Home Sugar Support™ Forum Fashion Coffee first date outfit, but in a swanky area?

This topic contains 3 replies, has 4 voices, and was last updated by SFwinefan SFwinefan 1 year, 2 months ago.

Viewing 4 posts - 1 through 4 (of 4 total)
  • Author
  • #39494


    Hi guys! I’m meeting a POT monday and he seems like a real catch. He wants to get coffee in the morning before a meeting in the area (perfect because no possibility of him “extending” the date). Normally I’d dress casually, but he want to meet in a very upscale, high class neighborhood near both of us. Should I adjust my outfit accordingly? If so, what on earth should I wear? My wardrobe is, frankly, not extensive, and I’m not sure what I should wear that’s between “casual coffee date” and little black dress. Any advice at all is appreciated!


    Some nice jeans, a blouse, and some cute heels. Anything better than an old t-shirt will probably be fine. I wouldn’t worry too much about it. Just don’t freak out that he’s gonna be overdressed (I assume) because of his meeting.


    I second what @strawberry.breanna.smoothie has to say and add that whatever you choose should be comfortable and make you feel confident. If your outfit makes you feel self conscious, it’s going to reflect in how you behave.


    @princess1098, the advice above it’s sound. If you want that extra level of assurance, you can go by the area a day or two ahead to see how casual people are.

    Remember, this is coffee so casual, comfortable, but done in a way that shows you off will be all an SD will be looking for. And much better than over dressing. Most people in a nice area will still be casual and in jeans, even in a nice part of town. Assuming it’s not after church on Sunday or in a business district early in the morning.

Viewing 4 posts - 1 through 4 (of 4 total)

You must be logged in to reply to this topic.