I love anything stripes, especially if it has some nautical flair. I took this casual look up a few notches by adding some strappy heels, which gives this outfit a "Boston Proper" feel. 

Get the look:

Sweater: Kate Spade* on SALE! // similar here // here 
Shorts: Ann Taylor // similar here // here
Shoes: Ann Taylor (old) but similar // similar here // here
Sunglasses: similar here 

*Thank you Kate Spade for having me as an Ambassador.