What to Wear on a Summer Date For Men
Photo Credit:@mr.danielocean
You finally got the date. Now you’re staring at your closet, thinking: What do men even wear on a date night? And why is it always 90 degrees when you have somewhere important to be?
Looking good without layering up is tricky. You want to be confident, not sweaty. Cool, but not like-you-just-left-the-gym casual. This guide gives you clear, low-effort outfits based on the actual date—not just “wear a polo and hope for the best.”
Whether it’s dinner, drinks, or something more unexpected—we’ve got you covered (without covering too much).
1. The Rooftop Drinks or Patio Bar Date
The vibe is casual but curated. You’re standing, walking, maybe sweating a little—and still want to look like you know what you’re doing.
What to wear:
Lightweight short sleeve button-down (camp collar or linen blend)
Chino shorts or lightweight drawstring trousers
Low-profile leather or canvas sneakers
James Shirt
Agua Bendita
$180
Lander Cargo Pants
PAIGE
$239
The Monterrey
$185
MOD tip: Go for patterns or textures up top to show personality—just skip anything that looks like a Hawaiian souvenir. Roll your sleeves once, stay cool, and don’t forget deodorant.
2. The Dinner Date at a Nice-but-Not-Fancy Spot
Think elevated casual—somewhere you need a reservation but not a tie. You’re sitting close, there’s a candle involved, and you don’t want to sweat through your fit by the main course.
What to wear:
Textured polo or knit tee
Slim, breathable chinos or tech pants
Casual suede loafers or clean white sneakers
Knit Crochet Short Sleeve Button Down Shirt
$328
Tuff Tony Jeans
Nudie Jeans
$220
2002r Sneaker
New Balance
$145
MOD tip: A quality polo makes you look more polished than a tee without making you overheat. Stick to neutral colors or earth tones—they read confident, not corporate.
3. The Daytime Stroll / Farmer’s Market / “Let’s Walk Around” Date
She says “let’s meet up and walk a bit,” which sounds chill—until you realize you’re sweating and there’s no breeze in sight.
What to wear:
Breathable crewneck tee (no logos, no cling)
Tailored shorts (7” inseam, not gym length)
Slip-ons or clean sneakers (with no-show socks)
Scripture Tank
ALLSAINTS
$199
Flynn Cargo Shorts
ALLSAINTS
$149
MOD tip: Go for neutral or washed colors that hide sweat and look relaxed. Sunglasses are a must—you’re not trying to squint your way through the date.
4. The Outdoor Concert or Street Festival Date
You’ll be on your feet, probably holding a drink, surrounded by people and humidity. Comfort is non-negotiable—but style’s still required.
What to wear:
Loose-weave button-down or oversized tee
Lightweight trousers or linen-blend pants
Retro runners or structured sandals (if you must)
Noll Short Sleeve Shirt
Theory
$185
Straight Cut Shorts
Theory
$185
MOD tip: If you’re wearing a tee, cuff the sleeves once for some structure. Add a chain or bracelet to look like you thought this through—even if you didn’t.
5. The Movie Date or Casual Night In (That Could Turn Into More)
You’re keeping it low-key, but you still want to feel confident. No ratty shirts. No pajama-adjacent joggers.
What to wear:
Textured henley or slub tee
Slim joggers or stretch cotton pants
Minimalist slides or sockless slip-ons
x Daft Punk Duo T-Shirt
Pleasures
$60
Modern Straight Jean
FRAME
$248
MOD tip: Fit is everything here. You’re not “dressing up,” but the right tee + tapered joggers = “this guy looks good doing nothing.”
