Ask Webster Style: Shoes for the grown up hipster

Q. Hi! Shoe question! I’m shopping for a 34 year old man who’s trying to graduate from Chucks. He has a casual, comfortable style but still with that hipster edge. Also, he’s an artist who wears straight legs jeans and a chain wallet. 😉 Thank you! If anyone knows, it’s you guys. 🙂

From South Carolina

A. Hey EJ,
Since he like chucks (I assume you mean Chuck Taylors), we have focused on mid to high top shoes. We have  also focused on shoes that have a casual but “dressy” look and feel. This way they will work well with jeans and slacks. We stuck with colors that will work with many different color combinations. Checkout the follow selections below, we threw in a couple of oxfords as well.

Best regards,


Milford Black by Aquila Shoes $189
Geary Navy by Aquila Shoes $199
Casual Suede Lace Ups by Aldo $130
Burlington Signature Saddle Oxford by Bass
Top-Sider® ‘Boat’ Oxford Saddle Shoe by Sperry $99.95

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