VIEWPOINT

I Tried On (Over) 100 Wedding Dresses In My Search For The One. Here’s Everything I Learnt Along The Way

Katherine Ormerod has worked in and around the fashion industry for nearly two decades and knows her personal style inside out – so why did the prospect of finding a wedding dress spark so much angst? Before marrying her long-term partner – and father of her two boys – in a “go big or go home” affair in the California desert this autumn, the 40-year-old bride-to-be embarked on an epic journey of discovery in search of a gown that reflects who she is now.
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This is not my first wedding rodeo. At 26, I got married in the second dress I stepped into. It was by Jenny Packham, made of unfinished chiffon tiers with a strapless neckline and a fishtail cut, and it worked perfectly for my end-of-the-Noughties Tuscan nuptials. Sadly, the fit was better than the flame and by 29 I was going through a divorce, adamant that I would never set foot down the aisle again. But if my thirties taught me anything it’s this: absolutes are a waste of breath. When my long-term boyfriend and father of my two sons proposed on Christmas day, aside from being so shocked I needed a foil blanket to calm my shakes, there was no question what my answer would be. 

What was far less clear is what the hell I would wear. Having worked in or adjacent to the fashion industry for the past two decades, and with almost 80,000 people now following my style on Instagram, you might be surprised to know I was fazed. I really know myself and have a good handle on my personal aesthetic, so why the angst? The truth is, however ballsy you may be, there is something about a wedding dress – this mythical concoction of tulle and taffeta that’s supposed to encompass the essence of your style while also making you look like your very best self – that is quite simply crippling. Even for a woman like me, who has likely worn more dresses than you’ve had hot dinners.

An ethereal veil at Danielle Frankel.

“I quickly realised I was in the market for proper drama,” says the bride-to-be, seen here wearing Markarian.

For starters, as a multi-faceted 40-year-old, with all the complexities that entails, I was concerned that no single dress could ever reflect my spirit. Unless a magician could conjure up a gown that said “Amish by day, vixen by night”, finding one that encompassed my, shall we say, oxymoronic personal style seemed unlikely. So, I decided to embark on an odyssey of discovery. I challenged myself to try on 100 different wedding dresses and write about the process. I planned to unravel my own ideas about what suits me, and stay open-minded. My quest would ultimately see me cross oceans and borders, and enlist the help of some of the world’s most revered bridal designers along the way. High street to high end, traditional to edgy, nothing was off the cards.

One piece of advice passed on by Rosie Boydell-Wiles, a stylist and bridal expert at Vivienne Westwood, has been ringing in my ears over the past five months: “Your wedding day isn’t the moment to experiment with your personal style.” She’s not wrong, and yet I initially found it hard to pinpoint exactly what my personal style looked like in the matrimonial context. Day-to-day, I wear feminine frocks by brands like Doên and Sea NY which juxtapose with my tattooed forearms, sharp inky fringe and long blood-red nails. By night, the look goes up a notch to incorporate naked dressing and a Le Smoking sans brassiere. I’m certainly not a wallflower, nor a minimalist, but then I’ve never felt I fitted into a singular style box. Others might say girly, but I don’t feel saccharine enough for that. More unhinged jolie laide perhaps? Know any designers who’ve made that their USP in the bridal market? Me neither.

Katherine plays the Vivienne Westwood bride.

Katherine loved Markarian’s Idra dress.

Trying on a design by the queen of modern bridal, Cecilie Bahnsen.

Courtesy of Katherine Ormerod

At The Own Studio in Shoreditch.

Courtesy of Katherine Ormerod

My first stop was Honor NYC – whose Instagram account I’d been stalking for weeks – on the back of New York Fashion Week. There, any thoughts of simply selecting a white-ish dress from one of my favourite catwalk designers immediately evaporated, as I experienced the immaculate construction of a made-to-measure wedding gown. I also quickly realised that I was in the market for proper drama. My ceremony is being held in a breathtaking architectural home in the Californian desert this autumn, so any notion of low-key restraint has already flown out the window – we are definitely in go big or go home territory. My favourite dress was a sheer nude tiered strapless style, which I came to realise looked remarkably like my first wedding dress. Even though 15 years had passed, it seemed I was reverting to type.

