I’m dreaming of little getaway weekends this summer. I love these bags. I think you could buy one and use it forever. They’re so classic and cool, effortlessly chic without trying. How about wearing some sort of simple Steven Alan or APC frock and wooden sandals (perhaps something like this?) and hitting the road?!:

1. Upper Playground: Taylor Travel bag
2. Rag & Bone: Mini Gladstone bag
3. Tori Birch: Gingham weekend bag