Navigating the 21st-century dating world — especially in 2020 — can be a taxing and tricky prospect, and that goes for established relationships, budding relationships and heck, marriage in equal measure. Are coffee dates still the norm in all three of these situations? In my estimation, yes — we’ll leave the rest of the questions to smarter folks, but today, we’re going to talk about what to wear on a weekend coffee date. A standby of enjoyable, relaxing time together, often pairing great coffee with (hopefully) great conversation — pick the right coffee shop, plan activities before and after … and yes, figure out what to wear on a weekend coffee date in the meantime. No matter how long (or short!) you’ve been with your partner, dressing for the occasion with your favorite men’s style essentials — much less style essentials for early spring — is always the right way to approach the situation (even if you’ve previously viewed your weekend coffee run as a necessity rather than event). So, from a new Faherty Brand Chore Coat to a classic crewneck sweatshirt and of course, a garment-dyed Oxford shirt for classic, laidback style, I think you’ll like what we’re brewing up today. The goal is to approach the situation (in matters of dress as well as mentally) with an air of casual cool — so, be yourself, dress the part, then enjoy the day. If you’ve got questions on what to wear for a weekend, let me know on Twitter. OK, order up!
Keeping things casual and cool for a weekend coffee date.
- The Jacket: Faherty Brand Chore Coat, $328 — Statement-making outerwear, the kind that’s eye-catching without going crazy, is tough to find these days — except the Faherty Brand Chore Coat, the ideal way to make a first (or second, or third) impression.
- The Sweatshirt: Taylor Stitch Crewneck in Natural Donegal Terry, $128 — Depending on the weather, maybe you won’t need this classic crewneck sweatshirt from Taylor Stitch. But if you do, it’s a classic layer that quietly nods toward timeless cool.
- The Oxford Shirt: Flint and Tinder Garment-Dyed Oxford Shirt, $118 — In keeping with the vibe we’re going for (calm, cool and collected), a garment-dyed Oxford shirt in a flattering color and soft fabric is your best friend (and possibly … your new favorite shirt?).
- The Denim: Flint and Tinder 1-Year Wash Jeans, $128 — Again, since it’s the weekend, we’re keeping things casual but not over-the-top — perfectly faded denim, especially from Flint and Tinder, is your go-to move.
- The Classic Boots: Astorflex Dukeflex Boots, $155 — When you want to look put-together without overdoing it, reach for classic chukka boots that are visually interesting and easy to wear with your favorite jeans.
- The Watch: Form-Function-Form Horween Leather Chronograph, $128 — Leave the heirloom-worthy watch or that rugged dive watch at home — a classic casual watch, particularly a Horween leather strap watch, is your move here.
- The Grooming Essential: Duke Cannon Solid Cologne, $25 — Again, making a great impression (regardless of how long you’ve been dating!) is a solid move any day of the week, and Duke Cannon Solid Cologne is subtle & high-quality — certainly, some of the best men’s solid cologne on the market.
- The Wallet: Red Wing Heritage Classic Bifold, $129.99 — Picking up coffee on this date is the right thing to do (in my book), and Red Wing Heritage is helping you meet that aim with one of the best men’s leather wallets — a classic wallet you’ll have for many dates to come, no doubt.
The key here, as with so many entries in our #OOTD series, comes with making the pieces you know and love — for instance, a garment-dyed Oxford shirt — work in harmony together in a way that’s polished and cool, yet memorable. That’s why we’re pairing your new favorite shirt with the right complementary pieces, including a classic crewneck sweatshirt and the Faherty Brand Chore Coat as shown above. This outfit has the makings of care and personal style without being too wild — sounds pretty great, right? In keeping with the laidback nature of a weekend outing, perfectly faded denim is a natural move (although rugged camp pants could also work if you wanted to go a bit more, well, rugged). Rather than wear a pair of lovingly worn-in sneakers — save those for the summer — go with classic chukka boots to add some polish to this look (keep those same boots handy to wear to the office on Monday, too). You’re going to be tying it all together with essential accessories, including a classic casual watch for noteworthy style (everyone loves a cool watch, no?). Haul your cash and cards with one of the best men’s leather wallets, and be sure to freshen up with one of the best men’s solid cologne for that extra finishing touch. Are you feeling ready for your coffee date? I hope so — to get more daily style inspiration, head to my Instagram.
The Style Guide 