now in the, well, Huckberry Sale Section, of course.

Shopping men’s boots at a discount at Huckberry is about as good as it gets, ehh? I’m personally impressed at the diversity of reliable, stylish men’s boots on sale at Huckberry at any given time, especially from trusted in-house brands like Rhodes Footwear.

There’s a dash of vintage Americana, from the classic chukka boot to the wedge-sole moc toe boot, not to mention, the hard-working nature of Vibram outsole Chelsea boots — most of which are made by Rhodes Footwear and marked down to some exceptional prices ($100 off on stylish boots for men at Huckberry, anyone?).

The bottom line seems to be that if you haven’t found the right pair of the best men’s boots — pairs largely fit for workwear-minded pursuits but also ready to wear to a casual office when cleaned up in a pinch – now is the time to lace ’em up or step right into ’em.

Rich suede, roughout leathers, even weather-ready leather uppers tend to pop up across the array of boots at Huckberry right now, and it bears repeating that the selection is utterly impressive. I’m tempted myself to score some Vibram wedge outsole Chelsea boots or lace-up boots fit for everyday style — whether teamed with olive chinos or expertly faded denim, of course.

Sizes in some styles of on-sale men’s boots at Huckberry are going fast, as to be expected with something so essential and utterly perfect for the season at hand.

It’s lke I say most days of the week at this style blog: If you can dream it up, Huckberry has you covered, and that surely holds true from the ground up in this instance with a wide range of the best fall boots for men — on sale at Huckberry ASAP, naturally.

Style Pick of the Week: Todd Snyder Donegal Crewneck Sweater – A Refreshed Take on a Seasonal Icon

Todd Snyder Donegal Crewneck Sweater.

What springs to mind when you think of the most classic, timeless pieces in your wardrobe? A vintage store find like a treasured waxed jacket? A favorite flannel shirt passed down through your family? Durable blue jeans with just the right amount of fading? Or perhaps, a burly, hard-wearing sweater like the one shown above from menswear legend and award-winning designer Todd Snyder.

The right classics in your style rotation remain that way for a reason, with durability, heritage — and in the case of the best men’s sweaters — warmth and performance top of mind.

And if you’ve read past Todd Snyder reviews on this very blog, you know that the designer can deliver, from breezy linen shirts in the summer to some of the most dependable, stylish outerwear (and more!) in fall and winter. This one carries on that lineage quite nicely, ehh?

But whether through time or general wear and tear, sometimes, even the best fall style essentials, the pieces you trust the most, can use a new look — that’s where the Todd Snyder Donegal Crewneck Sweater is ready to step into your seasonal sweater rotation with throwback good looks and plenty of rugged warmth on brisk fall weekends (and beyond).

Much like a refined yet rugged Todd Snyder flannel shirt, modern, luxe fabrication makes all the difference — in this case, Donegal wool gains durability and strength from the use of nylon and viscose, which should also help soften the Todd Snyder Donegal Crewneck Sweater in general.

With flecked tweed texture and the use of thick yet supple lambswool, this sweater adds plenty of character to laidback fall cabin weekends, yet can also be dressed up beneath a tan herringbone blazer or worn with crisp corduroy trousers and a white Oxford shirt for dressier seasonal occasions.

Color options like Espresso Brown are perfect for the season at hand, and the company even notes the silhouette — which should also wear plenty well beneath a waxed field jacket –is a personal favorite style of the designer himself.

At least in my experience, the Todd Snyder Donegal Crewneck Sweater strikes the right balance between rugged, classic good looks, seasonal warmth and even a dash of refinement when styled the right way. To bolster your own rotation of fall sweaters, from the humble cardigan to the dashing V-neck sweater, consider the Todd Snyder Donegal Crewneck Sweater a wise, retro-inspired move made to last.

The Friday Find: FRET12 Makes Some of the Coolest Gear and Garb For Music Lovers (And More)

Fret12 Chicago review.

There are certain pairings in the universe — yes, the universe — that go together well without even a second thought. An icy cold beer at an indie rock show, the perfect pair of boots alongside classic blue jeans, a chambray shirt and, well, another cold beer at an indie rock show — at least, that’s my outlook on the world.

What about a brand bringing a dash of that same sentiment and forward-thinking outlook together in one community, both online and IRL? A lofty goal and moment to meet, but Chicago’s FRET12 talks the talk and walks the walk — an ideal brand to dive into ahead of the weekend, right?

