Layering 2 Dresses + Boyfriend Jeans

Jeans: Gap // Heels: Forever21 (old–sorry!) // striped dress: Urban Outfitters (on sale $39) // race back dress:  Urban Outfitters (on sale for $30) // Bag: Madewell // Sunglasses: Quay // Hat: Nordstroms (similar) // Lipstick: Witty by Bare Esentuals

I bought a couple dresses for fall, mostly for layering. They’re both super discounted right now because ain’t nobody buying summer dresses any more!

I decided to get crazy and wear heels with a wide brimmed hat. It feels wrong to me. But sometimes you gotta break style rules, right?

I wore this to work for casual Friday. I realize that’s 4 days away but hey, take it as a little early week inspiration!

What do you guys think? Does this outfit work–yay or nay?