Style Pick of the Week: Frye Tyler Chelsea Boots – Best Men’s Chelsea Boots for Fall

Best men's Chelsea boots for fall

Among any list of the best fall style essentials — be it one of the best fall blazers or your new go-to henley — you’d also do well to consider some of the most rugged men’s boots, right? But there’s a fine line to walk, literally, if you want to maximize your versatility. While there’s a time and a place for hard-wearing work boots, you can still get fall-minded performance and style with *drumroll please* a pair of the best men’s Chelsea boots. In fact, at the current moment, there might not be a better pair of men’s boots for fall on the market than the FRYE Tyler Chelsea Boots.


You’ve hopefully encountered the brand through its penchant for making some of the best leather boots, period, but the American heritage footwear company continues to step up its game with timeless styles like the easy-on, easy-off Chelsea boot. It all starts, of course, with quality leather when it comes to the FRYE Tyler Chelsea Boots, and in this case, we’re talking a rich Cognac leather that wears well with plenty of fall style picks (everything from dark blue jeans to black denim to olive chinos).

The FRYE Tyler Chelsea Boots — which are selling somewhat fast despite a more investment-minded price tag of $328 at FRYE — also sit atop a sturdy leather outsole for traction on slick fall streets and through day-to-night pursuits (anyone up for a park stroll and brewery visit?). Better still, the FRYE Tyler Chelsea Boots are designed for a smooth ride, thanks to the injection of a rubber forepart in the leather outsole.


The end result is a pair of sleek yet hard-wearing boots, the kind you can team with wool trousers, stretch cotton chinos or your favorite pair of blue jeans without missing a beat. On your top half, go with rugged picks like one of the best men’s henleys or keep things a touch more refined with a cool cotton blazer. Either way, be sure to get as much wear as possible out of the FRYE Tyler Chelsea Boots, because they can take it.

The Friday Read: New York Fashion Week 2022

My friends, if you can believe it, the time is upon us again: It’s New York Fashion Week, one of the busiest times of the year for your Brooklyn style writer, and always an exceptionally exciting time. Over the years, I’ve had the chance to attend runway shows by the likes of Todd Snyder, I’ve experienced the delights of seeing new collections from up-and-coming menswear designers at New York Men’s Day, and I’ve enjoyed plenty of seriously cool parties with some seriously well-dressed people around.

Man and woman standing in a field looking at the camera wearing white tees and jeans

Through it all this week, I’ve done my best to stay on top of the menswear game in the meantime, including yesterday’s blog dispatch on the best men’s sunglasses and my latest Maxim dispatch on a stylish new Tudor watch. It’s always proven quite the balancing act, but one I always enjoy immensely.

Of course, the festivities kicked off in fine fashion with a J. Crew event on Wednesday night headlined by none other than… NYC rock legends Yeah Yeah Yeahs! Talk about worlds colliding, and talk about a dream night in and of itself.

Mercer Apricot

I’m off to more NYFW events today and this weekend yet still, including New York Men’s Day and the upcoming, Saturday night Tanner Fletcher runway show. For now, be sure to follow along with all the fun on my Instagram

The Thursday Buy: The RAEN Wiley Sunglasses are Some of the Best Men’s Sunglasses Under $200

Best men's sunglasses to buy now.

Bear with me here today, my friends, because we’re going to talk about an unlikely accessory you should still keep handy as part of your everyday carry essentials heading into early fall. The accessory in question? Of course, it’s a pair of the best men’s sunglasses — yes, I really do mean it.

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And although you might think of shopping for men’s sunglasses as a pursuit best undertaken in the spring and summer, the right pair of stylish shades can still work wonders for your look and of course, the comfort of your vision come fall (and winter). That leads me to the California-based eyewear masters at RAEN, purveyors of specs like the RAEN Wiley Sunglasses. What makes this pair some of the best sunglasses for men? My friend, I’m glad you asked.

Best stylish men's sunglasses.

It’s all about the right blend of style plus utility in terms of sunglasses for men, and the RAEN Wiley Sunglasses pack a nice wallop when it comes to both categories. Available in a seriously cool nine frame and lens combinations (all polarized for maximum visibility), your new favorite pair of sunglasses are crafted with a frame handmade from zyl acetate.

The construction is meant to be lightweight yet durable, and sturdy five barrel hinge hardware should only bolster the long-term wearability of the RAEN Wiley Sunglasses.

