How to Wear Sneakers with Dresses and Skirts Without Looking Too Casual

I Started Wearing the Shoes I Actually Wanted to Wear

For years, I think I had shoes divided into little categories in my head.

Tennis shoes went with jeans, shorts, leggings and anything involving a grocery store.

Dresses had their own shoes.

Skirts had their own shoes.

And if I was wearing something a little nicer, apparently my feet were expected to participate in the occasion whether they wanted to or not.

Somewhere along the way, I started questioning that.

Why was I changing out of the comfortable shoes I actually wanted to wear just because I put on a dress?

Why couldn't my sneakers come too?

Once I started paying attention, I realized tennis shoes could go with almost anything.

Dresses.

Skirts.

Satin.

Denim.

Florals.

Even outfits I would've automatically paired with sandals or boots before.

And once I started wearing them that way, I liked some of my clothes even more.

Because now I could actually live in them.

The Graphic Tee and Midi Skirt Combination

This is probably one of the easiest places I'd start if wearing sneakers with skirts still feels a little unfamiliar.

I'd pair a graphic tee with a midi skirt and sneakers.

The reason I like this combination is that nothing feels overly serious.

If the skirt is flowy or has a little volume, the tee keeps it casual.

I can tuck the front of the shirt in a little if I want more shape, or leave it loose if that's the look I'm going for.

With a graphic tee, I usually wouldn't pick a sneaker that is fighting for attention too.

A clean white sneaker works.

Black can work.

If there is a color in the graphic, I might even pull that color into the shoes.

Then I'd add a crossbody bag, sunglasses or maybe a baseball cap and call it a day.

This is exactly the kind of outfit I like because I can go run errands, meet somebody for lunch and walk around for a few hours without reaching that point where I'm quietly angry at my shoes.

We've all owned that pair of shoes.

Cute at 10:00.

A personal enemy by 2:30.

The Satin Skirt Doesn't Need Heels

This was one of those combinations I had to see a few times before it clicked for me.

A satin skirt with tennis shoes.

For some reason, satin can make me automatically think I need a dressier shoe.

I don't.

I actually like the contrast better sometimes.

I'd wear a satin midi skirt with a plain tee, fitted tank or casual sweater and then add sneakers.

The casual top matters to me because it connects everything.

If I have a dressier skirt, a dressy blouse and then athletic shoes, I may feel like three different outfits are having a meeting.

But a casual top brings the sneaker into the conversation.

If I'm wearing a leopard skirt, printed satin or something colorful, I'd probably keep the sneaker quieter unless I specifically want the shoe to stand out.

If the skirt is plain, that's where a red, burgundy, silver or interesting retro sneaker could be really cute.

I love this for dinner, a casual date or one of those situations where I want to look like I made an effort without looking like I spent forty-five minutes deciding what effort should look like.

The Denim Skirt Is Almost Impossible to Mess Up

If I can wear sneakers with denim shorts and jeans, it makes sense that I can wear them with a denim skirt.

That one doesn't require much convincing.

A denim mini skirt with a graphic tee and tennis shoes is easy.

A denim skirt with a fitted top, changes the look immediately.

I could also throw on an oversized button down over a tank and leave it open.

What I like about denim is that I can change the personality of the outfit with the sneaker.

A white sneaker feels classic.

A retro sneaker makes it feel a little more current.

A colorful sneaker gives the outfit more personality.

A black sneaker makes the whole thing a little quieter.

This is where I wouldn't overthink accessories either.

Small bag.

Hoops.

Sunglasses.

Maybe a cap.

Done.

Sometimes the outfit doesn't need eleven finishing touches.

Sometimes it needs me to stop touching it.

I Love Sneakers with a Floral Dress

A floral dress with sneakers has become one of my favorite examples of why we don't have to choose between feminine and comfortable.

I can have both.

I'd take a soft floral dress that I might normally wear with sandals and put on sneakers instead.

White is probably the easiest choice because the floral print is already doing something visually.

Then I'd add a woven bag, small crossbody or lightweight denim jacket if I need another layer.

I especially like this combination when the dress feels a little sweeter than what I normally wear.

The sneakers calm it down.

It doesn't feel so dressed up.

It feels more like me wearing the dress instead of the dress wearing me.

That difference matters.

I've had clothes that I loved hanging in my closet but rarely wore because I had mentally assigned them to some imaginary future event.

Brunch.

Vacation.

