The first time I went to London was also the first time I ever left the United States. I was 19 and from Kansas, but still worldly enough to be aware of how deeply uncool this made me.

I was traveling with my best friend, and we went to great pains to blend in—memorizing maps before we left our hotel, speaking only when necessary in an attempt to hide our flat American accents—but, still, it seemed as if we were haunted by the blunders of our countrymen at every corner: Yes, that was a Texan a few seats down at Wagamama, saying, “But I just want some chicken fried rice!” That mass of bright purple and red North Face jackets clogging the entrance to the Tube? Couldn’t be anything but.

And while a hallmark of the typical American tourist is that they see no need to heed the advice of “When in Rome…,” my traveling companion and I couldn’t have been more different. We tried as hard as possible to look “London” (I shopped so much that my credit card company called my apartment back home, worried about excessive overseas spending) but still fell far short of blending in. 

At the time, I chalked it up to the fact that I was a Midwestern college student. But returning to London just a few weeks ago, with five years of living and getting dressed in New York under my belt, I found that nothing had changed. I still felt more Jessica McClintock than Stella McCartney. 

New York and London are very different cities. London is civilized, while New York is bursting at the seams—a fat man one hamburger away from a heart attack. Try to find a place to eat in London at midnight, and you’ll be hard-pressed: the restaurants are closed because proper people ate dinner hours ago and are now home in bed. This pulled-together way of life seems to translate into the way people dress as well. On the plane over, I couldn’t help but notice that the British passengers looked comfortable in knee-high leather boots and fitted sweaters, while the American travelers had decided that the only way to do a red-eye was in their pajamas, or some version thereof. Within minutes of landing at Heathrow at 6:20 a.m., I saw a girl stroll by in a Karen Walker robot sweater and a sleek silver jacket, pulling her suitcase behind her and looking as if she’d just had eight hours of sleep and a facial. I, on the other hand, was ready to roll my jacket into a ball and make a bed on the baggage claim floor. 

This isn’t to say, though, that Londoners take fashion more seriously. Rather, it’s quite the opposite. Americans approach fashion with a studied lack of humor: We dress to be comfortable, dress to be professional, dress to be stylish. We want to wear what everyone else is wearing, only we want to wear it just a little bit better. In London, style is a personal issue: There’s less of a focus on how one should be dressing as there is on how one wants to dress. “There’s more of a sense of play in British style. I think in American style, we’re very conscious of wearing the ‘right’ clothes, the ‘it’ items,” says Sarah Maslin Nir, a NYLON contributor who’s a New Yorker by birth but now lives in London. “Sure, that comes into play in the U.K., but a major part of dressing stylishly here is out-funky-ing one another. But Brits do funky and still manage to look chic. There are just less limits, less worry about what everyone else is wearing.”

“I think [London style] is a little more reckless,” agrees London-based stylist Celestine Cooney (see her on page 126). “It can be quite haphazard, less controlled. Sometimes it looks like people have just put as much stuff on as they can and it doesn’t really work, but that’s not what it’s about in the first place. It’s about not being afraid to go out covered in plastic and fluorescent accessories or jeans so tight they restrict your walking.”

Topshop, the epicenter of the London fashion scene, is a world unto itself. My first time there was much like an acid trip. We dropped in, lost all sense of bearing and emerged hours later, not quite knowing what had happened but pretty sure that it was good. Topshop is inexpensive, but, especially thanks to the latest exchange rates, could never be called cheap. Its racks are full of frocks and coats that might be considered small-investment pieces. When I was there recently, I caught a peek at the names on the VIP discount list, and was able to spot Selma Blair and Kate Bosworth before the sales girl caught on to what I was doing, and slid the list back into its folder. Unlike American megastores, which are just big and crazy, Topshop is big, crazy, and cutting-edge. Their designer collaborations incorporate not just established big brands, but up-and-comers such as Richard Nichol, Markus Lupfer, Celia Birtwell, and Preen. It’s a testament to their fashion prowess that Topshop girls are clued in enough to recognize and covet labels such as these, and the store’s size, name recognition, and a location in central Oxford Circus mean that some of the city’s best fashion is not hidden away in a small side-street boutique, but is as easily accessible as Macy’s might be in New York.

London has always embraced fashion on a very street level, from punks and mods to the current more dubious wave of New Ravers, and now it seems that people feel free to pick and choose elements from each and make them their own. Thus, the lines between what is high-fashion and what is low blur in a very organic way. “With all the young designers here like Gareth Pugh and Carrie Mundane, there are spin off tribes and groups from these designers, and that creates a super-colorful street life,” Cooney says. “The Carrie and Henry [Holland] kids wear bright colors and have pastel hair, they look like toys, all rainbows and smiles. The Gareth Pugh kids are darker, they love a bit of Chanel and Rick Owens.”

“There is less of a divide between designers and their market here as well,” says Margaret Crow, an American student who’s lived in the U.K. for the past six years. “I see Christopher Kane or Gareth Pugh out dancing regularly and it’s not a big deal. Most of the designers here are clubkids themselves and design for that scene. Seeing Marc Jacobs isn’t exactly a rarity in New York, but he doesn’t mix like Danielle Scutt or Christopher Kane.”

Crow also notes something that was quickly obvious to me. “There has always been such a rich history of subculture here and it shows a lot more than in the States,” she says. “British cities and towns make the right environment for a goth kid to develop and be authentic. Middle England can be pretty bleak. When you compare a suburban American kid from an upper middle class family to a kid from the Lake District working the same look, it’s just obvious who will come off less of a poseur.” 

And it’s true: In the States, I’ve always responded to goth and punk kids with a bemused smirk, because I know that they probably drive Ford Tauruses and shop at Hot Topic. Walking through Camden, an area of London that sells everything from Tartan plaid creepers to tight, zipper-covered leather pants, pirate ruffles, and Jack the Ripper Coats, I was smitten with every little goth we met. I imagined them up all night in dingy apartments, listening to industrial techno and painting; waking at two in the afternoon to smoke cigarettes and drink black coffee. 

These kids elicited none of my scorn and all of my awe, which I’ve realized is my general response to London fashion. London style is inimitable because it isn’t trying to imitate anything, it’s just being itself. So on my latest trip, realizing that it was going to take a lot more than just a Topshop outfit to make me look British, I gave up, and spoke loudly in my annoying asking directions wherever I went.