A 10 Step Guide to Dressing Like a Street Style Pro

It’s not rocket science. Heck, it’s not even science. And if you’re a WWW regular, you probably know this stuff like the back of your well-manicured hand. But for those who are uninitiated to the seemingly arcane world of street style, we’ve broken things down into 10 easy steps.

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    Follow our lead and you’ll find yourself on the business end of Bill Cunningham’s lens in no time.

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    EXPLORE: Street Style
    PHOTO: Adam Katz Sinding of le21eme.com

    Always Come Equipped With a Pair of Look-at-Me Sunglasses

    These trusty shades work overtime, hiding tired eyes while serving as the kind of outré accessory that’s catnip to photogs.

     

    Image courtesy of Adam Katz Sinding

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    EXPLORE: Street Style
    PHOTO: Stockholm Street Style

    Ear Cuffs Are the New Arm Cuffs

    Equal parts punk and glam, ear cuffs were a ubiquitous sight during fall fashion week. Whether they’ll make a repeat performance for spring remains to be seen. In the meantime, however, we say, cuff ‘em.

     

    Image courtesy of Stockholm Street Style

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    Claire’s

    Coil Ear Cuff ($7)

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    Anita Ko

    Rose Gold Ear Cuff ($440)

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    EXPLORE: Street Style
    PHOTO: Vanessa Jackman

    Don't Shy Away From Pieces The General Public Might Deem "Ugly"

    This is fashion with a capital F, people. If your boyfriend/parents/boss thinks you look like a color-blind mental patient, chances are you’re doing something right.

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    Martine Rose

    Cropped Denim Jacket ($455)

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    EXPLORE: Street Style
    PHOTO: Stockholm Street Style

    DIY a Frayed Hemline for the Denim Look Du Jour

    But what about the standard cuff, you say? Nope. Totally last season. Ever since street style star par excellence,Yasmin Sewell, stepped out in a pair of chopped-off jeans at London Fashion Week last spring, the denim tides have been turning in favor of frayed hems. The Man Repeller even offers this handy DIY Tutorial.

     

    Image courtesy of Stockholm Street Style

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    EXPLORE: Street Style, ASOS

    ASOS

    Ripped Raw Hem Skinny Jeans ($58) in Blue

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    Frame Denim

    Skinny De Jean ($79) in Topanga Canyon/Fairfax

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    EXPLORE: Street Style
    PHOTO: The Man Repeller

    Wear Socks With Heels (Bonus Points if Said Footwear Is White)

    Given recent weather conditions (we’re looking at you, Polar Vortex), we wouldn’t be surprised if this ankle-insulating look gains more traction. Try it with both closed and open-toed shoes.

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    Gianvito Rossi

    Leather Pumps ($645)

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    EXPLORE: Street Style, Hue

    Hue

    Scalloped Pointelle Socks (3 for $16)

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    EXPLORE: Street Style
    PHOTO: Candice Lake

    Play Fast and Loose With Proportions

    This applies both to the whole ensemble (i.e. an oversized sweater and school boy shorts) and to the pieces themselves (i.e. the sweater’s dropped shoulders and structural sleeves).

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    3.1 Phillip Lim

    Laser-Cut Crepe Shorts ($395)

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    EXPLORE: Street Style
    PHOTO: Fuck Yeah Models Off Duty

    Messy Hair? Don't Care. Treat Your Mane like French Woman

    The cardinal rule in street style is to not look like you tried too hard. A bed-headed coif (a la our Gaelic girl crushes) goes a long way to this effect. Read on to see our sister site Byrdie’s product picks for achieving the look, regardless of hair type.

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    EXPLORE: Street Style
    PHOTO: Camille Over the Rainbow

    The New Power Couple? Leather Pants and Iconic Sneakers

    Both key trends in their own right, together this pairing is the fashion equivalent of Brangelina.

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    Mango

    Leather Pants ($252)

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    EXPLORE: Street Style
    PHOTO: Stockholm Street Style

    When In Doubt, Opt for a Bold Monochrome

    This outfit is a no-brainer— all you need are two, vaguely matching pieces—yet it always delivers the drama.

