One of the good things that came out of the COVID pandemic was the collective abandonment by women of wearing uncomfortable clothing to work. Pre-pandemic, women were more likely to pour themselves into Spanx or endure foot pain as they teetered around in heels. Post-pandemic, women just aren’t willing to make that level of sacrifice, at least not on a consistent basis. This shift was more profound than just giving up discomfort but instead very much rooted in how clearly the spotlight shined a light on the expansive professional inequalities between men and women. As I say in this post, as society finally woke up during COVID and realized what women knew all along — that they were all doing double the work, grooming twice as much, in charge of the majority of the household responsibilities, and more…while getting paid less — women appreciated their value and are now demanding more and apologizing less. 

It’s not that women are dressing like slobs, quite the opposite, actually. As the threshold of a willingness to be uncomfortable, today’s woman has figured out how to pair comfort with professionalism. Tailored pants with elastic? Yes, please. Comfortable performance fabrics in professional silhouettes? Definitely. Workplace sneaker looks that pass for client interfacing? Easy, figure-flattering professional silhouettes that don’t require shapewear? Flats that allow women to keep up with men while walking? Yes, yes, and yes. Women have learned that it is possible to look appropriate for work and comfortable at the same time.


This makes wearing sneakers to work, particularly with dresses in the summertime, incredibly appealing. However, as women are in their infancy navigating this look, it can be a hard one to master. The wrong sneakers, wrong dress length or silhouette, and instead of looking chic, you might as well put on one of those religious prairie dresses and learn how to French braid your hair. in today’s post, I have created some sneakers with dresses looks for work along with some tips on how to successfully navigate this style.


Shirt dresses are great silhouettes to pair with sneakers. The length of these dresses, or any dresses for that matter, is critical. You don’t want the hem of the dress to hit at the widest point of your calves. This style, from Argent, for example, is a longer, relaxed midi that sweeps around the lower calf to the ankle, depending on your height. What is also important, particularly with longer dresses, is that your sneakers aren’t too clunky or orthopedic looking unless you want to create that compound look. In this look, I styled the dress with a refined pair of Stan Smith Adidas sneakers and finished the look with a navy belt from The Fold and a toggle necklace from Jennifer Zeuner. Both the necklace and belt add refinement to this outfit and elevate the casualness of the sneakers.


A shift dress is another style that works well with sneakers because this style usually looks good with flats in general. Usually, the body shapes that look best in these dress silhouettes are ones with less defined waists and slim legs. When you wear sneakers you are shortening the visual length of your legs which also has a widening effect because when you optically shorten a body part, you also make it look bigger. it’s why women often stand on their toes while trying on pants. Even if their reason for doing this is instinctive, they can see the slimming difference this makes. For someone like myself, who has a curvy figure, heavier legs, and thicker ankles, wearing a dress like this is bad enough and would only be made worse if I threw on a pair of trainers.

For those of you who this style flatters (you have my envy) a style like this is great for sneakers because shift styles tend to look better with flatter shoes. I styled this shift from MM. Lafleur with leopard and gold-trimmed sneakers from Cole Haan. The look is further finished with gold drop earrings from Kate Spade.


sneakers with dresses

One skirt or dress silhouette that doesn’t work well with sneakers is a knee-length pencil skirt. This styling can often look very 80s workaday lady commuting home from the office. Pencil skirts tend to need heels. There are some exceptions to this but, typically, these pencil skirt styles are too casual for work. It can also be tricky to find that dress sweet spot when choosing styles that work with sneakers. If a dress is too corporate in look, the sneakers are too casual to pair with them or if the dress is too casual, with sneakers, the outfit can come across too weekend-looking.

This dress from Elie Tahari hits that sweet spot of being work-appropriate when paired with sneakers but also not too casual that it looks like you’re dressed for weekend fun. I styled the dress with these simple sneakers from Everlane and a multi-colored Gorgana necklace.


sneakers with dresses

As with the shift dress, the trapeze dress, like this one from COS, looks best on those with a silhouette that isn’t too curvy and buxom. In addition, the trapeze style has a shortening effect that is emphasized when paired with sneakers. I like this look but would recommend it for more of a business-casual workplace or for days when you can dress more casually.

I styled the look with colorful sneakers from Soludos and a pair of beaded hoop earrings from J.Crew.


sneakers with dresses

This dress skirts the line in terms of workplace appropriateness depending on the environment of your workplace. It’s an easy, relaxed, midi style from The Oula Company. With how casual many workplace environments have become, a dress such as this may be perfect, but before making the decision to wear a style such as this, be sure it is suitable for your day.

This dress was styled with Veja sneakers that pick up the blue of the dress and goldtone doorknocker earrings from Kenneth Jay Lane.

Sneakers with dresses in the workplace is very much a viable look for work as long as you choose the appropriate silhouettes for not just your body shape but also your work environment, and choose styles that pair well with sneakers. It should go without saying, as with your other work shoes, the sneakers you wear to work should always be clean and neat.