My girlfriend, fully dressed and ready to go out, turns away from her full-length mirror and asks me the eternally dreaded question: ‘How do I look?’
She is a rare beauty who is preternaturally fashionable, clairvoyantly attuned to trends, immaculately stylish and a keen September shopper. And yet today she has elected to wear an outfit that seems, to my male gaze at least, baffling in both its proportion and colourway.
Mannish, barrel-legged jeans that stop mid-calf with four-inch turn-ups; heavy, black, block-heeled, crepe-soled, glam-rockish zippered boots; a fluffy, oversized sleeveless angora jumper in a care-home teal tone, over a white, pie-crust collar blouse – very Lady Diana – with its long cotton shirt tails untucked and inexplicably flapping around beneath the jumper’s hem. Lastly, a trench coat so knowingly oversized that it’s on the roomy side for me – and I’m eight inches taller and seven stone heavier than she is.
Her overall look? A combination of 1970s Jackie magazine style pages, Alison Steadman’s Candice Marie character from Mike Leigh’s Nuts In May, and Julia from Motherland. All of those images, I will soon learn, are now being regarded as positive style references.
Wisely, having learned the hard way, I elect to offer nothing negative when she asks me that inevitable question. But my inner voice (which is equal parts bitchy RuPaul and an increasingly incredulous Victor Meldrew) is saying, ‘Yes, Lady Di was a beautiful woman, but she was never really stylish. She was square and Sloaney and those frilly collars made her look like an old lady even when she was in her 20s.’ Also, baggy, high-waisted, barrel-legged jeans make all women’s bums look huge, the turn-ups shorten even the longest of legs (and my girlfriend’s are long and slim), and that sleeveless jumper looks like something a children’s TV presenter might wear.
Simon Mills shares his bafflement at current women’s style trends – a confusing and unflattering mix of Lady Di, glam rock and care-home teal
Feathers – à la Sesame Street’ s Big Bird and Rod Hull’s Emu – have flown back into fashion
I am aware that women’s fashion is a riddle, wrapped in a mystery, inside a deliberately anti-chic, tonally jarring, continually goalpost-moving, body-hostile, man-repellent enigma of silhouettes, shapes and stylings that seem specifically designed to not just repulse the opposite sex but also keep us confused.
My two daughters, who are 32 and 27, are cut from the same cloth, turning up for our lunch dates in knowingly fugly vintage sports apparel, and dark, floaty nu-gothic getups. I have now been schooled to term these ensembles as ‘elevated athleisure’ and ‘dark academia’. Both are bang on trend for autumn/winter 26. And my girlfriend’s wonky white blouse? A ‘shirt with a twist’ no less, as seen in new collections by Dior, Armani and Erdem.
This fall (us chaps still call it ‘autumn’), the catwalk of confusion continues – on the rails, in lookbooks and in the wardrobes of spouses and daughters (who might even be borrowing Dad’s tuxedos, neckties and extra-large sweaters to stay in fashion).
Because masculine silhouettes are still with us, only this season they are oversized to comical dimensions, with one brand (Lacoste) hoping that a skinny, size-eight woman might like a classic trench coat cut to suit a man of James Corden’s build.
This AW26 iteration of loose and oversized – mannish suiting that is sloppy on the shoulder (Bottega Veneta, Givenchy, etc) with a voluminous trouser line that puddles around (now invisible) shoes – is termed ‘invertebrate’ tailoring. It also comes with a very, very long sleeve.
I’m a style-conscious (but fashion-clueless) man who has been brought up to admire classic Savile Row tailoring and is easily offended by the grim cheapness of thumb-scraping sleeves on mass-produced suits. To me, a long coat sleeve that engulfs the shirt cuff and hides the hands altogether looks messy and horror-movie sinister. Ditto long sweater sleeves, extended bomber jackets and blazer sleeves. Also, why would any woman want to dress up in clothes that make her look like a kid dressing up in her grandad’s old whistle (as in whistle and flute – rhyming slang for suit) for a school play? And, yes, I think I have just answered that question.
Lady Di-style pie-crust collars are also in trend, but can be ageing on a woman, writes Simon
This season has seen clothes oversized to comical dimensions, with one brand (Lacoste) showcasing a classic women’s trench coat – to suit a man of James Corden’s build
‘Wonky white blouses’ are creeping onto the catwalk, with British luxury fashion house Erdem exhibiting the garment at a 2026 runway show
An oversized mannish suiting that is sloppy on the shoulder and puddles around (now invisible) shoes – is now termed ‘invertebrate’ tailoring. Designer label Bottega Veneta seen at Milan Fashion week, 2026
Twelve-year-old-girl-raiding-fat-grandpa’s-wardrobe being the desired look on the creator’s moodboard, probably.
There has also been a resurgence of colour-blocking, the style for wearing blocks (separate garments) of contrasting or clashing primary colours in the same ensemble – this can be seen in the new collections by Chanel, Hermès and Prada. However, while Dame Prue Leith will be thrilled, crimson and scarlet should be a red flag for everyone else.
Primary tones, when worn by the older generation particularly, are thought to be part of a (slightly desperate) ‘peacocking’ process that kicks in when somebody stops getting noticed. The attraction reduction is compensated for via yellow spectacle rims, canary-coloured waistcoats and pink socks. The appraisers on Antiques Road Trip are big on this.
But the wrong colour combo – say, the red skirt and white shirt seen in Prada’s new collection – can easily make a girl look like she is wearing a Man Utd away kit, a Hi-de-Hi! holiday camp uniform or a 1980s air stewardess’s livery. So copy the look at your purple-and-pink peril.
Even more scary, certainly for a boy who grew up in the dour colours of the 1970s, beige, brown, mustard yellow, teal and turquoise have also made a return to the racks. Magnolia has been recast as ‘buttery beige’ (but still looks like margarine to me) while feathers – à la Sesame Street’s Big Bird and Rod Hull’s Emu – have flown back into fashion as seen in pieces by Alberta Ferretti and Christian Siriano.
Designers are loving the avian aesthetic; plumage has a delicate, fragilising, millinery effect on a woman. The body becomes a brittle, vulnerable artwork of diaphanous keratin and fluff. It is also a material that says, ‘Don’t touch me, I might break.’ Along with, ‘Can I borrow your coat while we walk to the car because I am freezing!’
Playing with the female form or abusing clothing’s conventional proportions for no other purpose than to put off the opposite sex is also back in the shape of dresses and separates with a flapper-girl style, low-slung or dropped waist. Why?
This autumn, Chanel is suggesting an outfit that incorporates a sleeveless V-neck jumper not dissimilar to my girlfriend’s Nuts In May woolly, with a skirt that has a waist hovering somewhere around the thighs. How the skirt’s leather belt stays in place is anyone’s guess. Even on a professional model, this produces a sort of dachshund effect with an extra-long torso and freakishly short limbs. I mean… who would want to wear that?
Before she leaves for her meeting (still in her barrel jeans and Lady Di collar), I show my girlfriend the offending Chanel catwalk image, hoping to experience a significant fashion moment of shared incredulity and bemusement with her. Instead, she takes a mental note, returns to her wardrobe and pulls out a new September purchase; yep – a buttery beige dress with a significantly dropped waist.
As for me? This AW26, and as with all previous falls, I will mostly be wearing a look of utter bewilderment and confusion. Predominantly in a 1970s colour-blocking palette.
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