Fedoras look great on square faces (and round faces too). Cowboy hats are suitable for those with square faces.

Popular examples of wide-brimmed hats include boater hats, skimmer hats, fedoras, trilbys, gambler hats, derby hats, and cowboy hats. [3] X Research source Bowler hats have a two-inch brim with a rounded top. This style was popular in 1800’s and early 1900’s. Western hats, sometimes known as cowboy hats were worn in the Midwest. These hats have characteristically wide brims. Derby hats are usually worn by women and have elaborate bows and are usually worn at derby racing. [4] X Research source

Try on different styles of hats to see what kind of material feels best on your head.

Kentucky derby hats can cost anywhere from $135 to thousands of dollars per hat. [7] X Research source Bucket hats are often constructed of cheaper materials like polyester or cotton. [8] X Research source

People with a warm tone look best in blues, greens, golden yellows, and creamy whites. People with cool skin tones look best in bright blue, lavender, ruby, gray, and navy. People with neutral skin tones look best in light peach, red, yellows, and off-whites.

A denim jacket, white t-shirt, and slim fitted jeans work well with a fedora or bowler hat. A flowing dress, sandals, and sunglasses go great with a derby hat. Wearing a baggy sports jacket or suit can make you look childish in a wide-brimmed hat. [10] X Research source Make sure that your hat color does not clash with the colors that you’re wearing on the rest of your body. You don’t want the hat detracting from the rest of your outfit.

If you can’t feel confident when wearing your wide brimmed hat, consider choosing another option for your hat.

If you don’t have a tape measure, you can download and print a tape measure online. You can also ask a professional hat maker or seller to measure your hat size for you. [12] X Research source

For instance, a 22 1/4 inch head circumference is a 7 1/8 sized hat in the US and a size 57 if you use metric measurements. [14] X Research source For Stetson hats, a size 7 1/8 is a medium.

If the hat is too big and you can’t find a suitable size in the style you want, you can apply felt pads to the inside of your hat.