How to Dress Well for a Date

So you're taking the love of your life out for a big night, splurging on a big-ticket meal and reveling in the romance until the wee hours of the morning. Maybe you're meeting up with your partner for a few quiet drinks at the local watering hole because it's been that kind of week. Perhaps it's a cocktail with someone you met on the apps. Whatever the particulars, it's date night. Which means you need to get dressed.

We're here to help. From what to wear for a chilled out evening at the bar to pulling out all the stops for a gala—yeah, a gala—we're breaking down the spectrum of date-night attire so you can stop worrying about your outfit and start worrying about whether your partner still finds you funny. (Just kidding. You're a hoot.)

Let's get into it.

Match your partner's level of formality. Yes, even if it contradicts the advice below. If your wife wants to get fancy as fuck to order beer-and-a-shot specials at a dive bar, you better dress to the nines right with her. If your boyfriend wants to test the limits of the restaurant's dress code in a sweatsuit, don't reach for a suit suit and try to outshine him. This is date night, after all. It's a chance to break from your routines, enjoy each other's company, and remind yourself that despite all the bullshit out there in the world, it's good to be together. You're a team. That means dressing like one.

That said, there is a sliding scale of formality, from casual drinks up to a top-tier dinner followed by a trip to the theater. Barring a style swerve of the romantic variety, it's best to align the vibe of your outfit with that of the location and occasion. So we've broken it down with a few examples below.

A cardigan keeps it chill but polished.

Meeting up after work? Convinced the nanny to stay a couple hours later than usual? Sounds like the perfect time to stop off for a couple of drinks at a bar you like. And unless you're both mixology obsessives or honest-to-god socialites, it's probably a pretty chilled-out spot. There's no need to get all gussied up for this one. The idea is simply to to look polished and comfortable.

You could throw on a sport coat or a chore jacket if you're feeling it, but a cardigan is more relaxed and does the job of the critical third piece—that is, the extra item that pulls everything together—just as well. Pair that with a simple white tee that's got a decent bit of heft and structure, because this is not the time for that threadbare shirt with the stretched out collar you wear while lounging on the couch. Jeans would be fine, but chinos with a straight fit and a sturdy cotton are even better. Skip the sneakers and opt for loafers that elevate everything without feeling out of synch with the rest of the outfit, and never underestimate the work a couple of good accessories—a woven belt, a watch with a mid-century vibe—can do.

In terms of brands, there's no real right or wrong answer other than this: Wear stuff from the same makers you like to wear for everything that's not a date. (That also goes for the rest of this story, by the way.) If you're feeling unmoored, lifestyle brands like Todd Snyder, Buck Mason, NN.07, Ralph Lauren, and J.Crew all offer a wide range of options that hit pretty much every point on the casual-to-formal spectrum, and their clothes all tend to play nicely with one another. But you don't have to limit yourself to just those companies. A good place to start, if you really want to get into the weeds and maybe find a new favorite label along the way, is with all of our previous style guides.

Yes, a sport coat and jeans can look great. Case in point: Redford.

We're not necessarily talking about the buzzy spot with the three-month wait for reservations here. (Though if you planned ahead and managed to nab a coveted 7:30 p.m. spot on a Saturday, we're sure your date will be impressed, and the advice still holds.) We're just talking about a nice spot that feels special. The kind of place where showing up in a T-shirt and jeans wouldn't get you kicked out, but might make you feel underdressed.

You don't want to be the underdressed guy on date night, do you? Of course you don't. And one way to ensure you aren't is to reach for a proper sport coat that shows you put some thought into what you're wearing. It should have some texture, to ensure it can never, ever be mistaken for an orphaned suit jacket (i.e., the one that's supposed to match the trousers you're not wearing tonight). Tweed is a favorite in the colder months. Linen or wool-and-silk blends are great for summer. You could easily pair that jacket with chinos or dress trousers, and no one would have anything negative to say about that. But if you want to bring some liveliness to the outfit, we'd suggest taking a page from Robert Redford's '70s playbook and pulling on jeans with a subtle bootcut instead. Wrangler's Cowboy Cut jeans fit the bill perfectly, and are tough to beat, especially at their price point. Keep the Western theme going without veering into costume territory by choosing a snap-front shirt in not-quite-white and a pair of side-zip boots. Finish things off with a slim belt (skip the ornamental buckle) and a watch that walks the line between sporty and dressy, and you're good to go.

Wearing a suit doesn’t have to feel like standard fare.

You scored a table at a Michelin-starred restaurant. You're going to the theater, the opera, the symphony. You're hobnobbing with the upper crusties and you're having a damn good time doing it. Nice! So, what are you wearing?

Let's get something straight: A classic suit-and-tie combo works great here. A charcoal or navy two-button, a white or light blue shirt, a tie with some texture (think silk knit) or a pattern, and a pair of nice lace-ups? That's a timeless combination, and it looks great on pretty much everyone. If you're feeling unsure, opting for something super classic is absolutely a good idea.

That said, if you'd like to mix things up a bit, we're not going to stop you. A suit is still advisable and encouraged, but there's no rule that you can't play with color and cut. Paul Smith has a double-breasted jacket with matching, belted trousers that have been a real hit amongst the celebrity set lately. Sterling K. Brown has worn them. So have Patrick Schwarzenegger and Jonathan Groff. Plus, as you can see above, Young Mazino even wore the suit on the red carpet on Emmys night. And if it's good enough for the red carpet on Emmys night, you can be sure it's good enough for your date, too. A shirt and tie would be a fine pairing, but a sweater polo in toasty brown brings some extra warmth. Add brown boots, a croc-embossed belt with golden details, and an expensive-looking watch that's actually quite the steal, and you've got a look that's ready to party—but with all due propriety.

If the invite says "black tie," you have to wear a tux.

If you're going on a full-blown fancy date—a gala, for instance—the invitation will almost certainly indicate the dress code. The dress code will almost certainly say "black tie." Which means you should certainly—not almost, but certainly—wear black tie. That means a tux. Wear a tux.