Fedoras are great for the top of your head, but not warm enough for my climate in winter. Also, they blow off in the wind. I think of them as purely decorative hats, much as I love them. Mr. Suz has one for dressy situations and for spring/ fall.

Carter, the photo you posted would be a perfect beanie for you (imho)

Yes, if you need recommendations on winter hats, definitely ask a bunch of Canadians! We're pros!!
Here's the link for the beanie I grabbed at Target, if you want to try a cheap and cheerful one - lots of colors and it's easy on the hair:
http://www.target.com/p/women-.....A-16463124

Cutting your hair short like mine actually minimizes hat head - although I'm sure that's not a solution for you.

WHAT A SWEET DOGGIE. xo

My beanies are cashmere.....a bit of a splurge but they are very warm, soft and have nice stretch so they don't squeeze my head/hair. Some are J Crew, one I got at The Bay. I watch for them to go on sale.

Good question! I really only put on a hat if I have nowhere to go later or it's late in the day. I can pull it off better if I'm wearing my hair wavy - it tends to bounce back. Otherwise flathead hat head for me too! Good luck

I like slouchy berets for this reason. Kinda like a beanie, but less length and a little more fullness. You can adjust it to cover the ears or not, depending on how much warmth you need. I have a little head though, so many hats that work for others are overwhelming on me.

Try Club Monaco for hats. I particularly like the Nora and it's on sale right now. I just added the Colleen, also on sale.

Wow. Look at all this wisdom! Today ended up being a very busy day, and I'm headed back out again in a minute. Just as well I haven't had time to shop yet...so many new suggestions here. I'll be back later to follow all your links.

I did do a quick search last night for ear bands. All I seemed to find were either gear-type or they had big rose decorations on them. Most were at least partially acrylic. Even still there were very few. Is there some other way I should be searching for these?

Angie...I was hoping for something a bit less radical than chopping off my hair;-)

The solution to hat hair is no hat. I choose earmuffs for colder temperatures, and prefer the hood of my puffer over the hats I own. The hood is large, so it doesn't give me too much hat hair, but unlike the hat, it blocks out the wind. Win-win. If you do choose a hat, you could add some dry shampoo indoors, which will help with volume.

I found the most totally awesome slouchy beanie at Nordies this fall and when I went to get the information to send, they no longer have it...Anyway, I went to the men's department and found a cashmere Rail beanie...It is TDF...I can just pop it on pull down a few bangs and I am ready...This one got about a million positive reviews so I tried it and hey I indeed liked it...Perhaps you could peruse the men's department and score a similar find...smile