Classic clothing with
a modern twist

Why locals love it

Named for the owner's shelter-rescued dog and cat, Sherman Pickey is a favorite among mid-Atlantic prepsters of all ages. Known for their trunk shows and abiding, enthusiastic customer service, Sherman Pickey has something for everyone (and if it's not their in your color, they'll order it for you on the spot).

Why you should visit it

There are many stereotypes of preppy life in these parts. Sherman Pickey especially curates their store to include the staple names (like Lilly Pulitzer and Petit Bateau) with local designers of clothing and jewelry. Mostly geared toward women, the store carries and stocks a notable amount of stunning handbags as well.