This article may contain affiliate links; if you click on a shopping link and make a purchase I may receive a commission. As an Amazon Associate, I earn from qualifying purchases.
When you're over 30, it's hard to know which sneakers trends are cool and which end up looking clueless. I wrote this post in 2019 but updated it for 2020 to include current trends and the most stylish sneakers that look fashionable, purposeful, and not try-hard for grown women. Below my advice on picking out the best trendy sneakers for grown women and how to style trendy sneakers.
What Kind of Sneakers are Stylish in 2020?
Does anyone else think of this clip from “Crazy Stupid Love” when they see the sneakers that are currently popular? Thing is that movie took place in 2011 and ever since New Balance and other “old school” sneaker brands have gained popularity. Sneakers that were hot in the 1990's are back en vogue, and there are plenty of new brands on the scene that give off a retro vibe. Even so, it's hard to accept the fact that shoes we mocked less than a decade ago are now cool. What makes it harder is there are plenty of people like Steve Carell's character who never knew they went out of vogue that continued to rock them in a very un-ironic manner. How do you show you're wearing trendy sneakers because they are comfy and cool not because you stopped caring about trends once you graduated from college?
How To Choose Stylish Sneakers as a Grown Woman
Rule number one: wear what you like. If you don't like my advice, my advice isn't for you. Rock what you think looks good, makes you feel good, works with your lifestyle and unique needs. However, if you're unsure where to start in searching for trendy street sneakers, read on.
When looking for street sneakers to wear with everyday clothing (denim, shorts, casual dresses, etc.) a low-contrast color may get you the most mileage. Especially if you're not confident embracing the trendy sneaker trend, choosing a shoe that isn't high contrast with your skin or your standard wardrobe is a good bet. If you plan on wearing these shoes with a lot of jeans and dark leggings, consider a pair in black, gray, or a deeper color. If you think you'll be wearing them more with shorts, dresses, and pants that expose your ankle you may want to choose a color closer to your skintone or less of a contrast (tan, camel, gold or rose gold, white, ivory, pale pink, gray, etc.).
Right now, puffy shoes like we wore in the late '80s are back in style. Air Force 1, Reebok Classic, Fila Disruptor, all the shoes we coveted as kids and teens are now en vogue. And if you like them, go ahead and rock them again with gusto. They look fantastic with slim leggings, pleated and bias-cut midi skirts of lightweight fabrics, shorter shorts and dresses with volume, and looks that balance the puffiness with softness, sleekness, or a length of bare leg.
Shop Trendy “Old School” Sneakers:
However, such shoes may not feel comfortable to you when looking at your reflection. If you're short, they can make you look more short. If you have large feet, your feet will look larger. If you have thick legs and/or ankles, they will emphasize it. If you care about such things, this kind of shoe can be hard to style effectively. You may wish for a lower-profile shoe that exposes more of the ankle and top of the foot.
I have had luck with Adidas, Puma, and Nike for finding retro-inspired sneakers that aren't like marshmallows on my feet. Brands like Veja and Cariuma have come on the scene offering low-profile cool sneakers with ethical practices and materials. Converse “Chucks” and Vans “Old Skool” are classic styles that are also low profile; Superga is a great alternative brand if you have wide feet or find Converse uncomfortable. Soludos makes low-profile canvas sneakers with colorful and boho-inspired embroidery. If your style veers towards preppy, consider a pair of Tretorns. If you're looking for comfort shoes that don't look like comfort shoes, ECCO makes really stylish pairs. For those who invest in a covetable shoe collection, Golden Goose sneakers and Comme des Garçons PLAY sneakers have been on-trend for a couple of years, are comfy, and have a low profile. Below is a carousel of shoes I found online that are stylish and low-profile:
Shop Trendy Low-Profile Sneakers:
Be Wary of OTT
OTT stands for over the top and a lot of trendy sneakers right now are going that route. A retro sneaker but with chiffon ribbons as laces. A cool sneaker… with velcro closures and platform soles. Sequins, mixed patterns, holographic fabric, studs, lights, bows, ruffles, wedge heels stacked soles… A shoe that is OTT is more likely to look dated by the end of the season. Also, an OTT shoe not styled by an OTT person who has an OTT wardrobe can look cheap and clueless far quicker than a shoe that is more subdued.
