Style Julia Stiles look-alike.

December 30, 2009 12:04 PM

I need a cute, warm, women's winter hat.

I look kind of like Julia Stiles*, but with an even rounder face. Which makes it hard to find hats that look flattering at all. Also, I have limp, long, straight hair that tends to get flyaways in the winter, so I'm adverse to polyester materials in hats. Something wool on the outside with silk on the inside would be a dream come true. Also, my ears tend to get cold, so I'd love a hat that covered them. Any ideas? I have tried on tons of hats and have never liked any of them.

*If you like how Julia Stiles you might think I'm bragging, but I favor the exotic brunette look, so I'm really not. She's just the celebrity I'm always told I look like, for better or worse.

posted by semacd to Shopping (10 answers total)

I like these hats which I saw at Renegade Craft Fair this winter. They have ear flaps and come in different materials. The one I tried on had a soft fake fur/fleece/something on the inside and was reversible. As a fellow round-faced person I understand your dilemma and think that the earflaps might help to make your face look less round. The price ($58) is pretty steep though.
posted by Bunglegirl at 12:18 PM on December 30, 2009

As a man, it is tough for me to recommend women's hats.

I can say, though, that my ex (who also looked a little like I imagine a person fitting your description would look) looked absolutely stunning in the few hats she had from Still Life NYC.

While the link appears to show their hats as quite expensive, it was our experience that if you go to the store or-if you do not live in NY (which we didn't)-call the store the prices were actually much lower as a result of sale pricing. On top of that, they are far and away the most well made felt and textile hats I have ever seen or owned, and that is coming from a rather obsessive hat collector who took two separate 1k mile trips to NY with the sole purpose of going to Still Life. The staff, owner and all around service are fantastic, and the product is great.

Okay, done gushing now. Seriously, though, call them up and ask what they have on sale. I am sure that post-Christmas they are stocked with bargains.
posted by broadway bill at 12:21 PM on December 30, 2009

I've always been a proponent of women wearing fur ear-flap hats. No, seriously, they're cute, you don't look anywhere near as goofy as you feel, although they require you wear a similarly bulky coat to keep you from looking top-heavy. That said, parkas are cute, too.
posted by AzraelBrown at 12:35 PM on December 30, 2009

Julie Styles would look awesome in a knit woolen slouchy, and so would you! They're warmer than they look, too.
posted by tapesonthefloor at 12:40 PM on December 30, 2009

Here is a good article on hats.

I wear lots of winter hats and I have found some things that help. Make sure some of your hair is showing under the brim in front on your forehead or on the sides. It softens the look and can be really cute. Earflaps can be really bad, hats that are tight, and anything that goes down around your chin.

I like hats that have bigger brims, like this . I usually fold the brim up, and it helps me if the hat is a little too big. It just looks better. Static guard helps with fly-away hair after you take off a hat, or you can use fabric softener sheets to stop static hair too. The cheap unscented ones are great. Throw them in a baggie and take them with you. I have a small container of hair stuff in my desk at work and I use that if it is really bad.

But I don't want to walk around with my head freezing in winter.
posted by chocolatetiara at 12:53 PM on December 30, 2009

A wool cloche. Either knitted or in boiled wool (the latter of which can have a silk liner). Love cloches.
posted by Kurichina at 1:10 PM on December 30, 2009

Hello, fellow round-faced person! I just wanted to second all the talk of ear-flap hats. I bought a cute knit one with a pompom on top, and I could not be happier.

That shape of hat comes in a number of styles, so find one that suits your coats the best.
posted by jess at 1:33 PM on December 30, 2009

I say look to etsy.com. if you don't see anything you like , you can come up with a design of your own then place a "wanted" add on the Alchemy page and crafters make bids. I recomend not wearing a hat that fits tight on the top because a little hieght will make your face look longer. Heres Julia!
posted by madmamasmith at 4:05 AM on December 31, 2009

Seconding a cloche. There are some beautiful ones on Etsy; I've had my eye on one from Piper and Paisley, although she's currently on vacation.
posted by transporter accident amy at 5:31 AM on December 31, 2009

Update: I tried on a bunch of hats and the ear flap style looked most flattering. And it's really warm. I got this hat from EMS. It's warm and comfortable because it's lined with fleece on half the inside.
posted by semacd at 7:26 AM on January 10, 2010