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If the Shoe Fits: Fall’s Hottest Shoe Styles and How to Wear Them

So fall’s finally here, and that means it’s time to break out your new slouchy cargos, boyfriend cardigan and skintight knee-high leather boots, right? Not quite. While this fall’s shoe styles are hotter than ever, by no means can you wear every style with every outfit. How you pair your kicks with your clothes is just as important as how they look on your feet. The right outfit can seriously up a shoe’s fierce factor, while the wrong one can cause a major footwear faux pas. HC is here to help you find the best ways to wear each type of shoe, including some new styles and your old shoe standbys (we all know you still wear UGGS, admit it).
The Flat

Whether it’s your trusty Tory Burch Reva flat or a more fashion-forward oxford, flats are a collegiette™ staple. We wear them from class to dinner to the mall and back again, without a second thought as to what they’re paired with. They really do work with almost anything—you could use them to dress down a sexy dress just as easily as to add some class to skinny jeans and a T-shirt. Jovana Mirabile, fashion designer and one of HC’s resident fashion experts, says you can wear flats with just about anything: “I think you can get away with anything with flats... they look great with leggings and an oversized sweater or t-shirt, or you can dress them up with a sundress or jeans. They’re probably the most versatile type of shoe.”
The Pump

The pump is a staple in every girl’s closet—it’s classic, it’s sexy, and it goes with everything. Well, almost. You can pump up (no pun intended) most outfits with this feminine, leg-lengthening shoe, but it’s important to keep your occasion in mind. For a job interview, they look polished and professional with a pencil skirt. If you’re going out, pair pumps with dark skinny jeans and a great top, but they look a little out of place with a super-flashy dress or sequined mini. Mirabile explains, “I think pumps are a more sophisticated shoe, they have a smarter look, so wearing a dress that’s too short or flashy with pumps doesn’t look right. Something tasteful and professional, or something trendy and casual for a night out looks great with pumps.” And finally, the cardinal rule of pump-wearing: never wear pumps with leggings. Mirabile says, “I don’t recommend it—instead, wear flats or boots with leggings. Pumps don’t go with such a casual look.”
The Sneaker

When we were kids, we didn’t even think about it—we wore sneakers to school every single day. But now that we’re college fashionistas, we have to put a little more thought into what we can wear with our comfy kicks. If your sneakers are running shoes, that’s all they can be—Running. Shoes. Wear them to the gym, wear them on a jog, wear them on a bike ride…and then take them off when you’re done. Athletic sneakers are comfortable, sure, but try not to wear them with non-athletic clothes—especially not when you go out.   More fashion-y sneakers, like Converse or Keds, are fine for class, but probably not the best with a tight skirt and sparkly top—they dress your look WAY down. Mirabile suggests, “If you’re looking for comfort, go for flats instead. Why dress it down with sneakers when you can look cuter with flats?” They’ll be just as easy on your arches without sacrificing any fashion cred!
The Boot

No fall wardrobe is complete without a great pair of boots. They’re cute, chic and totally functional in even the crummiest weather.  But not all boots are created equal, and therefore they must not be treated as such. Here are some general boot rules:

  1. Don’t wear knee-length boots with a knee-length dress or skirt. Mirabile says, “Make sure you always have a few inches of thigh showing above your boots—otherwise, your legs will look cut off.
  2. If you can, try tucking your boots into your jeans if they rise above mid-calf. Mirabile explains, “Sure, you CAN wear your pants over your boots, but why not show off your boots by tucking them in?”
  3. Uggs are never the best choice with any outfit, and they’re not waterproof enough to act as snow boots—but you already knew that, right? If you must wear them with anything (because they’re undeniably the most comfortable shoes ever invented), wear leggings or skinny jeans, and always tuck them in. Mirabile shudders at the idea of the shoe—“It’s the silhouette that makes them so unattractive”—but insists that if they’re worn at all, they must be tucked in. “Always ALWAYS wear them tucked into your pants, never wear your pants over them!” she warns.
  4. If you’re wearing over-the-knee boots, wear a dress that falls above your knee so your legs don’t look cut off, but be careful not to go TOO short. “Super-high boots with a super-short dress can look a little ‘hooker’ if you’re not careful,” Mirabile says. “Be sure to pair a flashier boot with a classier skirt or dress, or else skinny jeans or leggings.”
  5. Boots that fall halfway up your calf, especially clunky rain boots, tend to cut off your legs, especially if you’re wearing a skirt or dress; the most flattering styles are knee-and ankle-length. Mirabile says mid-calf boots look great with a skirt or dress—if you’re a model. Otherwise, be careful. Try a skinny jean instead—they look great tucked into boots. 

The Bootie

The bootie, which can range from practically a pump to a clunky lace-up hiking boot, has taken the fashion world by storm in the last few years, and doesn’t appear to be going anywhere. But just like with tall boots, with each type of bootie comes a different way to wear it. Booties, in general, can be split into three types, with some simple rules governing each one:

  1. Cutout booties: These fierce and fabulous boots are like updated pumps—they come in tons of different lengths, styles and textures, from slashed to cage to everything in between, but they’re all perfect with a miniskirt or dress, or even shorts. With pants, however, they can be a little trickier. Don’t wear cutout booties with long jeans or leggings, or with flared or loose pants; it loses the cutout effect. Go for cropped pants instead—they work PERFECTLY and really show off your fabulous shoes!
  2. Utilitarian booties: Lace-up and hiking-style booties are HUGE this season; they’re useful, rugged-chic, and totally fashion-forward. They, too, look amazing with a dress, skirt, or shorts, and even with skinny jeans or leggings, but you have to be careful wearing them when you go out.  Be careful wearing them with cropped pants—Mirabile says, “If your booties rise above your ankle (which almost all utilitarian booties do), make sure you can tuck them into your pants. Cropped pants that rise above the top of the bootie don’t look right.” And if you have oxford booties, try pairing them with a pair of slouchy trouser socks for a prepster feel.
  3. Classic booties: These old standbys (well, if 2008 means old) come in every imaginable color and texture, and can either be peep-toe or closed-toe. They can have a sky-high platform, or a low chunky heel, but either way they work with almost anything. Unlike cutout booties or utilitarian booties, these look AMAZING under flared jeans or wide trousers, and they work just as well with skirts and dresses. If they hit you below the ankle, like a pump (these are called shoeties, as in shoe + bootie), don’t tuck your pants into them—Mirabile says your pants should hit right at the ankle in this case—but if they rise above your ankle be sure your pants can be tucked in. Look for shapes that dip down below your ankle, and make sure to get a pair that matches with everything, because you’ll wear them all the time!

Jovana Mirabile, Fashion Designer and Student at Parsons the New School of Design

Amanda First is a senior English major at Cornell University.  She is Life Editor of Her Campus, as well as founding editor of Her Campus Cornell. She has interned for Cornell Alumni Magazine, Harper's Bazaar, and Parents through ASME's internship program.  Some of her favorite things include high heels, browsing ShopBop, yoga, The O.C. reruns (but only before Marissa dies), and Tasti D-Lite. After college, she hopes to pursue a career in magazine journalism.
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