The Sunday Sale: Enter to Win This $10K Vintage Rolex at Bespoke Post With Every Dollar Spent

The concept is simple with today’s stylish, ultra-covetable discount: Spend more, earn more (chances to win, that is). It’s an investment proposition of sorts from the good folks at Bespoke Post, all-around purveyors of some of the coolest gear for guys, period.

That includes a monthly series of the best subscription boxes for men, but the possibilities are nearly limitless if you scour the site long enough — and they make and sell so much of the best gear for guys, that each purchase puts you in the running for something as enviable as it gets.

Bespoke Post teamed up with luxury watch authenticators and resellers Bezel on a Bespoke Post vintage watch giveaway, and namely, the chance to win a $10K vintage 1997 Rolex Submariner. How’s that for a heck of a deal, with one entry for every $1 spent?

The 1997 ref. 14060, 40mm Oystersteel Submariner is a modern marvel, complete with a black tritium dial with some subtle aging if you look closely. It’s a tantalizing prospect as far as a watch and a giveaway-worthy opportunity is concerned, complete with the chance to also take home $5K in cold, hard cash via the Bespoke Post vintage watch giveaway.

You’ve got until October 31st to enter to win (entry via purchase through Bespoke Post on some of the best gear for guys, that is).

As if that wasn’t cool enough, the watch itself comes with its original box and papers, while it’s billed as coming in excellent condition overall.

Throw in that extra cash for good measure — plus the simple opportunity to score some of your new favorite style picks of the season when you enter the Bespoke Post vintage watch giveaway, and you could make the case it’s one of the coolest, sharpest things the much-loved online retailer has ever done.

Let’s say we take a closer look at the Bespoke Post vintage watch giveaway via your online purchase, and may the best guy or gal win this handsome watch.

The Sunday Sale: Save More Than 30 Percent On Outerknown’s Best-Selling Blanket Shirt In Time for Fall

Outerknown Blanket Shirt review.

You might make the case that there’s not a more classic or quintessential fall style move than that of the hearty plaid shirt, a timeless go-to in matters of rugged style, easygoing good looks and dependable performance.

While some variations are made from thick cotton flannel or cotton chamois, there’s also something to be said for a modern update to an icon, and that’s where the Outerknown Blanket Shirt has made waves in recent years.

Part of the steadily growing and eco-conscious lineup at legendary surfer Kelly Slater’s Outerknown line, the Blanket Shirt in its many richly crafted cotton twill variations has become a fan favorite in the modern era, and it’s not hard to see why. In fact, to hear the brand tell it, the style is “Outerknown’s most beloved item for all seasons and quality that feels so damn good every time you throw it on.”

That’s high praise indeed, but in my experience, the hard-working Outerknown Blanket Shirt lives up to the hype, and then some.

Add in the fact that select colors of the utterly classic Outerknown Blanket Shirt (including Dusty Red Cusco Plaid as shown here) are on sale, and you’ve got a surefire recipe for seasonal style success, my friends.

The Outerknown Blanket Shirt is bolstered by the use of soft yet sturdy organic cotton twill that’s further accented by two useful chest pockets and nut buttons — it can be worn on it own comfortably, or else as a dependable overshirt atop everything from a garment-dyed pocket tee to a thermal henley.

You’ll notice that the casually rugged Outerknown Blanket Shirt comes in a vast array of colors and patterns, all the better to amp up your off-duty wardrobe when paired with faded blue jeans or tobacco-hued chinos (both favorites in my style rotation).

The Outerknown Blanket Shirt is also finished with a contrasting chambray inner collar and back fabrication, and it’s worth noting that best-selling styles like this tend to avoid the proverbial sale bin for most of the season.

And yet, with fall and its many layering options all around us, it’s worth taking a chance (a very well-considered, stylish chance) on the reliable and reliably stylish Outerknown Blanket Shirt at the right price. Good luck, and we’ll see you out there, my friends.

