I think the thing that is "off" in look 2 isn't necessarily the fit (I think it looks really nice actually) but the colours on you. At a glance, you seem like a soft autumn, but you may want to look into seasonal colour analysis/colour me beautiful to look more into what colours complement you and which ones are making you look washed out. You definitely have lightish hair and warm skin, so the stark contrast of black and white in that top is stealing all the attention from your face.

I think you look good in stuff that hits at your waist, I would never have guessed that you were only 5'3" because your legs look pretty long. Anything cinched at the waist is going to make your legs look longer and I think it's a great asset for you to exploit. I don't really have the same body type as you so I'm gonna stop here.

If you wanna age up your style try on some full sleeve/sleveless blouses. Do some experimenting with what kinds look best on you. Linen is a great place to start for summer, but I also like polyester blends that drape nicer.. Pairing a breathable white blouse like this with those pink shorts would automatically age up your look.

Based on your style goals, you might really like my pinterest board for inspiration. I have similar leanings right now and I pin a lot of stuff in colours I think you would look good in. I like stuff with a high collar, high waisted and loafers or flat shoes. Lately I've been really into the idea of shirts under dresses if you can't notice.