How to Wear Sneakers and Look Fashionable, Not Frumpy

What is the number one item clients want in their closets? The right sneaker — 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?

3 Essential Sneaker Styles

Current 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.

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.

Nike and Adidas platform sneakers

High-top Nikes and platform Adidas | Image: Cynthia Kelley

Golden Goose shoes at H. Audrey

Golden Goose, available locally at H. Audrey | Image: H. Audrey

Multi-color Sophia Webster sneaker

Sophia Webster at Neiman Marcus | Image: Neiman Marcus

Pair of hi-rise skater P448 shoes

Hi-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.

P448 and Converse x Keith Haring sneakers

Low- and high-top sneakers with straight, cropped denim. Left: P448; right: Converse x Keith Haring design | Images: Shopbop

Zebra Print Statement Sneaker with Pink Dress

Zebra P448’s — perfect for a solid dress! | Image: Cynthia Kelley

RELATED: Cropped Flares: The Best Fit for Your Body Type + How to Style Them

The Staple Sneaker

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.

Veja Velcro sneakers | Image: Neiman Marcus

Veja Velcro sneakers | Image: Neiman Marcus

Keds at Shopbop | Image: Shopbop

Keds | Image: Shopbop

Golden Goose All-Star shoe available at H. Audrey

Golden Goose All-Star, also available locally at H. Audrey | Image: Revolve

White sneakers from ABLE

Neutral-toned Nera sneaker | Image: ABLE

Pair of P448 platform shoes

You 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.

Plaid dress from Free People

A long, flowy patterned dress pairs well with a white staple sneaker. Image: Free People

Skinny flare cropped jeans from Bergdorf Goodman

Skinny flare cropped jeans with a low-rise white staple sneaker | Image: Bergdorf Goodman

Distressed boyfriend jeans from Shopbop

White sneakers paired with distressed boyfriend jeans | Image: Shopbop

Veja sneakers paired with a cute fall dress

You can absolutely wear sneakers with dresses! Image: Cinq à Sept

RELATED: 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.

Veja sneaker

Veja sneaker | Image: Neiman Marcus

Pink Rag & Bone recycled sneaker

Rag & Bone recycled sneaker | Image: Rag & Bone

On Cloud Sneakers in Black and Maroon

On Cloud sneakers are ideal for walking all day! Find them at Oak Hall. Image: On

Luxe Alexander Birman sporty sneaker

Luxe 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!

Alice & Olivia + Paige joggers

Left: Casual Alice & Olivia leather joggers; right: Paige denim joggers | Images: Alice & Olivia and Paige

Rag & Bone jeans

A sleek sporty sneaker paired with cropped denim | Image: Rag & Bone

Woman posing in Veja sporty sneakers

Girl Boss in Veja sporty sneakers, paired with office attire | Image: Cinq à Sept

3 Sneaker-Styling Rules to Live By

  1. 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.
  2. 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.
  3. 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].

Thanks 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


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