The Sunday Sale: These Gustin Selvedge Jeans Are Every Bit as Good as Advertised, at a Fraction of the Price

There are certain menswear staples that, if you ask me, are assuredly worth the investment, and a pair of the best blue jeans for men certainly qualifies. There are also levels to that investment, as with any grea style must-have.

While some jeans are more affordable and made with a blend of traditional cotton denim and modern stretch fabric, others are made from what you might call “the good stuff,” a truly out-of-this-world fabrication known as selvedge denim.

And my friends, the good folks at Gustin make some of the best selvedge denim on the market, and they do so at a fraction of the price compared to other high-end men’s blue jean companies.

Of course, if you read this Brooklyn style blog regularly, you’ll have come across thick, hearty, sturdy pairs of raw (unwashed or untreated) men’s selvedge denim over the years, and there’s a true difference in the way this fabric wears, ages and molds to your body over time.

It’s exciting stuff as you consider your rotation of menswear essentials, and the Gustin 75 Okayama Standard Jeans are a best-seller from the San Francisco-based direct-to-consumer menswear brand, which specializes with great care in stylish men’s blue jeans and more.

It can be a big leap to buy a pair of selvedge jeans for the first time (pay special attention to the sizing specs for these men’s selvedge jeans on the brand’s Web site), but you can rest assured that this pair of sanforized raw selvedge denim measures up in every possible.

The Gustin 75 Okayama Standard Jeans boast a dependable 14.5oz. fabric weight for multi-season wear, while they fade to a medium blue with more wear over time (after starting as a deep blue indigo, of course).

And here come the savings, too: Gustin notes these jeans are “typically priced at $278-$417 in retail,” yet you can find several sizes of the Gustin 75 Okayama Standard Jeans available now for just $199. In my experience, that’s stellar value for some of the best men’s blue jeans. Between the savings, the style points and the stellar quality, you might have just found your new favorite pair of men’s jeans in the Gustin 75 Okayama Standard Jeans.

The Sunday Sale: Upgrade Your Everyday Carry at Huckberry With This Rugged Filson Wallet

When it comes to your everyday carry essentials, it’s best to not mess about. That means the gear you reach for every single day (as the name suggests) had better be up to par in matters of fabrication, quality and durability, and that includes one of the best leather wallets for men — as well as your money clip, your leather key fob and more.

And the good news is, you can find those hard-working staple selections at a place like Huckberry, known around these parts and elsewhere for being one of the best online menswear shops around.

Of course, that means a wide array of gear and goods passes through the site’s digital shelves, all the while getting a significant markdown — take the Filson Tin Cloth Outfitter Wallet, for instance. The site dedicates itself to scouring the market for the best gear for guys, period, and this handsome wallet from the heritage designers at Filson certainly qualifies.

It’s now on sale for almost 50 percent off, and while stock is moving quickly, it’s not hard to see why the durable Filson Tin Cloth Outfitter Wallet carries on the company’s legacy in such fitting fashion.

Naturally, Huckberry notes that the company’s “waterproof Tin Cloth has been a hardwearing icon for a century,” with waterproof capability on both the interior and exterior of this stylish leather wallet, for good measure. The Filson Tin Cloth Outfitter Wallet also boasts a subtle Filson logo with a debossed finish, while this surprisingly sleek and strong wallet has space for as many as eight cards.

Nylon thread enhances the durable design of the eye-catching Filson Tin Cloth Outfitter Wallet, which boasts a two-tone rust colorway in a distinctive build that Filson seems to perfect with each new season.

While it might seem that your old wallet is up to par, it’s assuredly not built quite like the Filson Tin Cloth Outfitter Wallet — upgrade your daily carry selection at a site like Huckberry, one of the best online menswear shops you’re apt to find these days.

