How to Wear Retro Sneakers Without Looking Frumpy

One of the big shoe trends this season is retro running sneakers, sometimes called retro runners or retro trainers. These are basically old school style running sneakers reimagined for a new decade… and for streetwear, not just athletic wear.

Whenever the topic of retro sneakers trending comes up, I get questions about how to wear them… and more specifically, how to wear retro sneakers without looking frumpy.

Madewell sweater (S) // Pistola Denim (29) // rag & bone Retro Sneakers (39)

I get what y’all are saying. I mean, for years, I wouldn’t even let one of my running shoes come in contact with a pair of jeans in my closet.

Okay, I jest. But you know what I mean. There is no more surefire way to look frumpy than to wear your running shoes with jeans… or so we’ve been told. But now that’s all out the window.

These days, women are wearing sneakers with everything from jeans and shorts to skirts and dresses. But how do we do that without looking like a fashion emergency?

I do think we women of a certain age have to tread lightly with this trend… pun totally intended. 🤣

Whenever a wardrobe item or style combo that has at one point considered frumpy suddenly becomes trendy, we must be very intentional about styling, and fit and quality matters more than ever.

I’ve been paying attention to how stylish women are wearing their retro sneakers and did some experimenting in my closet, and here are my best tips to participate in this trend without crossing over into frump territory.

How to Wear Retro Sneakers Without Looking Frumpy

Treasure & Bond sweater (S) // Frame Le High Denim (29) // rag & bone Retro Sneakers (39)

#1. Find the right sneaker for YOU. 

That may sound obvious, but there are a lot of options out there, so you want to find a pair of retro runners that you love and that aligns with your personal style. Some are big and chunky and some are more streamlined, some are bright and colorful and some are subtle neutrals.

Find a pair that makes you happy and that you’re excited to wear. I picked up these rag & bone Retro Sneakers in the Light Sand Suede at the #NSale back in July. I like that they’re more streamlined than some, and they have that luxe/casual vibe that I love.

I also wanted a neutral color other than black or white that will work into my existing wardrobe, and this sand color seemed like the right choice.

They’re definitely spendy, though… especially at full price. (I got mine on sale.) Fortunately, you don’t have to spend a lot to get the look. If you don’t already have a pair of retro runners, and you’ve been wanting to dip your toe into the trend… sorry, I can’t stop with the puns today… here’s a roundup of retro running sneakers at a variety of price points.

So now that you’ve found your retro running sneakers, how do you wear them without looking frumpy?

#2. Style them in a way that looks intentional.

There are certainly ladies who can wear this style of sneaker with chunky socks and a skirt and look really cool doing so, but because the runners are more sporty and athletic looking than a clean white court sneaker, I like them best with more casual outfits — namely jeans.

But what style of jeans?

Up until 5 minutes ago, I would have said to wear retro runners with jeans that end at the ankle bone and show a little bit of skin, like these slim straight cropped jeans. This shows off the sneakers and the slimmest part of the leg.

Another option would be crop flares. Here’s a side-by-side with two pairs that I have and love. These outfits are identical except the Mother Insiders (on the left) have a 26″ inseam, and the Citizens Isola (on the right) have a 27 inseam.

See how showing just a bit of skin at the ankle makes the whole outfit look better?

Evereve sweater vest (S) // Mother Insiders (28) // Citizens Isola (29)

Cropped jeans with the retro runners is probably the safest and easiest way to wear them without looking frumpy, but with full length jeans and relaxed fits coming back strong this season, we’re starting to see chunky sneakers with longer jeans.

Plus, I know someone will ask me what they should do in the wintertime, so I decided to try my retro runners with the AG Mari slim straight leg jeans. These have a 29″ inseam, which makes them almost full-length on me.

I think this look works okay, mainly because there isn’t much contrast in the colors of the outfit, but I really prefer the looks above with some ankle showing.

AG Mari  (28) // ATM tee (M) // rag & bone Retro Sneakers (39)

Look what happens when I switched to the same jeans in a darker wash. I don’t love this, but I need to try different tops to be sure. I’m not sure why I didn’t do that at the time.

