How to Wear Sneakers Fashionably
When you’re looking for comfortable shoes, it’s easy to gravitate toward sneakers. And sneakers, in recent years, have grown beyond comfort. They are now fashion essentials, and both men and women should have stylish sneakers in rotation.
But most people also wonder how to wear sneakers fashionably. Sneakers can feel like a risk with some outfits. What’s OK? And what’s not?
This post shares tips on how both men and women can wear sneakers fashionably, as well as 10 pairs of sneakers that you should consider adding to your wardrobe. Sneakers are “in,” so read on and find out how you can take advantage of this trend.
Tips for Men: How to Wear Sneakers Fashionably
This is Shawn, and I wanted to share just a few tips on how to wear sneakers fashionably before we get into the actual products. Here are 5 things to keep in mind as you’re considering sneakers and how to wear them:
- Don’t Go Too Casual: You always want to wear appropriate footwear. You can find upscale, leather options that are perfectly suitable for suits and business wear. And you can find casual options that are best with shorts and swim trunks. Don’t try to mix the two. Wear appropriate sneakers for appropriate occasions.
- Stick to Low Tops: When wearing sneakers to the office, lean toward low tops. Low tops mimic the silhouette of dress shoes, which makes them a nice fit when you want comfortable shoes at work. That said, I do recommend one pair of high tops below. Check it out to see why.
- Skip the Socks: Socks complicate the sneaker look. If you’re going to wear high tops, wear them without socks at all times — even when you’re wearing nice leather sneakers with a suit. Hailey notes this below, but showing off the ankle’s definition ever so slightly is important, and it’s difficult to do that when you’re wearing socks.
- Keep Them Clean: Keep your sneakers clean or get rid of them. When you’re looking to create ideal sneaker looks, dirty footwear need not apply. Dirty sneakers will ruin your overall outfit and make you look like a slob.
- Develop a Rotation: OK, so you need to keep your sneakers clean and you’re wearing them without socks. Two things you need to do: First, use foot spray or powder. And, second, develop a rotation. Having several pairs of sneakers will help each pair stay fresh.
Tips for Women: How to Wear Sneakers Fashionably
And this is Hailey — hi! I love wearing sneakers, and I want you to feel confident when you wear yours. Here’s a look at 5 things to keep in mind as your styling outfits of all kinds with sneakers:
- All About Ankles: The ideal sneaker look highlights the definition of your ankles. You can accomplish this by cuffing your jeans (or wearing jean with higher hems) and wearing your sneakers without socks. When the hem or cuff of your jeans falls just above your ankle’s most defined portion, the sneaker look reaches nirvana.
- Balance Your Colors: I love using colorful sneakers to add pop to neutral outfits, and I love to balance colorful outfits with neutral sneakers. Don’t go too far on the overall neutral or colorful ends of the spectrum. Use your sneaks to create balance.
- Leverage for Print Mixing: Mixing prints is tough to do. Luckily, we have white sneakers to help create a solid foundation for mixed prints. If you’re going to try mixing prints, make sure you have the right sneakers.
- Add Edge to Traditional Looks: I’ve included some edgy sneaker options below, but know that sneakers always bring a little edge to outfits. Find shoes that you typically wear that you replace with sneakers whenever you need a little edge. I mention this below, but consider using white sneakers as a heel replacement. You may just find that doing so opens up all sorts of new outfit opportunities.
- Create On-The-Go Ensembles: Accessorize sneakers as if you’re on the go. Wear with a small cross body bag that says: “I’m going to be on my feet all day, and this is the perfect outfit for it.” Hats, sunglasses, simple dresses. Anything that reinforces the ideas that you’re blowing and going in your sneakers is a good way to stylize.
Best Sneakers for Men
This is Shawn, here to tell you about your best sneaker options. Sneakers are everywhere these days. But it can be hard sometimes to tell what’s really fashionable and what you should take a pass on. We’ve shared a lot about how to wear sneakers, but what sneakers should you buy in the first place?
There’s one one-size-fits-all answer to that question, so I’ve shared a bunch of different options below. The right option for you will be based on your existing wardrobe, where you’re going to wear your sneakers, your budget and more.
I’ve tried to include something for everyone, so take a look at the options below, and find your perfect sneaker.
1. Lanvin Leather Fashion Sneakers — Best Overall
These are sneakers that demand shoetrees. Lanvin is one of the oldest fashion houses in the world, and the Lanvin Leather Fashion Sneaker is one of the most beautiful, stylish and comfortable sneakers you will ever encounter.
The structure of these sneakers is akin to Chuck Taylors. But Lanvin’s Leather Sneakers are made of leather (obviously), and they offer a uniquely distinguished toecap that ramps up the intrigue.
