WIW: loud, with amazing Converse wedges

I take my pictures in a mirror. Today I'm wearing a shirt with text, so I flipped all the photos, and boy does it look weird to see myself the direction people see me in real life!

Anyway. A WIW, and a handful of shopping decisions. The Gap had an incredible sale last week so I bought a bunch of their new fall items. I'm quite happy with the direction they're heading, but as usual I can't decide about fit & flattery.

1: First, what I wore: J Crew boys' t-shirt. I am so not loud in real life. This shirt cracks me up. After taking all these, I realized the sleeves look much better unrolled, but this is what you get.

And the Converse wedges from the NAS! They're amazing. They show up better in later photos.

2: Next, with a new Gap denim skirt. I love this skirt but I am considering sizing up. It's the right size but it hugs my curves in a way that's more bombshell than avant garde, and one size up hangs straight.

3-4: Same skirt, with a Gap "gwen" top. All cotton, structured, with a zipper in back. The XS was too tight in the arms. Is this (S) too shapeless on me? I rather like shapeless sometimes.

5: Not the Gap: a L'Agence silk dress with side zippers (invisible in the photo) and raw edges. I could shorten the straps 1/4". Keep? It was only $20 at Crossroads, and it looks great, but I'm not sure when I'd wear it and it smells strongly perfume.

6-7: Gap linen top - too much like scrubs? I think woven tops just might not work on my broader shoulders, after many attempts. I had to size up and I'm not sure the effect is great. I was going for a sort of Japanese / Eileen Fisher linen look.

Worn with slouchy Aritizia linen/tencel pants I found at Crossroads a while ago. They're my first foray into synthetic blends, and I'm happy so far. I'm considering adding wool/viscose blends also. I hate the feel of most synthetics on my skin for some reason, including pure tencel, but these are basically ok.

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