15 photos of real world vintage ladies wearing beautiful hats

Spring is well underway around these parts and I couldn't be happier about that fact. Even though, objectively, this winter was a fairly mild one (especially from early February onward), it felt like it went on for decades and I was quite excited to wave buh-bye to to the coldest chapter of the year.

The temps hadn't even hit double digits yet before my sundresses were rotated to the front of my closet and I was giving all of my summer hats and bags a once over to make sure that they didn't need any repairs before kicking off their time to shine once more.

As most of you know, I'm one of those folks who can never get enough of vintage hats. They're the one of my favourite items of clothing to wear and collect alike. Though I don't find too many around these parts any more, whether close to home, when I travel, or (occasionally, given the steep shipping costs on such) online, I'm always on the prowl for my next exciting old school topper and rarely go more than a few months without adding at least one new hat to my closet.

Hats are fantastic accessories. They can be expressive, bold, subtle, small, huge, lightweight, hefty, decorative, understated, one-of-a-kind, perpetual favourites (berets, for example), charming, chic, beautiful, exciting and at least a million other exciting things.

I've had a passion for them my whole life and have worn vintage examples frequently since my teen years (indeed, they were some of the first mid-century items I ever thrifted, back when finding them at thrift stores wasn't rarer than stumbling upon a pot of gold at the end of a rainbow).

These days my collection now numbers over 50 hats and shows no signs of slowing down (though I do keep reminding myself that I should prune through them at some point and sell or giveaway a tiny number that I don't wear very often; most however do see a lot of wardrobe action, so they're definitely staying put!).

Women (and men) the world over used to delight in the act of buying a new hat and doing so was frequently referenced in popular culture up until (at least) the 1960s. I will forever feel like we lost something great and gorgeous alike when most folks stopped wearing hats on a frequent basis, and love that many of us in the vintage/rockabilly/pinup world still keep this time honoured art alive.

With spring out in full force and my lighter, more seasonally appropriate hats (very much including all of my straw ones) making an appearance again, I thought it would be a lot of fun to kick off this week by sharing some wonderful photos that I've come across online lately of real world women from the mid-twentieth century wearing stunning vintage chapeaus.

While not all of these fifteen examples are strictly spring/summer related, they are each spectacular and can provide so much styling (and shopping/wishlist!) inspiring when it comes to how to successfully sport old school toppers in the scope of today's vintage looks that I felt it was a-okay to include them here, too.

Scroll on to soak up the vintage hat awesomeness, after which, I'm sure that like me, you'll be wishing for a time machine and a charge account at a mid-century milliner's shop even more than ever before! :)

15 photos of real world 

vintage ladies 

wearing beautiful hats

1. Lofty turban ruching over a hat form with long tendrils of millinery greenery jutting out of the back? Yes, pretty, pretty please! Here lace collar is really charming, too!




2. Though somewhat casual on the chapeau front of the day, each of these hats adds so much to their lovely wearer's ensembles, which would, at the time, have seemed at least a bit out of place without them. Plus extra styling points for the nearly identical belts.




3. Whimsical hats turn my knees to jelly and this double bow "antenna" style is doing just that big time! (While also reminding me of a similar vintage bow hat that I have and wear often.) Her companion's classic turban is pretty terrific, too - and can we take a moment to lose our heads over all of those fab bags!!!




4. A trio of gorgeous springtime perfect hats adorn the heads of these lovely ladies as they enjoy a Woman's Club Tea event while decked out in equally attractive printed daydresses.




5. Generously sized curving feathers that encircle the (front) brim of a hat are one of my favourite styles (see this example from my wardrobe, for example) and when they're partnered with a classic skirt suit like this you'd be hard pressed to find a more elegant 1940s daytime look (plus, how much do you love that she kept her gloves on even while touching up her lipstick - such a classy move!).




6. Let's all take a moment to appreciate the sharp styling of this well accessorized 1940s outfit and hat alike. This look would be great with almost any vintage hat of the era, but with this mile high topper it becomes a thing of Vogue magazine worthy brilliance.




7. Captured at a day out to Knott's Berry Farm, this charming 1940s group photo highlights a slew of beautiful hat, hairstyles and dresses alike.