Man and woman standing in a field looking at the camera wearing white tees and jeans

As if that wasn’t enough, the frame shape is squared-off and clean, the right sort of design if you want a more casual pair of sunglasses to wear with laidback looks like the best pocket T-shirt and lightweight jeans (topped off by a stylish bomber jacket, of course).

Perhaps the biggest benefit to snagging the RAEN Wiley Sunglasses right now? Of course, the multi-season wearability — and the affordable sub-$200 price. Are the RAEN Wiley Sunglasses some of the best men’s sunglasses under $200? Try ’em out yourself and let me know in the comments.

See Now, Buy Now: The American Giant Classic Full Zip Is the Best Casual Hoodie to Shop Now

Best hooded sweatshirt for men.

Sometimes, the simple things, made in classic, long-lasting fashion, tend to gain the most traction in your wardrobe — right? No matter how simple they might seem, like one of the best casual sweatshirts for men. What’s so great about a hooded sweatshirt, or rather, what’s so great about American Giant? They’re the company that makes perhaps the best hoodie on the market, and again, it’s simple: It’s the little things done right, like quality craftsmanship and even better materials. Both of those are what helped make the American Giant Classic Full Zip such a fan favorite over the past decade.

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In fact, one of the best men’s hoodies on the market just so happens to be celebrating its 10th anniversary — and your new favorite hooded sweatshirt has thousands of positive five-star reviews to back it up — so it’s worth diving into what makes this hoodie (and the company itself) a necessary part of any laidback wardrobe. You very well might know American Giant for its commitment to rugged USA-made gear like some of the best men’s work pants or the best lightweight hoodie (different than the one we’re talking about today, though!), but it only gets better from there.

Best casual men's hooded sweatshirt

You see, the American Giant Classic Full Zip is a certified modern classic in the annals of casual menswear for plenty of reasons. Perhaps you’ve noticed yourself dressing much more casually as you look for the best clothing to wear at home, and the American Giant Classic Full Zip delivers in terms of long-lasting durability.

Remmy Champagne Crystal

Chalk it up to the use of durable 100 percent combed ringspun cotton and a custom-developed heavyweight fleece for extra warmth and comfort, for starters. Take it from this menswear writer who often wears a hoodie to work from home: The American Giant Classic Full Zip can stand the test of time, no doubt about it.

Best American-made hoodie for men.

The American Giant Classic Full Zip also uses hardware like a custom metal zipper and grommets, and the small touches also make the difference as you search for one of the best men’s hoodies. What exactly are those small touches? That’d be the double-lined hood and reinforced elbow patches: Yes indeed, the American Giant Classic Full Zip is so well-made, you can even wear it out of the house.

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That’s another thing: This stylish hooded sweatshirt comes in a plethora of colors to suit every preference (11 as of right now), so you can wear it with your favorite pair of blue jeans for casual weekend outings aplenty. And because the American Giant Classic Full Zip packs such a punch in terms of quality and versatility, it’s worth the price: You’re ponying up $138 for this stylish men’s hoodie, but it’s worth it (again, take it from me). Put simply: The American Giant Classic Full Zip is a hoodie you’re going to have years from now.

The Tuesday Steal: Some of the Best High-Top Sneakers for Fall Are 25 Percent Off at Huckberry

If you keep up with the goings-on here at The Style Guide, you’ll surely know that Huckberry is a true one-stop shop for the best menswear essentials of all sorts, be it the company’s famed waxed trucker jacket or one of the most luxurious hoodies on the market. Yes, they can do it all, including stocking and selling an exclusive pair of the best high-top sneakers — a pair you’ll find marked down right now for 25 percent off in the always well-stocked Huckberry Sale section.

Crucially, although the field is crowded when it comes to the best high-top sneakers, there’s something especially about the U.S. Rubber Co. Colchesters Hi Sneakers. For starters, you’ll only find them at Huckberry, and you’ll now find them for just $90 (marked down from $120). It gets better from there, because this set of stylish high-top sneakers, featuring a rugged canvas upper, is based on the original basketball sneakers based on (wait for it)… pairs from 1892. Not a bad touch of retro-meets-modern style to add to your wardrobe, ehh?

Best high-top sneakers for men.

The U.S. Rubber Co. Colchesters Hi Sneakers deliver in terms of looks, to be sure, but they’re also a mighty fine set of sneakers when it comes to fall-ready functionality, featuring a durable canvas upper in two versatile colors: Black and Deadgrass. Either would look right at home when worn with, say classic tan chinos or dark blue rolled denim in equal measure.

