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collage of two women in oversized clothes © Getty

How to wear oversized fashion in your 40s, 50s and 60s

Trinny Woodall's stylist Annie Swain sharesher expert tips on wearing oversized fashion at any age

May 1, 2025
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Oversized fashion has spilled off the Saint Laurent catwalk and onto the high street in a major way.

But while the likes of 28-year-old Hailey Bieber manage to pull off the 'I raided dad's wardrobe' look with effortless style, can you still wear it when you are over 50? According to celebrity stylist Annie Swain, you can. "It's not down to your age, but a frame of mind about how bold you want to go," she says.

Having given fashion advice to the likes of second act favourites Elizabeth Day and Trinny Woodall, both early adopters of the oversized power suit, Annie says:  ''Rosie Huntington Whitely nails oversized fashion, but I also love Tracee Ellis Ross' (Common People actress and daughter of Diana Ross) killer looks and the way Grece Ghanem, a fashion influencer in her 60s, plays with colour and volume. 

Tracee Ellis Ross sitting on a chair in an oversized suit © Instagram
Tracee Ellis Ross look sensational in oversized attire

"Oversized fashion doesn’t have to be a slouchy look, it can look smart or sexy if it is styled the right way for your body, no matter what age you are," Annie reassures.

Styling oversized fashion in midlife

The oversized staple

''The most important thing in my wardrobe is an oversized blazer,'' says Annie. ''You can go as extreme as you like. Saint Laurent went full power shoulders with a masculine shirt and tie, which Hailey Bieber rocked.

Hailey Bieber poses in a suit look with a striped shirt and red tie© @haileybieber
Hailey styles her oversized look with a striped shirt

''But you can take a regular white t-shirt and jeans situation and just add an oversized blazer and it will update what you already have in your wardrobe.''

The size of the jacket should depend on your shape or your mood, she adds. ''And I always push or roll up my sleeves to give them a softer edge.''

The hardworking oversized essential

You should never underestimate the power and versatility of a big shirt to subtly maximise your look, says Annie.

''A simple shirt is a great starting point, and oversized shirts have many uses which appeal to me,'' she says. ''On holiday, I wear mine with a swimsuit, thrown over my gym gear and then make it look gorgeous with rolled up sleeves and jeans and accessorize with red lipstick and chunky jewellery.

''I have a huge selection of oversized shirts; some are wild and some more contained. I have killer big ones that are vintage men's Marks and Spencer and a Turnbull and Asser shirt where I cut off the collar but kept the huge cuffs. H&M and Arket always have oversized silhouettes and I have a sheer one from M&S that I love. Or steal one from your partner's wardrobe.''

How to go bold

If you want to make a statement, then go big, bold and beautiful in a full oversized suit. ''Maxmara kicked the full oversized trend off last season but there are loads of really great oversized suits on the high street,'' says Annie.

Trinny Woodall in a blue suit sitting in an armchair© Ken McKay/ITV/Shutterstock
Trinny Woodall pulled off this vibrant blue power suit

There are two ways you can embrace this full look: by playing it straight with a masculine city vibe, or soften it up with some pretty touches.

''You could add a feminine edge by wearing a mesh ballet pump, or kitten heel and show off a bit of cleavage with a sexy lace bra underneath.''

Elizabeth Day wearing a brown blazer, oversized T-shirt and pink trousers © Getty Images
Elizabeth Day demonstrates how to style oversized attire

If you are on the short side, consider cropped trousers, as they won't overload your frame. ''I am only 5ft 4, so I like to show a bit of ankle and my wrists if I am wearing oversized. I prefer not to look slouchy, but smart, comfortable, so you still feel dressed up or ready for the office - or even the red carpet like Elizabeth Day.''

How to play it safe

If you love the oversized look, but are not feeling confident enough to go all out, start small.

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''You can add an oversized element to your outfit with a big bag at first, then move on to a blazer,'' suggests Annie.

Also, to prevent the feeling you are drowning in fabric, pick one piece of oversized clothing and match it with something more fitting. ''Rosie Huntington-Whitely always does it beautifully when she wears a big oversized blazer and her long legs out.

Rosie Huntington-Whiteley in a larger blazer and fishnet tights © Instagram
Rosie Huntington-Whiteley demonstrates how oversized can be sexy

''It is the same for big flared jeans, which are on trend at the moment,'' she says. ''I was working on a shoot the other day and a 40-something producer and an assistant who was 25 both turned up wearing oversized parachute pants from Cos, one with a ballet pump and the other with trainers and they both looked amazing. 

'''If you wear a skinnier vest or a slim fit t-shirt or body suit to contrast, you won’t feel overwhelmed.''

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