What to Wear on a First Date

We’ve talked about what to eat on a date.

And about what to drink.

Which is all well and good, but what about what to wear? Unless you plan on going in your birthday suit (… do not go in your birthday suit. Ever.) you’ll need to think about which trousers go with what shirt, which pair of shoes with what skirt.

They like what each other is wearing, obv.

Wink’d is here – as always – to help. We like dating, after all. A lot. We especially like when dating goes well, when the potential romancers enjoy each other’s company, when love sparks and chemistry crackles… mmmMmm!

So here we go. What to wear on a date:


  • Crisp button-up shirt. Avoid any that have the vaguely crazy patterns resembling your Aunt Vernon’s curtains. Also avoid the shirt that has pale yellow stains from last year’s BBQ on the park. If it’s wrinkled, iron it.

Neither shirt looks to be a very good option

  • Casual, sophisticated t-shirt. Try it with a light blazer. This is perfect for an outdoorsy date, or one where temperatures are suspect. By sophisticated t-shirt, we don’t mean one that says “Get Laid This Way!” or “I’m with Stupid.” You’re on a date. You don’t want to be with stupid. Avoid anything that has holes in it, or that smells like your gym bag.
  • Light blazer. These are perfect for just about any occasion. Pair them with simple jeans for that casual, devil-may-care attitude, channeling your inner edgy rockstar. Or wear one with a pair of ironed dark slacks
  • Shoes. Wear good shoes. Not training shoes. Not dirty grungy flip flops. Nice, clean, decent, preferably dark brown leather shoes. Ladies and fashion-conscious men notice these things.


  • Show up wearing your sweaty gym stuff. Kath over at “After I Quit My Day Job” lamented about this recently. Moral of the story: sweaty dress does not equal fun, or sexy dress. Your date will want you to take your clothes off, but not for her enjoyment.
  • Wear a full suit. What are you, on a job interview? Unless you’re meeting straight after work, a suit will seem out of place. At least take the tie off.

Matching shirt to shoes? Good. Matching each other? ... hm.


  • Pull out that sweet summer dress. You’re a lady, after all. And dresses are sassy. They’re the perfect mix of fun (swirly! Swishy!), sexy (slinky! saucy!), and subtle (glimpses of ankles! delicate shoulders! pretty arms!) to impress your date.
  • Wear heels. But not too tall of heels, particularly if you don’t know how tall your date is. Heels give that little umph, that edge of confidence, that sass of a strut. Avoid anything insanely flouncy or floral. Stick to a nice black pair, or a crisp cutting stiletto.
  • Show off your best asset. If you’re proud of your shoulders, wear a one-shoulder top. If you like your legs, pair a crisp shirt with nice khaki or linen shorts and weather-appropriate shoes, like wedges for summer.
  • Add a little jewelry. Delicate earrings or a sparkling, simple necklace can make your outfit just that much more fun.


  • Channel your inner stage diva. By this we mean, avoid all things super sparkly, super glittery, super small. You may have an inner Beyonce just waiting to burst free, but why not save that for date two or three? You want your date to focus on you – not on seeing his reflection in your gleaming clothing.
  • Wear too little. You’re sexy, yes. And confident. But you shouldn’t show it all in one go. Men like that mystery of the unknown. Besides, you want a guy to be interested in more than just the very, very little that you’re wearing.

At the end of the day, what you wear won’t make or break a date. Wink’d realizes this. But all the little parts add up to make a whole, and that whole will impact whether or not date two (three? four?) happens.

What do you think?



About Wink'd

Wink'd is a fun, savvy social card that lets you make new connections with strangers, future dates, future flings, future partners or even simply future friends. The social cards can be anything from cute and flirty to sexy and mysterious to just plain funny. You can give them to anyone, anywhere, at any time - and they can make a connection back to you using your very own exclusive Wink'd written code and scanning code which links them directly to your Wink'd online profile and allows them to send you an anonymous message if they so choose. It's that simple: just Wink at someone by handing them a card and let them connect with you online!
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One Response to What to Wear on a First Date

  1. good shout on not wearing sweaty gym clothes. eeew!

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