8. Tipples, chic outfits (love the polka dots!), and good sized hats make for an extra fun night for these two stylish Australian gals.




9. Two beautiful ladies (seriously, they look like they could have just left a Hollywood movie set!) rock lush flower adorned hats on what appears like it could have easily been a sunny spring day, given that they've opted to remove their coats as they beam for the camera.




10. I feel like I need every awesome element of her plaid + brown hued ensemble in my life (and closet) right now, most definitely including that fantastic feather and netting bedecked felt hat.




11. Fab floral print dress? Check! Matching scarf/snood worn over one's head? Check! A killer handbag and pair of shoes? Check! Top it all off with a jaunty little nautical-esaue tilt hat? Check. It's outfits like this that make me love vintage fashion to the immeasurable degree that do.




12. A beautiful young woman posses with a girl that, I can only assume given how similar they look, is her sister, on the little girl's Communion Day, while rocking an awesome ruffled hat. I'd love to find something with a similar wreath of ruffles for my own hat collection.




13. I think that we can collectively agree that her ensemble - that mile-high hat very much included - is off-the-charts incredible! (It was worn for a fashion show in 1946.)




14. Stitched brimmed hats are the bee's knees - as are both of their fantastic dresses. I really like the look of a wide brimmed hat and a fitted, classic 40s frock like the example shown here.




15. This beautiful 1930s photo should be placed alongside definition of the word "elegance" in dictionaries the world over.

{To learn more about a specific image used in this post, please click on it to be taken to its respective source.}

♥ ♥ ♥

Over the years I've found, based on comments and emails that I've received on such topics, that the two areas of vintage fashion that the largest number of people seem to be leery of experimenting with are gloves and hats.

I get that big time on both counts. These accessories, especially outside of a utilitarian setting (baseball hat, snow mitts, etc), are not ones that most people sport anymore and they instantly stick out to all who see you as very distinct signs that you've consciously opted to dress differently than the mainstream twenty-first century norm (which, BTW, I commend you for!).

However, ultimately, hats are just like any other garment or accessory. The ability to wear them lies in your own confidence and how they make you feel when they're on your head. In all the years I've been capping off my looks (see what I did there?) with vintage hats, I honestly cannot remember ever once having received a negative comment about my choice of headgear and even if I had (or one day do), it won't phase me at all.

I feel sorry for those who don't know the joy first hand of wearing (let alone shopping for) a fabulous hat and how doing so seems to instill more confidence in you the moment you slip a killer chapeau on.

I hope that you'll follow both my lead, as well as that of all of these super chic yesteryear fashionistas, this spring and summer by giving your toppers plenty of outfit exposure, whether you're new to the world of vintage hats or have been delighting in them for ages now.

Here's to a joyful sunny season topped off, quite literally, with one fabulous vintage hat after another!

The Travelling Hat visits Penticton

Outfit details

1930s/1940s style tilt hat: Handmade by milliner Tanith Rowan
Brown plastic barrette: Goody
Black rhinestone stud earrings: Claire's or Payless
C. 1950s white blouse with black trim: Rue 23 Vintage
Royal blue blazer: Suzy Shier
C. 1950s royal blue rhinestone brooch: Gift from a dear friend
1940s/50s ruched light blue gloves: Unknown, had for years
1940s black felt and gold tone metal handbag: Possibly a gift (had for years)
1950s long black pencil skirt: Probably eBay or Etsy
Black seamed nude stockings: eBay
1940s style black faux suede pumps: Walmart
Lip colour: MAC Russian Red


Photography by Tony Cangiano

♥ ♥ ♥

My dear friend Tanith Rowan is, hands down, one of the most talented milliners practising this timeless art alive on the planet today (long time readers may recall that she made my bespoke vintage style hat dreams come true last year with this dazzling grey and pink chapeau) and her creations never fails to bring me to my knees.

I'm a devoted fan and follower of Tanith's work, so when she announced on her blog in November 2014 that she was going to launch a traveling hat project (dubbed, very sweetly, The Sisterhood of the Traveling Hat) that would see a single creation of hers traverse the globe and land on the noggins of stylish vintage ladies far and wide, I couldn't add my name to signup list fast enough.

