How To Wear Hats When Your Hair Is Short

If you've ever cut your hair from long to short, you know that certain adjustments must be made. I cut my hair from a shoulder-length bob to a pixie cut more than five years ago, and although I immediately knew that short hair was for me, I still had to make a few adjustments, including how I wore a hat. I changed how I dressed (for a while, I dressed much more femininely although now I'm at a comfortable middle ground). I changed the way I wore makeup, choosing to have more fun with colors and eyeliner than I did in the past. It also took me time to figure out how to style my pixie cut properly.

The hardest adjustment of all, however, was, as I mentioned, figuring out how to wear hats. It sounds silly, but for ages I was convinced that I no longer looked good in hats. Then the winter weather came around, and it was no longer a style choice so much as a necessity. Now, happily, I'm back to wearing all kinds of hats again. It simply took time for my brain to adjust to how I look in hats now, as well as the help of a few tricks that I picked up along the way to make hats look flattering with my short hair.

Here's the top 5 tips that I can offer to other short-haired girls trying to figure out how to make their pixie cut work underneath a hat:

1. Position knit beanies properly.

The key to wearing knit beanies when you have short hair is to position the hat properly on your head. You don't want to pull it straight down onto your head, covering your forehead; rather, pull it onto the back of your head at an angle, as seen above.

As you can see, my ears and the majority of my head are covered, but the hat isn't taking over my face. Plus it's not pulled on all the way, allowing the hat to have some floppiness in the back.

2. Let some of your hair peek out.

This is how not to wear your knit hat.

See how it's pulled down over my forehead and sticking straight up into the sky? Not a good look; I look like a Conehead. Plus, if you have short hair like I do, allowing the hat to swallow up my pixie cut entirely makes it look like I don't have any hair at all, which isn't the look I'm personally going for.

3. Experiment with different kinds of hats.

Sometimes when you go from long hair to short hair, you have to reassess what looks good on you. There's a lot of hats that I feel like I can't pull off anymore, such as baseball hats or cloche hats. On the other hand, lots of women with short hair have told me they love wearing those types of hats. In the past, I would have felt silly wearing a fedora but now it kind of makes me feel like Jean Seberg in Breathless .

So try on lots of different hats — yes, even fedoras — and keep an open mind.

4. Wide-brim hats are the best, no matter how short your hair is.

Floppy, wide-brim hats are awesome for two reasons: They add a touch of glamour to everyday outfits and they protect your face from the sun. If you get one in black or brown (or even burgundy or forest green) you'll be able to wear it year-round with almost any outfit.

This doesn't mean you no longer have to wear sunscreen, of course, but it does help protect you from the sun while making you look put-together.

5. Add lipstick.

Finally, when in doubt, always add lipstick. My go-to is NARS Velvet Matte Lip Pencil in Cruella (worn below); Revlon ColorBurst Matte Balm in Standout is a similar, budget-friendly option. A bold lip will help add some glamour to your outfit when paired with a large hat.

NARS Velvet Matte Lip Pencil in Cruella, $27, Sephora; Revlon ColorBurst Matte Balm in Standout, $6, Amazon

And it will also help to dress up a basic knit beanie.

NARS Velvet Matte Lip Pencil in Cruella, $27, Sephora

So remember: Always try to have some hair peaking out, don't tug your knit hat all the way down your forehead (keep it loose instead), try on lots of different hats, and always add a big hat and some lipstick for instant confidence.

Images: Kelly Dougher