Don't Buy Dupes
High fashion brands like Gucci and Balenciaga have gotten on the trendy sneaker train and carry stylish sneakers for sky-high prices. As with all designer accessories, lower-end brands and Made in China fast fashion companies come on the scene offering “dupes” of these designer pieces for a much cheaper price. If you're not sure whether the shoe you're admiring is a dupe or counterfeit, I recommend Googling the shoe description. For example, when you Google, “white sneaker with green and red stripes” the first hit on Google is authentic Gucci sneakers for sale on eBay. When you Google, “white sneaker with jeweled straps” Gucci also comes up in the first hits, and then a “dupe” by Steve Madden. I also recommend becoming familiar with the designer styles by perusing them on the website of a department store like Bergdorf Goodman so you get a feel of the trends and the specific designers' trademark styles. Whether they are truly counterfeit and pretend to be designer sneakers or they're made by a department store brand with so much of the designer elements you can't tell they're not the real deal until you're up close, it's not stylish to wear such a shoe.
The Right Socks
The best way to wear trendy sneakers is to have your ankles exposed, no visible socks. My favorite no-show socks are the Hide and Seeks by Smartwool. They really do hide under every pair of sneakers I own, they keep your feet warm in winter and cool in summer, wick away moisture, prevent foot odor, hold up for years, and don't slip down your heel mid-day. Bombas is my second-favorite brand for no-show socks. For every pair of Bombas purchased, they donate a pair to a homeless shelter.
Shop No-Show Socks:
How to Style Trendy Sneakers
Okay, you found a pair of sneakers that you think look cool, feel great, and are fun to wear. Now, how the heck do you style them for every day in a cool, grown woman style? Here are a few ideas to get your sartorial juices flowing using one of my favorite sneaker classics: The Adidas Stan Smith. This sneaker is low profile, low on details, come in all white or with details in black, gold, green, and occasionally other colors. This is a sneaker that is popular across the globe; this is a sneaker you can wear sightseeing in Europe and not look obviously like an American tourist.
Look 1: blazer | t-shirt | knit jogger pants | sneakers
This is one of my go-to outfits, in fact I shared a version of it with boots recently but more often I do it with sneakers. When you pair comfy jogger-style knit pants with a structured blazer, it achieves a more polished effect than with a hoodie. This is a great way to also rock another trendy look, the graphic tee, without looking too young. By having the joggers and the blazer both black it looks more polished and less like activewear. Be sure to pull up the cuffs of the joggers a bit to let a hint of ankle show. The t-shirt should either be tucked in or half-tucked; this post delves in ways to get comfortable with tucking in tops.
Look 2: dress | jacket | sunglasses | bag | sneakers
One of the most classic ways to rock sneakers as a grown woman; a t-shirt dress and denim jacket is great for weekends, casual activities, and sightseeing. By pairing the crisp white sneakers with rinse denim, this outfit feels modern and sophisticated.
Look 3: jeans | jacket | tee | belt | earrings | sneakers
This is a pretty typical look for weekends and casual situations; the way to make it feel modern is to focus on fit and proportion. These jeans, while coming in sizes 00-40, also come in lengths. You want to choose a length (or hem your existing jeans) to a length that shows the ankle bone to have them work well with sneakers. This not only elongates the leg, it feels more modern than having the jean hit the top of the shoe. A striped tee is a classic, but this one has a more flattering neckline and slimmer silhouette than in the past. Again, tuck or half-tuck the top and add a scarf or belt for interest. The field jacket nips in at the waist and also has a slimmer silhouette so it is clearly a fashion piece and not leftover from your fishing trip or safari. Adding a pair of interesting earrings shows you know current trends and like having fun with fashion.
Look 4: skirt | sweater | long necklace | short necklace | sneakers
Sneakers can be worn with dressier clothing and look chic, not sloppy. Again, the key is fit and proportion. Midi skirts are very on trend with sneakers, but to keep it looking sleek, choose a skirt of a lightweight silky fabric with drape so it doesn't add bulk and pair with low-profile sneakers that expose plenty of ankle. The sweater can be switched out for a tank, tee, or even a turtleneck. The key is to choose one that skims the body, either hits at the waist or can be tucked in, and is a soft or lightweight fabric. You don't want anything stiff or thick which will look bulky with the sneakers. Adding shine, in this case with delicate gold necklaces of varying lengths, makes the look purposeful and incorporates a popular jewelry trend.