Like myself, Tanith is a big fan of vintage tilt hats and so designed a breathtaking example of such to send out in the world for many a fellow vintage wearer to spend a bit of time with before passing Adelaide, as she was christened, on to the next Traveling Hat participant.

Prior to "her" arrival in the Okanagan Valley, Adelaide last spent time with another good friend of mine, Seanna from the blog Seanna Approved. And before that, she had shown up in various corners of Australia, Europe, and America, but I believe I'm the first Canadian to have her spend on this side of the 49th.

Like all of Tanith's work, Adelaide is a vision of stunning beauty and expert workmanship. She had been worn by several other ladies before I received her, yet she reached me in excellent condition - testament to the quality of Tanith's creations (as well as the care that each person has used in handling this hat).

I very much enjoyed seeing how the other Sisterhood of the Traveling Hat participants had styled this awesome vintage style tilt hat, forming ideas for my own outfit with each new look that Tanith shared on her blog (check them out here). However, when Adelaide actually landed on my doorstep and I held her in my hands, all of those previous concepts flew out of the window.

She was even more breathtaking in person and I was struck by how powerfully she channeled a late 1930s/early 1940s look that would have been right at home on the head of any leading Hollywood starlet of the era.

I don't own a lot of 30s garb at all, but I wasn't going to let that stop the vision for an ensemble that was cementing itself in my mind from coming to life. By blending vintage and vintage appropriate modern pieces together, I was able to come up with a daytime (or casual evening wear) look that I feel taps into the spirit of the late 30s/early 40s quite nicely.

This enchanting topper deserves to be the star of any outfit and I aimed to make that happen here, opting for largely understated pieces and fairly minimal (for me) jewelry, save for the gorgeous 1950s blue rhinestone brooch that I added to my blazer (I don't usually wear brooches that are same colour as the solid hued garment they’re pinned to, but of the about fifteen different brooches I tried with this look, both Tony and I felt that this one worked the best and so I broke my usual rule and just went for it!).

There was something so deeply wonderful about getting to spend time with Adelaide. Not only did I stop and reflect often on the fact that she had been in the hands of many of my vintage friends around the world, none of whom I've yet met in person, but also that we were creating a future vintage accessory in this traveling hat. Unlike so many (current) old school hats though, this chapeau's story is know and documented.

Wherever Adelaide eventually lands for her forever home, her tale is documented and shared, history in the making captured care of modern technology.

It was an honour and joy of the highest magnitude to spend time with this traveling hat. While here, she got to see Kelowna and Penticton, including both our home and my parent's house. I bonded with this gorgeous hat and saying goodbye to it was a bittersweet experience.

I wanted to keep her with me for years to come, yet at the same time was elated to send her off to be enjoyed by the next chic vintage sporting lady who will put her own unique styling spin on Adelaide's story.

Thank you, dear Tanith, for creating this project and for uniting so many of us scattered across the globe with one enchantingly gorgeous hat that I'm sure, much like myself, no one who spends time with her will ever forget.

Honoured to be featured on That's a Pretty Hat

Though, like many of you, I (proverbially) eat, sleep, and breath vintage fashion day in and day out, that doesn't mean I'm not inspired by other peoples' styles, too, even if they veer more on the modern side of things. This rings especially true if a fellow fashion blogger and I happen to share a passion for a particular brand, garment or accessory.

Earlier this year I discovered a wonderful blog that's helmed by a very stylish lady named Kathleen Lisson (pictured below in a sublimely lovely Ellen Christine hat and Reiss dress). What makes her site - called That's a Pretty Hat - especially noteworthy is the fact that Kathleen in a hat loving woman after my own heart. From casual to royal wedding worthy, this well dressed blogger's posts are jam packed with one inspiring, beautiful hat after hat another, each of which is paired with Kathleen's refinded, elegant modern style (which strikes me very much as being 21st Jackie O or Grace Kelly).

We've been commenting on one another's blogs for a while now, and it was with much excitement that I recently received an email from Kathleen asking if I'd like to be included in part of a post she was planning about hat fellow loving bloggers. As you can imagine, I jumped at the chance and enthusiastically wrote back at the speed of light.

