I know many of my relatives through their clothes. I know their dress sizes, the shape of the blouses they chose to wear, the costume jewellery they kept until they died. I know what they valued – whether it was a brightly coloured leather belt or multiple pairs of black, leather gloves all cut slightly differently. I know this because plenty of these garments and accessories have filtered down to me over the years.

My room is stuffed full of possessions that belonged to three previous generations of family members. It’s a jumble in there – items from maternal and paternal grandmas, great-aunts and grandfathers (as well as plenty stolen from my mum) hung together in my wardrobe or folded away in boxes.

For a while though, the most prominent things in that room were the hats. So many hats! They lined the top of my bookshelves, hung on the edge of my mirror, and ranged across every available service. At one point I even had two pin boards covered in an attractive range of shades: raspberry, cobalt, scarlet, khaki, chocolate, navy, russet, plum, electric blue.

Many of these ones had belonged to my maternal great-granny. They’ve experienced quite the journey. When that great-granny died, my mum donated nearly all of her hats to the local primary school I attended – retaining a few for our own dressing up box. After years of these trilbies and berets (and plenty of other styles of hat I can’t even categorise) being played with by infants, their days of use were nearly at an end. They were bagged up and set aside to send to a local charity shop.

As fortune would have it, my mum and I visited the school that day. Mum’s eyes fell on the jumble of colours plonked by the door. When we found out what was happening with them, she asked if we could rescue the lot – and rescue we did. We carried them home, spilled out the contents on the carpet, and inspected our spoils.

I took them all.

I can date this amazing discovery back to summer 2009 because I blogged about them shortly afterwards – styling lots of the hats and repurposing the lyrics of Eleanor Farjeon’s ‘Cats Sleep Anywhere’: 

Hats sleep anywhere, any table, any chair.

Top of piano, window-ledge, in the middle, on the edge.

Open drawer, empty shoe, anybody’s head will do.

Fitted in a cardboard box, in the cupboard with your frocks.

Anywhere! They don’t care! Hats sleep anywhere.

I’d begun my blog earlier that year – searching for an outlet to play around with vintage clothes and conversations about style. At that point, an outfit for my blog didn’t feel complete without lashings of accessories. These were my first fumblings towards assembling a sartorial identity that was all my own – removed from the expectations of school or social groups or what teens were meant to wear. I wore net gloves and big, crystal necklaces and brightly patterned silk scarves. I layered everything and stuck a belt on top. I used the term ‘granny chic’. And I wore a hell of a lot of hats. Alongside the various beautiful, brimmed things inherited from family members, I bought plenty second hand. They were the kinds of hats that on anyone over the age of 20 would resemble pretty tame wedding attire but, on a 14 year old with near-waist-length hair, just about worked.

Hats have turned up time and time again over the years on that blog. To give the briefest selection of choices, there was the cream beret with a bow on the front of it to dress up in a Susie-Pevensie-goes-to-Narnia inspired ensemble (complete with a vintage suitcase and some snow-covered fir trees); a black felt floppy hat to complement my sixties swing coat; a little, knitted green hat to keep my pinned up hair in place alongside a twenties-style flapper dress I made using film negatives; a children’s boater worn with a blue teadress; a seventies leather patchwork sunhat alongside a long, crocheted dress; a soft egg yolk yellow beanie to complement a grey wool dress I made from an old jumper; a bright orange hat atop a bright orange outfit inspired by the colours of Penguin Classics; a grey faux-fur hat (big enough to look like a small animal perched on my head) with a lilac satin princess dress; a red net and velvet fascinator to complete a striped velvet ensemble; feathers pinned to my head when emulating Isabella Blow… the list continues. I even did a Sherlock-inspired shoot with a deerstalker.

They’ve not just been for dressing up either. I have a core group I still wear with huge regularity. There’s one blue trilby in particular that I’d be devastated to lose. And yet, and yet… I’m still surprised to hear friends of mine say, “Oh, I have a great hat, but I’d need more confidence to wear it.” Where they were once seen as ubiquitous, being just another addition to an outfit, now they’re considered some kind of statement. Apparently it takes audacity to don anything brilliant or boldly shaped. It seems a shame when there’s such pleasure to be derived from them.

Yes, it may require a confident tilt of the head. But you’re much more likely to receive compliments than anything else. People tend to be impressed by a good hat. And all those pre-formed fears you might have about strange comments or people looking at you oddly? They’re mostly false. Besides, if they do stare, let them. You’re probably brightening their dull day. Take it from the girl who recently walked around a city centre wearing a zinging bright orange (very mini) mini-dress with a matching bow tied in her hair. Now that gets people staring. 

Sometimes hats don’t have to be eye-catching though. Sometimes, you know, they do have practical use too. I’ve been eyeing up various beanies and other cosy looking things recently, aware that the chill in the air means it’s time to assess what I can wear for purposes of warmth rather than general flamboyance.  Perhaps among them there’ll be one particular hat. It’s black and very, very furry – fitting close to the head. The kind of hat that’s ideal for bitter days when the wind cuts at your ears (even when, as in my case, they’re already hidden under a mound of curly hair). It belonged to Nana.

Nana, by the way (pronounced ‘Na-naa’), was my other maternal great-grandma.

When she died a few years ago I combed her cupboards, partly helping mum to box stuff up, partly searching for treasure. I wasn’t disappointed. Furry hats and collars aplenty, as well as some rather fabulous winter coats.  That sense of intense delight in unexpected acquisitions – new things to add to my outfits without paying a penny – has never faded. 

I wore it endlessly last winter – once on a day when my mum visited me at uni. A few days later she emailed to say that she’d found some pictures of Nana wearing that very same hat at her mum’s christening. There was my grandma, tiny in a white cotton robe, and my great-grandma – furry hat matching her coat perfectly.

Nana was also, obviously, the counterpart to the granny with all the colourful hats. Collectively, they’ve together contributed more to my hat collection than any other family members. The two of them never saw eye to eye, both angry that their respective children had divorced when my mum was a toddler. So much animosity between them, and yet their hats are in the same boxes, jammed together. Sometimes I can’t remember which one of them owned a particular item. I like that though. All that tension and resentment – yet their hats now sit side by side, years later, given new life each time they’re worn.

Rosalind Jana is a writer, editor and an English lit student. She tweets at @RosalindJana and blogs at Cameras, Clothes and Coffee.