What would you wear with the Lanvin Leather Fashion Sneaker? These shoes can be worn with a suit — that’s how high they fall on the fashion spectrum. But they’re versatile, too. I wouldn’t wear them with swim trunks to the beach, but they’re right at home in a pair of nice dark denim jeans and a tailored T-shirt.
You’ll hear me say this a lot in this post, but: Feel free to wear these sneakers without socks. In fact, I’d recommend wearing them without socks. But, make sure to take care of them, too. That means using foot spray or powder, and then inserting a desiccant that’s going to keep them nice and moisture free (and smelling good) between wears.
Is the Lanvin Leather Fashion Sneaker right for you?
2. Adidas Iniki Runner — Best Retro
But Adidas has changed that with its Iniki Runner. This shoe blends a style that’s right at home in the 70s with the most advanced running technology you’ll find in a casual shoe. The result is perhaps one of the most advanced retro sneakers that a man can get.
You’ll find tons of different color options, so feel free to add a pop to bland outfits by getting a red pair or a green pair. You can also add an interesting and attractive hue by grabbing a pair of the baby blues pictured here.
What would you wear with the Adidas Iniki Runner? I’d recommend jeans that show off just a little bit of ankle, or wear them with casual shorts during the hotter months. You’ll want to make sure to pair the colors appropriately if you go with something other than black or white. Don’t, for example, match your hat color or T-shirt color to your shoes — it’s just too much.
The Iniki Runner is so cool, so comfortable and much more affordable than some other retro options. Get a pair for your rotation.
Is the Adidas Iniki Runner right for you?
3. Converse All-Star Modern — Best High Top
The Chuck Taylor All-Star is a shoe that’s seemingly gone unchanged for 100 years. You can still buy a shoe that’s basically what it was when it first appeared on the market in the early 20th century.
But the All-Star Modern by Converse is a little different. This is an advanced take on the Chuck Taylor All-Star, and that allows you to get a leather high-top that works much like a boot.
What would you wear with the Converse All-Star Modern? This is the perfect fall comfort boot that goes to work with dark jeans or even tailored chinos. While it’s a high-top and it doesn’t necessarily match a dress shoe silhouette, it does offer a look that’s akin to higher-end boots — without the discomfort.
Kudos to Converse for the way it tweaked the Chuck Taylor All-Star without blaspheming. This is a modernization project that could have easily gone awry. But, instead, they did a nice job presenting a modern take on the original.
And you can still get the original, of course, so don’t pour one out just yet. In fact, we recommend the original in the last section of this post.
Is the Converse All-Star Modern right for you?
4. Tom’s Paseo Casual Lace Up Shoes — Best Workplace Option
This sneaker is super versatile. It comes in a number of materials and colors that make a great fit for the workplace. You can find brown, black and other neutral options in suede, leather and canvas, each of which will look great as part of a business casual wardrobe.
But many of the Tom’s Paseo Casual Lace Up option can also go to the beach or to the pool. They are lightweight, breathable and incredibly comfortable, which means you can walk the streets all day, or walk the halls of your office — all while looking appropriate and staying comfortable.
What would you wear with the Tom’s Paseo Casual Lace Up? Just about anything. Seriously. I’ve already mentioned wearing with jeans or chinos at the office, but you can also wear with shorts and even a bathing suit. Some outfits may be better options depending on what color and material of Paseo you choose. But this is a shoe that gives you a lot of freedom.
Tom’s hasn’t always been in the lace-up business. But the Paseo is an excellent option that does lace-up correctly, and that delivers us men an attractive sneaker that can truly go anywhere in style.
Is the Tom’s Paseo Casual Lace Up Shoe right for you?
5. Adidas Ultra Boost — Best Active
The Adidas Ultra Boost is really more than a sneaker. This is a shoe that truly represents that latest and greatest in Adidas innovation, and you could use it in your rotation (probably for tempo runs and speed work) if you were training for a marathon.
But we won’t get into the nitty-gritty on tech and specs because we’re talking about sneakers. And the Adidas Ultra Boost can also make a fashion statement. I love the off-white appearance of the model in the picture. These shoes are perfect for a Saturday or Sunday when you’re going to be moderately active — and a day when you want to look good and enjoy the comforts of advanced running design.
What would you wear with the Ultra Boost? Keep it pretty casual. There’s nothing wrong with wearing jeans or nicer shorts with this shoe, but I prefer pairing an active pair of kicks with active wear.
No matter what you wear with them, you’ll notice how the Ultra Boost responds to your foot, and you won’t have to wonder for long why they’re so highly regarded as true running shoes.
Is the Adidas Ultra Boost right for you?
