Olivia Singer distills her everyday style into something refined, black and glamorous. So how can she (and we) upgrade that look for the holiday party season?
OLIVIA SINGERDecember 23, 2025
I find it hard to raise the stakes when it comes to my everyday outfits, which mostly consist of an ever-growing rotation of black dresses. What most people consider eveningwear is, for me, basically loungewear. Much to the confusion of anyone travelling with me, my clothes stay the same no matter where I am: I wear the same thing during fashion weeks, on a remote ranch in Texas, or in the Atlas Mountains. Rick Owens on the prairie, Alaïa in the highlands – both surprisingly practical. The asymmetric cut of the first and the flexibility of the second are functional enough for me to swing a leg over a horse or sit on a quad bike.
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Long dresses don’t intimidate me either. Because of my profession, part of my wardrobe is reserved for grand, floor-sweeping gowns I’ve collected over the years – just in case, and on strict advice from a former editor, I never travel without one. The fashion industry loves to throw a random black-tie event out of nowhere. But the holiday season calls for a bit more than the usual – sometimes it’s simply nice to be more dressed up than necessary. The phrase party dressing, though, often conjures awful images of jewel tones and overdone details – everything that goes against my instincts. How do I avoid looking like I’ve stepped out of a costume drama, or worse, like I’m performing a different version of myself?
Thankfully, spectacular dresses have made a comeback in recent seasons – pieces with a dose of elegant extravagance and a whisper of indie sleaze; dresses that look fantastic but also like they’re made for having a good time. I came of age in the 2010s, an era now being revived through Hedi Slimane’s messy-chic partywear. And even though my wardrobe has embraced glamour and shed polyester and cigarette burns, I’ve kept that slightly undone aesthetic: the dresses are never perfectly adjusted or hemmed, and my heels are always scratched.
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I firmly believe there’s a modernity in that dissonance. In an industry that often worships the idea of immaculate perfection, there’s something deeply honest about the imperfect. Simone Rocha captured it perfectly after her last show, where dresses inspired by the 1920s, built on crinolines and panier skirts, were styled with T-shirts casually knotted at the waist or left half-open over delicate slips. “Disappointed debutantes,” she called her heroines. “Their elegance is ironic, with a dose of reality.”
Saint Laurent’s fall/winter 2025 collection under Anthony Vaccarello carried a similar spirit: monumental couture silhouettes paired with tousled hair, sunglasses, and attitude. When one of those dresses arrived on set, hovering between a black cloud and a giant jellyfish, I felt like a girl playing princess, only without the torture of rigid construction. A simple silk top fell loosely across my body, while a light, airy crinoline sat low on my hips, almost floating with each step. It was similar to McQueen’s exquisitely embroidered creations that Seán McGirr sent down the runway with a dose of nonchalance – when I slipped into one, I didn’t feel I needed more underneath it. Pure insouciance, as the French would say.
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Around this time last year, on the steps of Royal Albert Hall during the Fashion Awards, Caroline Polachek approached me in a floor-length, transparent McQueen gown – sheer from neck to thigh, traced with black, thorny embroidery. She looked like the coolest woman I’d seen in years: uninterested glamour, impossibly elegant, yet somehow light. “Cool means not too much of anything,” she told me later.
“I’m more afraid of looking ‘overstyled’ than ‘too simple.’ A good dress should speak for itself.”
The key is nonchalance: a major dress, which by definition should be dramatic, worn with minimal jewellery, modern shoes, and fresh skin. “My favourite styling looks like it was just thrown on me,” says Adwoa Aboah. “I love unpretentiousness. Even if it’s an opulent Saint Laurent dress, it should feel relaxed and effortless.” That spirit also inspired her new project, The Veil, created with her friend Georgie Wright – minimalist bags with interchangeable veils of embroidery, feathers, and beads, including special shimmering versions with a perfectly soft shape. “I feel like you’re often forced to choose between simplicity and extravagance,” she says. “The Veil sits right in the middle.”
Beauty, of course, plays its part. I recently surrendered myself to New York facialist Iris Maglanoc, whose microneedling treatments with exosomes gave me a glow younger than my actual age. But there’s a difference between a bare face on the runway and a bare face in real life. That’s where Isamaya Ffrench comes in – the leader of modern glamour, with products engineered for exactly the effect I want. “I feel most myself when I’m not overdressed, so if I’m wearing something big, I avoid complex makeup,” she says. “Glossy finishes and anything that reflects light add dimension to the face. And if you’re someone like me who doesn’t wear much makeup, you can just use that – nothing else.”
I’m obsessed with her transparent, creamy formulas applied with fingers, especially Face Glaze, a dewy gel-balm tapped over lids, cheekbones and lips. “Fresh skin and lips look natural, and I love that in our AI age,” she says. “Skin is what makes us human; it needs to be seen. And when someone feels completely authentic, even extravagance looks effortless.”
“There’s so much preparation before a big event – choosing the look, fittings, glam, posing, photographs. And then, when you’re finally there and the event is happening, it’s so easy to forget to enjoy it,” says Caroline. “I’m working on switching gears, so that when I finally arrive, I can enjoy the people, their company, their looks. That’s the real icing on the cake.”
“And have a drink,” Isamaya adds. “You stop worrying about your makeup and start actually having fun.” Dress up, then forget about it, and enjoy yourself even more. That’s definitely my motto for the season ahead.
Photo: Niall Hodson
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