I’m a hat person. I love hats. One might even venture to say I adore hats. Particularly vintage hats, of which I have several. For years at antique fairs I was drawn to every stall and vendor which sold old hats. Sometimes when I’d try them on, my friend Mary and I would attract a crowd of ladies who also loved hats. I still remember trying that burgundy one with the huge bow at the Perth Antique Fair in the eighties when the elderly lady with a cane who was watching me said that I had to buy it. So I did. I always do what I’m told. Ha.

So I love to own hats. Even though I don’t wear them as much as I should. Because here’s the thing about wearing hats when one has thick short hair. You might look okay in the hat, but you do NOT look okay once said hat is removed. Because my hair is think and short, it generally stays where it’s placed. Or where it’s squashed beyond repair by hats. So my hat must remain on my head from the time I leave the house until I return. Which can be problematic.

Some people manage this fine. My friend Margaret, who has a silky bob, looks great in a hat. She wears them regularly, removes them, fluffs her hair expertly, and after lunch replaces the hat deftly without the aid of a mirror. That’s a skill, you know. But the fact that I cannot manage that skill is moot. Because if I wear a hat, I simply do not take it off until I’m back home.

In the past couple of years I promised myself that I would try to wear my vintage hats more often. I wore this lovely, quirky, green hat to the Vintage Clothing Show in 2017. I thought I looked particularly fetching. But when I picked up my friend she said she thought I kind of looked as if I had a mushroom on my head. Sigh. Some people just have no appreciation for vintage hats.

Winter hats have always been a particular anathema to me. Nothing squashes hair better than a woollen winter hat. In fact, I think that Canadians wearing toques must have invented the concept of “hat head.” I steered well clear of toques or any form of winter hat for decades. Except when partaking of winter activities like skiing or skating, of course. Until last year. Last year I bought a soft cream woolly hat with a pompom and loved it so much I wore it all winter.

Of course woolly hats, and beanies, were in style again. And because I’m retired, I didn’t have to wear my hat into work and contend with hat head all day. I wore it below to lighten up a too dark outfit. My plan was to leave the hat on when I arrived wherever I was going because the hat went with the outfit underneath my coat. I even wore this hat into the spring during the long weeks of lockdown. Because, when worn on the back of my head, my woolly hat worked a treat covering up those dreaded covid roots. Not that I was in danger of anyone seeing them. Well, except for you guys.

Cream hat with black Max Mara jacket.
Lightening up an all black look with a cream woolly hat.

The other day when Hubby and I went for our Christmas tree, I wore this very old woolly hat, below, made for me by my friend Janet to match my handmade sweater… way back in 1981. I guess that makes it a vintage hat now. Ha. I also wore my new Ugg Adirondack boots for their first real outing. I am not sure what Hubby said to make me laugh here. He’s always making me laugh.

In my lopi sweater and matching hat, jeans, and white Uniqlo jacket, and Ugg boots cutting a Christmas tree.
Hubby always makes me laugh.

Later I announced to Hubby that I was sure I had a picture of me in my blue sweater with my niece Rebecca, my sister Connie’s daughter, wearing my matching blue hat. And I dug around until I found it. Christmas 1981, the Christmas Janet made my hat. Isn’t Beki sweet? Those big brown eyes. I could just squeeze her. Chocolatey hands and face and all.

Me in my Lopi sweater and Beki in my matching hat. 1981.
Ah, isn’t she sweet in my hat?

So, I seem to be coming around to the idea that wearing winter hats can be a good thing. The decades of being colder than necessary because I didn’t want to mess my hair seem to be over. But if I’m going to wear hats out in public, I will need to rethink what goes with my new hair and what doesn’t. My cream woolly hat, as much as I love it, does not look as good on white hair as it did on blonde. I bought this heathered grey hat with the creamy pompom while I was Christmas shopping recently. The colour goes perfectly with my grey Vince sweater.

On the waterfront in a grey hat from Indigo, grey Vince sweater, white Uniqlo down jacket.
I think my woolly hat is slipping off my head.

I wore my new hat and sweater with my white down jacket to my physio appointment today. And the good news is, once I removed my hat, I simply ran my fingers through my hair and it looked presentable again. That’s partly because my hair is softer and silkier since I let my colour grow out. And partly because of the looser, brushed back style which my hair seems to like. My hair naturally grows back off my face. Brushing my bangs forward, a look I wore for years, was only achieved with the aid of a straightening iron and lots of product. One day I’ll try a bangs brushed forward style again, or maybe even go shorter, but I’m enjoying this new look at the moment.

