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I Tried On Over 100 Wedding Dresses to Find the Perfect One: Here’s What I Learned

July 4, 2024
1 min read

Finding the perfect wedding dress is no easy task, especially if you’ve been down the aisle before. At 26, I wore a Jenny Packham dress for my first wedding. It was beautiful, but the marriage didn’t last. Now, at 40, with a proposal from my long-term boyfriend and father of my two sons, I faced the daunting task of finding another wedding dress.

Despite my extensive experience in the fashion industry and a strong following on Instagram, the thought of picking out a wedding dress was overwhelming. The pressure to find a dress that reflects my style and makes me look my best felt immense.

As a 40-year-old with a multifaceted personality, I was unsure if one dress could capture my essence. I wanted something that said “Amish by day, vixen by night.” So, I decided to try on 100 different wedding dresses and document the journey. My quest took me across borders, from high street to high-end, and enlisted the help of top bridal designers.

One piece of advice that stuck with me was from Rosie Boydell-Wiles, a bridal expert at Vivienne Westwood: “Your wedding day isn’t the moment to experiment with your personal style.” While this made sense, defining my personal style in a wedding context was challenging. Daily, I wear feminine dresses by brands like Doên and Sea NY, paired with my tattooed forearms, sharp fringe, and bold red nails. By night, my look includes daring outfits and a Le Smoking jacket without a bra. I’m far from a minimalist, but I don’t fit neatly into any style box.

My journey began at Honor NYC, a brand I had been following on Instagram. During New York Fashion Week, I realized the beauty of a made-to-measure wedding gown. I quickly learned I was seeking drama. My upcoming ceremony will be held in an architectural home in the Californian desert, so understated was not an option. My favorite dress from Honor NYC was a sheer nude tiered strapless style, reminiscent of my first wedding dress. Despite 15 years passing, I seemed to revert to my original style.

This experience taught me that finding the perfect dress isn’t about trends or fitting into a style box. It’s about discovering a dress that truly resonates with you, even if it takes trying on 100 dresses to find it.

Claire Stern

Claire Stern is the Senior Journalist of esquireus.in. Previously, she was Deputy Editor of Vogue.com. Her interests include fashion, food, travel, music, Peloton, and The Hills—not necessarily in that order. She used to have a Harriet the Spy notebook and isn’t ashamed to admit it.

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