Going to the mall:

 

High-waisted shorts + plain top + a lot of jewelry + boots + a good purse to carry your wallet in.

 

First date:

 

Jeans + boots + plain shirt or a graphic tee + cool leather jacket.

 

“You don’t want to seem like you care that much, so something low-key. Definitely no heels on a first date unless it’s casual—like jeans and a casual shirt. I would wear flats.”

 

Party at someone’s house:

 

A plain black tight dress + Rob’s Arthur George socks + simple black boots, no heels + sweater (if it’s cold) + necklaces.

 

“I love casual dresses. I have 10 plain black dresses.”

 

On the plane:

 

Cute sweats.

 

“On the way here I wore army green sweats that were tight on the bottom but then really baggy, I wore a plain black shirt that was all cut in the back and I tied a flannel around my waist and paired it with boots and socks. You can look cute and be comfortable.”