Every cool cat wears a hat—a wide-brimmed beach baby, a trés chic beret, a funky fedora.

So how come you put one on and you look like a goober. Fear not! Here are a few tips I gathered during a recent Boston opening of Goorin Bros. Hatmakers.

  • Start off with the right size hat. In other words, you shouldn’t look like a mini-me trying on your dad’s. It shouldn’t come down over your ears or fall off when you tilt your head. Conversely, it shouldn’t leave a red mark across your forehead when you remove it. If you have to fuss with your hat, it’s probably not the right size. Here’s a great sizing guide.
  • Your hat has to fit your face, not just your noggin. If you have a long face, don’t wear a hat with a lot of height. A super round face staring back at you from the mirror—you can definitely rock a tall hat.
  • Ladies, for most hats, pull your hair back in a low pony or let it hang down without styling it around your face. Unless you want hat head. Your call.
  • I hate to tell you this, but your face is all messed up. In terms of symmetry, of course. Nobody’s face is perfectly equal on each side, so let your hat do a balancing act by always tilting it a bit. If the hat you like doesn’t look right, try a different angle. Also consider the placement of the type of hat. Sun hats are meant to be worn on the back of the head; fedoras should be worn down over the eyebrows. Berets should be worn on one side. Trés chic.
  • Your hat is part of your outfit, so match it to your clothes. A fedora is wrong with a sundress, whereas a sunhat looks ridi in the winter.

With these tips, you can leave your hat on and leave off goober status.