30 Date Night Outfit Ideas for Men

Got plans tonight and don’t know what to wear?

Whether it’s your first date or your fiftieth, these looks help you feel confident, stylish, and ready to impress—without overdoing it.

1. Bold Stripes for the Win

This black and white striped shirt tucked into cropped navy pants is a stylish choice for rooftop drinks or an upscale dinner.

Pro Tip: Leave a few buttons undone for a confident, flirty vibe.

2. Casual Sophistication

A relaxed grey shirt with tailored pants and loafers keeps things smooth and polished. Perfect for dinner somewhere nice but not too fancy.

Pro Tip: Add a gold chain or watch for extra charm.

3. Clean and Classy

This cream knit shirt with navy trousers is great for cozy restaurant dates or movie nights. It’s calm, confident, and looks like you tried (but not too hard).

Pro Tip: Keep your sneakers spotless—white shoes make a big first impression.

4. All-Black, All Smooth

Wearing all black with white kicks gives major cool-guy energy without looking like you’re trying to be mysterious. Great for nighttime strolls or a lounge date.

Pro Tip: Layer on a simple chain or two—she’ll notice.

5. Sharp and Stylish

This olive green button-up and dark pants combo screams confidence. Those brown loafers make it perfect for date nights that might turn into dance nights.

Pro Tip: A fitted shirt shows confidence. Just make sure it’s not too tight to move in.

6. Laid-Back But Put Together

The striped knit polo and cream trousers give vintage date-night charm. Great for daytime dates or casual dinner by the beach.

Pro Tip: Tuck the polo and finish with fresh sneakers to keep it tidy but relaxed.

7. All Black and Slick

A fitted black shirt with matching trousers and polished shoes brings serious date-night energy. It’s bold, clean, and impossible to ignore.

Pro Tip: Open the collar and layer in a chain for that smooth, confident touch.

8. Bold Shirt, Relaxed Fit

This printed short-sleeve shirt over a white tank and wide-leg tan pants is perfect for a fun dinner or night out. Cool, laid-back, and full of personality.

Pro Tip: Keep the shirt open and the pants loose for effortless charm.

9. Beachy Stripes and Cream Tones

Soft stripes with light pants make this outfit great for sunset dinners or warm weather date nights. It’s relaxed but still polished.

Pro Tip: Match it with clean white sneakers and a simple chain.

10. Navy Knit and Dress Pants

A fitted navy polo tucked into beige trousers is a perfect balance of smart and cool. Great for grabbing drinks or a casual dinner out.

Pro Tip: Leather sneakers pull the outfit together while keeping it date-night ready.

11. Polo and Patterned Pants

This combo of a navy polo with light plaid pants is stylish but never loud. It’s an easy win for dinner dates that lean classy but chill.

Pro Tip: Cuff the pants and skip socks to keep it modern.

12. White Tee and Light Trousers

A crisp white tee with tailored grey pants is simple and clean—great for coffee dates or casual evening plans.

Pro Tip: Fit is everything here, so keep it sharp and well-fitted all around.

13. Polo and Cropped Trousers

A white polo and cropped charcoal trousers hit that sweet spot between casual and sharp. Great for a low-key dinner or grabbing drinks downtown.

Pro Tip: Black sneakers add a sleek contrast—just make sure they’re clean.

14. Denim on Black

A fitted dark denim shirt tucked into black jeans keeps things rugged but date-night ready. Ideal for chill bars or night walks.

Pro Tip: Black boots give this outfit an edge without overcomplicating it.

15. Striped Shirt and Black Pants

This short-sleeve shirt with horizontal stripes brings some personality without going overboard. Pair it with fitted black pants for an easy, stylish look.

Pro Tip: Open a few buttons and toss on a watch for added charm.

16. Layered Street Cool

A gray tee, white base layer, and green leather jacket with relaxed jeans give off effortless date-night confidence. It’s relaxed and modern without trying hard.

Pro Tip: Retro sneakers show you’ve got style and comfort figured out.

17. White Polo and Green Pants

Crisp and fitted, this white polo with slim green chinos is a killer combo for outdoor dinners or classy day dates.

Pro Tip: White loafers keep it bright—don’t be afraid to go sockless.

18. Denim Shirt and White Trousers

A tucked-in denim shirt with white trousers and brown dress shoes is polished but still fun. Ideal for a fancier dinner night or jazz lounge.

Pro Tip: Keep the shirt snug and sleeves rolled for that confident touch.

19. Black Blazer and White Pants

A black blazer over an open light blue shirt and white pants brings high-class style to rooftop dinners or swanky cocktail lounges.

Pro Tip: Velvet loafers and a drink in hand say you’re confident and know how to dress.

20. Ribbed Polo and Black Trousers

This ribbed tan polo with black pants keeps it sharp and simple. Great for casual dates where you still want to look put together.

Pro Tip: Tuck in the shirt slightly and add a watch to level it up.

21. Light Blue Polo and Gray Pants

This soft blue polo with cropped gray trousers gives off relaxed charm. It’s perfect for a laid-back dinner or a classy brunch.

Pro Tip: White sneakers keep it fresh—no need to overthink the shoes.

22. Open Shirt and Retro Sneakers

Loose-fit tan trousers and a crisp white shirt give chill energy, while the sneakers add some edge. Great for a cool restaurant or night at the movies.

Pro Tip: Unbutton halfway and toss on a chain for a bit of flash.

23. Retro Polo and White Trousers

A bold striped polo with bright white pants is a stylish nod to vintage flair. Perfect for day dates with drinks and good conversation.

Pro Tip: Loafers give this outfit that polished finish without needing a blazer.

24. All Black with White Sneakers

A fitted black polo and cropped black trousers paired with white sneakers is sleek and easy. Ideal for dinner dates that roll into something more.

Pro Tip: Keep the fit close and clean—confidence is in the cut.

25. Cream Polo and Dark Trousers

A clean cream polo paired with black trousers is a simple, classy combo that works for almost any date. It’s low effort but still shows you care.

Pro Tip: Fresh white sneakers pull it all together—keep ‘em clean.

26. Striped Shirt and Ripped Jeans

This green striped short-sleeve shirt layered over a white tee with ripped jeans is perfect for casual vibes. Chill, stylish, and not too serious.

Pro Tip: Roll the jeans and go with white kicks to keep it playful.

27. Rust Polo and White Pants

This rust henley-style knit polo with tailored white pants brings personality without overdoing it. A great pick for a dinner date or drinks outside.

Pro Tip: Brown slip-ons give it a polished finish without going formal.

28. Blazer and Black Trousers

A tan double-breasted blazer over a white shirt and fitted trousers is for when you want to impress. Classy, sharp, and great for a fancy night out.

Pro Tip: Skip the tie to keep it relaxed but elevated.

29. White Shirt and Brown Pants

A fitted white button-up tucked into brown trousers is timeless. Great for wine bars, dinner spots, or any place where you want to look refined.

Pro Tip: A simple leather watch adds just the right amount of detail.

30. Fitted Tee and Tailored Pants

A teal fitted crew neck paired with tailored beige pants keeps it fresh and clean. Perfect for early evening dates or rooftop lounges.

Pro Tip: Tuck the shirt in for a smarter look and finish with white sneakers.

Date night dressing doesn’t have to be complicated.

Just pick one of these looks and go enjoy yourself.

If one of these outfits gave you ideas, drop a comment, share with a friend, or pin your favorite fit for later.

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