#OOTD: How to Dress for a Fall Evening On The Town — The Right Way

So, you’ve done your research, you’ve made your reservation and you’re looking forward to an evening at your favorite cocktail bar, a secluded whiskey den or an old-school speakeasy — if it’s a special occasion, and even if it’s not, I’d bet you’re now on the hunt for what to wear out on a fall evening. Date night, weeknight, post-concert, pre-dinner … the right #OOTD can go a long way in terms of solidifying rock-solid fall and winter style, and I’m here to help you put it all together.

My go-to in a situation like this is usually my trusty Flint and Tinder Trucker Jacket, to go along with my neighborhood whiskey bar, Sycamore Bar and Flower Shop, but perhaps you want to step it up a notch (NYC’s The Dead Rabbit ought to do the trick!). Wherever you go, the best men’s style essentials are crucial in that regard — we’re talking subtle but stylish, considered and composed. Witness our picks below, from slim black jeans — sharp but not too stuffy — to rich cognac leather boots and more unique touches suited to an evening on the town. Case in point: Layers like a rugged work jacket and slick-but-classic touches like an organic cotton Oxford shirt. Of course, you’ll also find the best leather dress watch in this ensemble for the taking. The key here is putting together a look that’s sharp, versatile and comfortable — in my mind, this is a get-up you could wear to the office, and then right out to dinner afterwards. It all comes together in a fall-friendly black-and-tan combination that’ll quietly turn heads, and hopefully, impress your company. Like the look of this? Feel free to reach out to me on Twitter. 

Pairing up rich leather boots with dark denim and a workwear jacket — all in the pursuit of great whiskey.

  • The Slim Dark Denim: Bluffworks Travel Jeans 2.0 in Black Dark Wash, $98 — Invest in the best with these slim black jeans in a flattering fit — built-in stretch and handy hidden pockets ensure your everyday carry essentials are taken care of, while the silhouette is dressy enough for a refined bar or speakeasy.
  • The Jacket: Vetra French Moleskin Jacket, $229 — A modern update to the classic workwear silhouette, this rugged work jacket provides a nice contrast to your slim black jeans and white Oxford shirt — it’s casual but not too casual, and visually interesting all the same.
  • The Shirt: By Garment Makers Organic Shirt, $78 — A crisp, classic white Oxford shirt is a foolproof move, no matter the occasion — and when the occasion involves enjoying an Old Fashioned alongside pleasant company, well, you’d best look the part. This might just be the best Oxford shirt to snap up for fall and winter.
  • The Boots: Moral Code Jacques Wingtip Boots, $249 — The right leather boots can really tie an outfit together — and the pair of the moment has to be this pleasingly refined pair from Moral Code, featuring classically rugged brogue detailing. Certainly sharp enough for a distillery, a speakeasy or your favorite cocktail bar.
  • The Watch: Carpenter Watches G2 Brooklyn Gent, $724.98 — For a refined evening out and about, only the best leather dress watch will do. Carpenter Watches makes a nuanced, subtle and yet visually interesting timepiece, to say the least.
  • The Everyday Carry Essential: Rustico Traveler’s Notebook and Wanderer Pen, $120 — Especially when visiting a new locale (and even when visiting an old haunt), a stylish leather notebook will come in handy when inspiration strikes — or when you simply want to remember that exact cocktail recipe.
  • The Socks: Taylor Stitch Merino Socks, $22 — Don’t discount the importance of stylish socks, especially this comfortable, anti-odor pair from Taylor Stitch.
  • The Leather Wallet: Bellroy Slim Note Sleeve, $89 — Stay sleek, streamlined and stylish with a slim leather wallet that keeps your valuables safe — no extra bulk required.

From top to bottom, head to toe, I’d say you’re not going to go wrong with this look for an evening enjoying your favorite cocktails. We’re keeping your look fresh and modern by swapping a blazer for a rugged work jacket, and then pairing up that piece with a classic white Oxford shirt for go-anywhere seasonal style (and yes, you can wear that combo at the office, too). From there, slim black jeans help carry the day by providing a nice mix of edgy style and a sharp silhouette — again, critical if you’re visiting a hip haunt in town. Of course, the right pair of rugged leather wingtip boots has to be what makes this outfit all work; the pair shown here from Moral Code are practically begging to be worn out on a fine fall or winter evening. Excellent essentials are also critical to keeping your ensemble streamlined and stylish, from a slim leather wallet to stylish socks and of course, stylish leather notebook to jot down tasting notes, recipes or random musings. And when hitting up your favorite cocktail bar, the small details seemingly get a bit bigger — take your wristwatch, then upgrade it from the average with the best leather dress watch — then prepare to watch the compliments roll in. This ensemble might look a bit different from the look you were first envisioning, and in my mind, that’s A-OK — it’s all about unique style and nuanced, subtle details. This look might even make your whiskey taste that much better — but again, that’s all up to you. Thanks for reading, and happy whiskey hunting (and tasting!).

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