Sneaker Styling Tips
A few basic tips to help you style your trendy sneakers:
- Show some ankle. The same holds true for loafers and brogues; you need to have visible space between your pants and shoes to make the look purposeful. Nine times out of ten this will require a trip to the tailor. Be sure to bring your sneakers with you to ensure the right length. A shorter pant will still work with basic flats and pumps, there is no specific length that is “in” this season or the past few seasons so feel free to shorten and even narrow your pant to the specific length that works with your body, your personal style, and your shoe wardrobe.
- Balance volume. If you're rocking a pair of Nike Air Force 1, I bow down to you and your fierceness. With any shoe with a bit of volume, consider styling them with either a skinny pant and top or jacket with some volume, or a straight or a-line style dress around the knee, letting the legs show. A slim leg will let the shoes take the spotlight and give them an edgier vibe.
- If new to the trend, go low contrast. A pair of shoes that are close to your skin tone will blend the best into your wardrobe and personal style. Instead of white, black, or navy try a softer neutral like cream, tan, gray, or a soft metallic.
- Start with a classic. If you're new to wearing trendy sneakers, you may be more comfortable going with a popular classic. Adidas Stan Smith or Superstar, Puma Suede Classic, Tretorn Nylite, Veja V-10, Converse All Star, Nike Classic Cortez, Vans Old Skool, and Gola Coaster are a few types that have remained classic cool for a few seasons.
There’s a picture of a grey sneaker with looks like white stripes. I don’t see any info on them. Would you please tell me about them and where I can purchase them.
Alison Gary says
I think they are the Courtset style from adidas. I am positive they are adidas but not as positive about the style but these look very similar. They seem to be discontinued so there are limited sizes at different retailers: https://bit.ly/3ecF3MD and https://bit.ly/2ZoF8sE they may also be the adidas Gazelle, which I can’t find right now in grey but found in a soft greyish mauve color: https://bit.ly/2Tp54Aw
I was looking and looking and looking at the Tretons that you posted, trying to figure why I was experiencing a weird dejavu when I looked at them. And then I remembered that I wore Tretons for my cheerleading uniform back in the mid-90s when I was in middle school!! I absolutely hated them (because I had size 11s at the age of 11 and everything made my feet look huge and terrible in my eyes) but now I look at them and maybe they’re not so bad!? Thanks for the trip down memory lane!
This post is gold. You’ve inspired me—and I maaayyy have bought a pair of bright red sneakers. (I totally did. Am so ready for spring.)
I’ve had problem feet all my life. In fact, my mother used to say that as a child I detested walking barefoot and can be seen in photos tip toeing on the sidewalk. I’ve had over eight surgeries on both feet and still suffer with periodic aches and pain even now. So, wearing sneakers is my best option. I used to wear only them when commuting after switching from my dress shows, and then full-time on the weekends. Now, I wear them every day. I am a huge Nike fan, so 99.9% of my sneakers are Nike branded. I have every color and style, but, if need be, wear all black sneakers with my suits and dress clothing. I always wear sneaker no show socks and, usually use my orthotics. My feet feel better and I’m comfortable most days. I used to feel self-conscious of the look, but now, a lot of women is sporting this look as well. Thanks, Allie, for making this a talking point.
Jessica Valadie says
I am chuckling right now as I look at the brand new Vans that arrived this week on my doorstep. Good to know that I have good taste! Ha.
I absolutely love sneakers. They’re all I’ve been wearing for the past couple of years and my feet have never felt better, though I have to say most of my sneakers are slip-ons. Are those in the sneaker category or called something else?? Hmmmm. Anyhow, just wanted to say that getting some cheap, colorful laces through Amazon can bring new life to sneakers. I’ve got a pair of black and white Supergas that I purchased hot pink laces and gold laces for and I feel like I’ve got a new pair of sneakers when I change out those laces for the black ones the pair came with. It doesn’t take much to get me excited, lol.
I went all in for Bombas because of their business model, and the style of the sock. Donating to people in need? Heck yes! But I’ve not had very good luck with them. Several pairs have gotten holes in different spots. :-/ Really bummed because I was hoping to replace all my socks with them. Has anyone else experienced this?
