What to Wear on a First Date (Men): Outfits by Venue and Season

For most first dates, wear dark jeans or chinos that fit, a shirt with a collar or a plain, heavier T-shirt in a solid color, and clean leather shoes or clean minimal sneakers. Add a layer (overshirt, jacket, sweater) when it's below about 65°F. Dress one notch above what you'd wear to that place on a normal Tuesday. Fit matters far more than price: a $30–40 shirt that fits beats a $150–200 one that billows at the waist. Then adjust for the venue and the weather, which the rest of this post covers outfit by outfit.

The default first date outfit

If you only read one section, read this one. This outfit works for coffee, drinks, tacos, a brewery, most dinners in most American cities:

• Dark wash jeans, no rips, no fading at the thighs. Or chinos in navy, olive or tan.
• A shirt that fits through the shoulders: an oxford button-down, a solid knit polo, or a plain crew-neck tee in a thicker cotton.
• Clean shoes. White leather sneakers, suede chukkas or brown leather boots.
• A belt that roughly matches your shoes if your shirt is tucked or your pants have loops that look empty without one.

That's a uniform you can repeat for every first date for a year, and nobody will know, because nobody sees you on two first dates.

Why so plain? Because the point of the outfit is to make a good first impression for about four seconds and then get out of the way. You want her to remember the conversation, the dumb story about your neighbor's parrot, whatever. You don't want her to remember the shirt. Loud prints, slogans and very trendy pieces pull attention to the clothes, and they're riskier if her taste differs from yours. If you're rebuilding your whole wardrobe and not just one outfit, how to be more attractive covers fit and basics.

There's one exception: dress like the guy in your profile photos, roughly. If every picture shows you in a flannel and boots, showing up in a blazer will feel a little like meeting a different person.

What to wear by venue

Coffee shop or daytime café

Keep it relaxed. Coffee dates are short and casual, so overdressing reads as trying a bit too hard.

Dark jeans + a plain tee or henley in navy, gray, olive or white + a light overshirt or chore jacket if it's cool + white sneakers.

A crew-neck sweatshirt in a solid color (no logo) works here too, as long as it's in good shape and not the one you sleep in. Skip the hoodie. It's too close to "rolled out of bed."

Cocktail bar or wine bar

Step it up one notch. The lighting is darker, people are dressed a little sharper, and you'll be sitting close.

Dark jeans or chinos + a button-down (solid or a small, quiet pattern) with the sleeves rolled twice + leather boots or loafers + a jacket if it's chilly.

A dark knit polo is a good alternative if button-downs feel stiff on you. If the bar is on the fancier end (the kind with a dress code note on its website, or where cocktails run $16–20), wear real leather shoes and leave the sneakers home.

For a dive bar, brewery or sports bar, go back to the coffee outfit. Nobody at a dive bar is wearing an oxford.

Dinner at a sit-down restaurant

Match the restaurant. Look at its photos on Google Maps or Instagram before you go. If the diners in the pictures are in T-shirts, you can be too, just a nice one.

For a mid-range place, the type with cloth napkins but no host in a suit:

Chinos or dark jeans + a button-down tucked in, or a fine-knit sweater over a collared shirt in colder months + leather shoes or boots + a belt.

For an upscale dinner:

Wool trousers or dark chinos + a pressed button-down + an unstructured blazer (optional, but it handles everything from "nice" to "very nice") + leather dress shoes or loafers.

A suit and tie is too much for nearly any first date. It makes the dinner feel like a job interview, for both of you.

I'd also avoid white shirts at a restaurant that serves pasta in red sauce, mole or anything else that splashes. Navy and gray forgive a lot.

Outdoor or activity dates

A walk, a hike, mini golf, bowling, a farmers market, an outdoor movie. Dress for the activity first and look put together second.

Hiking or a long walk: athletic-cut chinos or clean hiking pants + a fitted tee or quarter-zip + trail shoes or sneakers that are actually clean + a light jacket you can tie around your waist without looking like a geography teacher.

Bowling, mini golf, arcade bar: jeans + a tee or henley + sneakers. You'll be bending, reaching and moving around, so nothing tight across the back.

Farmers market or street fair: the coffee outfit, plus sunglasses and sunscreen.

Wear real athletic gear only if the date is the workout itself, like a climbing gym or a group run. Even then, wear clean stuff. The shirt that's been in your gym bag since Thursday can stay there.

If you're still picking the plan, first date ideas has options at different energy levels, and the outfit usually follows from the place.

What to wear by season and temperature

American weather swings a lot depending on where you live, so go by the forecast for the hours you'll actually be out. The daily high can lie to you. A Denver evening in October can drop 25 degrees after sunset, which the Denver first date ideas post factors in.

Hot weather (80°F and up)

• Shorts are fine for coffee, a casual lunch, an outdoor activity or a beach town. They should hit just above the knee. No cargo shorts, no athletic shorts.
• For bars and dinner, go with lightweight chinos or linen-blend pants.
• Short-sleeve button-downs in linen or cotton, or a knit polo. Lighter colors help.
• Leather sneakers, canvas sneakers or loafers worn with no-show socks.
• If you sweat a lot, wear a thin undershirt under a lighter shirt, or pick a darker or patterned shirt that hides it. Bring a spare tee in the car if you're driving.

Sandals are a judgment call. Clean leather slides at a beach bar in San Diego? Fine. Flip-flops at a restaurant? I'd skip them.

Mild weather (60–79°F)

The easiest range. The default outfit works with nothing added. Around 60–65°F, especially in the evening, bring a layer: a denim or chore jacket, an overshirt, a light bomber or a thin sweater.

Layers help more than you'd think. If she's cold on a patio, you're not obligated to hand over your jacket, but you can offer.

