How to Dress on a First Date

3 How to Dress on a First Date
Giorgio Armani once said ‘Clothing is the outward expression of the inner person’, so what you wear will communicate to your date just what kind of experience she’s in for. Is she going to be spending an evening with a prep school ponce, or a paragon of modern manliness?

Though your own behavior will dictate a lot of how the evening will go, nothing will get you off on the wrong foot quite like showing up in clothes that fail to clearly communicate your ‘inner person’. With that in mind, EveryGuyed has a rough guide for anybody looking to impress on that first date.

Just Who Do You Think You Are?

Above all, stick with what you know, and what you’re already intimately familiar with. The first date is an unfamiliar situation, which doesn’t need to be further complicated by stress over what you’re wearing. A good place to start is any items in your wardrobe that consistently get compliments from women. Short on these pieces? Go with what you’re most comfortable in, as long as it’s acceptable in the context of your date location. Don’t use this opportunity to wear something brand new, and don’t choose an outfit that you’ve never tested out and about before.

Stick with what you know, and what you’re already intimately familiar with

So What Should You Wear?

You should stick with what you know, but that’s not to say you can’t fancy up your usual ensemble up a bit. For those wanting some more concrete help however, here are a few guidelines of what is unacceptable, and what options you have.


22 How to Dress on a First Date
Button up, or t-shirt? Full-length, or short-sleeve? Sweater, or sweater vest? We’ll make this simple for you. A good clean t-shirt can be great in warmer climates, but avoid ones with excess slogans, logos, or graphics. The same goes for button up shirts, since you should always opt for what’s clean, simple, and above all comfortable.

Always make sure that you’re shirts are clean, not just washed, but free any stain, missing button, or wrinkles. Never wear a shirt that you’ve just purchased without washing it, since it will have telltale folding creases, and heaven forbid, a sizing sticker or tag that you missed.


Dress for the weather, and dress smartly. Remember that you’re probably going to be taking your jacket off at some point, so make sure it’s as minimal as the weather will allow, since you might be carrying it around with you.

You’re not supposed to look like someone completely different, you’re just supposed to look like a more up-market version of yourself


61 How to Dress on a First Date
Jeans, khakis, dress pants, they’re all good choices, but just be conscious of what impression you want to give, where you’re going, and what she expects. Almost always, a quality pair of jeans is perfect in almost any situation. To be clear though, avoid distressed or ripped denim; blue or black in a nice trim cut always works.

Note: For the above categories, consider visiting EveryGuyed’s articles on ‘Dressing for your Body Type’ because none of the above advice is any good if the fit isn’t there.


13 How to Dress on a First Date
As long as your shoes are matched to your outfit, it’s hard to mess this up. The only key, and we mean key, is that you’re shoes are in good shape and clean. Those beaters you wear everyday, even if they are the most comfortable shoes you’ve ever owned, will fail to impress her; she’s not wearing them, but she is forced to look at them.


81 How to Dress on a First Date
Less is more. Keep the number of rings to one, and for god’s sake, it had better not be a wedding band. A quality watch is a nice touch, especially since you should avoid checking your cell phone, even for the time. As for scarves or gloves, just ensure their weather appropriate and remember that at the end of the night, you’d rather be holding her hand than carrying your excess accessories.

Dos and Don’ts

Here are just a few tips we’ve collected from around the office, and from personal experience:

  • Do: Remember that she’s probably as nervous as you; wear what makes you comfortable and she’ll pick up on how relaxed you look.
  • Don’t: Don’t be overly concerned about what you’re wearing, and don’t worry too much about unexpected stains. Women want a man who can dress, not a prima-donna.
  • Do: Ensure that anything you wear fits well. Let her get a sense of that body you’ve spend so many hours honing at the gym.
  • Don’t: Don’t get your hair cut on the day of the date. At least a week is needed for a cut to return to a more natural look, while still remaining styled.
  • Do: Make sure everything is clean, and everything that needs to be pressed or ironed, is.
  • Don’t: Over-accessorize. Overwhelming your look with too many superfluous goods like hats, scarves, gloves, earrings, and sunglasses can create a ‘busy’ look that comes off as more cluttered than cultured.


The important thing to keep in mind is that you’re not supposed to look like someone completely different, you’re just supposed to look like a more up-market version of yourself. New shoes, a haircut and a planned trip to the museum won’t help you at all if the shoes are too small, you hate the haircut, and you can’t stand the museum. If you need to be someone else to impress her, it might be time to consider that you’re mismatched as a couple.


Got any more first date tips? The perfect first-date location? Success stories you can’t wait to share? Use the comment box below to contribute!


Xiaoli Li
Xiaoli Li is an often-missed former editor at the EveryGuyed network. He's currently working as a freelance writer, and probably yelling at a soccer game somewhere out there.
Xiaoli Li

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