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5 shoes every woman should own, according to a stylist

Beef up your collection with these five essential styles.
Images of three different Women wearing fashionable shoes, a bootie, and blue shoe with a heel
TODAY Illustration / Kohl's / Aldo / Jeremy Moeller / Contributor / Getty Images / Michael Campanella / Contributor / Getty Images / Edward Berthelot / Contributor / Getty Images
/ Source: TODAY

Shoe trends come and go, but there are a few timeless styles that are always en vogue. If you're looking to build a shoe wardrobe that will last for years on end, there are five styles you simply can't leave out.

Shop TODAY consulted fashion expert and stylist Cindy Conroy to get some insight on how to rock them, and we're also rounding up a few shoppable styles we think you'll love.

Ballet flats

There is perhaps no other shoe that's as versatile and approachable as the ballet flat. It's a timeless style that will never go out of fashion and it's perfectly practical for busy gals who are constantly on the move but don't want to sacrifice fashion for function.

"With designers crafting ballet flats in an array of magical colors, patterns and shapes, they are the new classic that you can wear with virtually anything, all the way from jeans and a tee to a cocktail dress," Conroy explained.

Universal Thread Everly Round Toe Ballet Flats

You simply can't go wrong with a classic black flat. We could picture ourselves wearing this chic pair from Target with everything from jeans and a chambray blouse to a flirty dress and tights. The versatile shoe has a memory foam lining and a comfy round toe, and the price is certainly right.

Vionic Robyn Ballet Flat

If ballet flats are a mainstay in your footwear collection, it's worth picking up a pair that provides plenty of support — trust us, your tootsies will thank you. Vionic's Robyn flat has a contoured footbed that hugs feet without stifling them, and it even earned the American Podiatric Medical Association's seal of acceptance for its comfy design. It's also insanely stylish with its laser-cut detailing and the metallic color goes with everything.


Boots are great and all, but sometimes you just want the look and feel of the classic style without committing to a taller shoe. That's where booties come in handy! Ankle booties are easy to slip in and out of and they're one of the few shoes you can actually get away with wearing all year long.

"Sure, it’s cute as a button, but it also ticks all of the boxes when it comes to functionality. You can wear them with a midi skirt, cropped pant, an above-the-knee dress, wide-leg trousers, maxi dress, culottes or mini skirt. The list goes on and on," Conroy said.

SO Averyy Ankle Booties

At only $30, these faux suede booties are a true steal and have a comfy footbed and memory foam midsole to help keep your feet happy for hours on end. The 1.5-inch heel gives you just enough height but is still easy to walk in, making it a practical option. Plus, the shoe comes in basic black and a range of other neutral colors to fit every personality!

Franco Sarto Horrace Bootie

Leather booties are always a worthwhile investment because they'll last you for years on end, even when you wear them to death. We're currently crushing on this textured pair from Franco Sarto since it has a slight block heel that can dress up an otherwise casual ensemble or dress down a more fancy frock.

Multipurpose heels for summer and winter

Even if you don't rock heels in your daily life, it's great to have a few pairs in your shoe rotation for times when you'd like to step up your game a bit or need a little lift because you're wearing a maxi dress.

"Whether it’s summer or winter, every gal needs a good multipurpose heel to take her from meetings to dinner dates to weekend getaways," Conroy told us.

Kelly & Katie Caital Sandal

Floral and tie-dye, oh my! Summer is all about having fun with color, and we can't get enough of these bright heeled sandals from Kelly & Katie. Some of our other favorite features include the padded footbed, faux leather lining and adjustable ankle strap.

Aldo Velalith Block Heel

Beautiful in blue! We can't stop smiling whenever we look at these bright blue slide sandals. The slip-on style has a fashion-forward square toe and sturdy block heel, plus it's padded for optimal comfort.

A New Day Francesca Heels

You don't have to spend a lot to get a polished pair of pumps, and it's smart to keep one stashed away for job interviews and other important professional moments. This sleek, budget-friendly pair from Target features a comfy memory foam insole and a walkable 3.25-inch heel. Not bad for $30!

Sofft Lindon Leather Block Heel Pumps

When the weather is frightful, we opt for a classic dark block heel to help hide any dirt we might pick up as we're going about our day. Sofft puts a premium on comfort with this pump thanks to its contoured foam footbed and soft microfiber lining, and we can guarantee that it'll never go out of style.

Waterproof boots

Even if you live in a warmer climate, rain and snow boots are always nice to have on hand for sudden downpours or when you're traveling to an area with more precipitation. If you live in a colder climate, you pretty much need a basic pair of rain boots and a more solid pair of winter boots to survive.

"A quality pair will have you sitting pretty while enjoying this wardrobe classic for years to come. Because let’s be honest, when it pours, there’s nothing quite like a waterproof boot to keep your feet completely dry. Nothing else measures up," Conroy told us.

Chooka Tall Memory Foam Rain Boot

You don't really need to splurge on rain boots since they're not an everyday style, but you should keep your eye out for a few features like a solid sole that offers plenty of traction and a comfy memory foam insole. Luckily, this pair checks off all those boxes!

Sorel Whitney II Tall Lace Boot

If you live in a colder climate, a traditional rain boot simply won't cut it in the frigid winter months. This tall waterproof boot from Sorel takes on rain, snow and sleet like a boss while also keeping your feet nice and toasty with a microfleece lining. Totally worth the splurge, if you ask us!

Supportive sneakers

Whether you hate the gym or love to work up a sweat, a supportive pair of sneakers is a wardrobe essential you should always have on hand. It's also ideal for traveling!

"Both chic and practical, a supportive sneaker will cushion your feet from sunrise to sunset. Pair them with a floral dress, preppy pant and top combo or trouser shorts and a blouse for a stylish and comfy ensemble," Conroy said.

Dr. Scholl's Turn Around Sneaker

Designed for everyday use, these sporty sneakers feature faux leather and mesh detailing and a cushioned foam footbed. The style comes in several colors, but we can't take our eyes off the navy option that has pink and green color blocking.

Vasque Satoru Trail LT Low Hiking Shoes

Serious about fitness? If your sneakers quickly rack up plenty of mileage, it's worth splurging on a more heavy duty pair like these hiking shoes from Vasque. The lightweight style features breathable mesh detailing and a moisture-wicking lining that keeps your feet dry. Of course, it also provides plenty of traction and impeccable cushioning.

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