Up until pretty recently, I never thought I would be able to “pull off” the cool sneaker look. You know, like those people who can make them look effortlessly chic with a simple dress. I wanted to try but I thought, “I’m not the right size. I’m not cool enough. I don’t have the right clothes to make it work.” All of those thoughts were wrong and harmful for A LOT of reasons. So much like my journey to wear skinny jeans back in 2006 or wear a middle part in 2009, I just needed to let go of all of that noise and try it. Guess what? It went great and I have a hard time wearing any other type of shoe these days. And I am not the only one on the EHD team:) Wearing a heel feels like the wrong call when I could wear my extremely comfortable sneakers. But I know that there may be some of you that are still on the fence about this look, maybe even have some intrusive thoughts of your own. If that’s the case, may this post be here to quiet your mind and get you excited to try something new (or a minimum get you a comfortable cute pair of new shoes if you need them). I know for me, the biggest hurdle when it comes to trying new to me fashion trends is “the how” and/or “do I have what I need in my closet?” That is why we are starting this post with six easy inspo looks so you can confidently nail the sneaker look if you want to. Then we’ll get into our shoe picks. Let’s begin!
Fun Printed Midi Dresses
This is one of my favorites. The flowy patterned dress with a sick sneaker. The length of the dress can, of course, be shorter or longer depending on your preference but don’t these women look both super fashionable AND comfortable? I think the key if you have a bold pattern, like the one on the left and center, is to keep the shoe colors simple. Two solid colors max. That way the dress and shoes will complement each other instead of compete. Now, if you want to wear a sneaker with lots of colors and patterns go for it! This is just if you want an simple no-fail combo.
Cozy Sweater Dresses
What an easy and fun fall look! Just choose the sweater dress of your liking, then pair with some classic high-top converse (like the gal on the far left and my go-to) or choose a sneaker that has a color with works with your dress. See how the woman in the middle has different tones of green in her shoes? It works with the green of her dress without being matchy-matchy. Same goes for the pink dress. The hot pink in the shoes gives a fun edge to the outfit while still working within the color palette.
Chic Oversized Sweaters With Skirts
Look how cool our gal Suzanne looks! And this shoot was from 2019. It just goes to show that this look has longevity:) I’m sure a lot of us have a maxi skirt and an oversized sweater or sweatshirt in our closet too so let’s get into some more looks below…
Look at how versatile this combo is. I love that Karen styled that chunky orange sweater with that delicate silk shirt. Then to balance the sweater chose extra chunky sneakers. I would wear this in a heartbeat. I also like that each of these looks has sneakers that are neutral in color so that the clothes are the focus.
P.S. I just noticed that Jenna is actually wearing pants but it looked like a shirt when I picked it so I still think it’s good inspo. Ha. I mean that sweater is incredible.
Obviously, jeans had to be a category. Sneakers and jeans are basically the PB&J of outfit pairings. But now is the time to have a bit more fun in the sneakers department. Take these bright orange sneakers. This oversized white blazer and jeans would have been a cute look…but with those sneakers, it makes this outfit exponentially cooler.
But you don’t always have to have a bold color to make the look cool. You can also play with your hemline. All of these sneakers are cool and classic but notice the difference in hems. You can have it hit right at the ankle, give them a little rolled-up cuff, or have them extra long. It all depends on preference but don’t be afraid to play around.
Business (Extra) Casual
If I worked in a slightly more traditional office, THIS would be my look. A tailored trouser, blazer (or jacket), and fun sneakers. It’s a cool professional outfit that’s also actually comfortable. I love the idea of getting to play with color and pattern too. But speaking of casual…
This look makes me want to move back to the east coast ASAP! Sneakers and loungewear may be the actual PB&J of outfit pairings since there are very limited footwear options when it comes to sweatpants. Regardless this matching set/peacoat look is stylish and super cool. If loose sweatpants aren’t your thing, leggings are a great substitution. What a perfect running errands look.
So there you are with some inspo looks. Now onto our shoe picks. Some we own and love, some are in our carts but all are pretty great (if we do say so ourselves). To start us off we have Em in her new favorite pair. Enjoy!
From Emily: I originally got these for a Madewell shoot and quickly loved them. They are the perfect balance of colorful/neutral and sporty/everyday casual. They just make any of my casual outfits more fun which I am very into since comfort is still my #1 priority.
