'Annie Hall' Tailoring Is Trending: Here's The Modern Way To Wear It - The Gloss Magazine
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‘Annie Hall’ Tailoring Is Trending: Here’s The Modern Way To Wear It

How to dress like a dandy in 2025  …

There’s been more than one Annie Hall reference made in the fashion ether over the last few weeks. First, Michelle Pfeiffer starred in a campaign for French fashion brand YSL in a tailored suit and tie that could have been lifted straight from the era of Working Girl. Then, Nicole Kidman walked the red carpet at the Critic’s Choice Awards in a strong-shouldered suit from the same brand – with an essence of Diane Keaton – in lieu of a whimsical dress. Meanwhile, over fashion month, the hottest accessory for models and show-goers alike wasn’t a quiet luxury coat or an It bag … rather a tie. This season has been all about feminine fashion and soft colours, but are we finally ready to embrace masculine dressing? 

Fashion shows and red carpets aside, how do you approach the look in real life? In essence, it’s about putting a personal stamp on the look. “Avoid being too literal with it,” says Ruby Slevin, of Banshee of Savile Row. The female-led tailoring brand is fresh from debuting its AW25 collection at London Fashion Week, where models embraced dandyish tailoring that dined out on a distinctly masculine-feminine aesthetic. Waistcoats, ties and pocket squares were all on the menu. The knack is to convert the vibe on a moodboard to something you can really wear. “Whether it’s your choice of shoes, modern, fresh jewellery or your hair, you need to be yourself. In our AW25 show, the model purposefully had that Parisian, dishevelled hair. You don’t want to follow the original look down to a tee, because you run the risk of it being a bit hammy,” Slevin advises.

As for the tie, Slevin shares this golden rule. “A tie can have intimidating connotations. When I first started wearing them, I would go to vintage shops and find really bright-coloured ties, so they felt more feminine and approachable. Pick a tie in a fabric that you love, it’ll feel more safe,” she says.

You don’t have to commit to a three-piece and tie, either. See French fashion writer Monica de La Villardiere, who recently sported a tie and double denim combination to the Polo Ralph Lauren show at Paris Fashion Week. Similarly, journalist Jane McFarland is rarely seen without her trademark cream three-piece suits, which she offsets with bed hair and smoky black liner from French make-up brand Violette. The look is a lesson in insouciance. “Wearing a tie with a waistcoat and a shirt is really nice. And you don’t even need a full suit, which you could wear with a long skirt,” Slevin adds. 

If you aren’t going full dandy, a suit is still a statement of confidence. Twiggy recently stole the show in a bright pink two-piece layered with a slogan T-shirt underneath (a reminder to have fun with colour) at the Dublin International Film Festival, where she gave a talk about her new Sadie Frost-directed documentary. Equally, brilliant Irish artist Elizabeth Cope favours tweed suits as the colours mirror the landscape around her.

SEE MORE: Professor Vilhelmiina Huuskonen’s Preppy And Eclectic Wardrobe

A word of warning if you do embrace the look: make sure it fits. “That baggy, oversized look has been mainstream for quite a while now, but it doesn’t work on every figure. I think a lot of women, especially if they have narrow shoulders, feel they’re lost in that oversized shape – it swallows them up,” says Slevin. The solution? Befriend your tailor and alter a high street suit, or if budget allows, look into made-to-measure or bespoke options. “Even just where your trousers sit on your waist is so important, where it feels comfortable. For each individual, the right spot is so different – it’s like night and day,” Slevin says. 

Image: Instagram @monicaainleydlv.

Banshee of Savile Row AW25.

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READ MORE: What Stylish Women In New York Are Wearing Now

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