How to Style Shoes from Booties to Black Tie

How do you pair shoes with outfits? It seems like a simple concept. But whether you're slipping on some comfy flats, zipping up some thigh-high boots or sliding into some killer mules, it can sometimes be tricky to know how to style the rest of your outfit to go with your favorite new designer shoes. We're here to help.

When learning how to style shoes, you don't want to get too bogged down with fashion rules or, worse, get stuck in a style rut! Fashion is supposed to be fun, so play with proportions and make every outfit your own. The following are just a few clever tips for how to match shoes with clothes and take your ensemble up a notch.

Black Booties

Boots & Booties

Who doesn't love a good pair of designer boots? From stovepipe boots and slouchy boots to ankle booties and cowboy booties, a good pair of boots has the ability to slim the leg and make you look taller and leaner, all while pulling together your outfit in the best way possible.

Ankle Boots

Ankle boots can range from super casual to super fancy. And, depending on how they're styled, they can be perfect for nearly any occasion.

A casual ankle boot typically has an elastic side panel, laces, zippers, a low heel and/or a rounded or semi-pointed toe cap, and usually comes in a material like brown suede.

As for how to style these shoes, you'll want to keep it simple. Pair your shoes with a pant that can show them off, like skinny jeans that can be tucked or cuffed, or a pair of cropped ankle jeans. Then, toss on a sweater, white T-shirt or blazer.

If you have a dressier heeled pair of ankle boots in black leather or a print, you have a few styling options. For more of a daytime look, pair them with a great pair of boyfriend jeans, skinny black pants or a circle skirt, and an oversized sweatshirt, sweater or a denim button-up. For an evening look, slip into a sheath dress or a full-skirt dress and pop on a leather jacket for a touch of unexpected juxtaposition.

Knee-High Boots

Knee-high boots tend to fit tightly around the calves and typically have more rounded toes. Because these boots fall a little below the knee, you'll want to take special care when choosing your outfit as they can tend to make you look short if not styled correctly.

Try pairing these boots with blue or grey jeans and an oversized sweater, long cardigan or a turtleneck. We also love to pop on faux fur vests with this type of boot!

Thigh-High Boots

A great thigh-high boot has the power to give you that little extra boost of confidence to take on the day. It looks ultra-chic and can slim the legs while streamlining your entire look. Black, brown, grey — whatever color you choose, you're sure to look incredible.

For an easy daytime look, we like to style thigh-highs with leggings or skinny jeans. For up top, you can pretty much do anything; pair it with a sweatshirt, blazer, cardigan, blouse or bomber jacket. If you're looking for a versatile look that can take you from day to night, try pairing your boots with a flattering sheath dress or an A-line skirt. Just be sure to stay away from tight skirts or dresses — they tend to cheapen and date your look when paired with thigh-high boots.

Blue Espadrilles


Espadrilles are the epitome of island getaway fashion. The light shoe features a plaited, flexible sole made of jute while the uppers are made of canvas or a type of cotton fabric. Designer espadrilles come in many forms, from sandals to flats to wedges, so you can easily find a style for any look.

Since this is more of a summer or vacation type of shoe, you'll want to keep your styling pretty casual. Stick to light summer dresses, cropped pants, shorts, overalls, long skirts and floppy sun hats.

Light Pink Heels

Evening Heels

Galas, events, weddings, nights on the town — there's always an occasion for a killer pair of designer evening shoes. Formal footwear brings with it an air of confidence, elegance and grace, allowing you to shine. Whether you have a shoe obsession or just need a go-to pair of pumps to wear when a special occasion pops up, it's smart to know just how to style these shoes so you look your absolute best.

As the name implies, evening footwear is meant to be worn with evening attire. Opt for a gown, dress or formal pantsuit with a feminine edge. If you want your shoes to elongate your legs, opt for a pair of nude or skin-tone pumps. If you want your shoes to pop, make sure your outfit is more on the neutral side.

Outdoor Flats


A good pair of fashion flats or designer mules can take you from day to night in a cinch. Plus, your feet won't be aching come the day's end. From brightly colored loafers and bold-printed slingbacks to demure ballet slippers and rocker-chic mules, flats are both fashionable and comfortable (our favorite combination).

Whatever style of flat you opt for, you can typically pair them with anything as they're an extremely versatile shoe. Ankle-length trousers, jeans, shorts, skirts or dresses; you can pretty much wear it all when it comes to flats. Just keep in mind, if an outfit tends to cut you off, or make you look shorter than you are, you usually will want to stay away from flats and instead opt for a shoe with a bit of a heel.

Pink Pumps

Pumps & Slingbacks

We love a good casual pair of pumps or slingbacks. It's an easy way to add a touch of chicness (and height) to any outfit. Pumps and slingbacks come in a wide variety of styles, from neutral work shoes to high-fashion statement-makers.

For a daytime look, we recommend pairing these shoes with wide-leg trousers or jeans and a bold-printed blouse or fitted turtleneck. Wearing these babies for date night? Go with a fun pencil skirt, a gorgeous cocktail dress or a flowy jumpsuit.

Yellow Gold Strapped  Heels

Strappy Heels

Designer strappy sandals are a great alternative to pumps and offer a bit more support thanks to the straps. Whether you choose low heels, chunky heels or stiletto heels, strappy sandals have an innate ability to elongate the leg (while showing off that pedicure you just got!).

Not usually a work-appropriate shoe, we suggest wearing these strappy sandals for a formal event or a weekend outing — it's all in how you style them. For formal affairs, stick to dresses, gowns, skirts or fancy jumpsuits. Taking these stunners out during the day? We love pairing strappy heels with some unexpected straight-leg or boyfriend jeans and a graphic tee to bring a more casual feel to your ensemble. Try pairing a unique pair of hose with your shoes for a high-fashion look.

White Sneakers with Accents


Think sneakers can't be fashionable? Clearly, you haven't been paying attention. Activewear is and has been a huge trend in fashion for the last few years, and it's bigger than ever before. Top designers around the world are getting in on the sneaker game and we couldn't be more thrilled to see their take on tennis shoes. But how do you fashionably style these designer sneakers?

We love pairing sneakers with leggings and an oversized sweatshirt or flannel for an easy-breezy weekend look. Or, try pairing your kicks with some cuffed boyfriend or rigid jeans and a lace tank and jacket for an ultra-cool girl vibe. You can even toss on some sneakers with a silk and lace sheath dress for that just-rolled-out-of-bed 90s look. Sneakers definitely aren't just for the gym anymore.

White Daytime Wedges


Wedges are the perfect daytime casual shoe that gives you the height you want with the support you need. The heel of a wedge shoe runs under the foot, from the back of the shoe to the middle or front, making them sometimes much easier to walk in than heels. They range in height from almost flat to extremely high. While designer wedges aren't as sophisticated as formal heels, you can still wear them to daytime events like an outdoor wedding or picnic.

Wedges typically look best when paired with a maxi dress, summer dress, midi skirt or wide trousers. The style adds definition and shape to the ankle, which will naturally make them appear thinner. But the typical woven or foam heel tends to skew more on the casual side, so keep this footwear to daytime soirees or outings.

Learn How to Style Shoes and Shop Tootsies for the Perfect Pair

At Tootsies, we have a drool-worthy, must-have selection of women's shoes to choose from. Whatever style you're looking for, we have it and more. Browse online by style, size, designer, color and price to find just the pair (or pairs) for you. If you're in Houston, Dallas or Atlanta, check out our incredible selection in person. And if you have a question or need additional product information, reach out to our customer service department for help.

Contact Us Today