Next, I tried these same sneakers with full length flares. Even if I cut them so they wren’t dragging on the ground, I just don’t like this look very much. I think it looks sloppy, and that’s not my vibe at all. That said, it’s entirely possible I will be wearing this look by next spring. Who knows!

  Mother Denim (28) // rag & bone Retro Sneakers (39) // Caslon thermal top (S)

If you want to do the retro sneakers with full length jeans, it’s more trendy to pair relaxed straight leg jeans with sporty sneaker styles. Take a look at this look from Gap.

photo credit: Gap.com

It seems counterintuitive to pair something bulky with another bulky piece, but it can be a cool combination if it’s done right and if it aligns with your personal style.

That said, this might be a look best left to the younger set. That is because the baggy jeans and the retro sneakers are both very trendy items… and that brings me to #3…

#3. Don’t incorporate too many trendy items into the outfit, but keep the other outfit components current.

As we age, we look more stylish when we incorporate trends into our outfits sparingly. Wearing too many trends at once can look juvenile. My 16-year-old daughter can get away with that, but me? Not so much.

Since pairing running sneakers with your jeans is already a trendy styling technique, you don’t want to overdo it with a bunch of other trendy items. But you also want to be sure the other outfit components are current so it looks intentional.

For example, these straight ankle jeans in the washed black are a nice length with these sneakers, and the quilted plaid jacket is the perfect topper to this casual yet elevated outfit.

Fidelity Denim straight ankle jeans (28) // rag & bone Retro Sneakers (39) // Evereve plaid jacket (S) // beige tank (S)

Here’s the same outfit with a rust-colored fitted denim jacket. I really love this look! The colors work really well together, and I like the silhouette I created with the cropped fitted jacket and slim straight ankle jeans.

Fidelity Denim (28) // rag & bone Retro Sneakers (39) // KUT from the Kloth denim jacket (M) // beige tank (S)

And a thermal top is a nice casual top for an outfit with sporty sneakers like these.

Fidelity Denim (28) // rag & bone Retro Sneakers (39) // Caslon thermal top (S)

This cotton stripe sweater has a sporty vibe, so I like how it works with the jeans and retro runners. (As an aside, the dangly earrings look out of place with this outfit. I had them on from earlier in the day, but I’d wear a smaller hoop or simple stud.)

Treasure & Bond sweater (S) // Mother Dazzler Straight Ankle Jeans (29) //  rag & bone Retro Sneakers (39)

You guys said you wanted to see more of the looks that don’t work, so here’s a look I do NOT care for. In this case, the top is too dressy for the jeans and sneakers. It looks like I just threw the sneakers on with a business casual outfit to walk from the train to the office.

AG Mari (28) // rag & bone Retro Sneakers (39) // LOFT floral tie neck blouse (S)

#4. Pay extra special attention to fit and balance.

Your outfit should be color coordinated and balanced, just like any other outfit you put time and effort into. And because jeans and sneakers historically have been a sloppy combo, the fit of every item in the ensemble should be on point. Keep the entire outfit elevated and good quality, even if it’s very casual in formality.

Treasure & Bond sweater (S) // Frame Le High Denim (29) // rag & bone Retro Sneakers (39)

Some ladies may like the retro sneakers, but not with jeans. That’s just fine! If in doubt, stick with wearing your retro runners with athleisure looks like joggers or faux leather leggings. Top them off with a denim jacket or leather bomber to keep them less gym, more street style.

I plan to wear my rag & bone Retro Sneakers with crop flares and straight ankle jeans, and keep the tops casual and color coordinated. When I want to wear longer jeans, I’m going to opt for other shoes, like clogs and booties.

But as always with fashion, I reserve the right to change my mind in a few months. As styles and silhouettes change, so does our perception of what is stylish and flattering.

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56 thoughts on “How to Wear Retro Sneakers Without Looking Frumpy

  1. I think I now understand when people complain about old things being “new” again 😂

    My “uniform” in my 20’s and early 30’s were athletic sneakers with boot cut jeans. Zero variation. Now it looks weird to me since I love booties and other shoe types.