Founded in 2008 by Dan Tremonti, the brother of Creed guitarist Mark Tremonti, the company takes an ingenious approach to live music and culture — spurred on by the inventive and utterly fun “String Thing,” a found-art type of object that takes old, broken guitar strings and transforms them into lively action figures of sorts.

Chicago’s FRET12 does oh-so-much-more than that (which you can read about in my latest CoolMaterial feature on the brand!), including crafting a seriously cool, rugged lineup of the best gear and menswear for guys out there like you and me. The company also specializes in all sorts of music gear and emphemera, and if ever you get the chance to trek to the Windy City, a visit to the FRET12 space at acclaimed Chicago music venue The Salt Shed is very much recommended.

But back to that lineup of rock n’roll-inspired menswear. Take the FRET12 Studio Shirt, the kind of handsome denim or chambray shirt that wouldn’t look out of place on the back of one of your favorite guitarists (Aaron Dessner, anyone?).

It’s designed, cut and hand-sewn in Chicago from 100 percent cotton, and serves as the perfect complementary piece alongside, say, your favorite pair of black jeans and some trusty tan leather boots (feel free to mix and match, people!). I’ve gotten plentyof mileage wearing it alongside dark blue jeans at a music festival as well as alongside chino shorts in hotter temperatures.

Yessir, it’s a new staple in my rotation, but beyond that, Chicago’s FRET12 is an inspiring brand taking on a bit of everything at the intersection of rock music, craftsmanship, menswear and more (keep an eye out for collaborations with the likes of Huckberry, for good measure). This certainly isn’t the last time you’ll be hearing about FRET12 — plug in, score a new shirt in the meantime, and embrace the power of great gear and great rock n’roll, my friends.

The Thursday Buy: The Pladra Every Day Flannel Shirt is One of the Best Flannel Shirts on the Market This Fall

Pladra men's flannel shirts review.

There are plentiful flannel shirts for men on the market, right? And in plentiful varieties, from thick flannel workshirts to heathered flannel dress shirts and classic red-and-black plaid flannel shirts in spades. Many of these flannel shirts for men are assuredly worth their weight, and then some, but what if I told you there was a company out there dedicated only (or at least, for the most part) to making the best men’s flannel shirts on the market?

Too good to be true though it might sound, that’s the aim of Pladra, which focuses on a thoughtfully curated array of men’s flannel shirts with unexpected touches — like printed nature scenes beneath the collar and at the shirt cuff — alongside unexpected color combinations and handsome patterns.

Think of Pladra men’s shirts like a flannel shirt for the modern age — a relatively tailored fit, a vast array of solid colors as as well as plaid patterns, and a few easy-to-shop options broken down by weight and by usage.

For instance, the Every Day Flannel Shirt shown here is a personal favorite, the kind of shirt that’s crisp enough for an afternoon coffee meeting and just plain cool enough to wear underneath a trucker jacket at an indie rock show.

In colors like Portsmouth Blue or the aptly named Autumn Red, Pladra offers a lifetime guarantee alongside its shirts, and the soft, supple yet durable nature of the fabric speaks to that — seriously, Pladra flannel shirts are uncommonly soft while boasting a fit that looks positively great untucked or worn tucked in beneath a handsome cardigan.

For my own daily wear on the road through a Michigan fall or trekking elsewhere in my #FreelanceLife pursuits, I value the brushed midweight cotton flannel build of the Every Day Flannel Shirt — not too restrictive or heavy to wear atop a henley, nor too lightweight to buckle under crisp autumn air. Pladra bills the Every Day Flannel Shirt as one made for three-season layering, and there are options aplenty when it comes to Pladra heavyweight flannel shirts for brisk temperatures and a workwear-like nature.

A word to the wise: The Workhorse Elite Flannel bridges the gap between heavyweight and an everyday weight, but we’ll have more on some of my new favorite flannel shirts in the weeks ahead.

‘Tis the season for finding your new favorite flannel shirt and layering it on up, is it not, my friends? For now, I can’t recommend highly enough that you start off your fall shirt quest by scoring the Every Day Flannel Shirt from Pladra in a rich pattern of your choice — remarkable autumnal layering awaits, my friends.

