How is one expected to know how to dress oneself when there are so many other urgent and significant things, like Willow Smith’s Twitter, to think about? Allow moi to creative direct.
Layers: They can be your best friend or… your best friend. A great aspect of layering is how it can expand your wardrobe; unseasonal or uninspiring pieces can gain new life when paired with other items. Those summer dresses you have in the back of your closet? Wear one under a sweater with a blazer and watch as it transforms into your new favorite winter layer. Those peep-toe platforms you had to have but only wore once? Wear them with socks and a pair of cropped jeans.
Outerwear: it’s part of the outfit too! And in this city, sometimes it’s your whole outfit. Shopping is the first step to dressing better. You can’t slide down the slippery slope of sweatpants if you never buy any, and the same goes for outerwear; don’t underthink it. Locate a jacket that hits below the knee and pair it with shorts over tights and knee high boots. If people confuse you for Jane Birkin, just go with it. Embellished pieces? Metallics? Sounds good if you ask me. And you did.
Accessories: I need feathers! I need sparkle! And so will you when winter is going on its eleventh month and you’re too depressed to see the colorful half of your closet. A vibrant scarf styled loosely around your shoulders like Burberry Prorsum or a pair of earrings that weigh more than your bag can go a long way. Now say it with me: “belts!” If one doesn’t satisfy you, try two. Or three, à la Gucci 2008. You can never have enough bracelets. Or necklaces for that matter. Can’t hold up your head? Add one more. And hats are compelling even if you don’t live in London. Most importantly, never underestimate the power of a great accessory.
Attitude: Gestures on the runway stand the test of time long after the styles fade. More frequently than not, “looking good” has little to do with what you actually put on and more with how you carry yourself. Never forget that every sidewalk is your runway and every pedestrian is an activist holding up a poster for PETA getting in your way.
—Tips by Daga Samuels and photograph by Isa Giallorenzo
Journalist Isa Giallorenzo was born in São Paulo, Brazil and has elected Chicago as her beloved home since 2009. She runs the street-style blog Chicago Looks and wants to see this town become one of the fashion capitals of the world.