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First of all! Docs! <3 I have a brown pair and they are very comfortable once broken in. Kyra's right that they're a bit uncomfortable when breaking them in though. But, if you want to wear them, you can!

I keep imagining those floral ones with either a pair of black pants/jeans/leggings or a black skirt, for some reason, but maybe that's my style.

But maybe you can wear something comfortable but also nice looking. You don't have to go out all snazzy and get this fancy dress or anything, but I always liked showing off either my favorite outfits or new clothes I've gotten, so the Docs for you may be perfect!

I'd just say wear what you like! Maybe lay out some of your favorite clothes and do a bit of a process of elimination. You can mix and match, or even try on a few things to see what you like best!

I bet you will look great!