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Your Guide To Dressing for Valentine’s Day - Beau Hayhoe

Lounge Concierge

Tips for the year’s biggest date night – at home or on the town.

There are few holidays that call for you to put your best foot forward quite like Valentine’s Day. There’s the matter of finding the proper gift for your significant other, as well as planning a special day, whatever that might mean to you and yours truly. Of course, there’s also the question of your #OOTD for the day (and night).

Start with the question at hand: Does the occasion call for a dressy date night on the town? A carefully prepared meal at home? Not to worry: Our guide to dressing for Valentine’s Day ensures the perfect balance between stylish, refined and authentic, because as long as you’re dressing to impress and staying true to yourself, the rest of the holiday should be a breeze.

An Elegant Winter Sweater Or Blazer

Dressing for Valentine’s Day is a bit like preparing a “choose-your-own adventure” course of action. If you’re going to be on chef duty at home, you still want to put thoughtful care into your look. A handsome shawl cardigan– like the Buck Mason Herdsman Shawl Cardigan – is more elevated than a sweatshirt you’d wear on a normal night in. Dressing it up to hit the town? An elegant & seasonally friendly wool blazer (like Todd Snyder’s Madison Sportcoat) is an expert move.


An Effortlessly Cool Shirt

Just as you have your go-to cigar for reliable enjoyment, your wardrobe should have pieces you can trust in multiple situations. A classic Oxford shirt fits the bill for Valentine’s Day at home or out on the town – it’s a polished-yet-comfortable move for uncorking a bottle of wine at home, yet it can easily be dressed up with a knit tie for an evening dinner reservation. For both occasions, we trust the Bonobos Everyday Oxford Shirt, but you could also elevate your look further with a classic white dress shirt from The Tie Bar.


Go-Anywhere Chinos

Remember what we said about Valentine’s Day presenting options akin to a “choose-your-own-adventure” series? Here’s where a reliably stylish, versatile pair of pants enters the equation. The cotton chino is a workhorse at the office, but here we opt instead for a refined take on the style from luxury retailer MR. PORTER. And go a step further by choosing a deep, distinctive color that turns these into proper dress pants – at a cocktail bar or at home, because Valentine’s Day calls for the best of the best anywhere you go.


Expertly Crafted Chelsea Boots

A word to the wise: If your plans call for an evening in, away from the cold, you could always slip into some handsome leather slippers. If you’re out and about though, there’s hardly a better, cooler choice than sleek leather Chelsea boots, like this stylish pair from Tecovas. They’re a change of pace from your standard dress shoes and they’ve got some serious sex appeal, especially with crisply cut chinos. 


A Trustworthy Leather Watch

Here’s where consistency is key: If you have a reliable watch you love wearing for special occasions, perhaps an investment-level Rolex timepiece, then this part of your ensemble is already settled. And yet, if you’ve been searching for a wrist game upgrade without breaking the bank – something you can dress up on a Valentine’s Day date night – then the Armitron Charles might fit the bill perfectly.


The Finishing Touch

You’ve bought the flowers, you’ve gotten your hair cut and your beard trimmed, you’ve hit on every grooming point from A-to-Z – now, for the finishing touch. Opt for a rich, balanced scent like Perry Ellis Red Sky Eau de Toilette, which is distinct enough for this winter date night (at home or at a cozy speakeasy), complete with notes of cedarwood and rosemary.


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