The Sunday Sale: Take 25 Percent Off Sitewide at the Triple Aught Design Equinox Shift Sale

In the crowded world of menswear, it’s always worth taking a closer look at a brand that’s committed in steadfast fashion to sturdy, overbuilt gear, in the best way possible. That ethos certainly rings true when it comes to my friends at Triple Aught Design, the San Francisco-based menswear brand with a deep focus on tactical, performance-inspired, absurdly rugged gear fit for situations on land, in the air, on the trail and across the globe.

Lofty praise though that might be, it’s selections like one of the best denim jackets, or one of the softest yet most durable cotton henleys, or even a pair of the best selvedge jeans for men, that cement the company’s vision centered around performance and style.

And that’s what makes the Triple Aught Design Equinox Shift Sale so worth shopping — for the next three or so days, take 25 percent off sitewide on a stylish, hard-wearing, rugged assortment of gear, from your new favorite denim jacket to a tactical field coat, expertly fitted jeans and chinos, sleek base layers and much more.

While there are certainly some exclusions when it comes to savings on durable, rugged gear aplenty, the Triple Aught Design Equinox Shift Sale is perhaps the best chance in a good while to equip yourself for the season ahead, be that with sharp cargo pants, the company’s famously tough Ranger Jacket or the sturdy, endlessly wearable Haven CPO Shirt.

It doesn’t hurt that the offerings up for grabs at the Triple Aught Design Equinox Shift Sale are perfectly suited for the season ahead: Think strong-yet-supple cotton twill shirting, tough-as-nails work pants, even hard-working bags and everyday carry essentials.

It’s almost the Triple Aught Design way, at least in my experience: If you can think of a seasonal adventure or scenario where things could be upgraded significantly through tough-yet-stylish gear, then I’d wager the Triple Aught Design Equinox Shift Sale has something for you across the next few days. 25 percent off on some of the best gear for men beckons.

The Sunday Sale: This Line of Trade Sweater from Bespoke Post is an Expertly Crafted Style Steal

Best fall sweaters for men.

As we move into the best season for layering and menswear overall, I’d urge you — like me! — to take a good look at your roster of menswear essentials. Hopefully, that roster includes pieces fit for layering like one of the best sweaters for men.

There’s a wide world out there when it comes to men’s sweaters, from the hard-working shawl cardigan to the office-ready V-neck sweater and the layering friendly merino wool crewneck, to name but a few options I personally love.

At times though, you need to up the ante even further with rugged texture and burly construction in mind. That’s where you’re going to find precisely what you need on this fine fall Sunday at Bespoke Post — enter the handsome Line of Trade Norfolk Waffle Sweater, a discounted steal that delivers plenty of great looks and functionality in a durable package.

The Line of Trade Norfolk Waffle Sweater, fashioned from a ribbed blend of cotton and acrylic for texture, stretch and softness, positively delivers the rugged good looks every collection of sweaters needs this season, from the ribbed crewneck collar to the ribbed cuffs for a perfect fit and eye-catching style.

And unlike wool sweaters, the Line of Trade Norfolk Waffle Sweater should prove able to be layered comfortable atop a long-sleeve tee and beneath a denim jacket, for instance — all without overheating, which is sometimes a concern with beefy wool sweaters.

The set-in sleeves are a prime example of craftsmanship, the kind not often found on a sweater that retails for less than $50 on sale. Bespoke Post even recommends you wear the hard-working, layering-ready Line of Trade Norfolk Waffle Sweater atop a buttondown shirt (say, a white Oxford shirt), and that look should deliver style that’s as casually rugged as it is ready for a date night on the town.

Available right now in both Green Oak and Charcoal Heather, either option provides autumn-approved versatility and variety, with the functionality and warmth to match. For the season at hand, it doesn’t get better in terms of savings than this stylish Bespoke Post sweater.

The Sunday Sale: Save a Whopping 70 Percent On the Perfect Men’s Fall Shirt at Billy Reid

Best fall shirts for men.