    I really like the green sweater look and the striped sweater look. I got a hearty giggle from the thumbs down pic. I likely have some old pics of myself dressed like that 😂

  2. I think I like them best with the dark jeans! But you’re right, its a balancing act ….back in the day, I would wear my sneakers with hoodies and jeans for tailgating and didn’t care about ‘fashion’, just wanted to be warm and comfy..lol . Great post … I may look for some cheaper versions to wear – I don’t see this trend staying around forever.

  3. I keep eyeing retro sneakers. I wear my On Cloud sneaks with joggers and may try them with ankle jeans before I make the investment of buying a pair of retro sneakers. Because I have issues with two lower lumbar disks there are days when anything with a heel is hard on my back (and with high arches I have never been a flats girl). I like the IDEA of retro sneakers for those days when I need extra comfort.
    Question on jean washes, Jo-Lynne– I usually start putting my light washes away this time of year. Do you see yourself keeping your light washes out this fall and winter? And what about the shorter lengths of jeans? Once it gets cold, will you stick with full-length straight, bootcut, and flare?

      1. I also love the light washes all year long, love to pair them with a burgundy top/sweater in fall/winter. Loved the post today, wish I hadn’t gotten rid of my brown suede Puma’s couple of years ago!

  4. Thank you for the timely and very helpful suggestions. I work long hours at a casual women’s clothing store where we wear jeans almost exclusively because we sell them. We are always trying for comfortable shoes because concrete floors are murder on the feet after eight hours! As a woman “of a certain age” I will be following your advice regarding jean length and sneakers that will now likely include running shoes. Also agree that some tops are just too “dressy” for a running shoe.

  5. Thank you for all your fashion and life insights! I’m so glad tennis shoes are back in style for adults. They are so practical!

    Related to nothing in this blog…just wanted to tell you how great your hair looks! I love this color abs length on you. 😃

  6. Thank you for this post! You look great in this look but for me , it’s a hard pass. Never was and never will be a jeans/ sneaker girl.However, I do love then with joggers.

  7. Jo-Lynne – how often do you reorder that night cream from Amazon you recommended? I see that it’s much less expensive on subscribe and save, but don’t know how long it might last.

  8. Wow – I feel like I’ve been living under a rock. I’ve never stopped wearing athletic sneakers with jeans for outdoor events (an amusement park, the zoo, tailgating, etc.) and for work when we’re rearranging the library (which happens more often than you’d think). They are my version of “sensible” shoes.

  9. As a teenager growing up in Phoenix in the 70’s, we wore what we called “track shoes” with jeans that were longer and flared. I just assumed that’s how I would wear them again. I bought the Rag and Bone retro sneakers and they are soooo comfy, but I haven’t worn them yet. I better play around with the jeans I have and see how they work. What about white jeans? With maybe a beige top? Thank you for these “How to wear” posts. I really do need them!

    1. Yeah, I didn’t think to put them with white jeans! Not that I never wear white after Labor Day, but I guess I was so focused on my black and blue that I didn’t think about it. I do think that would be cute.

  10. EXCELLENT post!! I too have these r&b shoes in the sand (also bought black, but they’re sitting in my ‘maybe’ stack) but haven’t worn them because it’s not jeans weather yet where I live. BUT, I do think it’s important to differentiate I will not be wearing my actual exercise shoes with this street style. I bought these sneakers specifically as fashion. It’s when others wear their actual ON or NB or Asics as “fashion” that it looks frumpy. I’d love to see ON come out with a fashion retro sneak since they’re so good!

  11. You definitely are on with this post. I didn’t purchase the right ones and don’t plan to buy another pair at this point. I saw the JCREW ones….you also linked them, on Cyndi S. blog and she had them on with shorts on camping vacation. I liked them, so got them for a great sale….$30. I haven’t worn them yet. 🙁 After I got them the weather turned hot and has been all Summer and I never reached for them, as wanted sandals. Now with Fall coming, I just don’t care for them with any of my jeans, as they are too clunky. I like your more streamline ones. I guess you live and learn on impulse buying when you see it on someone else at the time and they are on sale. LOL 🙂 I love the look you have with the Burgundy stripe sweater……..so classy and they don’t look frumpy at all. If these are still in style next Spring, maybe I’ll put them on with shorts or now if stays warm enough for shorts, but I’m ready to put my shorts away. Looking forward to your Fall post to come. Great job. 🙂

  12. I just can’t get behind the retro sneaker trend. No matter how you style it, I can’t help thinking another shoe would look SO much better. Maybe it’s my age, but I’m gonna pass on this one and leave it to the younger ladies.

