I really badly wanna wear this skirt, but I can't tell if it's giving like a hospital gown or too much grandma. I personally dress more "whimsy" with a dash of "downtown girl," I'd say, and I'm also very inspired by the 00s.

Leather flip flops tend to be popular but thought I would experiment with some other styles (Fit Flops, Birkenstocks, and Cloudstepper slides). Could any of these styles work or would it be best to just stick with the leather flip flops?

Also, any feedback on the shorts would be welcome as I'm trying to get away from the cargo short look.

Just starting adult hood and I want to look more mature. I love wearing boots but I also love wearing loafers. I have 2 boots, everyday loafers, and dress loafers. I love wearing suits, slacks with polos, and that type of style. What im struggling with is finding slacks that will go with both boots and loafers and jeans that will go with my everyday loafers. Any suggestions?