My new grey hat with my Vince sweater and my cream Uniqlo jacket

But, you know, to make my winter hat wardrobe complete, I think I need another new hat. A beret. I was inspired by all the beret wearers on our Paris weekend. My brown vintage beret does me no favours now that I’m white-haired. So I need a new beret in a cool colour: maybe cerise, or black, or a cool burgundy. My friend Linsey told me one day while we walked the trail that she has five berets. Five! She was wearing a fuschia beret that day, the exact colour of her fuschia down jacket. It looked lovely on her. I tell you my friends, I need to up my game when it comes to walking gear. Especially if walking is pretty much the only place I’ll be wearing outfits that anyone but Hubby will see.

I was investigating a website recommended by a reader a while ago. All about colours. I cannot remember the site or the exact recommendation made by the writer. I’ve been reading about colour for a couple of years now, and frankly it’s all become a bit of a blur, except for the odd bits that I found I could apply to myself and my style. But one article did make me realize why dark outfits look sort of unfinished on me now that my hair is so light. Unfinished and imbalanced. Like furnishing a room with all dark on one side and all white on the other, if you get my point.

So I think if I am going to wear dark colours, I might try wearing something on the top of my head to kind of cap off my look. Pun intended. Like a dark beret, in a cool colour. Perhaps the hat will help offset the stark contrast between a dark jacket or sweater and my super light hair. I am going to give it a try anyway. Nothing ventured and all that.

I’ll think of it as just another stage in my new hair journey. And a good excuse to go beret shopping.

Here are some of the woolly hats and berets I was looking at today. I love that burgundy number. Looks a bit like my green vintage hat. And the navy Cos beret is definitely a contender.

So, my friends, I am a hat person. At least a person who loves to own hats. And I guess you could say that I am striving to be a person who wears hats more frequently. We’ll see how I get on with that.

What about you? Are you a hat person or non-hat person?

P.S. The clothing links in this post are affiliate links. If you make a purchase after clicking my link, I will earn a commission.


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54 thoughts on “Are You a Hat Person?”

  1. I am definitely not a hat person. However, summer in Australia does rather demand hats. I think that part of my dislike of hats is the associated hat hair. I have short, fine, very curly hair that goes so flat and damp that nothing can save it when I wear a hat in the heat. The other thing is that I just don’t like the look of myself in hat! Such is life.

  2. I am not but part of me would like to be. Just as I wanted to be a long hair person when younger but somehow couldn’t make it work. In the past I have owned a couple of beautiful wedding hats that I adored and which always drew comments (favourable) but in general, I avoid them. Mostly, I believe, because they make me overheat and I cannot bear that feeling. Even when I used to be a regular cold weather runner, hats were not part of the outfit. Hats on small children – quite another affair. Ah well. Enjoy your cosy head.

  3. I find hats very interesting historically . In old photos it’s usually impossible to spot anyone of any age without a hat unless they were just too poor to afford one . They seemed to be a sign of respectability. I can remember my parents hats & then there was a flurry of wide brimmed ‘hippy’ hats in the 70s before they became mainly a practical necessity to cope with the weather . I’d like to be a hat person . If I looked like you in them then I would be . If my hair was thick & strong instead of fine & soft then I would be . To keep hats on my head I have to jam them on & pull them down . Not a good look especially, as you say , when I take them off . So I have two winter woolly pull ons, one thick & one thin plus a handful of wide brimmed summer sun hats . They’re only worn when absolutely necessary .

    1. My mum always used to say before we left the house, “I’ll just get my hat and coat.” Even when she never, ever wore hats. I think it’s a generational thing. I love all the hats the ladies used to wear in the thirties and forties.

  4. Enthusiastic hat-wearer here! My favorite are Indiana-Jones-style brimmed fedoras, which I now have in black, olive, navy and maroon. Bucket hats are awful on me, but I’m dying to try berets. Yours look just adorable, and I love matching sweaters and hats!

  5. I am way too short to wear hats (or hold an umbrella, come to that), but these days I frequently wear one around the house in the mornings. Yes, you guessed it – trying to flatten my fringe (is that the same as bangs in Canada?) so it doesn’t stick up stupidly after a shower.

