The Right Shoes for Every Outfit

They can make or break your best outfit, and are the one accessory that sometimes trip women up.

Fashion Consultant Emily McCormick spells out what shoes to wear with what pants.

As women, we put a lot of time into choosing our outfit…making sure we have the right shirt, flattering pants, a statement-accessory. Shoes are the last thing you put on when you’re dressing, and sometimes it shows… they can look like an afterthought. And the fashion industry doesn’t make it easy on us! We have so many pant options…from skinnies, to straightleg, to cropped, to bootcut, to wideleg…not to mention it with the dozens of shoes from wedges to flats to stilettos to boots. It can be a recipe for disaster.

Let’s focus on three of the most commonly worn pants: cropped, skinnies and bootcut.


The crop-pant can be defined as anything that hits above the ankle. Really popular style of pant that was originally thought of as a spring/summer pant only, but in more recent years has crept into Autumn fashion as well.

Crop Pant Shoes: Ballet flats, simple, sleek, reminiscent of Audrey Hepburn. Oxfords or wingtips…fun more masculine style. Dress up cropped pants with wedges, stilettos, 1940s heels

The one shoe you should not wear with a cropped pant is the ankle boot. It adds so many lines…the hem, so close to the beginning of the boot. It draws so much attention to that part of your outfit and is pretty distracting, not super classy. The exception to this rule would be if you’re wearing a really tight-fitting crop pant, like a legging.

A little tip: when deciding what shoe to wear with any type of pant, is to consider the fabric. If you’re wearing a wool pant, you can’t wear a casual shoe like a Tom or a Sperry. Stick to a nicer shoe. Interestingly, this rule doesn’t go both ways. You can wear a casual pant, like a jean, and throw in a fur animal-print flat, or a patent leather wedge and you’re good to go.


Skinnies are any pant that tapers at the ankle. I think there was a large number of women who sincerely hoped this trend wouldn’t stick, but they have been in style for a few years now, and a lot of women who were skinny-averse at the beginning of this trend, are now incorporating them into their mainstream wardrobe.

Skinnies shoes: Casual flats including Tom’s, ballet flats. Boots-high and ankle, prairie boots, combat boots. Try a new look like the 1920s/40s inspired shoes like the wingtips or oxfords women wear now.

The only shoe that is a straight-up no with skinnes, is a chunky running shoe. You want to be careful with stilettos…it can create a really harsh look. Finally, we have long left flip-flop season, but if you are planning to wear flip-flops, you want to do a thinner, sleeker sandal…consider leather, as opposed to a chunky, rubber sandal.

With boots and skinnies, be sure to watch the length of boot. Because a skinny pant, by nature, shows the silhouette of your leg, it looks best if you have a boot that doesn’t hit right in the middle of the calf. Look for a boot that comes to the knee, or the ankle boot.


A bootcut pant is tight through the thighs and flares at the calf. The glorious thing about bootcut, is that despite what’s in style, what’s not, this type of cut is almost always going to be the most flattering on women. And, we’ve talked about this before, we’ll talk about it again, but wearing something that’s flattering/well fitting is ALWAYS a better option than wearing something that’s in style/trendy.

When wearing a bootcut, you can see just the toe. So, you can get away with anything from a ballet flat, to a Sperry, to cowboy boots. They really are an easy pant. You also don’t have to worry about length of boot.

Bootcut shoes: Flats, ballet flats, casual shoes, low-profile athletic, any kind of boot., stilettos, wedges, almost anything!

With a bootcut pant, pay attention to what the height of the shoe does to the length of the pant. Bootcuts don’t look good as floods. Skinnies can be short, and they work, but bootcut just doesn’t. Sell them really long…hem them according to the type of shoe you’ll be wearing with them. So, if you’re going with jeans…and you’ll be wearing more casual shoes like ballet flats, then hem them shorter. If you have a wool dress pant that you’ll wear with heels, make sure to hem them so that the pant hits not more than an inch above the ground.

Remember, shoes are such a fun, quick way to add color and class to an outfit. …isn’t it fabulous being a woman?! Animal print, patents, wingtips, wedges, stilettos, flats…live it up and try something new!

Emily B. McCormick is the co-founder of Shabby Apple. She now offers consulting for start-up companies as well as fashion consulting. Visit her online at:

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