Metal eyelets add even more durability to the U.S. Rubber Co. Colchesters Hi Sneakers, while the vulcanized rubber outsole stays true to the company’s original method. The reinforced toe cap also bolsters the durability of the surprisingly rugged U.S. Rubber Co. Colchesters Hi Sneakers, and again, you truly can’t beat the sub-$100 price tag. Shop ’em now at Huckberry while they’re still around (and note that there are sizes available from 7 to 13 based on the color you select). Happy hunting, folks.

See Now, Buy Now: Make the Buck Mason Storm Stopper Bomber Jacket Your New Favorite Fall Layer

Best men's jackets for fall.

I can’t be the only one dreaming about the chance to layer up with fall style essentials aplenty, can I? Especially when those essentials undoubtedly include one of the best men’s jackets, right? That brings us to today’s featured Monday pick, as great a way as any to keep a new month rolling: The Buck Mason Storm Stopper Bomber Jacket is but the latest in a long line of the best fall menswear from the all-American brand, and you’d do well to get it into your wardrobe ASAP.

Satchel and Page

Buck Mason is as apt any company out there at bridging the gap between seasons — in this case, the heat of summer and the breezy cool of early fall — and you can see that clearly with pieces like one of the best men’s overshirts. Of course, that aptitude for layering is also on display with one of the best men’s henleys from that very same brand, but the Buck Mason Storm Stopper Bomber Jacket belongs in a class all its own.

Best rugged fall jacket for men.

The Buck Mason Storm Stopper Bomber Jacket checks all the right boxes as you look for ways to step from late summer into early fall, starting with the fact that it’s cut from a soft, yarn-dyed 5.5oz. cotton-poly blend. The polyester gives the Buck Mason Storm Stopper Bomber Jacket a good amount of stretch, while the cotton should prove lightweight and airy, yet easy to layer up with, say, a Buck Mason T-shirt from day to night.

Best men's bomber jacket for fall.

The Buck Mason Storm Stopper Bomber Jacket also has plenty of classic styling potential — note timeless color options like Army-inspired Surplus or a crisp Commodore Navy color. You can use the snap-button hip pockets to hold your everyday carry essentials, and ribbed wrist cuffs ensure a snug fit.

Satchel and Page

A nice bonus? The Buck Mason Storm Stopper Bomber Jacket is filled with PrimaLoft insulation, so you can even layer it up quite nicely with a Buck Mason sweatshirt or a rugged Buck Mason thermal shirt when it gets particularly cold this fall. In the meantime, be sure to add it to your cart ASAP for the season ahead.

The Sunday Sale: Get 35 Percent Off this Versatile Olivers Apparel Shirt Jacket

Folks, now that we’ve hit Labor Day weekend (shockingly enough), it’s high time to really start gearing up for early fall in earnest, as we’ve talked about here on The Style Guide with fall style essentials aplenty as of late. The best way to do that? Find on-sale menswear that works for your wardrobe, like one of the best shirt jackets from Olivers Apparel.

Olivers has a knack for making performance menswear you can actually wear outside the gym and away from the trail, out on the open road, and the Olivers Gold Coast Shirt Jacket is a prime example of that approach. Best of all? Your new favorite shirt jacket is 35 percent off right now ($148, versus $228). How’s that for one of the best fall menswear picks to shop now, ehh?

Perhaps you recognize the brand for making some of the best stretch pants for men, for instance, and they’re truly a multi-season brand thanks to picks like the Olivers Apparel Gold Coast Shirt Jacket. It’s made from a sustainable blend of recycled polyester and merino wool — the polyester adds durability and stretch, while merino wool helps regulate your temperature and keeps you cool in breezy weather.

Best shirt jacket for men.

Think of this rugged shirt jacket like a durable, transitional style move to carry you into September and October without missing a beat. The good news is, either the Indigo or Natural colorways of this stylish shirt jacket are on sale right now and ready for layering up with, say, one of the best men’s henleys or a comfortable moisture-wicking T-shirt. And because the design is so timeless, this shirt jacket (or “shacket”) also works nicely with the best men’s chinos or your favorite pair of jeans. Lest we forget, you can shop the for 35 percent off right now — what are you waiting for?

