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What happened when I let AI dress me for a week


Every fashion editor worth their designer shoes knows that wearing head-to-toe leather is a major fashion faux pas. Even the A-list can’t pull it off.

Remember when Victoria and David Beckham did matching leathers on the red carpet circa 1999? Undoubtedly one of the dodgiest celebrity style moments in recent history.

And yet, it’s a Friday night and I’ve walked into a trendy London pub dressed in a biker jacket and matching trousers. 

As I squeak past the bar towards my friends, they erupt into hoots of laughter. I look like a spy-film assassin. I feel ridiculous, not to mention a little clammy.

So why have I subjected myself to such sartorial humiliation? Because an AI told me to. 

I LOVE ALEXA CHUNG¿S STYLE. HOW CAN I COPY IT? Given Alexa Chung¿s eclectic and vintage-inspired style, she would opt for a 1960s mini dress with a mod silhouette. This will capture the essence of the Swinging Sixties when paired with block-heeled shoes. Dress, £145, sisterjane.com; shoes, £145, boden.co.uk; bag, £45.99, reserved.com

I LOVE ALEXA CHUNG’S STYLE. HOW CAN I COPY IT? Given Alexa Chung’s eclectic and vintage-inspired style, she would opt for a 1960s mini dress with a mod silhouette. This will capture the essence of the Swinging Sixties when paired with block-heeled shoes. Dress, £145, sisterjane.com; shoes, £145, boden.co.uk; bag, £45.99, reserved.com

HOW CAN I GIVE MY JEANS A STYLE UPGRADE? A rugby shirt can add a touch of sporty sophistication. They are typically cotton or jersey, offering a relaxed fit. Match with jeans for the perfect balance between casual and put-together. Shirt, £48, joules.com; jeans, £40, and boots, £75, both riverisland.com

HOW CAN I GIVE MY JEANS A STYLE UPGRADE? A rugby shirt can add a touch of sporty sophistication. They are typically cotton or jersey, offering a relaxed fit. Match with jeans for the perfect balance between casual and put-together. Shirt, £48, joules.com; jeans, £40, and boots, £75, both riverisland.com

WHAT¿S A CHIC LOOK FOR A PUB BIRTHDAY BASH? Leather trousers paired with a motorcycle jacket can create a stylish and edgy look. The combination exudes a cool and confident attitude. To complement the look, wear a silk neck scarf. And add sunglasses such as aviators or oversized frames for a touch of glamour. Jacket, £39.99, bershka.com; trousers and shoes, both £35.99, zara.com; neck tie, £7.99, tkmaxx.com; sunglasses, £8.99, hm.com

WHAT’S A CHIC LOOK FOR A PUB BIRTHDAY BASH? Leather trousers paired with a motorcycle jacket can create a stylish and edgy look. The combination exudes a cool and confident attitude. To complement the look, wear a silk neck scarf. And add sunglasses such as aviators or oversized frames for a touch of glamour. Jacket, £39.99, bershka.com; trousers and shoes, both £35.99, zara.com; neck tie, £7.99, tkmaxx.com; sunglasses, £8.99, hm.com

With more than 180 million users, artificial intelligence app ChatGPT is like a smart chatbot — you ask it a question and it will scan the internet to formulate a convincing answer. And it can mimic human language patterns, so it’s like talking to a real person.

It can compose emails, fill out forms, write essays and even code computer programmes. Some have even turned to ChatGPT for help crafting their dating profile. But can it help me get dressed?

With two young children, a house renovation and a job to juggle, anything to help me put an outfit together is a godsend. The catch is, I need to look chic — I am a fashion journalist after all.

Does ChatGPT have a sense of style? I challenged it to dress me for a week to find out.

I start with my everyday look. I’m forever wearing jeans and a jumper and could do with shaking things up. I type into the app: ‘How can I make my classic straight-leg jeans look new season?’

In a millisecond, it responds with a vague: ‘Pair them with a trendy, statement top or blouse.’ I ask for examples and it reels off a selection of alarming options (off-the-shoulder sweater; a sleek bodysuit; a crop top — eek) before landing on a knitted rugby shirt, which feels more me.

In terms of where to find these clothes, it vaguely tells me I should look in ‘various clothing stores, online and in person. Options include H&M, Zara, Marks & Spencer, Boden, Phase Eight.’

On to something smarter, I ask for a contemporary outfit for a work event, to which it replies: ‘Consider a tailored blazer and pencil skirt.’