Kathleen asked me to share some of my thoughts on the wearing of hats as an accompaniment to the two photos of me (which long time readers may recall from this shoot last March) included in her post, which you can read here.

I adored getting a chance to share some virtual page space with a handful of fellow hat lovers, whose styles, though much more modern than mine, are certainly inspiring and joy to find myself amongst. If you haven't had an opportunity to discover Kathleen's blog yet, it's a definite must for hat fans of all sorts, whether you reach for the mid-century designs like I do, or straight-off-the-F/W 2012 runway styles. (and everything in between!)

Many sweet thanks for including me as part of your first post on fellow chapeau adoring gals, Kathleen. I can't wait to see, and be inspired by, future editions of this series!

I won the most darling Lagelle hand-knit, vintage inspired hat!

This post is massively overdue, and I really must apologize about that. Last December I was selected as the lucky winner of a giveaway that the fantastically wonderful Lagelle held on her blog, Lagelle, the Art of accessorizing.

Her contest was the first (and to date, only) blog contest I’ve ever had the joy of winning. Given the time of the year lovely news that I’d won arrive during, it literally felt like I’d received an early Christmas present.

Lagelle has a passion for the vintage fashions of several decades, as evident by the continually delightful array of wardrobe filled posts (both of herself and those she finds inspirational), and which shares through the wonderfully chic, delightfully fun hand-knit, 1920s inspired hats she creates and sells on her site, Lagelle.com.

Sweet-as-a-cupcake Lagelle gave me the choice of a few different hat styles and colour combinations to pick from, and I settled on a timeless mix of burgundy and grey (complete with a darling little knit bow) for my new hand crafted chapeau.

I honestly did not have a single cold weather hat when this winter rolled around, so not only was winning Lagelle’s giveaway a beautiful boost to my wardrobe, it also proved to be immensely practical in the face of a typically chilly Canadian winter.

I wore my new hat nearly every day over the course of the colder months and received scores of compliments and "Where’d you get that adorable hat from?" queries (from bank tellers, strangers on the street, people in line at the grocery store, cute hispster girls at the mall – even a charming elderly woman on the bus one morning). I was only too happy to inform each and every one of them that my hat was a handmade creation from Lagelle.com.



{An entirely “of the moment” snapshot (in other words, we didn’t plan a photo shoot) that my husband nabbed of me wearing my gorgeous Lagelle hat one weekend afternoon last January. We’d just returned home from a day of running errands in the bitingly cold winter wind – during which time my head stayed wonderfully warm thanks to this darling knit chapeau.}


While I’m eager to welcome spring’s arrival with open arms, one of the very few things I’ll miss come the dog days of summer will be wearing my sweetly adorable hat out and about wherever I go. Until next winter though, my charming Lagelle creation sits atop the head of a dear pink teddy bear of mine (a beloved gift from my mother many years ago) on my bedroom nightstand, ready at a moment’s notice for an unseasonably cold day or the first hint of autumn's return.

Thank you so very much, Lagelle, for selecting me as the winner of your marvellous giveaway! Receiving your timelessly pretty, soft wool hat was one of the highlights of this past winter for me. Functional and stylish, your hat makes me smile every time I see it and is such a fantastic reminder of the shared passion for vintage fashion we both share.

Pink, black and white, a dynamite colour trio {Monday Muses, July 20th}

As you may have gathered from prior Monday Muses posts, colour – in all its many splendid iterations – is a perpetual source of inspiration for me. I couldn't fathom looking at the world and not being continually overjoyed by the never-ending array of hues that exist everywhere. They can mirror moods, create beauty, convey sentiments, act as the background or foreground of a room, change the look of an outfit in a heartbeat, and fill us with powerful memories.

Each season and every month brings with it both obvious colour pallets (rust, gold and burgundy in the fall, for example) and those which may have meaning more to our own personal histories than to the rest of the world.

My Muses this week are pink, black and white, three bold colours that each speak of summer in their own wonderful ways. Pink is playful and energetic, sweet and just a little sassy at times. Black embodies the all-consuming heat of summer and also plays homage to scorching hot tarmac, evening wear, and midnight skies. White (which was last week’s Muse) is chipper and yet tranquil, it can symbolize the seemingly endless search for relief from the heat or a way to capture this season’s airy, bright beauty.

