There's one question I always ask members of Chicago's fashion community. Here it is: How would you describe the city's signature style? Defining "the look" of this particular city is hard. After all, how do you represent glitz-and-glam River North and "hipster" grunge Logan Square in the same sentence?
.... But back to that question. The answers I've received vary from gushy ("Chicago has the best style of any city of I've ever visited!") to realistic ("there are some stylish people, some not-so-stylish people in Chicago") -- but one thing remains constant: Everyone likes to point out that Chicagoans put a premium on practicality. We are functional dresses, always ready for the things about our city that we complain about most: the wind. The cold. The El.
Now that we know that this city is full of practical dressers, let's skip ahead a few steps to the next point: It is possible to be practical and still look put together. In fact, it's really quite easy, especially in the fall. Much of it is just a matter of avoiding these common pitfalls people (most of these apply to both men and women) tend to fall into during colder months.
Avoiding leather: Sure, it seems intimidating. It's got a little bit of sheen, it feels totally different under your fingertips than, say, cotton does. Leather seems more New York than Chicago -- edgy, sophisticated, trendy, expensive -- but it also adds a bit of polish (not to mention warmth) to any outfit. Jean devotees, try this: Layer a well-fitting leather jacket (real or faux, take your pick) over whichever pair you find yourself reaching for most mornings. Add a plain tee shirt, a good pair of boots, revel in the compliments you'll be bringing in all day. It really is that easy. If you avoid leather on the grounds of veganism or frugality, I reiterate: It's okay to go faux. It'll give you the same look for less cash and way less cruelty.
Wearing the wrong sweatshirts: I get it. There is nothing more comfortable than a well-worn oversized Bears hoodie. If you're sitting at home, taking an exam or attending a game then by all means, wear the Bears hoodie. But if you're going to Sunday brunch or a casual work environment, step it up. Opt instead for a hoodless sweatshirt -- a little bit retro, a lot more flattering, as they tend to be shorter and more fitted, You'll notice a theme here: Leather sweatshirts are also great, whether you opt for a completely leathered option ($$$$) or a regular sweatshirt with leather details ($$.)
Choosing black shoes over brown: Fall's favorite colors include maroon, olive green and navy. All of these colors come alive when you pair them with chestnut brown. Brown shoes can take you so far in the fall because they give any outfit a
richness that takes it to the next level. It's also decidedly more neutral and less severe than black. Speaking of black, pants in this color make an amazing canvas for a pair of brown boots. Old-school fashion rules be damned.
For the women -- relying too heavily on yoga pants: They're called "yoga pants." Not "work pants" or "class pants." Not "wear them to lunch pants" and certainly not "wear them out at night pants." Not even "wear them to run errands pants," though I suppose that's debatable. I will allow you to use them as "hungover pants," but only in dire circumstances.
For the men -- wearing the wrong shirt under your button down: It's cold and you want an extra layer between your skin and the wind, but if you must wear an undershirt, make it a fitted V-neck. Too many men wear baggy crewnecks under a perfectly good button-down shirt -- all this does is make you look lumpy and sloppy. Keep your inner layer as sleek and invisible as possible.
And there you have it. Of course fashion is subjective -- but if you're trying to dress for practicality (how very Chicago of you) without sacrificing style, these common fall fashion pitfalls may be the only things standing in your way.