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What to Wear on a First Date: 2 Go-To Outfits for Men

first_img The Best Men’s Chukka Boots for 2019 What to wear on a first date right now is arguably a very pressing question since Valentine’s Day is on the horizon, after all. But there’s never a bad time to reexamine what you’re wearing on a date. Heck, even landing a face-to-face date means you cut through the digital noise out there, so you might as well dress stylishly for the occasion. Make no mistake though, a date night can take on a life of its own, especially if you subscribe to the idea that one date can really become … two (dinner at one spot, drinks at another). So, we’re offering up two ideas when it comes to what to wear on a first date: Casual and dressy, each with its own merits. Good luck out there. The Casual EnsembleTravisMathew Matchmaker Jacket – $175You’re getting soft flannel fabric, plus the casual and rugged appeal of both a shirt and a jacket in this winter-ready piece. A more unique option than a standard winter puffer jacket, and one that you easily drape over your date’s shoulders if need be (people still do that, right?). This is a fail-safe top layer when it comes to what to wear on a first date.Shop NowTaylor Stitch California Shirt in Everyday Chambray – $118As reliably solid and timeless as can be, this crisp chambray shirt is a stone-cold classic from Taylor Stitch. No matter where you go or what you do, we think this stylish chambray shirt is going to impress your date, no questions asked.Shop NowProof Rover Pants – $98The Proof Rover Pants pull out all the stops when it comes to versatile (yet casual) date night style. With the look and feel of denim or classic canvas work pants, these are polished yet laid back. That sounds to us like the perfect pair of pants to wear on a first date.Shop NowBeckett Simonon Morgen Sneakers – $149While you could reach for a pair of classic leather or suede chukka boots, we think vintage-inspired sneakers are a neat change of pace, especially if you live in a more temperate climate. Think classy and sharp, without overdoing it.Shop NowV76 by Vaughn Styling Cream – $20Reach for a styling cream that nourishes and gives some structure to your ‘do. And leave the ball cap at home, even on a casual date night.Shop NowFilson Mackinaw Field Watch – $400There’s a solid chance Filson makes the bag you carry every single day — turn to this heritage brand for a reliable, rugged field watch that stands out quite nicely on, say, a more laidback brewpub outing.Shop NowDuke Cannon Solid Cologne – $25A new addition to your grooming routine, Duke Cannon’s Solid Cologne is an everyday essential that’s going to pleasantly upgrade your entire casual ensemble. The Land scent is at once subtle and classic. It’s exactly the right aura to project on a night out. Shop NowThe Dressy EnsembleIndochino Hemsworth Navy Suit – $369Does dressing up these days always have to mean reaching for a suit? Not necessarily, depending on where you’re going. But if you need to suit up, you might as well put on a well-fitted, classically designed navy suit that’s a heck of a steal in terms of price.Shop NowInstitchu Bedarra White Shirt – $89If you’re saving money on your suit, you should splurge on your shirt. After all, the right white dress shirt can work day after day, week after week, in situations where you don’t even need a suit. And the crisp, classic Bedarra White Shirt from Institchu exudes refinement and taste, plus versatility.Shop NowThe Tie Bar Burgundy Wool Knit Tie – $25Nod toward winter with a rich burgundy knit tie in a seasonally ready fabric like wool. While most knit ties feature a square, this tipped tie is just a little more dashing.Shop NowJack Mason Aviator Watch – $495Versatility is also key when it comes to your watch. The Jack Mason Aviator Watch, in both its black dial and white dial iterations, is equal parts rugged and refined. As they say, a watch is arguably one of the things to catch your date’s eye, so make yours a great one.Shop NowPantherella Cashmere Socks – $72These socks are loved by menswear aficionados and global jet setters alike for their durability, style, and comfort. They’ll prove just as effective on your date night.Shop NowRhodes Dean Boots – $220Shoes are every bit as critical as the rest of your outfit, especially when navigating slippery winter streets. The Rhodes Dean Boots deliver excellent traction, plus sleek, date-ready style. Shop NowIf you’re a planner and are just looking at this article to prep for a potential first date, but haven’t actually gotten one yet, here are a few useful tips on how to ask a lady out. Editors’ Recommendations Helpful Wine Terminology So You Sound Like You Know What You’re Talking About How to Shave With a Straight Razor The Ultimate Pillow Guide: The 6 Best Pillows for All Sleepers 16 Best Action Movies on Netflix Right Nowlast_img read more