Best Sneakers for Women
This is Hailey, here to guide you through the very best sneakers for women. I’ve tried to include something for everyone — options on the dressier and high ends, as well as active and inexpensive options. You should be able to find something that works for your feet and your style from among these options.
And one final note before we jump in: Don’t be thrown off by the colors you see in the photos. These sneakers, by and large, are available in a wide range of different colors. So look for a style you love, and then find the colors to match.
Sneakers can add so much to a wardrobe or outfit, so I’m thrilled to share some of my favorites. Happy hunting!
1. Valentino Garavani Women’s Open Leather Sneakers — Best Overall
A woman’s sneaker rarely straddles the space between incredible comfort and high-end style, but these Open Leather Sneakers from Valentino Garavani turn the trick. Perfect to dress up or dress down, these Open Leather Sneakers feature a prominent and thick sole, as well as a white body with a thick stripe that stretches across the arch.
I love this stripe in gold (as pictured), but you can also find it in silver, burgundy, navy and other colors. It helps create the perfect differentiation from on-trend white sneakers — you get to stand out from the crowd a little.
What would you wear with the Valentino Garavani Women’s Open Leather Sneakers? I love these for almost any outfit. Don’t be afraid to wear a mini skirt or pencil skirt with them. Also, the fit perfectly with the safest sneakers look — cuffed jeans that show off your ankles.
But you can also wear these with casual or active wear. I’m telling you: The Open Leather Sneakers are equal parts tennis shoe and high-end footwear. It’s a combination that’s rare to find.
When you get these Open Leather Sneakers, you’ll find all sorts of fun outfit combinations to play with. And, when you stick to gold or silver, these shoes offer just enough pop to be interesting and just enough neutrality to pair easily with colors.
Is the Valentino Garavani Women’s Open Leather Sneaker right for you?
2. New Balance Women’s 620 Sneaker — Best Retro
This is retro perfection in a sneaker. I fell in love with the New Balance Women’s 620 Sneaker long ago, and I love keeping a pair in rotation. New Balance is a fixture in the running world, but they’ve become known also for their casual lines of footwear that feature throwback styles and modern comfort.
The 620 Sneaker is a great choice for a lot of reasons. First, it looks great, striking that retro appearance casually and without trying too hard. It’s incredibly comfortable and affordable, and I’ve found that the right pair is versatile, too.
What would you wear with the New Balance Women’s 620 Sneaker? This shoe is perfect for skinny jeans cuffed at the ankle. Try pairing with a tailored blazer for a smart office look — add a simple top for colorful 620s, or go with a more colorful top if you wear a neutral pair of sneakers.
But you can also pair these shoes with tights for an active morning, a simple dress with a scarf, a leather mini skirt, a tailored pencil skirt, boyfriend jeans and more. A lot of this just depends on your personal style, but have fun with these shoes — that’s what they’re meant for.
Is the New Balance Women’s 620 Sneaker right for you?
3. Adidas Women’s Superstar — Best Classic White
The Adidas Women’s Superstar is part of a family of classic kicks that have found their way onto the feet of tennis players, rappers, as well as fashion-forward women who want to add some sportiness to their style.
You can find the Superstar in tons of different colors, which gives you power and flexibility as you search for the perfect white sneaker. What you’ll find, no matter the color, is that these sneakers pair effortlessly and that they’re always comfortable. No wonder so many women are gravitating toward these classic Adidas for outfits all along the dressiness spectrum.
What would you wear with the Adidas Women’s Superstar? Think of the Superstar as a replacement for heels when you want a look that’s just a little chicer and a little more street. Add them instead of heels when wearing simple dresses, short- to mid-length skirts, jeans, trousers, shorts, etc. Any outfit becomes just a little edgier with a pair of Superstars.
If you want to lose the trademark three-striped appearance you get with most Adidas, try the Stan Smith model. These white sneakers ditch the three stripes for a more solid white sneaker look, and you can find all sorts of options that include fun accent colors on the heel and tongue.
Whether you choose the Adidas Women’s Superstar or another model, make sure to add some go-to white sneaks to your shoe collection. They revolutionize everything with edge and comfort.
Is the Adidas Women’s Superstar right for you?
4. Kenneth Cole New York Women’s Kam Fashion Sneaker — Best Workplace
This leather sneaker is my favorite answer to the all-white shoe trend. I love having white sneakers in my rotation, but I also love having the Kenneth Cole New York Women’s Kam Fashion Sneaker, which is available in all sorts of darker colors, too.
Check out the black leather, navy (pictured) and nude options. These colors are easy to match with other items in your closet, and you’ll find that you love the distraction-free simplicity of this shoe. They look great, they are comfortable, and they draw all of the right kinds of attention.
