Laying It On Thick
Prints in Proportion (Jeremiah)
Don’t be afraid to mix patterns and colors, as long as you pay attention to proportions. Jeremiah’s look, which he described as “fresh, but formal,” pairs a skinny black-and-Technicolor-striped tie with a soft, yellow-plaid blazer. To avoid looking like walking wallpaper, finish it off with a pair of simple pants, like these J. Lindbergh straight-leg trousers.
Beyond Basic Black (Heather)
This “California girl in New York City” look struts boldly past the standard-issue Manhattan black. A funky, flowered dress, which Heather picked up from a vintage store in California, takes an urban twist with a chunky, military-inspired black coat and simple brown boots. If you’re bold enough, top off the outfit with an oversized print bag.
Dress to Impress (Corey)
The hoodie-blazer combination may not be new, but Corey takes it to the next level with four layers in varying hues of blue. For ultimate winter warmth, play with necklines—a collared polo in royal blue pops underneath a navy v-neck sweater, which becomes casual again with a light blue hoodie, which is finally dressed up by a charcoal-blue button-down. Whew! Lest you think the tailored pants make the outfit too serious, add a kooky winter hat (which Corey purchased from a street vendor) for a look you can wear anywhere.
Simple Done Right (Bon)
Bon described his unique style as “classy, but with a touch of street.” The street look gets wise here with the baggy jeans tucked into clean white Keds. But the centerpiece is the gray wool coat, which has enough details—chunky, gold zippers and large sweater-style hemming in a different and bold shade—for everyone on the block. You can afford to add a few more pieces to this sparsely-layered look, so why not try topping it off with a retro throwback. Fedora, anyone?
Summer Solstice (Joanna)
To transition a light summer frock like this Derek Lam dress into winter wear, pair it with tights and one of this winter’s most ubiquitous trends, the ankle boot. Cover up your shoulders with a bold, unexpected piece, such as a waist-length military jacket that instantly makes over girly silk into winter warrior fiber. A thick, heavy wool pea coat will be sure to keep you as warm as the summer temperatures you’ve been dreaming of.
Always a Safe Bet (Jacqueline)
When in doubt, throw on a large, chunky knit for instant warmth and unexpected chic. Jacqueline’s geometric knit sweater is a flea-market find, and the large arrows in alternating colors make it more eye-catching than any old cardigan.
Top Heavy Yet Bottom Light (Ramsi)
Ramsi is a true fashion inspiration. After all, who else can work a classic, gray vest with a T-shirt and hoodie? Or beads and a multi-hued scarf, for that matter? The rugged leather jacket finishes off the look, and he keeps the rest of it simple—black skinny jeans with blue and gray Dunks. The pairing’s so eclectic that the fanny pack, whose rugged leather almost matches the jacket, looks new again—not a bit touristy.
When in Doubt, Punk it Out (Joanna)
Take a cue from the UK streets with a plaid wool jumper. But for the blustery New York weather, try a slim turtleneck underneath with a cape-like cardigan on top. This winter, three-quarter length sleeves are being daringly pulled over long sleeves for a look at once daring yet classic. Knit, textured tights upgrade the classic legging for the winter, and knee-length, leather high boots add that touch of street punk Luella Bartley is famous for. To really play with volume, complete the look with a trapeze, flared A-line jacket—a trend seen all over the fall ‘06 runways.