Cool weather (40–59°F)

• A sweater (merino or cotton) over a collared shirt or tee.
• A field jacket, waxed jacket, suede jacket or wool overshirt.
• Boots start making more sense than sneakers.
• Darker, heavier pants. Corduroy is good here.

Cold weather (below 40°F)

This is where a lot of guys default to a puffy ski jacket over a hoodie. If that's all you have, it's fine for a casual date, but a wool or wool-blend overcoat over a sweater looks noticeably sharper and doesn't cost a fortune (about $100–200 at department stores, often less on sale in late winter).

• Wool coat or a clean, dark, slim-ish puffer.
• Sweater or flannel underneath, so you look dressed when the coat comes off. You'll take it off inside, and what's under it is what she'll look at for the next 90 minutes.
• Scarf if it's really cold. Gloves and a beanie are fine; take the beanie off indoors.
• Waterproof boots if there's snow or slush. Wipe off the salt stains before you leave.

Fit over brand

Nobody on a date can tell what you paid for your shirt. Everyone can tell whether it fits.

A quick fit check in front of a mirror:

• Shoulders: the seam on a shirt or jacket should land at the edge of your shoulder, not halfway down your arm.
• Chest and waist: a button-down shouldn't pull into an X shape at the buttons, and it shouldn't have a parachute of extra fabric at your waist when tucked.
• Sleeves: long sleeves end at the wrist bone. T-shirt sleeves hit mid-bicep and don't flare out like wings.
• Pants length: a slight break or no break at the shoe. Several inches of fabric stacked at your ankles makes even good pants look sloppy.
• Pants seat and thighs: comfortable to sit in for two hours. If you're tugging at them when you stand up, they're too tight.

Tailoring is underrated and cheap. Hemming pants at a local tailor or dry cleaner usually costs about $15–25, and taking in a shirt at the waist is often $20–35 (prices vary by city, so ask first). That turns a $30–50 shirt into one that looks like it was made for you.

If you're shopping fresh for a date, two or three pieces is enough: one good pair of dark jeans, one oxford or knit shirt that fits, and if your shoes are in bad shape, shoes. Mid-range mall and online stores sell all of these for about $30–80 each. You don't need anything more expensive than that.

Shoes

People notice shoes. Maybe more than they should, but they do, partly because shoes show whether you take care of your stuff.

Good first date options, roughly from casual to dressy:

1. Minimal white or off-white leather sneakers (clean ones, which means scrubbing the soles too)
2. Suede chukka or desert boots
3. Brown leather boots, like a Chelsea or lace-up
4. Leather loafers
5. Leather derbies or oxford dress shoes

Brown leather goes with almost everything from jeans to wool trousers. If you're buying one pair, buy brown boots or brown loafers.

Avoid running shoes (unless you're actually walking a trail), beat-up skate shoes, square-toed dress shoes from a 2009 office job, and anything with a visibly worn-down heel. And wear socks that match the pants or the shoes, with no holes. Bowling alleys, some apartments and the occasional Japanese restaurant with floor seating will take your shoes off, and you'll be glad you checked.

What to skip

Most outfit mistakes on first dates fall into a short list:

• Graphic tees, slogan shirts, band shirts you'll have to explain.
• Anything stained, faded, pilled or wrinkled. Check in daylight, because a bedroom lamp hides a lot. A handheld steamer fixes wrinkles in a few minutes.
• Visible logos across the chest. A small one is fine; a giant one turns you into a billboard.
• Sports jerseys, unless the date is literally at the ballpark.
• Gym clothes anywhere other than a gym.
• Clothes that are too tight to sit in or too baggy to see your shape.
• Brand-new shoes you haven't broken in. Blisters by the second bar make for a long walk.
• A baseball cap indoors, or sunglasses on your head all night.
• Lots of accessories at once. A watch is great. A watch, two bracelets, a chain and a ring starts to compete with you.
• Too much cologne. One or two sprays. The grooming checklist covers that, along with haircut timing, beard, nails and the rest of the non-clothing prep.

The night before

Lay the whole outfit out the night before, socks and belt included. Try it on, sit down in it, raise your arms. If the shirt untucks or the pants pinch, swap now while you have time.

Check the weather again on the day. Bring the layer even if you don't think you'll need it, because the date might go well and turn into a walk after dinner, and walking around shivering in a short-sleeve shirt is a bad look for anyone.

Then stop thinking about it. Once you're dressed, the clothes have done their job. Whether you two click comes down to the conversation (what to talk about on a first date has openers if you want a few ready), and whether she wants a second date is her call. A good outfit helps you feel less awkward walking in. It won't change her mind about chemistry, and if she's not interested, a nicer jacket wouldn't have fixed it. Thank her for coming and move on.

FAQ

Should a guy dress up or down for a first date?

Slightly up from what you'd normally wear to that specific place. Look at what people wear there on a regular night and go one step nicer: a collared shirt instead of a tee at a bar, leather shoes instead of sneakers at a nicer restaurant. If you're unsure, a dark button-down and dark jeans is almost never wrong.

Can I wear a T-shirt on a first date?

Yes, for coffee, casual daytime plans, outdoor activities and most breweries or dive bars. Pick a solid color, a thicker cotton that doesn't cling, and make sure it fits through the shoulders and still has its color. Add an overshirt or jacket if you want to look a little more put together.

What colors should I wear on a first date?

Navy, gray, olive, white, light blue, brown and black are all safe and easy to mix. Navy and light blue suit nearly every skin tone. One color with some contrast to the rest is plenty; skip head-to-toe black at a daytime coffee shop, where it can look a bit severe in bright light.

Jeans or chinos?

Either. Dark jeans are slightly more casual and more forgiving of spills. Chinos look a bit sharper at dinner and are better in hot weather. If you own one good pair of each, you're covered for almost every date on the first dates list.