See Now, Buy Now: Amp Up Your Outerwear With the Stellar Flint and Tinder Dry Wax Field Jacket from Huckberry

It feels like there’s always room for improvement — or at least, room to scour the market itself — when it comes to the most rugged, functional and dare I say, simply the coolest outerwear on the market. Shoulder season presents an optimal time to wholeheartedly revamp your jacket rotation, shoring things up for the brisk weather at hand.

While a peacoat or topcoat cover more formal matters, and a trucker jacket covers casually rugged style situations, a touch more coverage is needed at times — the coverage only of the best men’s field jackets can bring, an aim met quite handily by the new Flint and Tinder Dry Wax Field Jacket. It starts off in fine fashion with the use of durable British Millerain Ranger wax canvas, a modern innovation building off the English company’s penchant for durable, water-resistant and abrasion-resistant fabrics.

After all, Huckberry calls the company “a pioneer of waxed cotton fabric since 1880,” and this particular fabric should feel crisp yet lightweight. It’s in keeping with the already impressive lineup of Huckberry waxed jackets, including its famed flannel-lined trucker jacket and a rather more recent take on the Harrington jacket in waxed cotton.

The dry wax on the aptly named Flint and Tinder Dry Wax Field Jacket represents a different treatment than Huckberry’s other waxed jackets while still developing a patina and proving plenty easy to wear, thanks to its nylon sleeve lining for an easy-on, easy-off approach.

And helpfully, added coverage is the name of the game with the longer cut of the Flint and Tinder Dry Wax Field Jacket, which comes in a handsome trio of color options like Olive, Reddish Brown and of course, British Khaki. Each gets a contrasting moleskin brown collar, while flannel lining delivers warmth that shouldn’t cause any overheating, even when worn atop a flannel shirt.

Huckberry has certainly thought of just about everything when it comes to the best field jackets for men, including a highly useful set of six external pockets, an added touch for your everyday carry anytime you step out into the field. And as it were, you’re going to want to step out into the field just about as often as possible this season wearing one of the best men’s jackets for fall — Huckberry delivers an ace in the hole once more, my friends.

The Tuesday Steal: Add Olive to Your Style Rotation with these Easygoing Todd Snyder Jeans

There’s an array of potential ways to upgrade both your off-duty and your business casual uniform, starting from the ground up. Of course, if you keep up with this Brooklyn style blog, you know that all too well, from your selection of stylish chukka boots to expertly crafted socks, but can you find a pair of jeans fit for both the office and hours off-duty? Once again, the answer is easy, my friends, and that’s: Yes, of course you can — if you know where to look.

And the place we happen to be looking today is menswear extraordinaire and award-winning designer Todd Snyder, with a fresh outlook on timeless Americana that includes a crisp new spin on classic jeans — beyond just the timeless blue jean, at that.

The Todd Snyder Garment-Dyed Jeans shown here are a departure from the GQ-approved designer’s normal array of expertly faded denim and inky blue selvedge, yet not in a bad way. In fact, the Olive colorway adds plenty to your style rotation, whether paired with a simple heather grey tee and a blue denim trucker jacket or styled with a dark blue chambray shirt and an unlined navy wool stretch blazer at the office (take heed as you plan your next fall #OOTD, my friends).

With their more relaxed, classic straight-leg fit, these Todd Snyder Garment-Dyed Jeans are also designed to stand up heartily to fall — try ’em on for size with sturdy work boots or Chelsea boots with a slightly more workwear-inclined silhouette, and then pay close attention to what Todd Snyder calls “quality, vintage-inspired details” like oxidized rivets.

With a mid rise and a straight cut through the leg, these jeans are polished without proving too slim or too baggy — a just-right fit akin to Goldilocks, as it were.

And despite that garment-dyed finish, these are in fact crafted from cotton twill selvedge making ’em a downright steal for your wardrobe at under $100. Add a dash of earthy color to your denim rotation, and your wardrobe will prove all the better for it this season, folks. Sizes are moving quickly as part of plentiful Todd Snyder menswear deals right now, so act accordingly to score a versatile set of denim for your seasonal roster.

See Now, Buy Now: The Taylor Stitch Moto Jacket is An Undeniably Cool Fall Jacket for Men

Taylor Stitch Moto Jacket review.

Ever come across a piece of menswear that’s so jaw-dropping, so instantly memorable, you immediately need to have it — or at least, you immediately need to add it to your wish list? That’s what this writer first thought upon seeing the remarkable, investment-level, seriously cool Taylor Stitch Moto Jacket — a long-running fan-favorite that arrives every autumn like a welcome, brisk breeze amongst the rustle of the changing leaves.

