How to Wear Sneakers and Look Fashionable, Not Frumpy
Finding the right sneaker — and styling it to look fashionable, not frumpy — can be daunting. Southern stylist Cynthia Kelley offers up three essential sneaker styles, plus a set of styling rules that should never be broken.
What is the number one item clients want in their closets? The right fashion sneakers — and an arsenal of go-to looks for wearing them, without looking frumpy.
Finding the right sneaker can be overwhelming with all of the current sneaker options. Shelves are stocked with high-tops, mid-tops, colorful, neutral, sporty, canvas, suede, and platform sneakers, just to name a few. They span from super comfortable to super luxe.
So, how do you choose which ones to purchase? And how do you style your sneakers with your current wardrobe?
PinCurrent sneaker trends vary widely in rise, color, and price range — but sneakers can be styled for any age range or personal taste. You’ve just got to find your perfect fit! Image: Cynthia Kelley
Sneakers are a footwear trend that grossed $79 billion in 2020, and they’re my very favorite item in the continued athleisure trend. They can be worn as daywear, in the workplace, and even for smart-casual affairs. Sneakers are seen on catwalks, as sportswear, and in daily street style. They can make any outfit look fashionable and put together (if you have the right sneaker) and allow you to feel confident yet comfortable walking out the door.
First, I’ll break down sneakers into three must-have styles — the statement sneaker, the staple sneaker, and the sporty sneaker — and share ways to dress to suit each style. Then, I’ll share my three essential sneaker-styling rules to live by. This guide will make it easier for you to find the right pair to work with your lifestyle needs and what’s already in your closet.
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The Statement Sneaker
Personality Plus. This is the outfit ‘highlight’ that allows you to totally express yourself. Before we talk about how to style these, here are some examples of on-trend Statement Sneakers, often characterized by bright colors and patterns.
PinHigh-top Nikes and platform Adidas | Image: Cynthia KelleyPinGolden Goose, available locally at H. Audrey | Image: H. AudreyPinSophia Webster at Neiman Marcus | Image: Neiman MarcusPinHi-rise skater P448, styles available at Gus Mayer | Image: P448
How to Style the Statement Sneaker
The statement sneaker speaks for itself and allows you to express your individuality or current mood in a fun way. This category includes more mid-top (about even with your ankle bone) and high-top (about an inch over the top of your ankle bone) options than the other two categories we’ll address later, but you can also find low-top statement sneakers.
Style this sneaker with mainly solid pieces and simple looks. Remember, the shoe is the conversation piece. They are a casual look and work especially well with white, black, or blue denim, along with leggings and joggers.
Pick a shoe that draws your eye — one that is different or original and really makes you smile when you look down.
PinLow- and high-top sneakers with straight, cropped denim. Left: P448; right: Converse x Keith Haring design | Images: ShopbopPinZebra P448’s — perfect for a solid dress! | Image: Cynthia Kelley
This sneaker is the daily go-to and will get the most wear of any shoe in your wardrobe. It is neutral and works with very casual and elevated casual looks and can even work professionally with the addition of a blazer. And of course, the staple sneaker is perfect for the work-from-home wardrobe.
Based on my experience with clients, I think the most comfortable sneaker seems to be the P448 brand as well as Golden Goose, which has removable arch support. Your ‘new’ good-old Keds are still a very cute, budget-friendly option. I also really like the sustainable Vejas, though they sometimes take a few wears to break in. But, as with any shoe, it takes some trying on to find your perfect ‘wear with anything’ necessity.
PinVeja Velcro sneakers | Image: Neiman MarcusPinKeds | Image: ShopbopPinGolden Goose All-Star, also available locally at H. Audrey | Image: RevolvePinNeutral-toned Nera sneaker | Image: ABLEPinYou can still enjoy patterns on your staple sneaker — just stick to a neutral color palette. Image: P448
How to Style the Staple Sneaker
The staple sneaker is easy to style. It is neutral, so it really goes with any outfit — colors, solids, or patterns. It is easy to throw on with jeans from straight to flare, trousers, or wide-legged pants. It works with short and midi dresses. The sneakers really pull the outfit together with a more casual, chic look. And as I mentioned, being comfortable in really cute shoes is always a plus.
PinA long, flowy patterned dress pairs well with a white staple sneaker. Image: Free PeoplePinSkinny flare cropped jeans with a low-rise white staple sneaker | Image: Bergdorf GoodmanPinWhite sneakers paired with distressed boyfriend jeans | Image: ShopbopPinYou can absolutely wear sneakers with dresses! Image: Cinq à SeptRELATED: 3 Summer 2021 Fashion Trends That Are Easy To Wear
The Sporty Sneaker
This sneaker is very comfortable and athletic looking, but still fashionable. The sporty sneaker is the more everyday version that evolved from the running shoe. It’s a cool, comfortable look that appeals to both the young and old. It comes in retro and vintage looks along with on-trend colors and details.
This sneaker is for everyday wear, but a few can also double for light/moderate exercise. It is perfect for traveling, especially for trips that require lots of walking.
PinVeja sneaker | Image: Neiman MarcusPinRag & Bone recycled sneaker | Image: Rag & BonePinOn Cloud sneakers are ideal for walking all day! Find them at Oak Hall. Image: OnPinLuxe Alexander Birman sporty sneaker | Image: Saks Fifth Avenue
How to Style the Sporty Sneaker
The Sporty Sneaker looks great styled with athleisure and fitness wear like leggings, athletic shorts, and joggers. But, it is also very on-trend this season to pair sporty sneakers with day wear and even business casual (see the blazer photo below). Sporty sneakers are generally a bit more chunky, so an ankle-length pant looks best. Pair them with straight jeans or leather joggers — and definitely a fall shacket, when the temperatures start to drop. They’re back again!
PinLeft: Casual Alice & Olivia leather joggers; right: Paige denim joggers | Images: Alice & Olivia and PaigePinA sleek sporty sneaker paired with cropped denim | Image: Rag & BonePinGirl Boss in Veja sporty sneakers, paired with office attire | Image: Cinq à Sept
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3 Sneaker-Styling Rules to Live By
Always show some skin in between your shoe and your jeans, joggers, or dress. Jeans should hit about an inch or two above our ankle bone.
Don’t wear socks that show. Wear no socks at all or no-show socks. *The exception: The higher sock that is on-trend if you are a little bit younger.
Buy the ones you love (not like) and you will always find a way to wear them.
I hope this helps you navigate the huge sneaker market. If you find the perfect fit, it will be your favorite shoe in your closet. Use the styling tips that work with your lifestyle, and you’ll be wearing your sneakers for many occasions this fall — even the ones you might not expect!
Got a burning question for an upcoming Style File? Email us at [email protected].PinThanks to my shoe modeling crew. Left to right: Celia Turner (P448), Betsy Caldwell (Golden Goose), Eliza Hawkins (ABLE), Evie McKenzie (Retro New Balance), and thanks to @ShopAliceNashville for having us for the shoe shoot! Image: Cynthia Kelley
Known for her fresh and modern styles, Cynthia Kelley is a Nashville-based personal stylist who provides custom expert advice to clients throughout the Southeast.
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