The Thursday Buy: Shop Huckberry’s Annual Pappy Van Winkle Giveaway Right Now For a Chance at $12K (And Rare Bourbon)

Huckberry Pappy Day 2024.

My friends, the time is now upon us once more. Or rather, if this caught you off guard, it’s time to hit the pause button and head over to Huckberry to shop a deal that only comes around once a year: The famed retailer is giving you (yes, you!… and me!) a shot at some serious cash and some ultra-serious bourbon.

Pappy Van Winkle Family Reserve Bourbon.

The maker of your favorite trucker jacket, the perfect pair of jeans and some of the best men’s boots on the market (among many other things, naturally) is bringing back its 11th Annual Pappy Day, a heck of a deal for lovers of rugged fall fashion and some of the best whiskey on the planet.

Here’s the deal: Now through September 26th, spend $75 on any U.S. order of the best menswear and gear from Huckberry, and get entered to win $12K in cash and a bottle of the covetable Pappy Van Winkle Family Reserve 20 Year.

How’s that for a standout deal on your new favorite fall menswear (and your new favorite bourbon)!? If you ask me, not much more needs to be said today, although might I recommend picking up a pair of the best men’s Chelsea boots or the iconic Flint and Tinder Waxed Trucker Jacket?

Here’s wishing you all the best of luck, the best of shopping some new seasonal style favorites, and hopefully, a toast with the best bourbon on the market. We’ll see you all tomorrow, my friends — now, start that shopping spree.

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!