If you’ve kept up with the blog in recent weeks, months and years, you’ll see that in my many freelance writing pursuits, I tend to wear.a lot of hats. From keeping up with the best menswear to buy from Huckberry to covering a range of new whiskey releases (including the debut of a new Old Grand-Dad expression!), it’s been a great way to turn my passions into a reality and a seemingly daily series of adventures.

Yes, I certainly am grateful, and it all tends to come to a head — in the best way possible — at times, especially this past week as I trekked once more down to Louisville and the heart of American whiskey country.

This trip was at the intersection of two of my favorite things: Rugged, distillery tour-approved menswear from Huckberry, and the debut of a special, limited-edition bourbon from cult favorite distiller Penelope Bourbon. Naturally, the release of the luxurious new Penelope Bourbon 2024 Estate Collection presented more than ample reason to hit the road to Louisville’s sleek, chic 21C Hotel.

Within the stylish confines of the hotel-meets-art-gallery, Penelope Bourbon co-founders Mike Paladini and Danny Polise toasted the occasion, showcased the whiskey itself and rang in the exclusive release in fine fashion.

I was outfitted for each occasion — a more rugged distillery visit, and a refined cocktail party — accordingly. Huckberry menswear, especially Flint and Tinder 365 Pants and durable brown leather boots, met the moment properly, while a double-breasted Wax London blazer (shown below) was an elegant way to suit up for the evening’s festivities.

It felt like proper attire, all the better to get the most out of the ultra-exclusive release hailing from 24 barrels of experimental Straight Wheat Whiskey (aged between 9 and 11 years, for those keeping score at home). A consumer sign-up waitlist was an instant hit, while the release itself drew crowds to the distillery to score a bottle — there’s no finer way to ring in Thanksgiving next week, and the holidays in general, with some standout new bourbon.

For now, consider it a nice complement to a stylish weekend, with two blog posts covering the best new menswear headed your way in short order here on the blog — thanks for reading and for following along!