Now that my hair is chin length, I am happier with how I look in a hat. However, I have a ‘bump’ behind my right ear and if my glasses or a hat rub it it can be painful. My LLBean and Sunday Afternoon sun hats are a size too big and work perfectly (I do not look in the mirror while wearing!!) My winter caps are all knit by me and have soft ribbing that doesn’t bind.

Slouchy hand knit beanies in winter, big straw sun hats in summer. Finding sun hats that fit my big head is always a challenge but I persevere. (Back in the days when I still went to stores in person I had a habit of trying on the sun hats every time I saw them. You never know. I haaaaate that women’s hats almost never come in multiple sizes. Hat sizing is technically unisex but that only works if they make more than 1 size!)

Also fancy fascinators/wedding hats for formal occasions (like the one in my profile pic) but they haven’t gotten much play lately.

And whooooo these pictures are old; I miss having nice short hair! (Hopefully in a couple of months I’ll be able to go get it cut again....)

Some gorgeous hats on this thread! Angie, you in a stetson is unexpected, but it looks amazing! Diana, your hats are spectacular! Did you make the knit one?

I am a bore when it comes to hats, though I admire them on others so much! I wear knit caps in the winter for practical reasons, and occasionally a baseball cap in the summer for sun protection.

I wear the following:
- a variety of straw hats in summer
- caps all year
- wool beanies in winter
- I do have two winter brimmed hats that I like but rarely wear. I need to be more confident in them!!

@Irina, I have a small head too - used to buy EXPRESS' sun hats when they've had two different sizes ( XS/S size - now it's "one size only" ).
I've got "shapka" from GAP a few years ago and same style from BR for husband and daughter.
Last time I saw the sun hat that fit me was at REI ( forgot the brand ).

I love hats but prefer those where the crown is not very tall so I guess that is why I prefer berets over beanies. I have several fedoras and straw hats, cloches and bucket hats. I wish I liked baseball hats since we attend a lot of games.

I'm a fan of all kinds of hats and caps but I have to say that the safe bet is the fedora, always very elegant and noticed.
Otherwise, newsboy caps and flat caps are still nice and famous. The choice is vast and in fact, every hat has its season.

In real winter, pretty much always a toque/beanie/watch cap. I need the double layer around my ears or I get cold! And I like that they stay put when it's windy and layer easily under a hood. I have some slouchier knit styles that are more like a beret or tam and wear those more often in the spring and fall when it's chilly but not freezing.

For summer, I'll wear pretty much anything except a true baseball cap (makes me feel too much like a camp counselor). I have full-brim hats in cotton canvas, faux-straw, and nylon, plus a linen baker/newsie cap and a really old canvas cadet cap -- the flat top looks much better on my head than a rounded baseball cap. Mesh-back trucker caps, which are very trendy with the outdoor rec crowd, also look completely ridiculous on me. I often look at them longingly because companies like Patagonia and Prana release lots with cool artist-designed prints.

I wear several types of hat, baseball/sun visor, wide brim and knit beanies. If it is structured (not floppy) I also might wear a newsboy style cap. These hats seems to work regardless of my hair length. My all time fave is a baseball cap.

This is my go-to hat now that my hair has grown out to my shoulders.