  6. I love hats, and have worn them for many many years since I was a teenager. I grew up with most of the women in my family wearing them, so it just seemed the thing to do, then I started to enjoy many different styles. The summer ones are put away now, and after giving a few away, still have well over 20 of those, and the box of berets, pull ons and touques is rather full. I just can’t resist a new burgundy, plum or silver/grey that is just slightly different from the collection I have, not that anyone would notice, but I love wearing them. P.S. my hair is shortish and curly grey so does not look the same after I take the hats off, but a good fluff and it can be presentable. You certainly do look great in your hats and that new grey one is gorgeous with the sweater.

  7. I love hats and needed them for my cold commutes and recess duty. Those days are over ; )). But I used to suffer from hat hair as well when it was so very thick, and oh, the dry hair static! Now I’ve noticed my hair has thinned and I can get away with hats more easily. I don’t like anything that crosses my forehead so no horizontal headbands, beanies or toques for me. That being said, I have one toque that smooshes down in the back so I can wear it off my face, but it is thin, and doesn’t work well in really cold weather. Berets mostly work but don’t cover my ears as well on cold, cold days. Another issue is that I wear glasses and a hat & glasses can be too much for my small face. Somehow sunglasses work, though, for those sunny, sunny frigid February days. Carol in VT

  8. I have to wear a hat when I walk here in So Ca. The sun is very strong. My short hair goes flat when I wear hats or berets in cold weather. I’d like to get a pompom topped knit cap for when I go to cold weather places. I have a vintage mink beret that I used to wear before I grew out my silver hair. I’m with you on trying to figure out what looks best with the new hair color, dark colors or light or bright.

  9. When I was young and thin, a very long time ago, I was a model for Christian Dior Chapeaux. In those long off days every hat looked good on me. I still love hats, but they don’t love me any more. I buy them every now and then, and I even put one on when getting ready to go out. But once I get to the hall mirror and give myself the new once over, off it comes!

  10. My husband bought me a black custom beaver made hat in Santa Fe. I never leave the house without it on my head fall, winter and spring. In summer I have a store bought one in black with and one in beige similar style. I never feel really dressed without a hat. (I was brought up in the 40’s and 50’s.) It seems to complete the outfit. You can see it on my website.

    1. I love the hats of the forties and fifties. Most of my vintage hats are from that era. Except for a black cloche from the twenties. I just spent some time perusing your site, Barbara. What wonderful paintings, and that hat… love that hat. 🙂

  11. There are times that I NEED to be a hat person—playing golf, shoveling snow, sunning at the beach, etc.—but I have yet to find a style that I feel looks good on me. Yes, I do wear hats when I have to, but I never like them. I think the problem is that I have short hair and a small head that appears even smaller when a hat squishes my hair down. Although I so badly want to wear a cute baseball cap or a knit hat with a pompom, I seem to need a style with more of a crown. And I haven’t found that perfect fedora.

  12. Agree with Lisa,it is cute indeed. Your hat/berets are lovely,Sue! This year is ideal to wear all your beautiful hats- no staying indoors more than fifteen minutes,so you can wear them all the time!
    I love hats,especially berets,they are beautiful,add the colour to the outfit,but my main reason to wear them is actually to save my hair from rain,fog,snow and other enemies ….
    I love hats with a brim (like Fedora f.e.,or Cloche) and am allergic to knitted wool hats -I’ll try cashmere beret (pink!)this year-we’ll see…

  13. I love wearing hats now, but I didn’t used to. I struggled to find one that fitted, having a large head (apparently 😂) and thick hair. Plus, I always felt uncomfortable and self conscious in one. This changed when we started travelling to Switzerland in the Winter and I needed to wear one in the snow. It became something of a challenge to find ones that fitted and that I enjoyed wearing. I have a few favourites now, from colourful to black. Then one winter at home I discovered berets and like D, I began to appreciate how they protect my hair, or at least some of it, from the dreaded frizz! I wear them a lot now, especially if it’s cold or damp and love how they really complete an outfit. I also have a couple of “wedding hats” Again it took me a while to find ones that worked. Ones I could simply pop on my head and forget about!
    You look really great in hats Sue. I’m glad you’re wearing your knitted ones now. I remember you telling me previously that you didn’t really wear that style.
    Also, I’d love to see a few pictures showing that gorgeous jumper and matching hat in more detail … it’s really lovely! It looks to be such a beautiful shade of blue.