     

    Image courtesy of Stockholm Street Style

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    Sonia by Sonia Rykiel

    Crepe Pants ($385) in Peony/Black

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    Equipment

    Signature Silk Shirt ($151) in Magenta

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    EXPLORE: Street Style
    PHOTO: Vanessa Jackman

    Jump On Next Season's Trends Now

    In other words, the early street styler gets the adoring throng of photographers/fashion bloggers. Case in point: Giovanna Battaglia (pictured), who seamlessly incorporated the S/S 14 pleats motif into her fall wardrobe.

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    Christopher Kane

    Full Accordion Pleated Skirt ($840)

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    Twin-Set

    Pleated Crepe Maxi Dress ($272)

Shop this Story
Anita Ko Rose Gold Ear Cuff

Anita Ko Rose Gold Ear Cuff

Anita Ko, $440
SHOP
ASOS Ripped Raw Hem Skinny Jeans

ASOS Ripped Raw Hem Skinny Jeans

ASOS, $58
SHOP
Twin-Set Pleated Crepe Maxi Dress

Twin-Set Pleated Crepe Maxi Dress

Twin-Set, $272
SHOP
Christopher Kane Full Accordion Pleated Skirt

Christopher Kane Full Accordion Pleated Skirt

Christopher Kane, $840
SHOP
Claire's Coil Ear Cuff

Claire's Coil Ear Cuff

Claire’s, $7
SHOP
Equipment Signature Silk Shirt

Equipment Signature Silk Shirt

Equipment, $151
SHOP
Frame Denim Skinny De Jean

Frame Denim Skinny De Jean

Frame Denim, $79
SHOP
Gianvito Rossi Leather Pumps

Gianvito Rossi Leather Pumps

Gianvito Rossi, $645
SHOP
Hue Scalloped Pointelle Socks

Hue Scalloped Pointelle Socks

Hue, $16
SHOP
Illesteva Leonard II Stripes With Blue Mirrored Lenses

Illesteva Leonard II Stripes With Blue Mirrored Lenses

Illesteva, $285
SHOP
Kenzo V-Neck Oversized Jacket

Kenzo V-Neck Oversized Jacket

Kenzo, $825
SHOP
L'oreal Volumetry Powder Fresh SOS Refreshing Spray

L'oreal Volumetry Powder Fresh SOS Refreshing Spray

L’oreal, $16
SHOP
Lavett & Chin Original Sea Salt Texturizing Mist

Lavett & Chin Original Sea Salt Texturizing Mist

Lavett & Chin, $30
SHOP
Le Specs Sphinx Cat Eye Acetate Sunglasses

Le Specs Sphinx Cat Eye Acetate Sunglasses

Le Specs, $55
SHOP
Mango Leather Pant

Mango Leather Pant

Mango, $252
SHOP
Martine Rose Cropped Denim Jacket

Martine Rose Cropped Denim Jacket

Martine Rose, $455
SHOP
3.1 Phillip Lim Laser-Cut Crepe Shorts

3.1 Phillip Lim Laser-Cut Crepe Shorts

3.1 Phillip Lim, $395
SHOP
Adidas Rod Laver Mesh Shoes

Adidas Rod Laver Mesh Shoes

Adidas, $30
SHOP
Sonia by Sonia Rykiel Crepe Pants

Sonia by Sonia Rykiel Crepe Pants

Sonia by Sonia Rykiel, $385
SHOP
Topshop Oversize Contrast Check Shirt

Topshop Oversize Contrast Check Shirt

Topshop, $60
SHOP
EXPLORE: Street Style, newsletter-1, Anita Ko, ASOS, Twin-Set, Christopher Kane, Claire’s, Equipment, Frame Denim, Gianvito Rossi, Hue, Illesteva, Kenzo, L’Oreal, Lavett & Chin, Le Specs, Mango, Martine Rose, 3.1 Phillip Lim, Adidas, Sonia by Sonia Rykiel, Topshop, street style, Shopping, How to Dress Like a Street Style Star, How to Look Like a Street Style Star
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