Like everyone else on the planet I spent much of the countdown to Christmas watching rom-coms. It doesn’t matter if they’re funny, if I’ve seen them before, or if they’re even any good, there is something to be said about the feel-good factor of a nostalgic romantic comedy when there’s nothing else on the tv. However, it struck me for the first time when watching The Holiday (for the 6th time) that instead of concentrating on the plot, I was sidetracked by Cameron Diaz’s wardrobe.
Amanda Woods arrival to the cottage makes almost no sense—why a stiletto heel for a long haul flight let alone the english countryside? Why so much impractical cream? But after watching her slowly but surely fall in love with Jude Law and Aran knits I realise, what the character is wearing is almost as important as the dialogue itself; and Amanda follows in the footsteps of some incredibly influential movie heroines. Think about it, would Pretty Woman still have been as iconic without the thigh-high boots? Can we imagine a Miss Congeniality without that bodycon mini dress reveal? And really, there is no Coyote Ugly without the spray-on leather trousers and cropped tank tops.
After bringing the topic of the best rom-com movies to my Who What Wear colleagues, I not only have a list of films I’d forgotten (sorry, You’ve Got Mail), but also some very good outfit inspiration, revealing in the process that everything that we’ve worn in the last 12 months can actually trace it’s roots back to one iconic movie heroine. Don’t believe me? Keep scrolling to see the swoon-worthy characters that we fell for so deeply that we inadvertently started dressing like them too. They had us at hello.
Style Notes: Yes, before “cottagecore” even had a name Cameron Diaz’s Amanda Woods was eating a cheese board in bed in a cable knit jumper, and if that isn’t peak winter inspo, I don’t know what is. Yes by the end of the film she’s back in a pencil skirt, but let’s not overlook all of the shearling and neutral knits that happens in between. Kick off your heels and layer up, this is an aesthetic designed with comfort in mind.
Just so snuggly.
The perfect winter co-ord.
I want one in every colour.
Indoor or outside, you’re guaranteed to be cosy in these.
Style Notes: On rewatch, there are certainly some problematic issues with Maid in Manhattan (the main lesson being that we do not need to pretend to be anyone else to win someone over) but, if it was seeing J.Lo in that all-white ensemble that truly won Ralph Fiennes over, that is totally understandable. Everything about this outfit says “I’m rich” without a single logo in sight—enter the quiet luxury phenomenon that we’ve been loyally committing to over the last two years. Cream is an obviously luxurious choice, but I think the key here lies in the head-to-toe-tonal styling decision. After all, just imagine how good this would also look in camel… or chocolate brown… or black… or slate grey…
Yes, you read that correctly. This is from the high street.
The Row set the agenda for modern luxury.
Such a great wide-leg fit.
Everyday hoops that go with everything.
Style Notes: No, this is not a screenshot from an Urban Outfitters campaign, of course it’s Julia Roberts unforgettable turn as Anna Scott, Hollywood A-lister incognito. From the oval sunnies to the leather blazer, everything about this look feels so current it’s spooky (even down to the pristine pair of black Vans just out of shot). The jeans are straight-legged, the t-shirt is white, and accessories are stripped back—90’s minimalism at it’s finest, and if you want a really good outfit moment other than this, it’s her wearing a full suit and tie to do press junkets. I have no notes.
This could have been hanging in Julia’s wardrobe.
The ideal length for wearing with an ankle boot.
It just wouldn’t be a comprehensive minimalist edit without something from Toteme.
So cute!
Style Notes: If you needed any convincing that Elle Woods walked so that Margot Robbie’s Barbie could run, it’s high time you rewatched Legally Blonde. Everything about Elle’s technicolour wardrobe is so utterly charming that we can’t help but root for her. It’s camp, it’s brash, and it’s unapologetically her, and the fun we had watching this film prepared us to embrace Barbiecore with open arms. If we learnt anything from this exceptional character, it’s how to find the joy in dressing up again. Oh, and the bend and snap.
How to do a pop of pink.
Margot, eat your heart out.
These would be so good with an all-black outfit.
So much more exciting than black.
Style Notes: Okay, we’ve all had the same panic at one stage in our lives. We’re invited to an evening event—whether that be a dinner, a birthday, a wedding, anything that requires formal dress, and our first thought it “what am I going to wear?” Thanks to How to Lose a Guy in 10 Days, I’m convinced that my answer is now always the same. A silky slip dress. There is no occasion that this won’t work for, and if it’s black tie just dress it up with some sparkly accessories, and if you want to keep it casual add a blazer and flats. Simple. There’s a reason that Andie’s no fuss approach to evening wear is the standout moment in the entire film, and in the words of Who What Wear commercial writer Florrie Alexander “I think about the yellow dress in that film at least once a week.”
Style Notes: It was Bridget Jones that TikTok had in mind when it coined the term “the Frazzled British Woman” aesthetic. And while the mildly offensive phrase does imply that single British woman above a certain age posses a chaotic energy that most actually don’t, it does conjure up an image of the exact trope we can find in any Richard Curtis rom-com. She’s practical, though dresses in a hurry, doesn’t bother with superfluous styling, but you can imagine carries a massive handbag, and is more likely to sport a block heel than a stiletto, but isn’t that why we love her? Despite the big coats and cardigans there’s still a playful mini or two in the mix. No, skirt is not off sick.
You’re going to need a sensible coat to contend with the Great British weather.
Just add opaque tights and a knee-high boot.
Because there’s always a scarf.
When you’re not wearing a skirt, you can tuck in leggings.
Style Notes: There are a lot of truly bonkers outfits in Never Been Kissed, but most of these happen when lead character Josie is first attempting to masquerade as a 17 year old. As soon as she becomes confident in her own skin and stops trying so hard (cue the character development moment), her wardrobe shifts from Y2K excess to a romantic, floral dream. All of the coquette sign posts are there: bows, pastels, cardigans, and chiffon, and this palette cleanser is a welcome relief after the white feathers and pedal pushers. All this girl needs is a Lana Del Ray soundtrack and she could have stepped straight out of TikTok tutorial.
Style Notes: And finally to the poster girls for movie outfit inspo, the cast of 1995’s Clueless. It’s true their look has been copied and pasted relentlessly since the film’s release, but thanks to a new generation discovering it for the very first time, a revived love for preppy chic has been trending on socials. Add a Gossip Girl reboot, Miu Miu runway references and a dash of Hadid sisters and you’ve brought the look bang up to date. And before you think “ugh, as if!” at the thought of a wardrobe influenced by American schoolgirls, if you own a pair of Prada loafers, a Ganni tank top, or a Frankie Shop waistcoat, you may have already been convinced.
Just screenshotting this entire look to copy later.
