How to Wear Sneakers and Look Fashionable, Not Frumpy (2024)

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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?

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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.

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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.

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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.

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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.

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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.

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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!

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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 [emailprotected].

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About the AuthorCynthia 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.

How to Wear Sneakers and Look Fashionable, Not Frumpy (2024)

FAQs

How to Wear Sneakers and Look Fashionable, Not Frumpy? ›

The combination of a sneaker with baggy jeans or oversized pants might not appear overly unique but is definitely trendy for today's style. This look is extremely comfortable to carry, versatile, and makes women look classy with minimal effort.

How do I look chic with sneakers? ›

The combination of a sneaker with baggy jeans or oversized pants might not appear overly unique but is definitely trendy for today's style. This look is extremely comfortable to carry, versatile, and makes women look classy with minimal effort.

How to wear sneakers after 50? ›

Wear them with cropped jeans, wear them with a dress pant as long as they don't drag. Sneakers and dress pants that are too long will look frumpy. Wear them with skirts and dresses as long as they coordinate. Wearing a neutral sneaker like THESE will be easier for you, but some like THESE will have more personality.

Can a 60 year old woman wear sneakers? ›

Engineering and science have made huge strides in the performance aspect, and an entire culture with many sub-variants supports sneakers-as-fashion. There's no age limit to any of those reasons to wear them, and in some cases, it makes them even more perfect for senior women.

How do I look feminine in sneakers? ›

  1. Wear a Shirt Dress. Wear a shirt dress that blends perfectly with your pair to look chic with sneakers. ...
  2. Pair with a Denim Jacket. ...
  3. Sport a Loose T-shirt with High-Waist Shorts. ...
  4. Opt for Oversized Pants. ...
  5. Go for the Classic Sweatpants. ...
  6. Rock That Miniskirt. ...
  7. Use the Right Accessories.

Can sneakers look classy? ›

Pair with Dresses or Skirts: Contrasting sneakers with dresses or skirts can create a stylish and feminine look. This combination adds a touch of casual charm to your out.

What color sneakers go with every outfit? ›

Classic White Sneakers: These timeless sneakers are the perfect foundation for any outfit and will never go out of style and are perfect for any casual or fancy look. They can be paired with jeans, skirts, dresses, and more for a clean and classic look.

Should seniors wear sneakers? ›

The risk of falling while wearing loafers or laceup oxfords was 30% - 50% higher than while wearing sneakers. The low heel, strong-grip bottom and the firm but flexible support offered by sneakers make them the best choice of footwear for seniors.

How not to dress frumpy after 60? ›

Don't Wear Baggy Clothes

It's an easy option when we're older, have a long to-do list, and want to opt for comfort first. But baggy clothes are extremely unflattering: they cover up your shape and send you directly into the frumpy zone and make you look years older than you actually are.

How can a woman over 60 look classy? ›

5 tips for dressing in your 60s
  1. Big patterns, bold colors. First, let's toss the old “rules” and expectations for how a 60+ woman should dress. ...
  2. Breathable fabrics? A breath of fresh air. ...
  3. Balance timeless with trends. Trends are for everybody. ...
  4. Layer mixed textures. ...
  5. Accessorize with dressed-up details.

What should a 70 year old woman wear? ›

In your 70s, it's a good rule of thumb to avoid looking too prim, too girly, or preppy. However, it's the perfect time to experiment with arty styles like tailored sweater coats, wide-leg pants, unusual clutches, and colorful patterns.

Can 60 year old woman wear leggings? ›

Comfortable, practical, and easy to wear wherever you go, leggings can be dressed up or down, depending on the occasion. In the past, leggings for older women were considered an almost scandalous fashion choice, but in recent years, they have evolved into versatile wardrobe staples suitable for women of all ages.

What kind of dress can you wear with sneakers? ›

Wear it with a baby doll or flowy dress for that nostalgic summer dress with sneaker look. For a sportier look, match a pair of white leather sneakers with a dress. Achieve that perfect daytime look with a simple knit dress and a pair of classic Adidas Grand Court sneakers.

Are high top sneakers in style 2024? ›

Level Up. "The chunky sneaker trend continues to stomp its mark on 2024, but with a more refined, sculptural twist," says Marie. "High tops are getting more attention with innovative materials and patterns, giving a nod to vintage basketball aesthetics."

How do you wear sneakers with nice clothes? ›

Colorful Sneakers

Create a dopamine-inducing color-blocked 'fit by wearing sneakers and accessories in the same vibrant shade and a dress in a contrasting color. Alternatively, you can go for a monochromatic moment by picking two-tone sneakers that match your dress and outerwear.

What type of dress can be worn with sneakers? ›

Maxi or midi length dresses work best with these types of sneakers and when it comes to white sneakers – Don't be afraid of a colorful or printed dress! Perfect way to balance out the look.

How can I look super chic? ›

How to Be Stylish
  1. Wear clothes that flatter your body type.
  2. Stick to classic cuts.
  3. Choose muted, neutral colors and bold accents.
  4. Avoid busy prints and textures.
  5. Buy strategically.
  6. Create an interchangeable collection.
  7. Take care of your clothes.
  8. Get items tailored.

Can I wear a fancy dress with sneakers? ›

If you're someone who wore sneakers to prom and can always be found in coolest gym shoes, wearing a dress with sneakers is likely your vibe. It's an elite combo, after all. Just because you're wearing a fancier outfit doesn't mean you have to wear heels, so why not swap the stilettos for cushy kicks?

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