Style Pick of the Week: Billy Reid Indianola Chukka – A New Classic Pair of Fall Boots

Best fall chukka boots for men.

I’d guess that, if you read the blog on the regular, your wardrobe has more than a few of the best men’s style essentials, particularly on the footwear front when it comes to, say, the best chukka boots for men. But what about when things get shaken up a bit and your favorite menswear designer re-enters the men’s footwear space in a big way, just in time for fall?

That’s what Alabama-based Billy Reid is doing with the reintroduction of Billy Reid footwear, which should provide plenty more competition for your rotation of the best men’s boots. Let’s take a closer look, shall we?

Best leather moto boots for men.

Now, I already wrote about new boots from Billy Reid yesterday on the blog, but let’s talk about a highly versatile pair in particular. After all, the collection includes just two new pairs for now: First up, we’ve got the Billy Reid Paglia Moto Boots, made in Italy from overdyed pebbled leather with a slight edge to it.

Those boots are sleek and dressy yet road-ready, but we’re here today to talk about the Billy Reid Indianola Chukka Boots. They’ve certainly got the pedigree you’d expect from a designer known for making one of the best pea coats and the best dress shirts on the market,

The Billy Reid Indianola Chukka Boots are very nearly what you’d precisely expect from a designer with a commitment to timeless style and craftsmanship. Light brown kudu leather gives these a bit of texture right out of the box, but these stylish men’s chukka boots will develop their own distinctive patina over time.

Best men's chukka boots.

Comfort flex soles provide ease of movement out of the box — these shouldn’t feel overly stiff or uncomfortable. The famed menswear brand has even burnished the toe cap for a bit of a rugged-meets refined feel when it comes to the Billy Reid Indianola Chukka Boots.

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The profile on these should prove streamlined enough to dress up with the best corduroy pants or your favorite pair of chinos, yet classic brown leather chukka boots also wear very well with timeless dark blue denim.

Keep in mind that although the Billy Reid Indianola Chukka Boots are an investment (they’ll set you back $448), you’re getting a truly classic pair of men’s boots that can be dressed up or down, a pair that’s made in Italy from the finest materials on the market. It sounds to me like your new favorite pair of chukka boots could be just a few clicks away.

The Friday Read: New Men’s Footwear from Billy Reid & Classic Fall Whiskey from Castle and Key

Billy Reid men's footwear.

My friends, here we are on the brink of what promises to be another most excellent fall weekend — it might be a blustery and rainy one in New York City yet again, but I’m equipped with the proper fall style essentials for the task at hand, including my trusty Shinola leather watch (and many more).

Best chukka boots for men.

With today’s post (or yesterday’s post on the best shirt jacket for men), hopefully, you feel the same way. On that note, let’s talk some of the best fall boots — and from an unlikely source, at least until recently: Billy Reid. You see, the famed Alabama-based menswear designer, one of my favorite brands and menswear companies, period, hadn’t made footwear in recent years — that all changes now though, with two classic styles that should cover plenty of style scenarios.

Billy Reid footwear now includes both a sleek pair of leather moto boots and a stylish pair of chukka boots, and you can certainly look for much more on two of the best pairs of shoes for men this weekend on the blog (hint, hint). I don’t know about you, but it’s an exciting prospect that one of the best menswear designers in the country is now making some of the best men’s boots — it’s almost worthy of a toast, don’t you think?

And a toast or two was once again the focus of my week, as I trekked to the lovely, rolling hills of Kentucky and Bourbon Country itself. The mission? Visit the historic Castle & Key Distillery outside Lexington as part of my spirits and freelance writing pursuits, a trip that included a tour of its famed grounds and plenty of sipping on Castle & Key Restoration Rye.

Speaking of rye whiskey, you should also check out my latest Maxim.com feature on an excellent new rye whiskey from the spirits innovators at BHAKTA. But in the meantime, back to Castle & Key.

We also visited charming Lexington restaurants like Eppings on Eastside, and spent a very memorable day sipping bourbon and watching horse racing at the iconic Keeneland race track. Consider this just a taste of what’s to come regarding this heralded, fast-growing spirits company.

It was once again another reminder that I’m so fortunate to do what I do, be it covering menswear on this very blog or trekking around the country visiting the best distilleries and menswear factories in the business.