What would you wear with the Kenneth Cole New York Women’s Kam Fashion Sneaker? Much like you can wear the Adidas Women’s Superstar with almost anything, the same goes for the Kam Fashion Sneaker. Try it out with jeans of any color or trousers in the workplace.
You can also find all-white options when looking at the Kam Fashion Sneaker. I prefer the Kam for its darker alternatives, but you may find that you like its looks and feel as your go-to white sneak.
Is the Kenneth Cole New York Women’s Kam Fashion Sneaker right for you?
5. Nike Women’s Free Rn Flyknit Running Shoe — Best Active
This is a real running shoe. You can find plenty of throwback, running-style shoes that are designed and manufactured for casual wear. The New Balance Women’s 620 is one of those. But this is a real running shoe, one that you could run miles and miles in.
As a training shoe, the Nike Women’s Free Rn Flyknit is known for its smoothness and comfort. It’s lightweight, too, which is nice. And you reap all of these benefits even when using it as just a sneaker. The Flyknit can make you feel like you’re walking on air.
But my favorite part about the Flyknit is its modern look? This is a sleek shoe that doesn’t scrimp on design. Pictured here you see the Ocean Fog and White-Blue Glow version, which features fine detailing throughout the shoe body. It’s at once simple and complex, and I love the way it looks.
What would you wear with the Nike Women’s Free Rn Flyknit? I’ll agree with Shawn on this: Modern sneakers like this are best paired with active wear. Yes, you can wear it with anything you like, dark jeans included when you’re looking to dress them up. But the Flyknit is most at home with yoga pants as your hustling to get errands done or on days when you’re going to do tons of walking.
Is the Nike Women’s Free Rn Flyknit right for you?
1. Converse Chuck Taylor All-Star Low Top — Best of All Time
Are you looking for the GOAT in tennis shoes? This is it. The Chuck Taylor All-Star Low Top is the beginning and the end in sneakers. It first appeared on the market more than 100 years ago, and it’s still around. Can you fathom that staying power?
What would you wear the Chuck Taylor All-Star Low Top with? Anything. Truly, anything. This is perhaps the most versatile shoe of all time, in addition to being one of the most popular shoes of all time.
One word of warning: You can find the All-Star in almost any color, but please be judicious in how you pair those colors. Don’t start matching. You don’t want a top or hat or bag or really anything else that perfectly matches you Chuck Taylors.
And you don’t want to go too bland or too outlandish with your overall outfit. Pair loud colors with neutral outfits and neutral colors with louder outfits. You’ll find that the balanced look does great.
Is the Chuck Taylor All-Star Low Top right for you?
2. Vans Classic Slip-On Skate Shoe — Best for Edge
This is another classic, though one that emerged in skateboarding early generations in the 70s and 80s. The Vans Classic Slip-On and its checkerboard style are both widely noticeable and largely accepted. It’s an iconic fashion statement that isn’t for everyone, but that’s accessible in both look and price.
These are simple shoes with an unmistakable appearance. You’ll find that they are inexpensive and comfortable, which makes them an attractive option, too. The question is: Are Vans Classic Slip-Ons right for your wardrobe?
These shoes tend to be a little edgier, a little more street-wise. And that’s fantastic for a lot of men and a lot of women. You can work it into preppier looks — it can provide a nice and unexpected balance to, say, a polo shirt and khaki shorts for men. But most who dress on the preppier end prefer boat shoes. Which, OK …
What would you wear with the Vans Classic Slip-On Skate Shoe? Shorts or casual jeans for men work great. For women, try pairing with a leather mini or pencil skirt to create a street look, and take them out for a casual spin with boyfriend jeans.
The Vans Classic Slip-On Skate Shoe is in the Sneaker Hall of Fame for delivering an outlandish and stylish look with a budget price tag. If this sneaker is right for your look, get a pair into your rotation.
Is the Vans Classic Slip-On Skate Shoe right for you?
Final Thoughts on How to Wear Sneakers Comfortably
One last time, here’s Hailey to take you home …
I have one rule when it comes to shoes and another rule when it comes to fashion in general. I want to share both here because they both apply.
First, on the shoe front, find something stylish but make your ultimate choice based on comfort. Life is too short to wear shoes that don’t feel right, just because you like the way they look.
And, second, on the fashion front, be true to yourself. You know your style and what makes you feel irresistible, so find sneakers that create that feeling. You still need to take risks and get out of your comfort zone. But don’t go for sneakers that feel out of your range just because that’s what everyone else is doing.
Did we miss your favorite pair of sneakers? Let us know in the comments section below, or get in touch with us directly through our contact page.
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