From Jess: These are my go-to, goes with everything, effortless everyday sneakers that I LOVE. I first saw them on my cousin and they always looked extremely cool on her. So finally one day I asked if she’d be okay if I bought them too. She of course said, “DUH, yes!” and I haven’t looked back since. Also at $24 you can’t be it. 10/10 and they come in kid sizes too:)
From Caitlin: I love a loud/statement shoe (shocker) but these are surprisingly wearable – the olive background and snakeskin trim really make them feel a bit more neutral and the pink and blue are such unexpected and fresh pops of color. (They also come in a whole bunch of other colorways, if you want to get a bit louder!) These REALLY dress up a plain white t-shirt and jeans – huuuuge fan.
From Emily: I’ve been living in these sneakers right now. I lost one of my checkered Vans but these are solid summer sneakers, that feel graphic and cool and better for long walks than the Vans are anyway.
From Ryann: These are my favorite sneaker to wear when I am running errands, want to look cute and stylish, and also am living on a prayer that I’ll get myself to the gym at some point. They really are so versatile as they can be worn with so many outfits but are also supportive and comfortable to walk or even run in. I have them in an off-white and tan colorway with the orange swoosh. I truly wear them constantly and cannot recommend them enough!
From Caitlin: CLICK THROUGH!!! These velcro shoes are SO MUCH COOLER than the side profile alone indicates – there are 11 different colors (!!!) and the color-blocking on each pair is so cool and fresh. I get more compliments on my Charlotte Stone shoes than literally anything else I own (have been screaming about their platforms for the past 2 years!) and these are no exception. I love the profile, the exciting reimagining of velcro, and that they feel like a party on your feet. LOVE:)
From Mallory: The Air Force 1 has always and will always be one of the most popular sneakers on the block and I’m not gonna lie it’s taken me a long time to finally “add to cart” for this reason: I wanted a neutral (ish) pair but not the classic white one that everyone has, so when I came across this white pair with an orange paisley swoosh I was immediately sold!! I LOVE the way these look with denim & I am incredibly obsessed with them. Please note the sizing can be tricky (it’s been an ordeal over here). It’s recommended that you go a half size down, but I wanted mine snug & I wanted to be able to slip them on and off & never lace them all the way (and the leather will stretch a bit over time), so I ended up going a full size down. The full size down is a bit snug at first but they end up molding to your feet which is cool and incredibly comfortable.
From Jess: I’m a sucker for a light tonal sneaker and how pretty is that beige!? I also love the cool lug sole that makes them feel a little more on trend (but not too “on trend”). I also was an exclusive Adidas sneaker wearer in middle school and high school so those three diagonal stripes take me back in the best (and subtle) way. These just feel elevated but still fun/sporty.
From Emily: Ok so I haven’t actually got these delivered yet but I am SO EXCITED. They are extra sporty, look great for walks, and I love both the colorway and that cool thick sole. Also, the design is really fun and feels very Portland:) I seriously can’t wait to wear these.
From Ryann: These are almost the exact colorway as my Nike Daybreakers that I LOVE and wear constantly. I am considering buying these because I’ve wanted Nike Air Max’s for a while and I already know that I love how these colors look with so many outfits. They might even be more comfortable and supportive than my Daybreakers! I am also considering ordering them in black and white because I don’t have a black and white sneaker currently. Either way I am dying to try these and can see myself wearing them with jeans, trousers, and definitely loungewear.
From Caitlin: Click through again – coming in hot with another pair of multi-colored shoes! These have a pretty chic and retro profile (and they also have laces, if that’s important to you). They’re a new drop that I haven’t tested out yet, but again – can’t go wrong with Charlotte Stone shoes. Cheers to supporting a small, women-owned business with cute and fun products!!
From Ryann: You might recognize this shoe from a very little-known movie called Forest Gump :). Needlessly to say they are iconic and bring a retro 70s flair to any outfit. I love wearing them with black Dickies that fit like trousers, and a white t-shirt. They make a very simple outfit feel effortless and cool.
There you have it! Any thoughts? Are you ready to slap some sneakers on? Any other recommendations? Let’s chat,
Love you, mean it.