Even though I love tailoring and any excuse to go for menswear-inspired style, I have to admit to being a tad Waistcoat Wary. From 1980s rockers to bartenders and croupiers, if you’re not careful, the classic black vest can quite easily swerve from corny to cosplay.
One of my favourite tailored vest enthusiasts is Ayo Edebiri, who teams hers with supersized Loewe cargo pants and sunglasses. The American writer-turned-actor now tops my gentlewomanly list of outstanding waistcoat wearers – and she’s in good company. Other devotees include Patti Smith, Janelle Monáe, Diane Keaton, Madonna and Marlene Dietrich.
The ongoing trend is for a waistcoat with nothing but a bra underneath.
Saint + Sofia
Astrid Waistcoat – Black
My black Jigsaw waistcoat is now sold out, but this is a similarly classic, flatteringly fitted black waistcoat that can be dressed up or down. It’s a timeless piece to invest in now and wear again and again.
Nobody’s Child
Brown Gingham Tailored Longline Waistcoat
Levi’s
Blue Denim Loose Vest
I have my eye on a Levi’s loose vest for its casual-meets-tailored dual appeal. You can never go wrong with denim, it’s such a classic, and can be used to create so many different looks from boho to something more urban.
Before attempting this look, it is important to wave goodbye to arm paranoia. Remember, we are the generation shaking up the style game, ignoring outdated fashion rules and wearing what we damn well like.
On holiday, I bare my arms without a second thought. On a scorching hot day in London, no one is looking at my triceps; they’re too busy wondering where to refill their water bottles or charge up their battery-operated, handheld fans.
Trying something new is always an excellent way to unleash fresh outfit combinations. Go for boho style by pairing the tailored vest with a tiered maxi skirt and cowboy boots.
Layer a waistcoat over a white T-shirt and faded jeans – or whoop things up with leopard print trousers.
For a smarter vibe, try Annie Hall-inspired pleated trousers. This summer, in a nod to 90s minimalism, I’m planning to wear mine with a black silk slip skirt and flat slingbacks. Day to evening in a dash.
There are many ways to wear the waistcoat – just don’t ask me to take your drinks order.
Tips for styling waistcoats
Pictured: Albaray gingham waistcoat £65, sizes 8-18 (sold out), Albaray gingham skirt £50, sizes 6-18 (limited stock), Le Specs sunglasses £55, Jigsaw necklace £100 (sold out), Next bag £78 (sold out), M&S shoes £45
Tu dress £35, sizes 6-24 (sold out), Mint Velvet waistcoat £89, sizes XS-XL, Warren James earrings £33, Dune bag £149 (sold out), Zara shoes £39.99
(Image credit: Retailers)
Go long or go home
I’m into the longer length waistcoat that’s been trending for a while – Albaray has gingham [now out of stock], butter yellow and pinstriped versions that look great with midi skirts – and was seen on the autumn/winter 2025 catwalk at Ami Paris. This style has the added benefit of not looking like you’re about to pull a rabbit out of a hat.
Tailored top, slouchy bottom
Still in doubt? Offset the smartness of a tailored design with slouchier trousers, jeans or cargo pants to shake off old waistcoat associations.
Try waistcoats in casual fabrics
Instead of going straight for the classic black waistcoat, take a look at casual fabrics, such as cotton twill, denim (I’ve got my eye on the Levi’s loose vest – oh hello, Beyoncé!) and linen.
Casual layering
Having said that a waistcoat with nothing underneath is a chic look, if temperatures dip to the cool side, you can slip one on over a simple white t-shirt or striped Breton top and still look on-trend.
Or if your personal style leans more towards the retro-tastic, try wearing your waistcoat open over a pussy-bow blouse or maxi dress.