  14. Grew up wearing hats to church on Sunday. Raised my daughters and granddaughters in bonnets. My bonnet babies always got lots of attention, nothing like chubby cheeks and a bonnet. That being said, no I don’t like hats. My hair is too thin and too frizzy, hat hair is unavoidable and unfixable. Only in extreme wet and cold do I pull on my cream colored knit hat with pom-pom!

  15. I too am guilty of being a hat owner, not wearer. Same hair issue, plus a big head! I love the idea of them, and always wear one in the sun, but it has to stay on.
    Thanks for the recommendation for “Such a Fun Age” a great read and very thought provoking, it warrants further discussion when I find someone else who has read it.

  16. I love this post! I like hats too, but like you, once they’re on my head they smash my short hair! I totally get it. You’ve inspired me to keep wearing them.

    1. I’m okay if I can leave them on until I get home. One good thing about the pandemic is that I’m not going out to lunch anymore, so I don’t have to worry about taking hats off this winter.

  17. I love hats but don’t wear them as often as I should. Had to go to a very posh (very not me) weekend polo event about 15 years ago where dressed to the nines and woman all wore hats. Bought a beautiful white hat trimmed in black (worn with a black sheath and white linen jacket and black patent Feragamos–probably the most stylish outfit I’ve worn this century). Still have that hat, but don’t think I’ve worn it since. Wear my mom’s old black Kangol (at least 55 years old) when I travel in winter. Or else, I wear a Kate Spade knit cap with a small knitted bow at the nape. Have several cloches in different colours; a rain bucket hat bought in John Lewis that I wear a fair bit in bad weather; and, an assortment of summer hats with decent, but not overly large brims (wore one to your house during your first “virtual” party). I’m too short for big flowery hats–always have to be careful not to “over-brim”.
    All I need to do now is wear my hats a bit more often.

  18. I am and always have been a “Hat Person”. I own and wear many hats of all types. There is a comment prior to mine from someone wanting to find a fedora…..I suggest Conner Hats (conner hats.com) because they have more versions that you can imagine and they come Sized so you can get one that actually fits properly

  19. Hi Sue
    It seems I’m more comfortable wearing winter hats than summer wide brim hats. I love them but I feel it’s a confidence thing. I’d love to try a berets but my ears need to be warm and they seem to avoid the ears. Toques for me.
    After reading the Paris post in my big comfy chair I let out a huge sigh…turn my head and looked out my window…dreaming of how much fun a trip with the ladies would be. After reading all their comments thru the years I thought how nice to truly meet. I really enjoyed our adventures shopping with Liz. I also appreciate your writing skills making me believe I was really away! xx

  20. I knew we were twins separated at birth. Not sure how that works considering the fact that I’m older than you, but whatever! I am a hat lover who owns lots of hats, including a navy beret bought in Paris last year, but who doesn’t wear them as often as I should because of what they do to my hair. I was determined to wear them more often this winter, but I’m not sure how that’s going to work considering our new Covid restrictions introduced yesterday. Maybe I’ll have to start wearing them around the house!

  21. I have an issue with hat hair, so other than fir outdoor warmth, I don’t wear them. I have two berets that don’t look good on me and a bucket hat I am donating this yr. Interestingly, I was looking at a cream hat like you have, just yesterday at Nordstrom Rack. I put it back for further searching, but I think I will go back for it.
    Funny story, when my sister and I were little, she had a darling brown felt hat, much like the burgundy one with the little sprig on top. I inherited this hat as a hand me down. Our sprig was green. I am sure it was adorable, since my mom had impeccable taste and dressed us well I think it matched a coat. Well, we thought it was silly and were very embarrassed by the sprig on top. My sister took that hat and put it under the seat cushion of a chair probably to hide and squash the sprig. It didn’t work, and I inherited it and felt exactly the same!

  22. They look wonderful on you…I LOVE hats. But they do not love me. Doesn’t keep me from trying, though.

  23. I totally agree with you about hats. When my hair was short (also thick) I never wore them. Now that it is shoulder length they look much better on me. However having hair like we do it is always tricky once it is removed!

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