If you’ve got the date, we’ve got the outfit. Because whether it’s a coffee meet-up, a long-awaited anniversary dinner or a casual Friday-night hang, what you wear sets the tone. And with Valentine’s Day coming up (or any night you want to make a great impression) now’s the perfect time to step up your style.
The good news? Looking great doesn’t require a complete wardrobe overhaul—just a few reliable outfit formulas, a couple smart upgrades and some pro-level fit tips from our expert Stylists.
But before we dive into date night outfits for men, let’s cover a few simple rules our Stylists swear by—their go-to guidelines for getting date style right every single time.
- Keep it clean, fitted and intentional: when in doubt, fit > fashion. Because even a simple outfit looks great when it wears well.
- Match the vibe of where you’re going: a brewery doesn’t call for a blazer, and a nice restaurant deserves more effort than joggers. Also, if the weather decides to get dramatic, bring a light layer so you stay comfortable without overthinking it.
- Pick one standout piece and let it lead: a structured jacket, a nice sweater or clean leather sneakers can carry your whole look. Keep the rest simple and balanced, and you’re set.
Alright, rules covered? Now for the fun part—the outfits.
What to Wear for a Daytime Date
Daytime dates like neighborhood walks, museum visits or weekend brunch call for a look that says you’re put together… without looking like you overthought it. Stylist Mathew’s best advice for a casual date outfit: “Don’t be afraid to mix formal and relaxed pieces,” he says. “You can elevate a simple T-shirt and jeans just by adding loafers or boots, plus a great jacket.”
A textured knit layered under a clean, structured barn coat also hits that balance perfectly, especially with straight-leg denim and boots. It’s easy, confident and reads as intentional without slipping into the “trying too hard” territory.
If you’ll be outside for part of the date, Stylist Erin has a go-to formula: “A charcoal waffle knit with dark-wash jeans topped with a warm shirt jacket and a simple beanie is weather-ready and looks pulled together in all the right ways.”
Easy style upgrade: Always bring an extra layer for winter weather, but skip the hoodie. A bomber jacket or quilted puffer is a simple upgrade that also keeps you warm.
“A charcoal waffle knit with dark-wash jeans topped with a warm shirt jacket and a simple beanie is weather-ready and looks pulled together in all the right ways.”
-Stylist Erin
What to Wear for an Active Date
When your date involves movement, comfort is king—but don’t confuse comfort with sloppiness. Elevated athleisure is the answer. For a hiking date outfit, Stylist Jackie swears by sueded fleece: “It makes your hoodie and joggers feel more polished while still being totally functional,” she says. Add smart layers and a couple of easy accessories (a beanie, for starters), and you’re good to go.
For more laid-back activities—think mini golf, bowling or a neighborhood walk —Stylist Caro suggests upgrading the basics. “Soft wool-blend joggers with a structured quilted jacket instantly refine your look,” she says. Even a modern hoodie paired with chinos and retro sneakers can hit that same elevated-but-easy vibe.
Easy style upgrade: When in doubt, go monochrome. It reads as intentional and pulled-together with zero effort. Then, bring in personality through a knit beanie or sneakers in a standout color.
If you’re still struggling to style your next museum date outfit or a mini golf date outfit, you can now chat directly with one of our expert Stylists! Head to our app to access Stylist Connect and start your conversation with a Stylist. Ask all your outfitting questions or even collaborate on your next Fix together!
“Soft wool-blend joggers with a structured quilted jacket instantly refine your look,”
-Stylist Caro
What to Wear for Dinner + Drinks
For a night out, you’ll want to take your look up a notch. The goal is approachable confidence, and pieces like dark denim, textured sweaters and structured jackets make an easy winning combo.
Stylist Mathew suggests swapping a basic button-down for a textured sweater. “It’s relaxed and refined without feeling stuffy, and pairs perfectly with jeans or dress pants.”
A sharp outer layer takes it even further. Top things off with a bomber, suede jacket or a classic topcoat for effortless polish. And don’t skip the small details—a belt, watch or freshly shined shoes can make a big difference.
Easy style upgrade: The condition of your date night shoes matters more than you think. Leave the running sneakers at home and go for trainers or crisp, clean sneakers to pull your whole look together.
“Swapping a basic button-down for a textured sweater is relaxed and refined without feeling stuffy, and pairs perfectly with jeans or dress pants,”
-Stylist Mathew
What to Wear for Valentine’s Day (or a Special Night Out)
When the occasion feels important, your men’s date night outfit should show it. Tailored trousers paired with a quarter-zip knit or sweater polo instantly feel polished, and adding a blazer takes the outfit from good to memorable.
Want to dial up the style even more? Stylist Caro suggests playing with colors and textures, especially for a men’s Valentine’s date outfit. “A tailored velvet blazer in deep burgundy or midnight blue adds luxe texture and warmth to your look,” she says. “Even subtle patterns like tonal checks add depth without stealing the show. This combo is perfect for anniversaries, Valentine’s Day or any night that calls for a little extra flair”
Easy style upgrade: Don’t overlook the small details—interesting sweaters, a great belt and thoughtful accessories can level up your look with minimal effort.
Still a little unsure about what to wear on your next anniversary date? Try our new feature, Vision. It utilizes AI to generate personalized images of you styled in the latest looks and trends. You can then browse and shop these styles instantly!
“A tailored velvet blazer in deep burgundy or midnight blue adds luxe texture and warmth to your look.”
-Stylist Caro
Get Styled by Stitch Fix for Your Next Date
Ready to make dressing for your next date more fun and effortless? Your Stitch Fix Stylist has you covered. Take your style quiz, order a Fix and let your Stylist do the work for you. They’ll choose just-for-you pieces to save you time (and a trip to the mall). Keep what works, and return the rest—or keep 5+ pieces and get 20% off your entire order. Shipping and returns are always free—no subscription required. It’s as easy as 1, 2, 3.
