Hats, like good wine and best friends, never go out of style. Choosing the right hat to match your suit, though, is a skill most often left for connoisseurs to master. Hats can be stylish, on trend and add just the right amount of swag to any look – if you know what you’re doing. So we’ve taken the three most versatile hats of all time and paired them with their best looks to help you get it right.
- Trilby. A trimmed and sleeker version of the fedora, the trilby hat is a favorite of male celebrities and is among the most versatile. Wear a brown or navy trilby with the Madison Navy Suit, oxford shoes and light blue men’s dress shirt. From Frank Sinatra to Justin Timberlake, celebrities also prefer the streamlined, narrowed brimmed headgear.
- Flat cap and Newsboy. These caps are favored by the more ‘artistic’ types but work well for anyone paired with the right outfit. Wear a flat cap or newsboy with dark colored jeans, Henley T and sport coat. Try the Flat cap with a pair of dark denim jeans, T shirt and our Classic Blue Herringbone Blazer for a simple on-the-go look for casual Fridays or weekends.
- Beanie. Great for fall and winter, the beanie or slouch hat has become a fashion favorite among A list celebrities, sports stars and musicians. David Beckham, Bradley Cooper and Jeremy Piven have all been spotted sporting this slouchy, knitted cap. Works best with casual wear or men’s dress shirts and pullover sweaters.
