#OOTD: Wear This New Menswear to Your Next Coffee Date

Just getting back into the dating game (or still hanging in there?), and wondering what to wear on your next coffee date? Or, looking for a way to switch up your dating routine — in style? Today’s #OOTD has you covered. We’ll start things off with a versatile denim jacket from Taylor Stitch, and then go from there. Depending on where you live — even neighborhood by neighborhood here in Brooklyn — maybe you’ve got a favorite coffee shop; maybe, you’ve also got a partner (or a new potential partner!) who’s a coffee aficionado. Thus, hit up that coffee shop, dive into your favorite coffee, listen to some amazing music, and enjoy yourself — dressed in style, of course. It’s a casual, laidback setting that still requires you put your best foot forward, and today’s menswear essentials certainly reflect that.
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Since it’s likely a weekend date, we’re going with casual, cool picks that exude versatility and confidence — nothing too fancy, nothing too over-the-top. Take a rugged denim jacket, then pair it up with pieces you’ve likely already got in your closet: Your favorite Oxford shirt, a classic pair of tan chinos, and stylish chukka boots that can go anywhere. I think you’ll find this is the sort of outfit you can mix and match — switch out the classic Oxford shirt for a chambray shirt or a stylish graphic tee, if you feel so inclined. Just remember: Confidence often starts with what you’re wearing and how you’re feeling — dress accordingly, and good luck out there!

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The casual, cool, confident #OOTD to wear on your next coffee date.

  • The Jacket: Taylor Stitch Long Haul Jacket in Organic ’68 Selvage, $188 — Exceptionally versatile, casual and cool enough for a coffee date, and quite possibly the best denim jacket on the market — that’s Taylor Stitch for you.
  • The Shirt: Flint and Tinder Garment-Dyed Oxford, $108 — With just enough polish and plenty of casual style thanks to the garment-dyed finish, this classic Oxford shirt is almost a no-brainer for a casual coffee date.
  • The Chinos: Flint and Tinder Cool Chinos, $98 — Just as with your classic Oxford shirt, a timeless pair of American-made chinos are a fool proof way to stand out quietly and stylishly.
  • The Classic Chukka Boots: Astorflex Greenflex Chukka Boots, $165 — A pair of durable, stylish chukka boots are another menswear classic that just make sense if you want to project a confident, stylish vibe (which, yes, you do!).
  • The Watch: Jack Mason Solar Field Watch, $375 — This solar-powered watch is a total head-turner and conversation starter, in a good way — people certainly notice if you’re wearing a stylish watch, and this one just so happens to be quite unique.
  • The Everyday Bag: Filson Dryden Ballistic Nylon Brief, $175 — Let’s say this coffee date is the first stop on the day’s errands or work — haul your everyday carry essentials in this durable Filson brief (plus, it’s another head-turning accessory).
  • The Grooming Essential: Bespoke Post Lather Box, $45 — If you feel so inclined, you can sign up for Bespoke Post and get the keys to a clean shave for your next date — crucial, if you happen to be a non-beard wearer.
  • The (Other) Grooming Essential: Duke Cannon Big Ass Bear Soap, $9.50 — You want to look, feel & smell your best every day — particularly on a first date, even if it’s just an afternoon at the coffee shop. This Duke Cannon soap, made with Deschutes’ Fresh Squeezed IPA, is essential.

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We threw a lot at you there, from a stylish outerwear upgrade to some new grooming essentials — how do you feel? Ready for that coffee date? The key is dressing for the occasion in a way that’s authentic and true to you — leave the dress shirt at home, and instead, switch things up with the best denim jacket on the market and corresponding gear that’s laidback, cool & ready for — perhaps a second date. In that case, I’m talking about a classic Oxford shirt and tan chinos, plus stylish chukka boots— to me, these are the building blocks of an outfit that’s going to look great nearly anywhere (and they let your personality do the talking, crucially). Accessories like an eye-catching solar-powered watch and a durable Filson brief are nice touches to add to this #OOTD. And because grooming is so critical, the Bespoke Post Lather Box is the perfect way to clean up your stubble or your beard — of course, a date all starts with how you prepare, and Duke Cannon’s Big Ass Beer Soap is one way to feel refreshed and smell great on the daily (coffee date included). Keep in mind that these are essentials that’ll work anywhere, and especially for a lovely afternoon at your favorite coffee shop. Have any feedback on date outfit suggestions? Reach out on Twitter. Thanks for reading!


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