Hats are a fantastic way to top off any outfit, whether you’re just running errands or pledging your love on your wedding day. But hats—especially dressier hats—can be tricky. How do you wear one without looking costume-y or that you’re trying too hard to be cool? Equally Wed has four fantastic picks to help you look wonderful.



Perfect for the vintage-loving groom. Inspired by The Chairman of the Board, who was known for his classic style as well as his singing, this pork pie hat is sophisticated, not “late 90s SoCal alternative rock fan.” Priced at $58, the Frank Sinatra Bewitched Pork Pie Hat is available from Village Hat Shop.




This fedora won’t make you look like Panama Jack, we promise. The two-tone number is a great touch for a seaside ceremony, providing great style as well as sun protection. Made for the Mr. Green collection by Louise Green Fine Millinery, Style M611KTPA is priced at $175.




Straw hats can be especially tricky. The key with straw hats is to consider size. If too big, they can be comical. This Paul Smith by Christy’s Black Trilby Hat will have people swooning, not laughing. At $207, this cool number is available at Paul Smith.



For all you rough-and-tumble cowpoke readers, you can make cowboy hats chic. The trick is to stay with a classic style. Much with the straw hat, the larger the cowboy hat, the more costume-y it’ll be. Also, leave the spurs and bolo ties at home. Priced at $85, “Open Road” by Stetson is available from Hartford York.