HOW CAN I STYLE A SATIN MAXI SKIRT FOR WINTER? Pair your satin skirt with a chunky sweater for a cosy but chic winter outfit. Add a scarf for warmth and elegance. Finish with trendy ankle boots. Coat, £99, and skirt, £35, both riverisland.com; sweater, £110, peregrine clothing.co.uk; boots, £102, boden.co.uk, scarf, £90, chintiandparker.com

HOW CAN I STYLE A SATIN MAXI SKIRT FOR WINTER? Pair your satin skirt with a chunky sweater for a cosy but chic winter outfit. Add a scarf for warmth and elegance. Finish with trendy ankle boots. Coat, £99, and skirt, £35, both riverisland.com; sweater, £110, peregrine clothing.co.uk; boots, £102, boden.co.uk, scarf, £90, chintiandparker.com

WHAT¿S ON-TREND FOR 2024? In 2024, jumpsuits continue to be fashionable. They offer a one-and-done outfit solution that effortlessly combines style and comfort. Jumpsuit, £335, wiggykit.com; trainers, £195, meandem.com

WHAT’S ON-TREND FOR 2024? In 2024, jumpsuits continue to be fashionable. They offer a one-and-done outfit solution that effortlessly combines style and comfort. Jumpsuit, £335, wiggykit.com; trainers, £195, meandem.com

As it’s not 1987 and I’m not a lawyer, I demand something ‘more modern and fashionable’. It comes back with high-waist, wide-legged trousers teamed with a blouse, knit top and loafers. I pull these out of my wardrobe, and feel happy about the result.

I’m starting to realise ChatGPT’s styling advice is hit and miss. It comes up trumps for cold weather ideas for my slip skirt (chunky knit, ankle boots, tailored coat) and correctly identifies that a muted colour palette and jumpsuits are key for 2024.

However, when I request a cool, comfy outfit to wear to take my children to the playground, the app recommends a T-shirt ‘featuring cute animals, cartoon characters or whimsical illustrations kids will enjoy’.

Although my three-year-old thinks this is brilliant (he asks for one, too), in my Miffy the rabbit T-shirt and red trousers I look like I’m about to present an episode of Blue Peter.

Where ChatGPT excels is in taking me out of my style comfort zone. I wear a mini dress for the first time since university after requesting an Alexa Chung-inspired look for lunch in town with a friend.

When I ask for date night outfit ideas, the app puts me in a cocktail dress and heels. While I feel overdressed for the local Italian, my husband gives me a wolf whistle as I walk down the stairs. The app even points me in the direction of kiss-proof lipsticks.

But just as my AI style guru is on a roll, Leathergate strikes. The brief: a chic, low-key outfit for a pub birthday party. The result: Hells Angels with a sauvignon blanc.

WHAT SHOULD I WEAR FOR A DATE NIGHT? Cocktail dresses exude a sense of refinement and grace. Red is a classic colour associated with passion and romance. Don¿t forget to wear confidence as your best accessory. Lip stains or lip tints provide a lightweight and long-lasting colour that can withstand kissing! Dress, £250, meandem.com; shoes, £35.99, zara.com

WHAT SHOULD I WEAR FOR A DATE NIGHT? Cocktail dresses exude a sense of refinement and grace. Red is a classic colour associated with passion and romance. Don’t forget to wear confidence as your best accessory. Lip stains or lip tints provide a lightweight and long-lasting colour that can withstand kissing! Dress, £250, meandem.com; shoes, £35.99, zara.com

WHAT TO WEAR WITH CHILDREN AT THE PLAYGROUND? Opt for a cool graphic T-shirt with a fun and playful design featuring cute animals, cartoon characters or whimsical illustrations that kids would enjoy. Keep your hair out of your face by wearing a ponytail. Jacket, £29.99, newlook.com; T-shirt, £22, daisystreet.co.uk; track pants, £177, chintiandparker.com; trainers, £35, marksandspencer.com

WHAT TO WEAR WITH CHILDREN AT THE PLAYGROUND? Opt for a cool graphic T-shirt with a fun and playful design featuring cute animals, cartoon characters or whimsical illustrations that kids would enjoy. Keep your hair out of your face by wearing a ponytail. Jacket, £29.99, newlook.com; T-shirt, £22, daisystreet.co.uk; track pants, £177, chintiandparker.com; trainers, £35, marksandspencer.com

When I query the choice, ChatGPT doubles down, reassuring me that it’s ‘a trendy outfit which exudes a cool and confident attitude’.

As if this combination weren’t suspect enough, I’m told to add a neckerchief and big sunglasses for an ‘edgy and elevated casual vibe’. I can only assume the app is glitching as nobody could consider this a passable look. Sack the stylist? Absolutely. I’ll stick to dressing myself for now.



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