If you follow this style blog on the regular, it might seem that we’ve been preparing for fall for weeks at a time — and, well, that’s largely true, since opportunities arise rather quickly to amp up your #menswear rotation for fall.

Starting with shirting (and starting with savings on shirting, no less) is as good a way to go as any, and the menswear masters at Billy Reid have precisely what you need to add a fresh outlook to your style roster heading into a new season.

It gets even better: One of the most versatile shirts for men is a whopping 70 percent off via the award-winning Alabama menswear designer, and although it might sound too good to be true, it’s certainly worth a closer look.

A holdover from last season, yet every bit as wearable now and into fall as any offering from the designer’s namesake brand, the Billy Reid Shadow John Shirt is meticulously crafted and features a multi-season, linen-like weave. Don’t let that fool you when it comes to the Billy Reid Shadow John Shirt (marked down below $70 right now!).

Helpfully, the shirt boasts easygoing everyday construction, with the kind of fit that looks especially great untucked with expertly faded blue jeans — but the real kicker with the crisply cut Billy Reid Shadow John Shirt is its fall and winter-ready Honey Plaid design, with a tasteful faded melange look.

All the details have assuredly been accounted for when it comes to the reliably stylish Billy Reid Shadow John Shirt, which also boasts a split spade chest pocket in a contrasting variation on the shirt’s handsome plaid pattern.

And although it’s woven from 100 percent cotton, the weave itself is looser — that means it won’t prove too thick or too stuffy to wear beneath a shawl cardigan or underneath a classic V-neck sweater this fall and winter.

The company recommends wearing it alongside a pair of the brand’s stellar chinos and elegantly rugged leather chukka boots, and when it comes to the Billy Reid Shadow John Shirt, I’d tend to agree.

And the best part is, I’d wager you’ll find plenty of ways to wear such an affordable yet stylish shirt, including atop a thermal henley alongside indigo selvedge jeans this fall and winter. With a shirt as well-fitting and well-crafted (and as affordably priced!) as the Billy Reid Shadow John Shirt, the possibilities in your style lineup are endless when it comes to one of the best shirts for men. Shop and save while sizes are still up for grabs, my friends.

The Sunday Sale: Take an Extra 15 Percent off the Best Men’s Gear and Menswear at Huckberry’s Labor Day Sale

Huckberry Labor Day Sale 2025.

Some offers in the world of the best menswear and gear are too good to overlook, even if you’ve already spent at least part of this fine Labor Day weekend taking care of some online shopping needs. The reason why this sale offer is simply too good to pass up?

Well, it’s the continuation of as stellar a summer close-out as any: The Huckberry Labor Day Weekend Sale slashes prices on some of the best gear and men’s style essentials on the market, from rugged Western shirts to ornate leather belts, versatile leather sneakers, crisp Aviator sunglasses, stylish stretch shorts and much, much more.

Even if you’ve given the Sale section a look already as you scour the market for the best Labor Day sales, it’s worth looking again, because the Huckberry Labor Day Weekend Sale goes a step further and gives you an additional 15 percent off already discounted sale items.

That means these are simply some of the best prices of the summer on selections that you can buy now, wear now and keep handy (for the most part) heading into fall.

For instance: The Relwen Yarn-Dyed Poplin Shirt is a multi-season favorite that will serve you well now and in the months ahead, as will selections like Huckberry sunglasses and leather sneakers and boots from brands like Astorflex.

Each of these selections are up for grabs now through tomorrow night (that’s September 1st!), so the waning hours of the Huckberry Labor Day Weekend Sale deserve to be shopped ASAP. If you know, you know — and now, you know that plentiful savings abound at Huckberry. Find your new favorite seasonal must-haves while the gettin’s still good, folks.

The Sunday Sale: Bespoke Post Is Now Offering a Discount on these Rugged SeaVees Sierra Adventure Boots

Best sneaker boots for men.

Stepping from one season from the next — from late summer into very early fall — is often as simple as making your transition from the ground up.

