So, Valentine’s Day is coming up. Whether you’re married or in a relationship (an old one or particularly, a new one!) or still looking for love, the question might be on your mind: “What the heck am I going to wear?” Based on your plans (Dinner? Drinks? Both!?), you might be faced with a dilemma. But I think the below #OOTD checks all the right boxes, no matter what. First up, stick with a classic winter blazer, and then layer up accordingly — in this case, that means a cozy, tailored flannel shirt from Faherty Brand, slim navy chinos and rugged leather boots from my pals at Huckberry. It’s truly foolproof.
Granted, we’re not going full-on tuxedo here, nor are we recommending you wear one of the best flannel suits for a night out, but it’s still a sharp look that can work for a refined dinner-and-a-show outing, plus a nightcap. The key with dressing for Valentine’s Day comes in staying true to yourself — seriously. If you and your partner keep things low-key and make a nice dinner at home, leave the Grayers sportcoat behind. Heck, if you feel like wearing that same blazer out to a solo cocktail at your favorite bar, sure — go for it! The same building blocks are going to carry you through, from crucial outerwear like a tailored topcoat to accessories like a slim leather dress watch. We’ll top things off with a great Valentine’s Day gift, too. It’s all below, and I hope these picks lead to an enjoyable (if Hallmark-led) holiday — no matter what you do!
- The Blazer: Grayers Hutton Wool Sport Coat, $195 — A casually cool, yet still polished, winter blazer from Grayers that blends warmth with tailored style.
- The Shirt: Faherty Brand Brushed Alpine Flannel Shirt, $148 — This stylish flannel shirt is also casual and cool, yet able to be dressed up or down depending on where your plans take you.
- The Trousers: Taylor Stitch Slim Chinos in Organic Navy, $98 — It’s tough to go wrong with slim navy chinos from Taylor Stitch — cut sharp to help you look your best on Valentine’s Day.
- The Overcoat: La Paz Heavey Coat, $364.98 — A tailored topcoat (particularly this one from La Paz) is exactly the right way to top off your #OOTD when it comes to what to wear for Valentine’s Day, right? Right.
- The Stylish Boots: Rhodes Dean Boots, $220 — Sharp, classic leather boots from Huckberry that’ll provide traction on slippery surfaces — and a ton of winter-ready style.
- The Watch: Armogan E.N.B. Watch, $220 — A refined dress watch is truly a must-have accessory if you want to put your best foot forward on Valentine’s Day.
- The Daily Essential: Flint and Tinder Heritage Boxer Briefs, $28 — What’s underneath your slim navy chinos from Taylor Stitch is as critical as the rest of this look.
- The Gift for Her: Soko Pia Pendant, $74 — OK, so this lovely pendant isn’t part of your #OOTD, but it’s among the best gifts for Valentine’s Day for her, yes indeed.
Even if this ensemble doesn’t quite line up with your Valentine’s Day plans, it’s hard to argue against the type of versatile building blocks it offers up — right? Starting with a winter blazer from Grayers gives you the flexibility to take your date (or heck, just yourself) out to drinks at a cool speakeasy or a refined sit-down dinner — or both. The stylish flannel shirt seen here is also made to be worn more casually — untucked at home, watching your favorite TV show — and it works in dressy situations, too. It could just be the best shirt for Valentine’s Day.
The same can be said for slim navy chinos from Taylor Stitch, which work for a ‘staycation’ or a night at home. You’ll also stay weather-ready with the Rhodes Dean Boots, some of the best winter boots out there — it helps that they provide great traction and killer style. We’re keeping things on-point with a slim camel topcoat, and we’re further driving home that refined aesthetic with a refined dress watch. Of course, it’s also of the utmost importance that you pick up a great gift for Valentine’s Day. And lest we forget … yes, you need good-looking underwear. Flint and Tinder can help. Feel free to let me know your plans for Valentine’s Day on Twitter — to see how I’m spending mine (likely enjoying a delicious craft beer!), you can check out my Instagram.