What to Wear on a First Date

It’s hard sometimes to decide what to wear on a first date, particularly if your date is someone you don’t know very well (or at all).  Here are a few tips for choosing what to wear.

  • What is generally expected in your area?  Not all areas are big on dressing up, so you should keep your city in mind when deciding what to wear.  For instance, where I live dressing up isn’t as common or expected as in other areas, so jeans and a dressy top are a pretty common outfit for a first date; while in other places, dresses are the norm at restaurants.
  • Try a little too hard.  I know — you usually don’t want to look like you’re trying too hard.  But think of a first date kind of like an interview — not that you need to wear a suit, but that you want to make a good impression.  If you arrive in torn jeans and a smelly T-shirt, and she’s wearing a dress, you will probably (and ought to) feel a bit sheepish.  It’s always better to exceed expectations — just a little.
  • To thine own self be true.  Ignore the fact that it’s poetry for a moment — it’s also true.  Don’t dress in a manner that is not reflective of your true personality.  If your date doesn’t like the way you dress, they are probably not the right person for you anyway!

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5 Comment(s)

  1. On Jun 1, 2009, Doreen said:

    I always try to ask where he plans to take me so I can have an idea what to wear. But sometimes they don’t want to say and since they’re boys, they don’t really know how to describe a place.

    But anyway, sometimes, I just ask them what I should wear, whether it’s dressy or casual or what. And I also take into account the time of the date.

    So far, it’s gone pretty good.

    Great post!

  2. On Jun 6, 2009, Cari said:

    I usually base it on the time of the date. If it’s a night, I usually wear a dress. If it’s daytime, I wear jeans/pants or something that’s easy to move around in.

    Great post!

  3. On Jun 13, 2009, Sheila said:

    Oh I know! It’s so hard! I just try to ask my date beforehand to give me an idea of what I should wear.

  4. On Jun 13, 2009, Jenny said:

    No matter what I wear on a first date, I always wear something that meets my approval. If you dress up with what other people is the right attire, then that person isn’t worth it, I believe.

  5. On Jun 13, 2009, Dana said:

    I live in the city so dressing up is normal here. So I sort of have an idea what to wear most of the time.

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