Alison, I love your posts and this one was just the right timing for me. Only in the past few years have I embraced being a sneaker girl – and this is coming from a 52 year old executive with big (size 10 or 11) feet. For years I thought looking professional meant uncomfortable shoes and boy am I happy to be wrong. My career continues to flourish even though I am comfortable:) I just ordered black joggers similar to the ones you shared, and the same t-shirt because I have the black jacket and shoes already – time for me to put it all together into a new look. Keep up the great work on all your posts including those awesome weekend reads. You rock:)
Sometimes I feel flummoxed for not buying into the white sneaker thing. I love the look, and I feel like the trend is here to stay, but all I can think about is how they’re going to look dingy almost immediately. Perhaps it’s because I’m a mom of 2 and am often walking through wood chips, etc at the park. I’m always looking for sneakers that don’t have the stark white on the outer sole and leather uppers, but they’re hard to find unless you’re doing all black in something that looks like an orthotic shoe. I got a pair of Columbia Bridgeport Slip shoes a couple years back, but I wish there were more options like that out there. Maybe I just need to get into the habit of cleaning my shoes more often, but I am cleaning everything else enough!
The solution to this is easy, though not minimalist. You buy two pairs: one pair for kicking around, and another pair to keep “nice”.
Such a great post – Thank You! I just got a pair of sneakers last week. However, they’re for extremely high volume feet, with room for orthotics, and some kind of posture-improving technology in the sole. That means they look more like a high profile trendy sneaker, but in cream and grey, so neutral colours. Although they’re very comfortable they are a bit of a puzzle to style! Should anyone be interested, the brand is Danish and called Wallin (wallin-shoes.dk)
This, and the other post you linked to, had so much great information — but I think I’ve (maybe) come to terms with not being a sneaker girl. I felt sad after reading your post and trying (again) to imagine myself in sneakers — in fact, I daydreamed back to elementary school when I so wanted a pair of Tretorns, saved my allowance, bought a pair, and never, ever wore them b/c I just looked so ridiculous in them.
I do appreciate your recommendation to lower the contrast between skin and shoe color — that’s a great tip.
(PS. The elementary school kid in me loves the plaid Tretorns I just saw at the Nordstrom site, LOL!)
I have difficulty finding shoes to work with girlfriend jeans. Are sneakers like these the go-to? How snug should the pant opening be? Would love to see a post on how to style these pants and shoes since I have to wear shoes with forefoot padding and support, and have unattractive (arthritis) ankles! Thank you for you blog!
I’ve had knees replaced and multiple leg surgeries. Have to avoid trendy and go with support (thank you Brooks Glycerine!) But I’ve found All-Birds to be comfortable and they’re all-wool for those of us who never wear leather.
Yes, I’d also like to plug All Birds! Wearing them to the office right now for casual Friday with jeans and a striped top. 🙂 I think they are easier to style than many sporty brands.
Kelly Rigotti says
I wore Allbirds on a recent trip to London, walking all day, every day, and my feet never hurt. I’ve never had that happen.
In my experience we all look younger/thinner/smarter/richer/more attractive when our feet feel good and we can easily take a purposeful stride. For me that means I’m in a shoe that stays on my foot when I move and doesn’t involve thinking abut the take off and land of every single step.
My take away here is that a white low profile sneaker should be in my Summer wardrobe.
OMG, I think “disheveled poli sci professor” actually IS my look, with a little bit of “disheveled English-lit professor” thrown in when I wear a dress, and I am going to embrace it for all it’s worth!
Alison Gary says
Yes! Nothing wrong with it if you own it and rock it!
I am 32 and love wearing sneakers, I am so so sick of ballet flats, and booties and sneakers feel fresh.
I have black slip on eccos, black adidas sambas, red shoreline converse, gray toms, hightop vans, slip on leopard hightops from target, millenial pink, black perforated, and gray glitter slip on sneakers, hightop navy sneaker-booties. Its an addiction.
I have a casual job and sneakers really fit my needs. I wear jeans, striped tee/solid longsleeve tee add an accessory/scarf or lipstick and big earrings and add a sneaker and it works
Alison Gary says
Sounds as though you have a fantastic collection!
Great ideas – I just bought a pair of Saucony Jazz sneakers, my go-to for fashion sneakers. I can’t wait to rock them this spring and summer. I’d love to start now, but have to wear regular crew socks due to a leg injury, that requires me to wear a full-leg brace.