  13. Love the outfits less the sneakers. Too forced to be on trend. I’m sticking with my leather and suede clogs and loafers. Sneakers staying with converse blue canvas with leather knit tie laces and Nike white leather classics.

  14. Love this post and how you’ve styled the retro sneakers! I personally love this style and just received the Nike New Day from Nordstrom to add to my collection.. I totally agree about balance and just playing around with the styles., for me I love my skinny or slim straight jeans and for me I have to have some ankle showing.. and I prefer the lighter wash… adding a crop jacket or blazer over a tee is a great way to wear them… or of course with a jogger. You cannot beat the comfort of this style! And my feet much appreciate it:)

  15. I totally agree about wearing a casual top with the retro sneakers. But I actually prefer the look with the full length jeans vs the ankle length. I think it’s because I have long legs and the ankle length screams 1999 high waters to me! Lol! It’s hard to embrace the looks you strived to avoid at all costs 20 years ago!

  16. I may lean, slowly, into this trend. As far as not looking frumpy doing so, and lest someone complain that you’re pigeon-holing women “of a certain age”, I think you’re spot on. Can we wear whatever we want? Sure. But, should we? I can’t stop thinking that younger women look for ways to set themselves apart, fashion-wise, from their mothers/aunts/grandmothers and when we start dressing “like them”, they change direction! And, as you said, we DO have to be more intentional about it. It’s not as easy for us to just throw any old thing on and have it look good, as younger women typically can. Our bodies, faces and hair don’t always “look right” with fashion designed for a youthful appearance. And, the fashion world isn’t necessarily styling with the older women in mind. We seem to lag behind and have styles created for us AFTER the younger generation has adopted a new style/trend (and by then, they’ve probably moved on!). As far as retro sneakers for fashion, I agree that any old running shoe just doesn’t look as stylish as these that were designed for fashion.

  17. Could you explain the difference between fashion sneakers and “retro” sneakers? I used to think I knew–retro sneakers had a thicker heel, rounded toes, etc., but now it looks like retro sneakers are fashion sneakers. Could you give examples of some pure fashion sneakers?
    By the way, great post! I’m convinced it looks better to show some ankle –just need to figure out the weather in the frozen tundra.

    1. Well, both are rather nebulous terms, lol. And they definitely overlap. Retro just means an old style reimagined for current fashions. These are specifically retro RUNNING sneakers – they have the “old school” running sneaker style, but other sneakers styles can be retro too.

      Fashion sneakers just means a sneaker designed to be worn as streetwear, to make a fashion statement, as opposed to the athletic shoes you work out and run in. So these are actually fashion sneakers, in the running shoe style. They aren’t meant to actually run in, but they draw on that styling.

  18. I have seen actual running shoes styled with jeans on other blogs. However, I find that my super comfortable Hoka Bondi 7s are NOT that comfortable when worn all day. Weird.

    1. I’m not surprised. Really, anything goes these days, and it’s all about personal style and wearing what you like. I don’t like that combo, it doesn’t look polished to me, but I realize not every woman is going for a polished look. 🙂

  19. Thank you for showing us how not to look frumpy when wearing retro sneakers. The pictures of the different types of jeans really helped! I don’t wear retro sneakers, but do have several pair of Naturalizer Marianne slip on sneakers that I love and wear with jeans. Do you feel the rules on how to style retro sneakers apply to these slip on sneakers?

  20. Speaking of fashion sneakers, can you think of any that would look acceptable with skirts or dresses? I’m healing a heel spur and have been advised by my podiatrist to wear sneakers, even to work.

  21. Yes great post…wonderful explanation!
    As a woman of certain age, I will wear my
    Skechers lol!!! But I also hv white Cole Haan
    that I struggle with because of the color.
    I do think length of jeans, the type jeans and
    the addition of cute jackets elevate all of these looks.