Back home in London, I wanted to reset, so I booked appointments with some of the city’s iconic bridal designers. At Halfpenny London’s Bloomsbury atelier, designer Kate told me to drown out the noise and focus on the feeling. How did the dress move? Did I feel supported? Could I breathe? Had I considered how it looked from every angle? Her infectious confidence gave me a boost, and I fell in love with a champagne silk halterneck gown called Cheryl. I also learnt that ivory isn’t my colour – something warmer is better on my skin.

Over on the Fulham Road, Sassi Holford told me she loves dressing brides of my age, and women who, like me that day, attend fittings alone. Indeed, too many cooks can create an issue. Early on in the search, I found a dress that I adored, but it was punchy. After three friends recoiled in shock and told me I’d regret it, I did begin to doubt my own barometer. Everyone has an idea of how “a bride” should look, and it is inevitably influenced by what they would choose for themselves. While I did bring friends with me to about a quarter of the appointments (free fizz, beautiful spaces, what’s not to love?) I found it easier to connect with my style radar alone. It turns out that I actually don’t want anyone else’s opinion.

Wearing a gown by Cinq at The Fall.

Courtesy of Katherine Ormerod

Katherine in a blush gown by Galia Lahav.

Courtesy of Katherine Ormerod

A nipped-in jacket and tulle skirt option at Self-Portrait.

Sampling bridal suiting at The Own Studio

Trend-wise, there were a lot of dropped waists, and the faintest pink blush was everywhere. Another more fundamental shift is the rise of more relaxed bridal studios, with a slip-on-and-go attitude. I visited The Own Studio and The Fall, both in Shoreditch, and revelled in the ease of the designs. Directed by The Own’s co-founder Jess Kaye, I came away dreaming of a bubble-skirted dress slashed across the neckline, which made me feel like Audrey Hepburn. At The Fall, it was the Claire dress by Cinq that seduced me with its Botticellian feel and tendrils of gossamer fine gauze.

For the full bridal experience, I couldn’t miss two of the world’s most famous stores: Kleinfeld in New York, with its 5,600 dresses and reality TV show (Say Yes to the Dress), and Pronovias on Bond Street, Barcelona’s most bedazzling export (also home to Vera Wang’s ready-to-wear bridal). On the topic of keeping an open mind, one of the things I learnt in my years as an editor is that you can find pieces you love in the most unlikely places, and that snobbery when it comes to style actually isn’t that chic. The ability to see past labels to discern what you do and don’t like in any setting is the real route to style success. At Pronovias, I swooned over a vintage square-neck style which looked straight out of Four Weddings & a Funeral (in a good way). It was about a third of the price of some of the other dresses in contention. Over at Kleinfeld – overlooking the fact that each dress was missing beads or pearls and the cheesiness of the public trying-on (I loved it really) – I was swept away by a laced corset Pnina Tornai number.

At a fitting at Honor NYC.

Courtesy of Katherine Ormerod

Katherine was “sucker punched” by Danielle Frankel’s Rosalie dress.

Courtesy of Katherine Ormerod

Speaking of public fittings, there is undeniably an element of body confidence and politics at play when bridal shopping. I am a size-privileged, slim woman, but I tried on plenty of wedding dresses that wouldn’t do up, or pinched my flesh in ways that didn’t appeal to my not uncritical eye. There was talk of weight loss during a couple of appointments, which felt uncomfortable. As a straight-bodied gal, I also found the emphasis on an hourglass shape tough at first (so much so I wrote a Substack on it). But by the time I passed the 100-dress mark, whenever my underarm flesh was skewered by a strapless neckline or buttons failed to make it past my middle, I simply shrugged. Practice often makes perfect when it comes to managing negative thoughts, and I do feel a renewed sense of body acceptance. After three pregnancies and 40 years on this planet, it’s simply time to stop speaking to myself in certain ways in front of the mirror. I feel very glad to have been reminded of this before my wedding day.