Alison Gary says
Wishing you a speedy recovery!
My 44-year-old daughter wears her wardrobe of sneakers effortlessly and always looks chic. Your post is SO helpful as at 68, I had no idea how to go about adding sneakers to my wardrobe. I’ve never been a sneakers person, but always have loved trendy shoes. Now you’ve given me some ideas to try out, I’m going to check out your links.
Alison Gary says
Oh I’m so glad! I think I’ll need to revisit this topic again and go more in depth!
An “Over 40” blogger (she’s 46 I think) did a big sneaker try on. It is actually very good and informative, and then she did a post where she put together like 9 outfits with the sneakers and stuff she already had in her closet. I’d highly recommend both posts for anyone looking into jumping on the fashion sneaker trend. It really helps to see the sneakers on a person and from different angles and she gives really detailed pros and cons (including weight of the shoe) for each sneaker. And of course seeing the sneakers styled with different outfits (not just a flat lay) really gives a better picture of the proportions. I’m not sure if I am allowed to say who the blogger is (is it rude mention another blogger? There is not an entry on this topic in Emily Post), but if you google 2019 fashion sneaker review you should find it.
Alison Gary says
Oh sure, I adore Jo-Lynne and she has a great site. And this post is a fantastic resource! https://jolynneshane.com/fashion-sneaker-review-comparison.html
Jo-Lynne Shane says
I saw this post pop up in my stat counter and popped over to read. Thanks for the shout-out! 🙂
I love all of your tips and you make some great points about how to style them and how to choose the right pair. A lot of people told me I should have kept the Golden Goose, but I felt like they were OTT (love that acronym!) for me personally. Very happy with the Veja I ended up with. Classic but fashion forward – and they have that low profile you mention, which is what I really liked about them.
This post is a great resource! Off to share on my FB page…
Alison Gary says
Aww thanks so much! <3
Thank you for this!!! Feeling “old” at almost-52 these days.
Alison Gary says
Woman, you are NOT old! It’s just there’s only so many things one can fit in their brain, and keeping tabs on trendy sneakers isn’t high on your priority list. But that’s the benefit of reading blogs, we do research on your behalf!
Elizabeth Kay says
Thank you!! I actually do own a pair of tan leather ECCO sneakers and I love wearing them. Kind of look like Keds. They are fun — but I’m always wanting to wear my wonderful grey and pink Nike trainers but don’t know exactly HOW to style them. This article is a great help:) I enjoy your photo outfit collages. And…You are adorable:)
Alison Gary says
Aww, thank you!
Nicole K says
Another brand, though super pricey, that I love for cool sneakers is Paul Green. But I try to find them on eBay!
Love all your styling ideas. Eyeing that plaid blazer…
Alison Gary says
I love eBay for things like that! And a plaid blazer is a hot thing for wardrobes now and through the rest of the year!
Just bought a pair of Supergas and I’m hoping to incorporate them into lots of outfits. These, in sage grey: http://bit.ly/2EkfV6l
Alison Gary says
Oh I like!
Reporting back – they are awesome. Comfy, small profile, look cute with jeans and leggings (and probably shorts when the weather is warmer). So happy to have found these!
I do wear sneakers to walk the mile from parking to office so I do worry that is what any sneakers will look like, this gives me hope.
Alison Gary says
I’m glad you found it helpful!
Teresa Sheedy says
i’ve been big into this…I”m never wearing heels again (maybe) I wear my sneakers with dresses, pants, whatever…I’m comfy, I feel cute, and my back and feet don’t hurt.
Alison Gary says
Thank you, Ali! I went ahead & bought those New Balance Shoes after I’d emailed you. Your ideas are great! So far, I’ve only worn my shoes with skinny jeans but I got SO many compliments on them (I love shoes, & these are adorable, imo). Thanks to this post, I’ve got several more ideas on what to wear them with as the weather warms up. I also own a pair of Tretorns that all white, so I think those will give me more casual options as well. It’s pretty crazy that these retro-shoes are back in style, but it’s also nice to be comfortable. Thanks again for this post!
Alison Gary says
My pleasure, a great question that I knew would help others so I had to turn it into a post! Enjoy your cute shoes!