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.
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
#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?
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.
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!
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.
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.
And a thermal top is a nice casual top for an outfit with sporty sneakers like these.
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.)
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.
#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.
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.
Stay In Touch
If you liked this post, be sure you’re signed up for my email newsletter. In addition to my most recent blog posts, you’ll receive exclusive newsletter content like special sales, my newest favorite finds, and an occasional peek behind the scenes — all delivered right to your inbox.
I would also love for you to join my JLS Fashion Insiders Facebook Group! This is a friendly place to discuss all matters of fashion and style with other women, share your outfits, get advice, and stay up to date on all the happenings in our community.
This post contains affiliate links. When you shop through my links, it helps support my business (at no additional cost to you) so thank you!