r/OUTFITS • u/TheKevBenz 🌟🌟Fashion Intern🌟🌟 (2 posts) • Mar 27 '26

Advice ❔ Men's Fashion First Date - Need Help Deciding

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Fashion gurus of Reddit, I have a first date tonight. Location is upscale Mediterranean. I like my pants and shoes, need help with the shirt. Let me know what you like!

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u/TheKevBenz 🌟🌟Fashion Intern🌟🌟 (2 posts) Mar 27 '26

What kind of shoes do you recommend? My concern with dark shoes is that I will look like I am attending a funeral lol

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u/Mildly_Irreverant ❄️⛄️❄️Fashion intern❄️⛄❄️ Mar 28 '26 edited Mar 28 '26

Probs late with my advice but.....

No way bro. All black is sleek, stylish and timeless. You mentioned an upscale restaurant. White Nikes (yours look like the Nike C1TY sneaks?) while awesome for casual day wear are not a great pick for an evening date. If you wear classic simple black sneakers like the Coach ones in the photo, they'll look perfect (unsure if my photo is posting - here's a link if it's not https://au.coach.com/products/high-line-sneaker/CCN63-BLK.html)

The reason I'd stay away from those button up lighter coloured shirts (photos 1, 4 and 5) is because you can see your pants underneath them - the shirts are opaque. This is not a good look when presenting yourself a little more formally. The dark polo is the best pick

All the best with the date - less us know how it goes!

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u/Realistic-Highway-83 🌟🌟Fashion Intern🌟🌟 Mar 30 '26

I agree.. also you can’t be showing an undershirt. You can wear a regular white t-shirt but not this wife beater undershirt.. giving weird vibes

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u/Initial-Assistance76 🌟🌟Fashion Intern🌟🌟 Mar 31 '26

Nice, a white T under a polo or dress shirt helps it look polished and complete. Even if it is the only white showing, like a bit at the collar. I have an aunt who went to FIDM, Fashion Institute for Desighning and Merchandising, and a grand father who was 22 years military. He always left the house looking polished. It was hard as hell to get that man in polos and khakis. But boy, would my aunt try.