Four surprisingly flattering ways to style a shirt – including wearing it back to front
If you were to peer into any woman’s wardrobe across the country, you’d almost be guaranteed to find one perennial classic hanging there: a button-down shirt. From plain white to striped, in a classic cut or consciously oversized, there is a shirt style (or three) to suit everyone. The beauty of this low-key workhorse is that it will never fail you: dress it up with red lipstick for the evening, wear it as a base layer at the weekend and let its crisp smartness do the talking at work. What lies behind this versatility? The fact that a humble shirt can be worn in myriad ways, making it the secret star of countless outfits.
Here are just a few styling tricks to try…
The ‘half tuck’
Katie Holmes recently stepped out in a white cotton shirt, only half tucked into her leather midi skirt. The trick lengthened her legs and gave her outfit the kind of undone sexiness that’s only possible when you don’t look too put-together. “It’s my favourite technique,” confesses influencer and stylist, Sarah Corbett-Winder. “It’s an ‘I’ve made an effort, but I haven’t really’ sort of tuck.”
An update on the popular ‘French tuck’ – which involves tucking in the front of your shirt, while leaving the back loose – this is a knack that works with even the simplest of outfits. Just look to Queen Letizia of Spain, who half-tucked her navy shirt into black flares for a recent engagement.
The back-to-front switch
Businesswoman and midlife style guru Trinny Woodall is so inventive when it comes to styling a white shirt that she’s devised 23 different ways to wear one – including tucking in the collar, using a skinny scarf as a tie and adding shoulder pads for structure. One of her most divisive recommendations, however, is to wear your shirt back to front (a hack also seen on the catwalk at Dries Van Noten).
You’ll need a slightly looser, less structured shirt to make this look work; try flipping around Reformation’s ‘Andy’ style, which has the perfect boxy cut. Wear it in the evening with jeans and party heels, like the silver ‘Maude’ slingbacks from Florrie London.
The ‘full tuck’
This is probably the most traditional way in which to wear a shirt – but switching up textures and proportion will keep the look fresh. “I love tucking a smart shirt into a pair of jeans,” says Danielle Windsor, founder of Yaitte. “It’s an effortless uniform for me. In winter, a chunky knit layered over the top is essential.” Try the brand’s ‘Buoy’ striped shirt in oxblood red, which looks preppy in the best way peeping out from beneath Artknit Studios’ black wool polo.
Pip Durell, founder of the fashion crowd’s go-to shirting brand, With Nothing Underneath, agrees. “I like a cinched waist and then a really good billow in the body of the shirt,” she says. “It’s simple proportion play.” She recommends choosing the brand’s bestselling Tencel fabric, as “the drape makes it perfect to tuck”. The just-baggy-enough ‘Boyfriend’ style in white, with navy details on the collar and extra-long cuffs, would serve you season after season.
The layered look
While adding a crewneck jumper over the top of a shirt is a time-honoured formula, Corbett-Winder suggests trying “a thin polo neck, ideally red or striped” underneath a button-down for a more modern spin – the best are in cosy merino wool, from Cos. “At this time of year, I love layering,” says Durell, who favours a white tee with one of WNU’s brushed cotton shirts, topped with a blazer. “It’s such an easy, casual look.”
Windsor is in the same boat and explains that she “always keeps a statement blazer on hand” to layer over a shirt when she needs to look “pulled together”. If you don’t want to look too corporate, Aligne’s velvet ‘Daphne’ style would be extremely festive with a silk shirt beneath it.
A few more tricks to try…
Windsor loves a “quirky” popped collar, which “adds a bit of personality and confidence to what is otherwise a classic silhouette”.
Try only doing up the top three buttons of a shirt, which will give an unexpected (but surprisingly flattering) flash of upper midriff when worn with a high waisted skirt or trousers.
A cuff pulled right back is a great way to show off a statement bangle and works well in the evening. “This is best done when I’ve stolen one of my husband’s very stiff shirts,” says Corbett-Winder.
Durell is also borrowing from the boys this season and plans to wear one of WNU’s traditional dress shirts “with leather trousers and sparkly jewellery – come January, I’ll wear the same shirt with jeans to meetings”.
Corbett-Winder is “very partial to a top button done up, with a scarf tied under the collar”. If you’re feeling brave, she even recommends wearing a shirt as a dress, “with red ballet flats or patent burgundy boots – but make sure it’s oversized!”
