How have you guys branched out?

I’ve grown up as a tomboy, and I still feel as though I am. It’s led to me having a very baggy, laid back wardrobe, but sometimes even I want to feel cute with more going out tops or something appropriate for a girls night out or a date.

Every time I go out and try on something new, like a tighter top or just something more feminine, I feel really insecure and never end up buying it. And even if I do, it just rots in my closet.

I’ve been trying to find a middle ground between the two styles, but I just feel like I can’t find anything that suits me at all. I also really hate wearing cropped clothing, and it seems like it’s all that’s available.

How have you guys branched out to different styles or clothing types while still feeling confident? I feel like I’ve had this problem for a while and know I can’t be the only one.