How long do you keep dressing your best for the initial dates?

I've asked this girl out to town and I'd put on my best outfit, an informal dress shirt with vest matched with white pants, it makes me look taller, leaner, and more mature than usual. I think she fell for me because of that - my normal casual attire hardly gets any reaction like that.

But obviously I don't have that many nice outfits to wear, so I was wondering, at which stage of dating would you be okay with dressing down. e. g. just going T-shirt, jeans, or shorts maybe. Perhaps it depends on the location and what you're doing, so perhaps you can share some of that advice too. :)



Most Helpful Guy

  • Unless you're an oil tycoon and have an endless supply of cash, I think it's okay you don't have tons of fancy and expensive outfits. You can still "dress down" while being classy about it, but I think women like men best when they're comfortable. No, not with a wife beater T with a mustard stain on it with the hairy beer belly protruding out from under it; but like you said, depending on what you're doing and where you're going, you can make some casual stuff look well put together and stylish.

    You can also take your best stuff and mix it around with other clothes that might go together with it, so it looks like you've got more fancy stuff than you actually do. I did that all the time with suits and sport coats because those damn things were very expensive.

    You'll be fine. As long as you have good hygiene and are confident, then the girl isn't going to worry too much about what you're wearing.

    • Actually dressing that nicely made me feel more confident and comfortable with myself lol, cos long sleeve shirts just give you that nice tight fit, it's really cosy.

      The part about mixing it up with other clothes seems workable... Thanks for your advice!

    • You're welcome, my friend, and good luck with this new girl you're seeing.

What Girls Said 1

  • You should dress nicely every time except when your home.

    • There's dressing nicely, and then there's dressing super nice haha. I'm referring to the super nice part.

What Guys Said 1

  • Sounds like you're dating her, ask what she likes on you.

    For me it just totally depends on my mood, sometimes I feel like GQ-in' it up with a vneck, blazer, my Gucci jeans and Vans.

    Other days, hoodie and gym shorts. That is the GOAT comfy combo.