If there is any moral to this story it is this: I found my dress in a store I would never have visited if I hadn’t been writing this piece. I don’t want to give too much away, but before that appointment, I didn’t associate myself with the brand – I didn’t see myself as that woman. But the moment that zip went up, I realised that actually, that is who I am. Powerful, sexy, a little defiant.

Which is not to say I haven’t since been tempted by alternatives. It’s a really good idea to stop trying on other dresses the second you put your deposit down. Due to this commission I didn’t do that, and a few weeks after committing I found myself back in New York at Danielle Frankel’s ethereal studio, sucker-punched by a chiffon number named Rosalie. Quite frankly, I’m still thinking about her, but consoling myself with the fact that the dress I’ve chosen encapsulates more elements of me. (Plus, I am not a bride who can afford to lose a deposit on the biggest purchase of her life, so there is an element of needing to get real and pull myself together.)

I would love to tell you that no one needs to try on 100 wedding dresses, but I had tried on 97 others before this latecomer rocked my world, so it would be a bit rich to offer that guidance. What is certain is that the admin of organising 17 appointments has chafed, ditto the frequently punitive cost of attending – from the fitting fees (some of which were waived due to this piece), to the childcare to the taxis – the search was an investment in itself. If I were to do it all again, I would take a week off of work and blitz the whole thing at once – although that would require significant forward planning. Some ateliers were unable to slot me in, even though I’m writing for Vogue and have a social media presence, which gives you an idea of the bonkers level of demand, even when you’re dropping the price of a small car.

Katherine couldn’t not make a stop at Kleinfeld, as seen on the reality show Say Yes to the Dress.

Trying on wedding dresses in public is cheesy… but fun.

Courtesy of Katherine Ormerod

Katherine wearing Halfpenny London.

Courtesy of Katherine Ormerod

Experimenting with shorter hemlines at Annie’s Ibiza

On the subject of price, I tried on dresses that cost £15,000, and dresses that cost £500 (head to Reformation, Reiss, Self-Portrait and Rixo). I’ve been trying on dresses I could never afford for much of my career, so I’d never advise steering totally clear of brands that are beyond your budget – I believe in making space for fantasy. But I would recommend approaching it dispassionately – as if trying on rare vintage or museum pieces.

As for tuning into my own feelings, I learnt pretty quickly that I was looking for an element of theatricality, and that I was happy for a dress to be tight around the waist, but I couldn’t bear a high neckline or a full skirt beyond a certain volume. The Grace Kelly via Elie Saab gown I tried on at Browns Bride was a style experience I will never forget, but I couldn’t wear that on my wedding day – I’m not sure I’d make it out of the hotel room. As Danish designer Cecilie Bahnsen counselled me: “If you can’t lift your hands up in the air, how are you going to climb on a table to dance?” Other sage notes from the queen of modern bridal? “Remember that you are the sparkle, not the dress.”

Katherine in a Sassi Holford gown…

Courtesy of Katherine Ormerod

… a dramatic train at Pronovias.

Courtesy of Katherine Ormerod

Katherine, seen here in Rixo, did not limit her search to designer gowns.

Wearing a dress from the bridal line at Whistles.

My final takeaway is a little like my philosophy on men: I don’t really believe in the idea of finding a soulmate in silk. Six of the 120 dresses I ultimately tried on (evidently once you start, it’s hard to stop) I would love to wear on my wedding day (honourable mentions go to Markarian’s Idra, Galia Lahav’s Izzy, Sassi’s Bella and Cecilie’s Beth). That is probably about the same ratio of men I could cohabit with. If you can drop the notion of finding one fabled needle in the haystack and instead accept that there will be multiple dresses out there that fit the bill, the whole thing can become one of the most tender, touching experiences – and a real romp, too.

People keep asking me if trying on so many dresses has confused me, and I can totally see how that could happen. But actually, I feel more clarity than ever. All that’s left to say is see you in October – just pray for me that I’m in the dress I’ve already paid for.