Style Pick of the Week: Flint and Tinder Bone Button Western Shirt – The Most Rugged Shirt for Fall

Most rugged shirt for men.

There’s no time like right now, an early September Saturday, to start really ramping up your assortment of the best style essentials for fall, right? That’s absolutely right, and if you read The Style Guide on the regular, you know that Huckberry is as great a source as any (and it’s one of the best online menswear shops around, after all). Of course, you likely know the brand from making rugged must-haves like the Flint and Tinder Waxed Trucker Jacket, but the entire lineup of Flint and Tinder menswear is also packed with, well, other must-haves.

Chief among those must-haves? The Flint and Tinder Bone Button Western Shirt, one of the best shirts for men and an outstanding way to switch up your shirting rotation from time to time. It hits all the right notes as far as classic Western shirts are concerned, and then some — starting with Western-style stitching and detailing throughout, right down to the back shoulder yoke. It only gets better from there.

Crucially, the Flint and Tinder Bone Button Western Shirt is made from a durable 100 percent cotton with a rugged natural nep design, and finished off with uniquely authentic burnt cow button snaps. Between that touch and the front button chest pockets (stitched in the Western style, of course), the Flint and Tinder Bone Button Western Shirt is about as durable, hard-wearing and authentic as it gets.

Of course, it’ll look right at home paired up with the Flint and Tinder Waxed Trucker Jacket or really, any essential pick from Huckberry this season. Go to it and layer up accordingly, my friends.

The Friday Read: The Best Labor Day Weekend Menswear Sales & Huckberry’s Fall Collection

Best Labor Day menswear sales.

Here’s the deal, my friends: It’s a special edition of sorts in today’s Friday Read, given that we’re — rather incredibly — rolling into Labor Day weekend and the official (unofficial?) start of fall. Or at least, early fall. If you’ve been reading the blog as of late, you’re hopefully well-prepared with some of the best fall menswear, like that of the rugged Huckberry Fall Collection (as seen at the top of the page).

Satchel and Page

If you’re not quite there yet? Well, there’s a plethora of men’s style essentials to go around in my roundup of the best Labor Day menswear sales. Now, because your time is important, and brief, I kept it relatively short — I’m talking all about the best Labor Day sales from 15 reliable, stylish brands, many of whom you’ve seen on the blog before. If not? Consider yourself in luck, because there’s no time like the present to shop the best fall menswear picks. For now, I’ll leave you to it — thanks for reading and happy shopping, my friends!

That’ll bring today’s Friday Read — Labor Day weekend sales edition! — to a close. For now, be sure to let me know via Twitter or Instagram if you scored any of the above deals or favorite picks. As for me, I’ll be on the lookout for an icy cold beer in Brooklyn as I enjoy the season opener for my Michigan State Spartans football program tonight. Go Green and thanks for reading!

The Thursday Buy: Get the Best New Sunglasses from Huckberry For Under $100

Just when you thought you had your wardrobe all squared away with the best style essentials for men, allow Huckberry to re-enter the fold and deliver the accessory you didn’t know you needed this early fall. The accessory in question? Why, that’s easy: Some of the best sunglasses for men, from a new in-house brand developed by the hard-working folks at one of the best online menswear shops.

Walden Sunglasses hit all the right marks in terms of style, functionality, price and design — how’s that for going four-for-four to close out summer? Make no mistake, you still need a pair or two of the best men’s sunglasses even as summer draws to a close — heck, you can make the argument you need to wear your favorite pair of sunglasses all year long, even in winter. Luckily, Huckberry’s Walden Sunglasses make it easy on you in every way possible. Let’s dive in, yes?

Best new sunglasses for men

Walden Sunglasses draw from vintage design inspiration (like the 1950s inspired Walden Woods Sunglasses, or the classic square look of the Walden River Sunglasses), and in the process, they strip away “unnecessary details in favor of simplicity,” as Huckberry says.

This, my friend, is great news for you. Along the way, the Walden Sunglasses use sturdy, durable and eco-conscious materials, like a recycled steel internal frame, nylon lenses made from materials like fossil carbon, and external frames made from bio-based content.

It’s an impressive approach to design that only gets better when you consider that these pairs are under $100, and they’re made to wear well with, say, plenty of Huckberry Bestsellers. If it seems like Huckberry thought of everything when designing your new go-to sunglasses, it’s because, well, they did. Secure your pair now for effortless early fall style, folks.