For now, I’m going to put some Billy Reid men’s boots on my wish list, and later, I’ll be enjoying some Castle & Key bourbon on a crisp fall night. I hope you consider doing the same! Cheers, and thank you for reading!

See Now, Buy Now: Billy Reid’s Leroy Shirt Jacket is the Perfect Early Fall Layer

Best men's shirt jacket.

In my experience, the best menswear essentials are the pieces that, as I often say, can do more than one thing well — the sort of picks made to go the distance, like the Billy Reid Leroy Shirt Jacket. The famed Alabama brand, led by Reid himself, nails the perfect balance between rugged and refined, including one of the best shirt jackets for men.

And this particular number is one of the best layers for shoulder season: Those nights when it’s breezy and a touch brisk, yet not quite chilly enough for your winter outerwear rotation. The Billy Reid Leroy Shirt Jacket is part of the Fall 2023 Billy Reid Collection, with enough durability to be worn now and into the months ahead in just about any way you see fit.

Best shirt jacket for men this fall.

The key here is the use of waxed cotton fabric from Scottish fabric maker Halley Stevensons, which is then turned into a remarkably rugged piece lined in cotton for softness and finished with a double-layer collar for durability.

The vintage match pocket on the Billy Reid Leroy Shirt Jacket is an exceedingly cool touch, proving that great style (and versatility) is all about the details this season (and beyond). Find out for yourself with the Billy Reid Leroy Shirt Jacket today, my friends.

Style Pick of the Week: Billy Reid Bold Plaid Tuscumbia Shirt – A Refreshed Version of A Classic

Billy Reid Tuscumbia Shirt review.

When I shop my favorite menswear brands, I tend to look for consistency and reliability, and of course, a distinct sense of style. That’s where Billy Reid often comes into play: The classic-meets-modern Alabama menswear brand makes iconic pieces with a fresh sensibility, be it the best shirt jacket for breezy nights or a rugged indigo Western shirt.

They also have their own lineup of tried-and-true classics, like the flagship Billy Reid Tuscumbia Shirt. Here’s where it gets even better: They update some of the brand’s best pieces in every season in new colors and fabrications, each cooler than the last, like the Billy Reid Bold Plaid Tuscumbia Shirt.

It arrives just in time for fall, and it’s a nice change of pace from a more standard (yet always classic!) blue or white Oxford shirt, for instance. The fun doesn’t stop there, though.

Best men's shirt from Billy Reid.

The iconic modern brand already calls the Billy Reid Tuscumbia Shirt a “cornerstone of lived-in luxury,” what with its use of custom brushed plaid cotton (in the case of this shirt). The plaid pattern itself on the Billy Reid Tuscumbia Shirt is also rich and visually appealing, with plenty of layers to it.

That gives it a bit of an edge in terms of style over other more classic red plaid shirts, for instance — the Billy Reid Tuscumbia Shirt is crisp enough to wear beneath your favorite fall blazer in dressier style situations for the season ahead. The next time you need a shirt that refreshes an already-iconic design, opt for this number from Billy Reid.

See Now, Buy Now: This Billy Reid Knit Jacket is a Perfect Layer for Cool Summer Nights

Best lightweight shirt jacket for men.

Part of bulking up your wardrobe of menswear essentials (at a proper pace, not too suddenly!) is all about preparation, and about building a rotation that’s got you ready for just about anything. That holds true for the dog days of summer, and especially if you find yourself squeezing in one last beach vacation, for instance.

Here’s the rub: While it might be blazing during the day, it’ll cool off at night, and whether you’re on your back patio or sipping a cold beer around a bonfire, you’ll need the right gear for the job at hand. Enter one of the best shirt jackets for men, a crucial piece you can wear with ease now and on into fall.

Best shirt jackets for men.

And of course, you can trust one of your favorite menswear brands to deliver a reliable option. That’s where the Billy Reid Summer Fleece Knit Jacket is going to exceed expectations in terms of comfort and rugged style.

Part tailored jacket, part sweater, all versatility.

It doesn’t hurt that one of the best men’s shirt jackets can pull double-duty at home or on the road, particularly one made from a soft, sweatshirt-like cotton fleece. It’s also constructed similar to a handsome Billy Reid shirt, with geometric flap pockets, elbow patches and antique brass snaps — assuredly, the Billy Reid Summer Fleece Knit Jacket is a major upgrade from a beach shop hoodie.