So while items like classic blue jeans and a sturdy henley are men’s style essentials well-suited for multiple seasons, it’s sometimes a wise move to work a pair of rugged leather boots (or in this case, stylish sneaker boots) back into your rotation slowly but surely — as summer wanes and fall approaches, of course. And there might not be a pair of men’s sneaker boots as well suited for the moment at hand as the SeaVees Sierra Adventure Boots.

As you might recall if you read this Brooklyn style blog frequently, Bespoke Post and SeaVees teamed up on the perfect pair of men’s winter boots at the end of 2023 – as luck would have it, select pairs of the handsome SeaVees Sierra Adventure Boots are still up for grabs as summer draws to a close.

The SeaVees Sierra Adventure Boots are now 50 percent off, with sizes going fast in two exclusive Bespoke Post colorways, designs that the upstart NYC retailer says were “inspired by the SeaVees ‘60s-era “California cool,” reflecting the shared commitment to quality and innovation from both companies.

The result? An on-sale pair of rugged, adventure-ready footwear that starts with a durable oiled leather upper blended with water-resistant Ventile cotton canvas. The SeaVees Sierra Adventure Boots also boast a hard-wearing natural rubber lug outsole for maximum traction on hiking trails, rocky coastline and dewy fall morning grass, while eye-catching touches like rawhide leather laces finish off the dependable SeaVees Sierra Adventure Boots in stylish fashion.

The design takes its cues from SeaVees’ popular Mammoth and Mariner Boots, but features touches exclusive to Bespoke Post, including an embossed heel logo. With an ankle-high design and sturdy construction, these hard-working boots are well-suited for everything from late summer yard work to early fall tailgates and brewery beers.

And for 50 percent off right now, it’s almost an imperative that you score a pair of the SeaVees Sierra Adventure Boots while they’re still around (although take heed, since sizes are rolling away quickly). Welcome the season at hand from the ground up, as we’ve said, and you’ll be more ready for fall than ever before.

The Sunday Sale: This Bonobos Performance Polo is an On-Sale, Ultra-Easy Style Upgrade

Best polo shirt for men.

There are certain style upgrades that are so easy to make, you almost might forget you even made said upgrade. In my book, that can be something as simple as swapping an ultra-soft, laidback polo shirt in place of a stretch dress shirt or even a T-shirt, and that’s where the Bonobos Pima Performance Polo makes the ultimate difference.

You’re getting all the benefits of a breezy top layer, one you can wear with chino shorts, linen trousers or light wash jeans, yet the design comes with the polish of a crisp collar.

And a stylish men’s polo shirt like the handsome Bonobos Pima Performance Polo still offers plenty of mileage as far as wearability is concerned — starting right now and rolling past Labor Day, especially if you find yourself needing to dress for Casual Fridays or a day at the links.

In my experience, a comfortable, moisture-wicking polo can also prove the ideal travel shirt — it moves with you, it’s soft to the touch, it stands up to a long day’s travel and it even looks, dare I say it… a touch nicer than an average T-shirt as you move through the TSA Precheck line.

Yes indeed, there’s much to love about the Bonobos Pima Performance Polo, including the fact that it’s on sale right now through the famed New York City retailer.

The Bonobos Pima Performance Polo comes in a useful, lightweight 50-50 fabric blend of Pima cotton and proprietary performance acrylic fabric for softness, stretch and breathability, while the option to pick one up in either Slim or Standard fits provides variety for every body type (helpfully, sizes also run from XS to XXL).

Right now, the Bonobos Pima Performance Polo in a highly wearable Light Beige retails for under $60, but a host of other colors are yours for the taking for just $75 — a steal in its own right. Consider scooping up at least one color of your new favorite polo shirt, then wearing said shirt underneath a lightweight navy blazer or else on its own with stretch chino shorts to end summer — how’s that for a style steal you can make work for you right now? Cheers to shopping and saving in style, my friends.