  22. And, it looks like it’s OK to actually tie the laces?? I struggle with “to tie or not to tie” and BTW, how do you keep them on your feet if you don’t tie!!

    1. I tie these, although there might be a “cooler” way to to it — I’ve seen some women do something funky where they tuck the laces underneath the tongue. I dunno. I do get irritated that I have to tie and untie every time, so maybe I should try to find an alternative method, but for now, I’m just tying them. I do tie my P448s to the side, and they stay on just fine. https://www.youtube.com/watch?v=reCxDexhPr0

  23. I work in a business casual office environment, so I don’t usually reach for sneakers with my jeans except for Fridays. This is super helpful, not just for work, but also for traveling! There’s nothing worse than having uncomfortable shoes when you have lots of walking to do, but don’t want to wear typical athletic shoes with denim! This post will help me to be both fashionable and comfortable on my travels! Thanks so much for your hard work!

  24. Great post! And I agree with other comments-LOVE your glasses and your hair! I have been studying your posts on the new denim styles and what shoes to wear with them. Do you think similar sneaker guidelines apply to wearing ballet flats with longer denim and cropped flares? Thank you for all the hard work and effort that goes into these posts!

  25. I think the risk if you wear the trendy look (with the baggy jeans) is that it may look like you’ve been wearing that look since the 90s, whereas a 20 something clearly hasn’t. Kind of like how women our age can’t carry off “mom jeans.” That said, the looks showing a bit of ankle look great! Thanks for this helpful post.

  26. I really like your new eyeglasses! The frames are great. Thanks for doing this post and all of the examples you shared. I agree that letting a bit of your ankles show is more pleasing to the eyes, and the outfit looks better.

  27. I admit, as a mom to preschoolers and a 7-year-old in her early 40’s, current fashion sense probably eludes me. But your least favorite look…the long flared jeans with the sneakers…was probably my favorite, and the way I’d most likely wear it. Perhaps it’s my age, and what was trendy at a crucial time of my youth…we were all stepping on the backs of our flared long jeans and ripping them up, haha. Part of it is body type; I’m very small and thin, thus ankle-baring looks aren’t flattering on me. I look like a 12-year-old boy with big bird legs! That said, the photo I like best of you in the sneakers is the one after the ‘thumbs-down’ pic–the striped sweater with the slim-fitting ankle jeans. I need a very non- clunky low-profile retro sneaker, like a canvas Converse one, to counteract the Big-Bird ankle effect with ankle-exposing pants.

  28. Just catching up here…..lots of comments on this post Jo-Lynne! I’ve had the R&B sand colored retro sneakers in the “saved for later” part of my Nordstrom cart for a few weeks now unable to decide if I’ll really wear them. Now seeing you style them in different ways (even the ways you don’t like 😄) convinces me I should buy them. I actually do like them paired with longer bootcut and flare denim and can see myself wearing them that way as well as with cropped flares. When I go to my college alma matter football games this fall and tailgate, I like to wear an elevated casual vibe and these sneaks have that look to me. I see them in the fashion category for sure and don’t think I’d ever wear them for athletic activities. Thanks for the post! You made me want to buy them! 😊

  29. I have two pairs of retro sneaks. These are definetly one of my favs. I agree with you when to wear these with some skin / bare ankles showing. Defenitely look good on moms that are always on the go. You may also try them with a no showing laces look, and a bit looser on the foot. They will look more chic, especially if you’re not wearing socks with them.

    Thanks for sharing ideas about these sneakers.


  30. Nicely put together! My office has been jeans casual for all the 15 years I have worked there, so it’s good to know I am trendy now LOL. (Basically, this is how I have been dressing for the past 15 years, I do on occasion wear “real shoes”, but I have mostly sneakers, too many pairs to count. I love shoes; that’s an understatement haha). I think I am going to have to buy that plaid jacket, I absolutely adore it!

  31. Hi Jo-Lynne! I too love your Longchamp glasses. Can you provide the style number? It starts with LO then a few digits. Pretty frames are hard to find!

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