Wear it over a breezy cotton T-shirt or your favorite henley, but just make sure the Billy Reid Summer Fleece Knit Jacket is close at hand in the next few weeks ahead. Oh, and did I mention it’s on sale? Sounds like a deal worth shopping right now.

The Thursday Buy: The Billy Reid Indigo Western Shirt is a Rugged, Refined Summer Classic

Billy Reid Western Shirt.

One of the things I love the most about the menswear world is seeing how brands put a new spin on their own time-honored favorites. And for my money’s worth (and in my own experience wearing the brand!), American menswear stalwart Billy Reid‘s namesake brand does as stellar a job at this as anyone.

This holds especially true for subtle, straightforward picks like one of the best men’s T-shirts, and it holds true for styles that are a bit trickier to perfect, like a stylish buttondown shirt. Make no mistake, it’s hard to improve upon a modern classic like the Billy Reid Western Shirt, which has been in the company’s rotation (and Billy’s personal wardrobe) for more than two decades.

And yet, one glance at the Billy Reid Indigo Western Shirt tells you all you need to know: The award-winning brand has indeed managed to improve upon a classic, and that’s just terrific news for your summer wardrobe.

Best denim shirt for men.

This exceedingly handsome shirt is part of the new Billy Reid Indigo Capsule, which harnesses the magic of indigo dye and turns it into a stylish offering of T-shirts, ultra-soft sweaters, buttondown shirting and more. The Billy Reid Indigo Western Shirt is a standout of the entire capsule, with a deep indigo color, contrast plaid stitching and genuine dark horn buttons.

Best indigo denim shirt for men.

It should come as no surprise that Billy gets all of these details correct, and throws in a few more for good measure. The flap chest pockets boast a unique spade shape, and heirloom ribbon detailing is a subtle touch beneath the bottom shirt placket. Of course, the Billy Reid Indigo Western Shirt is a winner every single step of the way.

Part tailored jacket, part sweater, all versatility.

Take heed, though. All of this ultra-premium construction comes at a price, and Billy Reid is offering up this long-lasting shirt for $228 right now online. If you ask me though, most anything from Billy Reid is worth investing in, so shop accordingly this week. Thanks for reading, my friends!

The Tuesday Steal: Billy Reid’s Short-Sleeve Tuscumbia Shirt Is On Sale for 30 Percent Off

Best short-sleeve shirt for men to wear this summer.

If it seems like I’ve been talking an awful lot about Billy Reid menswear in the past few days, that’s because, well, I have. It’s not for nothing, though: Right now, the Billy Reid Summer Event runs through this coming Thursday, so there’s quite literally never been a better time to score a few new favorite summer style essentials at standout deals (try 30 percent off, my friends).

Let’s dial it in a little bit more today, though, as one of the best men’s shirts for summer is up for grabs via that outstanding sale. That shirt would be the Billy Reid Tuscumbia Short-Sleeve Shirt, which is — as you might have guessed — a summer-friendly iteration of the brand’s best-selling Tuscumbia Shirt.

The key here is the use of yarn-dyed linen in a custom plaid colorway for a washed-out, pleasantly breezy summer feel, and the details only get better from there.

Best men's short-sleeve shirt.

The Billy Reid Tuscumbia Short-Sleeve Shirt features a standard fit for an easygoing feel, while the collar forgoes a more casual buttondown design in favor of a straight collar. The impact is a breezy shirt that even looks polished enough to wear underneath your favorite summer blazer, sans ties.

Of course, you can also style the Billy Reid Tuscumbia Short-Sleeve Shirt on its own with stylish Billy Reid shorts for plenty of summer weekend shindigs, and it still looks crisp enough to wear with your favorite pair of chinos. However you choose to wear the Billy Reid Tuscumbia Short-Sleeve Shirt, it’s a guaranteed summer style winner, complete with a great price tag (until Thursday!) to match.

See Now, Buy Now: This Billy Reid Trucker Jacket is an Affordable Summer Style Move

Best trucker jacket for men.

Summer might seem like an obvious time to take a more breezy approach to dressing, what with temperatures on the climb day in and day out. But there’s also an opportunity to layer up on cool nights with one of the best trucker jackets for men.

