“Oh my God, what are you wearing?” every on-the-street interview begins. “Start from the top.”
This is an account on Instagram where a young-sounding girl stops people around Aspen who she thinks have great style and asks them what they’re wearing. It’s a lot of fun, and no doubt Aspen is the perfect fashion playground for people who love designer clothes and have plenty of money to pay for them
The girl squeals with delight every time she documents another $1,000 cowboy hat from the designer western goods store in town — and most everyone she documents has one. Most people she features wear designer clothes from head to toe, especially cowboy hats, cowboy boots and turquoise (which I always thought was more Santa Fe than Aspen, but whatever)
The idea of documenting what people are wearing is exploding on Instagram, and it’s got me thinking about what defines true style. I have always been mystified by trends and the way we all blindly follow them, thinking it’s our own original idea, only to discover it’s the easiest way to blend in. Maybe our desire to fit in is so strong that we automatically gravitate toward ways to do that
It amazes me how trends — not just in fashion but in all forms of design — inadvertently document the passage of time by being obtusely associated with the decade they were popular. Why is it that so many people come up with the same idea at the same time? Are we that incapable of original thought that we blindly follow the masses, all the while thinking it’s all our idea?
True style is something that comes not from clothes, but from poise and confidence. People who are self-possessed have the courage to pair the unexpected, or turn something basic into something extraordinary by how they wear it. It’s not about what they wear, and it’s certainly not about flaunting expensive labels
To my eye — and please correct me if I’m wrong here — the person who decides to wear every single western-style item of clothing or accessory they own (especially ones from designer boutiques) at the same time is either a tourist, a part-time resident who comes for two weeks a year or the guest of a part-time resident. Like, you can buy a lot of that same stuff at the co-op in Carbondale for tens of dollars, just saying
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The other night I had a chance to put my own style to the test when I was fortunate enough to be invited to the Twilight Beach Polo event hosted by The Purist magazine and my dear friend Alex Halperin. Alex has incredible style and is the master of scouring “NWT” (new with tags) designer clothes at various thrift stores and discount sites. She has two sisters she is besties with, and they are all beautiful, classy women in their 70s who can rock a look like no other, and I want to be like them when I grow up.
So, I get invited to this fancy polo event, and for three days before it I’m thinking about what to wear. I even made a video, in my bedroom, getting dressed just like these people on Instagram, like I am 10 years old all over again and pretending I’m the host of a popular kid’s TV show. I do think this is what roughly half the population loves about social media — anyone can put themselves on camera and pretend to be a star, which satisfies some primordial compulsion to admire our own reflection.
The other half of people are voyeurs who never post but only look. And then perhaps 10% of people, the ones who have class and self-respect, don’t participate in social media at all because they value their privacy and have nothing to prove. But I digress
I settle for a maxi dress from a surf label with inexpensive white canvas cowboy boots from Dolce Vita, a western-style hat I got at Heirlooms for $20 that is adorned with lace and beading on the brim, and a rabbit fur shawl I bought at Suzy’s a million years ago that is a staple in my closet
I get a few compliments on the boots and several on the rabbit shawl — which is the only true stylish thing I have on — but I look nothing like Julia Roberts in “Pretty Woman.” The tall boots aren’t flattering on my short muscular legs, and I look more like a jockey at the track than someone going for western elegance. I broke my own rule by wearing the hat and the boots — platform sneakers would have been more my style. The top of this dress is way too low cut and the rubber pasty things I wore in lieu of a bra keep poking out. I did not feel good in this outfit. It felt like a costume. It was a fashion miss for sure.
True style isn’t about what you wear but how you wear it. The women I know who wear clothes well (rather than letting the clothes wear them) put unexpected things together and it works. They are also good at thrifting and understand that treasure, by definition, is about rarity, not popularity. It’s not that we don’t all love cowboy hats, because we do. It’s just knowing when, and how to wear them
Ali can be contacted
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