December 10th, 2008
I love the look of a lass in a fabulous hat, but you might need to persevere if you aren’t one of those people who looks naturally good in headgear. The shape of a hat alters the size of your head and face in relation to the rest of your body, which can make it tricky. It’s a question of trying on several styles to see which works. Berets, newsboys, cabbies, cloches, buckets, caps, fedoras and beanies, there’s a look for everyone if the proportions, fabrication, style and colour are spot on.
I like it best when there is hair peaking though from underneath the hat. Lasses with long hair wear hats particularly well and I think it’s because the abundance of hair adds balance, softness and interest to the look. I look awful in most hats because I have a small head and very short hair. Hats seem to overwhelm my facial features. But this does not prevent me from wearing one when it’s freezing cold. Hats, like scarves and gloves, keep you wonderfully warm. I’ll happily forego a little aesthetic for extra warmth.
I hope you’re wearing hats if you look great in headgear. They make a superb statement and can become part of your signature look. It doesn’t need to be freezing in order to wear them either. Often in Europe, people gravitate towards hats and scarves before a Winter coat.






A few of my favourite hat styles: beret, knitted cap, slouchy cabbie, fitted cabbie, newsboy and cloche. Hats are such a fun accessory. If I looked good in a hat (and my hair behaved after wearing one), I’d be all over the look.
25 Replies
Posted on Wednesday, December 10th, 2008 at 7:57 am
I love hats and have found styles that work for me but it does ruin my hair after even a short time wearing them. I get horrible static electricity and really bad flat head. Does anyone have a solution other the wearing the hat all day?
Posted on December 10th, 2008 at 8:11 am
I love hats and wear them all the time. I’m sure I’ll have some to post soon. I do get a bit of flat head hair but I usually just run my fingers through it and it perks up a bit. The additional flair hats add are worth the hair issues for me.
Posted on December 10th, 2008 at 8:33 am
I just saw a mom yesterday at the day care with a super fab hat– fitted cabbie I think. Unfortunately, she walked by before I had a chance to compliment her. Hats are critical for me to keep my ears warm– I wore mine today. I don’t really feel like I have a good handle on choosing them but I probably just need more practice in trying them. My head is also small so I have to watch for fit as well.
Posted on December 10th, 2008 at 8:38 am
I have always liked hats, but never worn them. This might just be my first year! I love the cream one on the second row in the center.
Posted on December 10th, 2008 at 8:43 am
I like hats and wear them all the time when outside in winter. I have long hair, so I only like how they look when mu\y hair is down, if I put in in a ponytail then I look quite silly.
I am currently wearing a grey newsboy one more often, but plan to get a few new ones after Holidays, during sales. That red Milly one is gorgeous, too bad the price is quite ridiculous.
Posted on December 10th, 2008 at 9:01 am
i wear heats all the time. living in TX i wear them everyday in the summer for sun protection and then i just got used to always having one on. i wear them mostly for function, which does end up making a style statement.
i’m hoping to get this one for winter. http://www.tilley.com/detail.a.....ductNo=TF1
ironically my mom was known for wearing hats everyday. i never appreciated that about her, but now i have come into it myself unintentionally.
i have really long hair and it does help the hats feel stylish.
Posted on December 10th, 2008 at 9:14 am
I love hats and think they really suit me. My husband has a small head. . compared to his body, heheh, so I try to get him to wear ones with some sort of brim. . but instead he keeps wearing awful toques which look like a condom on him!! Hope that’s ok to say here.
My favourite hats come from this designer: http://wildhagenwear.com/
I can’t recommend them enough.
Posted on December 10th, 2008 at 9:41 am
I love hats on other people but they draw out my worst features. They seem to put the focus on the lower part of the face, right?
I do have a cute hat, but it’s not that cute on me. I wear it when I need coverage for walking the dog and such.
Posted on December 10th, 2008 at 10:11 am
I love hats on other people and hope to see some fun pictures of YLF forum members sporting hats
For myself, I haven’t found a flattering hat style. Maybe they just aren’t for me, or maybe I need to try harder…
Posted on December 10th, 2008 at 11:08 am
I love the hats pictured in the post, but I don’t really have any in my wardrobe. I have one winter hat that I wear when absolutely required, like when I have to shovel the driveway.
Luckily, my commute involves walking from my car to the office building so I’m not outside too often and I can get away without a hat. I might have to try some hats on for fun next time I am in the store. Maybe I will stumble upon something cute!
Posted on December 10th, 2008 at 11:09 am
I love hats, but I don’t wear them very often, because I forget about them while getting out of the door. Thanks for clarifying about the hair, Angie – I was never sure if I should be wearing newsboy hats with long hair. I thought you have to have something like a bob. I also like berets a lot, but I am never sure when they are in fashion.