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It’s all the better if the trucker jacket in question comes from A) One of the best menswear brands on the market and B) Can be bought right now for a very nice discount indeed. I’m talking, of course, about the Billy Reid Tupelo Trucker Jacket, which is currently part of the Billy Reid Summer Event.

It’s part of select styles marked down by 30 percent right now, but take heed: The sale only runs until Thursday, and the Billy Reid Tupelo Trucker Jcket is assuredly a rugged men’s jacket worth scoring right now. In fact, today’s must-have trucker jacket retails for just $243, marked down from $348.

Best men's trucker jacket to buy now.

The key with this jacket is the summer-ready fabric, which just so happens to be breezy, pre-washed linen. It’s a nice change of pace from heavier denim jackets, the kind that might not work as well as a layering piece on a hot summer day. The details, as with other Billy Reid menswear essentials, are on point when it comes to the Billy Reid Tupelo Trucker Jacket.

Billy Reid trucker jacket for men.

Those details include antique brass tack buttons for a handsome touch of contrast against the navy linen, plus interior jacquard ribbon stripe detailing. The fit on the Billy Reid Tupelo Trucker Jacket should prove classic but nicely tailored, with enough room for layering it over everything from a rugged Billy Reid henley to a classic Billy Reid men’s shirt.

The next time you could use a breezy layer on a cool summer night, make sure it’s the Billy Reid Tupelo Trucker Jacket you’re wearing — and do yourself a favor by saving some cash on that purchase right now.

The Sunday Sale: Save 30 Percent on Menswear Classics with the Billy Reid Summer Event

Billy Reid Summer Event

This Sunday, it’s like I always tend to say here on the blog: The chance to score menswear essentials on sale, and pieces you can wear right now and for years to come, isn’t an opportunity to pass up.

If ever you’ve read the blog, and if ever you’ve shopped the enviable assortment of stylish menswear at Billy Reid, from classic chinos to one of the best men’s peacoats to one of the best men’s shirts, you know that certainly holds true.

But here’s a little something else worth keeping an eye on right away: The Billy Reid Summer Event, which runs into next week and offers the chance to save 30 percent on select styles from the famed Alabama-based menswear designer.

What exactly is on offer right now at the Billy Reid Summer Event? A little bit of everything, from the Billy Reid Tuscumbia Shirt (a certified classic) to a rugged Billy Reid trucker jacket tailor-made for breezy nights this summer. Bear in mind that the Billy Reid Summer Event only runs until this coming Thursday, June 29th, so it’s in your best interest to strike while the iron’s hot and save big money on stylish summer menswear. Cheers, my friends.

The Thursday Buy: Billy Reid’s Hybrid Swim Shorts Are the Go-Anywhere Pair to Wear All Summer

Best hybrid swim shorts for men.

These days, it seems everything in your wardrobe of menswear essentials serves a dual purpose, and that’s not a bad thing. In my experience, the more versatile your favorite pieces can be, the better. That goes for your chambray shirt (either a rugged shirt jacket or a stylish swerve with a blazer), as well as more beach-ready pieces.

Take the Billy Reid Moore Hybrid Swim Shorts. They look like a standard pair of classic chino shorts — the kind you might wear with a stylish denim shirt from the famed Alabama designer — but there’s so much more to them than meets the eye.

You’ll find them, first and foremost, in the always well-stocked Billy Reid New Arrivals section, and that’s where our journey (and your journey to finding your new favorite swim trunks — or shorts!) begins.

With the Billy Reid Moore Hybrid Swim Shorts, it all comes down to the fabric. That fabric, of course, is a 100 percent quick-drying nylon material, yet from afar, these stylish hybrid shorts look like, well, classic chino shorts. They’ve even got sharp details like a flap coin pocket at the waist, not to mention side slant pockets for a clean and dressy look.

Best hybrid swim shorts for men.

Plus, the Billy Reid Moore Hybrid Swim Shorts come in a cool textured black pattern, or a more classic khaki. If you want to lean more closely into the timeless stylings of chino shorts, opt for khaki. If not, opt for the patterned black option — yet, there’s really no wrong way to go with the Billy Reid Moore Hybrid Swim Shorts.

The great thing is, these stylish hybrid shorts pair up as easily with a USA-made T-shirt as they do with your favorite linen shirt from Billy Reid. As the designer says, from the beach to the bar, you’re covered with these dependable-as-can-be shorts.