What to Wear: Valentine’s Day in Two Outfits

What to wear on Valentine’s Day is a question that’s on the minds of, well, just about every guy this time of year — yes, even if you’re just dressing for a night at home. Like it or not, Valentine’s Day is still a situation that deserves attention and your very best effort, and that’s where we come in. We’ve put together a guide to two outfits that work for two different situations: A casual date night in or at, say, a nice brewpub, and then what you might call the best of the best: A no-holds-barred, exceptionally fancy outfit for dinner at the hottest spot in town. Either way, you’re going to like these picks and you’re going to look (and feel) your absolute best on one of your biggest nights of the year.

If You Feel Like Dressing Up

Let’s start things off on the right foot. We guarantee that a slim topcoat is a reliable starting option in any situation — especially a dressy Valentine’s Day. It sets the tone for the rest of the outfit (which we think looks pretty great to begin with).

Can you go wrong with an utterly classic-yet-modern suit? Reach for one that’s cut smart and available in a range of neutral colors, each well-suited to pairing with winter style staples this coming Valentine’s Day.

It’s hard to go wrong with a white Oxford dress shirt, which just simply can’t be beat, any day of the week — especially when the occasion calls for something tailored and crisp. But what to wear on your neck?

Now, if James Bond consistently reaches for a classic knit tie — which he’s been known to do — then, there’s no reason that you shouldn’t do the same. Right? Right. In terms of what’s on your wrist, we think that’s an easy choice — go with something your father or grandfather might have worn.

And if you didn’t think boots could be dressy, think again. Reach for a pair that can both combat slick roads and look great sitting under your perfectly tailored suit trousers — it’s as easy as that, and the entire end result is a winner.

If You’re Keeping It Casual

Let’s talk casual style for Valentine’s Day — dressing for this scenario definitely doesn’t have to be hard. For layering up accordingly, we think a durable field coat strikes the right balance between  outdoorsman and handsome gentleman, as do the rest of our picks.

A pleasantly rugged-yet-refined cable crewneck sweater is a unique, admirable choice when it comes to dressing for such a tricky occasion — the rest of your ensemble should follow suit.

We’re looking for that just-right balance of laidback and yet sharp enough for a Valentine’s Day date. Luckily, a new Grayers dress shirt fit the mold of casual yet still stylish. It’s also true that no guy looks bad in blue jeans, especially dark ones in a flattering Bonobos cut.

That’s the pair you want to wear for a casual Valentine’s Day — finish ‘em off with beautiful wingtip boots from Thursday Boots absolutely hit the nail on the head in terms of dressy-yet-rugged style.

And your accessories game should be equally sharp. On that front, Timex has stormed back into the hearts and minds of watch lovers everywhere with many of its recent releases, but the Weekender Chrono remains an utterly essential watch offering that will work nicely to round out this easygoing Valentine’s Day ensemble.