One outfit, four types of hats.
General tips on how to wear all types of hats
- My biggest piece of advice for looking good in a hat and being a “hat person” is to know your head and face. If you have a large head/face, you’re best to choose large hats. I typically shop for my hats in the men’s section and go for larger hats. If you have a small head/face, you also need a small hat. Seems simple, but I think this is where people run into the most problem.
- Your hat needs to frame your face. Experiment with keeping the bill (front) of the cap/hat straight or curved.
- Experiment with a slight tilt in the hat. I love doing this with an oversized baseball cap with a straight bill. Here’s a photo shoot I did with this cap.
- Experiment with wearing the hat toward the back of the head (great for berets, fedoras, and felt hats-third picture) or wearing it so the forehead is somewhat covered (great for flat caps-first picture, newsboy caps-second picture, and knit beanies-fourth picture).
- If you’re new to wearing hats, try wearing your hats with stick straight hair parted down the middle. Make sure your hair covers your ears. This hairstyle is the easiest to pull off all types of hats.
Four types of hats to try this fall and tips on how to choose and wear them
Flat cap:
I bought this at DSW in the men’s department. This hat is great on people with big heads/wide faces because it has a wide, flat bill. If you have a small head/face, I would instead recommend this kind of hat. The thinness of the tapered bill looks great on a small head/face. The flat cap should be worn without a tilt. It looks great paired with this kind of cardigan for that grandpa inspired look: (keep unbuttoned)
Similar caps that are great for large faces/heads:
Newsboy cap:
For pulling off this shape of a newsboy cap, make sure to bend the bill of the cap to make it super round the way I did in the picture. This cap is pretty tricky to choose. The crown of the cap can’t be too loose or too flat. It also can’t be stiff. I would recommend choosing a newsboy cap where the crown doesn’t overflow onto the bill. This means it’s too loose and will sit too wide on any head. This hat needs no tilt.
Similar caps that are great for large faces/heads:
Felt hat:
For a great looking felt hat, I have found the key is that the crown is not too high. The indention on the top of the crown should touch your head. That’s how you know it’s the right fit. Also the bill shouldn’t be so big that it looks like a floppy hat. Unlike the other three hats, a felt hat looks great pulled towards the back of the head, not covering the forehead. Since this hat already runs large, I got it in the women’s department. The crown of the hat should be a little bit longer than the bill of the hat, but not by much. For the felt hat, I prefer a crown that indents at the top and a thin band around the crown (as opposed to thick) The bill should be flat all around otherwise if it’s upturned in the back, it looks like a fedora or if it’s upturned on the sides, it looks like a cowboy hat.
Similar hats that are great for large faces/heads:
Knit beanie:
If you have a large head/face then opt for a beanie that is bigger and generally feels looser, like the knit weaving isn’t super tight. A general rule of thumb is if you have a smaller head/face, then choose a beanie with thin yarn. If you have a big head/face, choose a beanie that uses thick yarn. Also, if you have a big head/face, then you don’t want a beanie that tapers off at the top like this. That kind of beanie is better suited for smaller faces/heads. A beanie for big heads/faces stays round on top. The only exception is if you’re wearing a slouchy beanie and the tapered portion falls toward the back but looking straight forward you would still see a round top as is the case with this beanie. It shouldn’t feel too snug when you wear it. Take a step back and look at your reflection. If the beanie makes your face/head look bigger or smaller then it is the wrong fit. It should sit atop your head and frame your face. So remember, round top for a big head/face, and pointed/tapered top for a small head/face.
Similar beanies that are great for large faces/heads:
With hats, you have to always be on the search for a good one. They are hard to come by. Keep trying all types of hats and be super picky. That’s the real secret. Hope these tips helped! Good luck!
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