Artful Dressing: Finding Real Style and Inspiration from Street Fashion

Posted on October 06, 2015, 11:00 am
9 mins


Today’s street style fashion game has become a platform for style editors and fashion bloggers to make a name for themselves or the businesses they represent. As their influence has grown, the business of fashion itself knows the immense influence these “style stars” have on the brands, trends, and therefore sales. Looking at the development of fashion and style in past decades, it is easy to see the distinction between the fashion elite and those who marched distinctively to their own drum, but those lines have become blurred.

The internet has opened the opportunity for anyone with a big budget and the right connections to become a “fashion star,” but those who excel at marketing themselves aren’t necessarily the most talented or original. So how do we find our way through the forest of pretty, paid-for pictures with no real content to find the people with valid voices, with a unique take on the fashion?

Look to the streets. From the swinging 60s London and Warhol’s arts stars in New York, the Punk era of the late 70s, on to the present, street style is deeply rooted in the youth culture, new art and music. Some may dismiss fashion as superficial and frivolous, but for many it is a way of true self expression. Styling can be an art form unto itself. (Look at fashion rule-breakers like Iris Apfel—no symbol of youth culture, mind you—who finds her accessories and garments in far flung locales and also flea markets and little stores around the corner.) Before the darlings of the internet preened for the spotlight, there were those who showed real street swagger and made an unabashed statement about who they were, without the benefit of photoshop.

Legendary street photographer Bill Cunningham recently sat down with Fern Mallis for her “Fashion Icons” series at 92Y and had an interesting and insightful take on fashion today. He says:

“I think the fashion world needs to come to grips with reality. The reality is you have the whole country electronically connected. They’re educating the insides of their heads, as they should, and not [dressing] the outside with a fancy hat or a dress. Simple clothes, that’s key, and I think that’s what the fashion world should really think about.”

What speaks to me about Cunningham’s statement is he is not saying to have simpler designs; he is telling the fashion world to get back to the beauty of the clothes themselves and the creative process that makes this art form come to life—for everyone.

I am often the most intrigued by photographs of those who take a serious look at what it means to be creative in the process of getting dressed. Let’s face it: Most of us can tell the difference between those who try to hard to be cool, and those that truly are. Our editorial inspiration for the month is the Artful Dodger—Dickens’ serious, street-smart urchin dressed in adult clothing—and so I have created three looks inspired by those who show thoughtful inspiration and serious style every time they get dressed, who can put forth an adult appearance while still having a youthful heart.

The Artful Dodger

I am in complete awe of Rosie Assoulin and her dramatic silhouettes, which have a playful feel to them. They are the kind of piece you wear when you are completely in LOVE with fashion and you dress to stand out in the best way possible. These Rose Assoulin Tilt-A-Whirl Flare Pants will really up your style game. Pair them with the off the shoulder lace top from Zara for a little high/low ensemble, then go big with this super cool COS mohair oversized sweater. Add a little 70s glam with these vintage tiger’s eye and gold hoop earrings from 1st dibs, which is a fascinating place to shop. The streamline Chloe Mini Drew Ayers Handbag emulates a 70s style bag, and so do these rock star Palma Sandals by Tibi. Check out the Tibi shoe collection, if you haven’t yet. It is amazing.

Artful Dodger #2

The first leather jacket I ever bought came from the Men’s department at The Bon Marche. It was a distressed brown bomber that was oversized and the more I wore it the better it got. I wish I still had it. You can always borrow from the boys to give your look something unexpected, and J.Crew’s Mens Leather Flight Jacket is just the ticket. I chose my favorite go-to tanks from J.Crew to wear underneath the bomber. Wear them doubled up, one on top of each other. The anchor of this outfit is Tamara Mellon’s Signature Fringe Red and Black Skirt, which is a major trend of the moment. These woven Proenza Schouler Sandals gives texture and balance to the outfit without competing with the skirt. Plus, they are incredibly cool shoes. Finally, LEGO® is having a handbag moment, so why not carry a cool Mira Mikati and Les Petits Joueurs collaboration box clutch studded with the handbag designer’s signature LEGO® embellishments of Mikati’s colorful cartoons. The architectural design of these geometric earrings by Sarah Loertscher give the look a very modern edge.

Artful Dodger #3

Layering can appear to be a tricky business, but it is really a matter of finding a common thread with the things you wear together. Mismatching and mixing patterns is considered street-smart dressing these days, and personally I always love the unexpected, hence my obsession with the skirt or dress over pants look. I chose my favorite pair of Frame denim jeans, the fitted “Le High Skinny” Destroyed Jean, to wear underneath the MiH Patchwork Suede Mini Skirt. Wear a tie neck blouse, another big look for fall, and then add a pair of leopard Manolo Blahnik “Taylerbi” D’Orsay Pumps to pull it together. Street stylers love having original pieces, so vintage is often a great way to show some originality in your look. I found this 1950s Military Vintage Jacket that is off-the-charts amazing. Local Seattle store Moorea Seal has Pyrite Electric Ear Jackets that are the perfect jewelry touch. The beautiful midnight blue leather and suede Large Club Clutch from AllSaints translates perfectly from a day bag to an evening piece.

Being original isn’t always the easiest path. We are creatures that have a serious need to be a part of the pack. Showing originality in how you present yourself to the world isn’t necessarily a matter of being the loudest voice in the room—it is listening to your own true voice. “There are dark shadows on the earth, but its lights are stronger in the contrast.” ~ Charles Dickens

Lisa Cole is the fashion and style writer for Vanguard Seattle, and her work includes covering fashion news and events, runway shows and boutiques. She has her own fashion and lifestyle blog,, and is a member of Independent Fashion Bloggers and Fashion Group International.