Posted on December 10th, 2008 at 11:27 am
I LOVE hats. I always wear a bucket hat when we do our neighborhood walks – a necessity for the fair-skinned in sunny LA.
I have struggled to find a casual, every day hat, though. I have tried a few “cloche” hats, but with my tiny head and short curly hair, I haven’t found the right one yet. Most seem too dressy for every day outfits.
I am rapidly moving toward “eccentric lady” with my love of scarves and hats. What’s next? Gloves?
Posted on December 10th, 2008 at 11:38 am
I have a small head too-LOL- but it doesnt stop me from trying to wear them, especially living where I do (brrr..). I LOVE the red flower one from Shopbop you have pictured-but the not the $150 price tag (it is cashmere, but still).
Posted on December 10th, 2008 at 11:51 am
I completely adore hats, am told I look good in them, and own quite a few … but my hair is such a delicate ecosystem, that I don’t wear them as often as I’d like. Cloches, like that gorgeous one you picked, Angie, are among my faves!
Posted on December 10th, 2008 at 12:02 pm
I too LOVE hats, and have dozens of them. While my hair doesn’t always fill out the back, I do let my bangs peek out and maybe a few frontal locks. On bad hair days, I just tuck most of it up under the hat and wear it all day, even indoors, as it’s part of my whole ensemble. I get so many complements I wonder why I don’t wear them more…
Posted on December 10th, 2008 at 12:15 pm
I have the opposite problem of many who posted – I have a huge head! I also live in the middle of Canada which means it is VERY cold for 4 months of the year, so consequently spend a lot of time looking for hats to cover my big head. In the winter I never go out without a hat – you lose 50% of you body heat through your head so it is essential for the climate I live in!
To prevent static cling I sometimes spray the inside of my hat with Static Guard and I also use a product on my hair by Sebastian called Laminates Sheer Smoothing which is also an anti-static product.
I love all of the looks you showcased. I find it is also important that the style of the hat fits the style of the coat I choose to wear. The cute cabbies and newsboys are difficult to wear with my necessary down-filled coat, but I’ve managed to make it work by combining it with a funky scarf.
Posted on December 10th, 2008 at 12:21 pm
Hats look great on other people, but I look ridiculous in them. And, like Linda, I have a huge head. LOL A stylish hat would never fit me, and a regular winter hat squeezes my brains out. Plus, I just look stupid! I’ll wear them only out of necessity if I have to spend any amount of time outside in the cold. Even though I have long hair, my face is just too long to pull off a hat. I need my hair showing completely in order to balance me out.
Posted on December 10th, 2008 at 3:44 pm
I adore newsboys and could wear one every day if I had enough variety in my hat collection.
Interestingly, my face is a similar shape to the girl pictured here in a newsboy.
Posted on December 10th, 2008 at 4:07 pm
I love these posted hats (especially the cloche). Since I live in New Hampshire and I have yard duty at school, they are a necessity. I never feel quite comfortable in hats, but I found a style that works for me . Last year I purchased a hat and matching gloves to go with my 1930s or 40s fitted black coat with fur collar.
Take a look at the Red Rover website.
http://www.bumbley.com/RedRover.html
They are pricey, but I found them at a local shop for half price in January . The pictures do not do them justice, and the quality is excellent.
Posted on December 10th, 2008 at 4:39 pm
I enjoy wearing hats and gravitate towards knit caps and cloches. I have long hair and it is true that they only look good with hair down. I also have a couple of berets and one straw hat with a brim, but somehow I don’t like how they look on me–maybe it has to do with having a round face?
Posted on December 10th, 2008 at 7:23 pm
I’m glad that there is a “youlookfab wearing a hat” consensus.
Tanya and Athena, you look utterly adorable in hats and I’m glad you wear them. Sarah, I hope you’re encouraged.
Nice tip about the static spray, Linda.
Joelle, I have a client with a round moon face who looks fabulous in hats. Don’t give up!
Posted on December 11th, 2008 at 8:39 am
that red flower hat is gorgeous!!!
i actually never wear hats in winter…i have a very small head and a mass of curly hair that keeps it warm. Also i work hard at keeping a bit of volume on top so adding a hat i don’t plan to keep on all day wouldn’t work out that well…
but i love them on other women and i think they’re a great way to add some pop and style to an outfit for cheap! I’m jealous!
Posted on December 11th, 2008 at 9:17 pm
I love hats and I think I could wear them well…I just need to find some I like! I will probably hit the after Christmas sales and get a few.
Posted on December 13th, 2008 at 3:07 am
I love wearing hats and have found a great shop. It’s called the Queen of Hats in Portland, Maine. Here’s a link to their website: http://www.queenofhats.com/
Posted on December 20th, 2008 at 5:00 pm
I have a round face and would like to find a warm winter hat style for my shape…for snowshoeing or skiing.
Posted on January 10th, 2009 at 1:08 pm
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