Three Date Night Outfits for Him

Little Black Dress

Does your guy’s idea of dressing for date night involve a Kanye tee and too-worn sweats? Never fear. We’ve put together three common dating destinations – and all that he’ll need to dress to impress.

Before we begin, we have two “rules” that apply to all of our looks. The first: fit matters. Your guy can wear the most expensive shirt out there, but if it’s ill-fitting he’ll always look schlumpy. In comparison, pick up a bargain shirt that’s cut perfectly…well, he’ll look like a million – even if he didn’t spend it.

The second “rule”: look like you’ve made an effort, but not too much of an effort. English clothing designer Hardy Amies said it best, “A man should look as if he had bought his clothes with intelligence, put them on with care and then forgotten all about them.” And we happen to agree. This is the key to looking effortlessly cool whether donning jeans and a top or blazer and button-down.

Ready to get your guy date ready? Read on!

Dinner Date Men's Attire
Date Night

All relationships need to have a strong foundation, so investing in wardrobe staples like dark wash jeans and a crisp shirt are essential. But that doesn’t mean his look has to be boring – this button-down sports a fun novelty print. Top with a velvet blazer when the occasion calls for extra swagger (or he needs instant polish for meeting your parents). Plus, all these pieces work great mixed, matched and layered with stuff he already has in his closet.


After-Work Drinks

Meeting him after work for a quick cocktail? Snag him some denim. A denim button-down is sure to become the most versatile piece in his wardrobe. Layer with a bomber jacket to dress it down. Or dress it up with a vibrant tie – an easy way to add a punch of color. Chilly night? Pop on a sweater to bring warmth and texture to his look.

After-Work Drinks Men's Attire

Movie Night Men's Attire
Movie Night

Just because he’ll be in the dark doesn’t mean he has to dress like it. Remember those jeans from the dinner date? Bring ‘em back for ultra-cool style while watching the big screen. A sweater is always a cozy option – and great for burrowing your face in if you have a penchant for horror movies. Seek out interesting collar details, like the shawl collar, to add serious flavor to his look. Take it downtown with athleisure kicks or head uptown with polished leather lace-ups.


Sure, the “what to wear on a date” scenario can be very unnerving for your guy. Above all else, he should make sure that whatever he wears, he feels comfortable. Because that’s when his true self shines through. And that’s what fashion is all about: looking good and feeling great.

Category: Your Family

Tags: mens

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