Yes, that’s lofty praise, but this stylish men’s leather jacket is an utter classic for a reason, at least among the modern parlance of men’s leather jackets. And yes, it’s back this fall and simply better than ever.

We’ve talked about an array of the best leather jackets for men on this site in recent weeks, but few can match the construction and quality of this West Coast style staple. And while the price is assuredly investment-worthy and perhaps quite the splurge, I’d say you’re getting your money’s worth with the Taylor Stitch Moto Jacket, and then some. Taylor Stitch worked with its partners at Golden Bear to craft this jacket, one that was inspired by a vintage leather jacket built for the long haul, as the San Francisco brand says.

Crafted in the United States of America – no easy feat these days, my friends, each of the three variations of this handsome jacket are fashioned from hard-wearing, full-grain, drum-dyed 3.5-oz steerhide that should become more supple with each wear.

It’s fully lined and features flannel-lined pockets for added warmth — while it’s not quite a beefy puffer jacket or winter parka, you should be able to wear this jacket atop a flannel shirt and henley on especially brisk autumn days.

The specs on the Taylor Stitch Moto Jacket only get better from there — it also features Thinsulate insulation for substantial depth and warmth on the open road, with articulated back construction and a cropped fit for added mobility. Antique brass hardware, including a two-way YKK zipper and antique brass snaps, lends a further air of rugged durability to a jacket that’s bound to become your new favorite.

Perhaps unsurprisingly, this standout leather jacket, one of the coolest fall jackets for men, is moving quickly in leather shades like Espresso Steerhide. No matter which of the trio you select, this jacket is just about as ruggedly stylish as it gets when paired with classic dark blue jeans and a thermal henley, or else a plaid flannel shirt jacket and trusty Taylor Stitch moto boots (another personal favorite of mine).

For remarkable quality and durability, for almost limitless style potential and with longevity in mind, I’d wager it’s tough to beat the wearability and utility — plus fashion points aplenty — of the Taylor Stitch Moto Jacket. Inquiring minds, head to Taylor Stitch to learn more.

The Sunday Sale: These Rhodes Footwear Vibram Wedge Boots from Huckberry a Dependable Fall Footwear Move

Huckberry men's boots review.

Are you sick of talking about the best boots for men yet? I’d surely hope not, as fall presents prime opportunuties aplenty for lacing up and stepping into downright rugged, essential men’s footwear, as useful in the garage or the shop as they are in the yard or out far afield.

Perhaps the best boots for men are merely a pair you need as you strive to build the perfect bonfire and then admire your handiwork — either way, they can stand up to wind, rain, fall leaves and debris while also wearing stylishly with your favorite pair of blue jeans off the clock.

Let’s get even more specific: The selection of men’s boots at Huckberry has long been positively outstanding, running the gamut from sleek suede chukka boots to durable moc toe boots and the handsome Rhodes Footwear Vibram Wedge Boots shown above.

It gets even better once you know your new favorite boots are on sale at Huckberry right now for a rather impressive 40 percent off — that adage we always talk about on this menswear blog about striking while the iron is hot certainly comes into play here.

The goods are certainly delivered and then some, as Huckberry’s own Rhodes Footwear takes classic silhouettes, like the lace-up work boot, the chukka boot or the plain-toe dress boot, and livens them up with premium footwear construction hailing from Leon, Mexico, arguably a hotbed for crafting some of the finest footwear for men on the plane.

The hard-wearing Rhodes Footwear Vibram Wedge Boots feature chestnut suede (be sure to treat them with waterproof suede protector), but the real winner here in matters of constructing some of the best boots for men is the use of that anti-slip, deep-lug Vibram 2060 outsole for sturdy performance, from cobblestone streets to the yard and back.

With a profile that can be dressed up slightly with olive chinos or worn in more rugged fashion with canvas work pants, the Rhodes Footwear Vibram Wedge Boots are also built out with features like bovine and suede leather lining for breathability and comfort that molds to your foot over time, right out of the box.

Huckberry notes the utterly stylish, classic Rhodes Footwear Vibram Wedge Boots also feature an anti-shock EVA foam midsole for added rebound and support. And at a price like that — under $170, marked down from $268 — you’re adding an ideal blend of style, savings and performance to your wardrobe. You can’t beat that from Huckberry now, can ya, my friends?