As it so often does, Flickr offered up a treasure trove of vintage inspiration featuring these three marvelous hues, which I compiled into the mosaic below.


1. Vogue 1954, 2. Memories, 3. Vintage 1950's rockabilly dress sewing pattern, 4. IMG_4101.JPG EDIT, 5. Visiting my friend in Stockholm, 6. kitty in pink, 7. Vintage Pink & Black Dishes, 8. Pink Poodle Planter, 9. la vie en rose, 10. Glamour Girl Zipper Pouch , 11. oriental peach fan brooch, 12. 50s glamour girl, 13. new shoes! {Click on a link to see a larger version of a particular image and/or for photographer information.}


From there a sprint around etsy and other corners of the web revealed a score of wonderful, summer worthy items in pink, black and white (sometimes all together, in pairs or as single hues), which I hope will fill you with the upbeat, mid-July spirit I feel they posses.

♥ ♥ ♥


{With its simple, timeless design this all black cloche hat instantly calls to mind the 1920s, but would work with a variety of vintage (and modern) styles (many thanks to Loose Leaf Tigers’ blog where I first spotted this wonderful hat). $49.00 (US) from ModCloth.}



{Though the seller lists these pretty floral drop earrings as being from the 1980s, there is something unmistakably art deco about their design that would make the wonderful companions for 1920s and 30s styles. $4.00 (US) from etsy seller Mole Hill Treasures.}



{You’d want to get caught with your hand in the cookie jar when it’s as fantastically adorable as this vintage kitty cat one is! $58.00 (US) from etsy seller Junkyard Gypsy.}



{What better place to store your favourite old fashioned cookie recipes (or those for any other dish) than in this incredibly cool vintage rotary style recipe filing container. $30.00 US from etsy seller Sunset Vintage.}



{Large roses are splashed across this lovely, almost antique looking “kiss lock” purse, making it a wonderful way to bring the beauty of a summer garden into your wardrobe all year round. $37.99 (US) from Modcloth.}



{There is something so strikingly pretty about this fantastic pair of flower shaped rhinestone brooches! $16.00 (US) for both pins, from etsy seller She’s Fancy.}



{This beautiful hot pink, faux leather (pleather) rose belt would be so much fun paired with a huge range of dresses, skirts, cardigans or tops! $28.00 (US) from Igigi.}



{For another terrific way to adorn your waist with pink, black and white, why not slip on this whimsically adorable vintage apron that features a bevy of old fashioned ladies and gentlemen taking their beloved dogs for a stoll. $28.00 (US) from etsy seller I.W.O by Courtney Jane.}



{If you’re a fan or sweet black licorice, why not add some flare to your candy dish with these charmingly old fashioned looking Black Taffy sweets? $2.19 (US) for 10oz, from Troyer County Market.}



{Whether you serve up pink lemonade, white floating islands, or black jelly beans on this sweet flower bedecked vintage tray, it’s sure to be the star of your table. $17.99 from etsy seller Bella Blue 96.}



{Adorned with wonderful pink and black cross stitch this vintage table cloth is almost too pretty to use. $48.00 (US) from etsy seller Dishy Vintage.}



{Isn’t there something compellingly beautiful at this vintage black and pink glass bead necklace and earring set? I think it would be the perfect jewelry to wear to a cocktail or dinner party. $45.00 (US) from etsy seller The Eclectic Diva.}



{Wouldn’t this elegant black and pink lace vintage jewelry box look incredible on a dresser or vanity? $54.50 (US) from etsy seller 5 Gardenias.}



{Give the classic LBD a cheery shot of colour with this magnificently lovely vintage velvet and silk evening dress. $98.00 (US) from Etsy seller Voodoo Lounge.}



{The soft pink hue of these absolutely lovely 2.5 inch heels makes almost them surprisingly easy to pair with a wide array of different colours. $29.99 (US) from ModCloth.}

In searching for the items above, I discovered there is actually a really good sized number of vintage pieces that feature pink and black together (often with white thrown into the mix as well), which is great to know as I’m a big fan of these colours (one of my about thirty different dream kitchens would encompass these three colours paired with steel or chrome). Are you a fan of this trio of July inspired hues, too?