How Low Can They Go?

By reader request: Carly's guide to styling longer shorts!

outfit is an old GAP tee (similar here), Jeanerica Belem Shorts (I opted up two sizes!), and taekwondo sneakers.

Hi friends. I am excited to share that Carly Semack, The Stripe’s Creative Projects Manager, will be taking on a monthly column here, helping us style trickier (at least for us millennials and older) trends. I had polled you in the chat to see what trends…