A nice lunch.

Somewhere with flowers and outdoor seating apparently.

Then I finally realized I can wear the dress to Target if I want to.

Nothing happens.

Nobody comes over the intercom and asks me to explain myself.

A Tank Dress and Sneakers Might Be the Easiest Outfit I Own

Give me a comfortable tank dress and tennis shoes and I'm halfway out the door.

This is especially good when I want one piece of clothing to do most of the work.

I don't have to figure out which top goes with which bottom.

The dress already handled that meeting without me.

For a fitted tank dress, I'd probably choose a cleaner sneaker and then add a light jacket, cardigan or button down if I want another layer.

A baseball cap can make it sportier.

A nicer bag can make it look more polished.

Sunglasses help almost everything.

This is also one of my favorite travel outfit ideas because I can walk comfortably and still feel put together.

And that's really where my feelings about fashion have changed.

Comfort doesn't automatically mean I gave up.

Sometimes comfort means I finally got smarter about getting dressed.

The Black Slip Dress Changed My Mind

A black slip dress can look completely different depending on what is on my feet.

Heels make it one thing.

Sandals make it another.

Sneakers change it again.

I especially like a black slip dress with black sneakers because the darker colors make the outfit feel more pulled together.

I'd add a black bag, sunglasses and maybe a few pieces of jewelry.

That's it.

If I wanted more contrast, I'd wear white sneakers instead.

If I wanted the shoes to be the interesting part, I'd try a sneaker with color.

I think this is where a lot of us get stuck with sneakers and dresses.

We assume the sneaker needs to disappear.

It doesn't.

Sometimes I want the sneaker to be part of why the outfit works.

An Oversized Shirt Can Become the Whole Look

An oversized button down with a short skirt is another outfit I really like with sneakers.

The loose shirt against a shorter skirt creates enough contrast that the outfit already feels styled before I start adding anything else.

I'd probably wear white sneakers or a low retro style sneaker here.

Then I'd carry a tote or crossbody bag.

The same idea works with an oversized shirt dress.

Sneakers underneath it keep everything relaxed and give me an outfit I can actually move around in.

I can shop.

Walk.

Travel.

Spend the day out.

And my shoes aren't the first thing I'm thinking about.

That's usually a very good sign.

I Don't Automatically Reach for White Sneakers Anymore

White sneakers will always be useful.

I still love them.

But I've stopped acting like they're the only sneakers allowed near a skirt.

Sometimes black looks better.

Sometimes red makes the outfit.

Sometimes burgundy pulls a color out of a print.

Sometimes a retro sneaker gives a basic outfit more personality than another accessory ever could.

Silver and metallic sneakers can also be fun when the rest of the outfit is pretty plain.

The easiest way I think about it is this.

If my dress or skirt is already busy, I usually let the shoe settle down.

If my outfit is basic, I can let the sneaker have a little fun.

That one idea has saved me from standing in front of the mirror changing shoes six times.

Usually.

I'm still me.

The Outfit Has to Look Like I Meant to Wear the Sneakers

This is probably the biggest thing I've learned.

I don't want my sneakers to look like the shoes I put on because my real shoes hurt.

I want them to look like they were always part of the outfit.

Sometimes one little thing makes that happen.

It might be matching a color in my sneakers to my bag.

It might be throwing a denim jacket over a dress.

It might be wearing a casual tee with a dressier skirt.

It might be picking a sleeker sneaker instead of a bulky athletic shoe.

I also pay attention to proportions.

If my skirt is really full, I may want a more fitted top.

If my dress is long and flowy, I might choose a sneaker that has enough presence underneath it.

If I'm wearing a shorter skirt, I have a lot more freedom because almost any sneaker shape can work.

But I don't think there needs to be a complicated formula.

I look in the mirror.

Does everything look like it belongs at the same party?

Good.

We're leaving.

I Don't Want Clothes I Have to Suffer Through

I think that's really what changed for me.

I stopped believing looking nice required some level of inconvenience.

I don't need uncomfortable shoes to prove that I dressed up.

I don't need to save dresses for special plans.

And I don't need to look at a skirt and immediately start wondering which sandals or heels I'm supposed to wear with it.

Sometimes I want my sneakers.

So I wear my sneakers.

And funny enough, wearing comfortable shoes has actually made me wear more of my clothes.

I'll reach for the dress because I know I can walk in it all day.

I'll wear the skirt because I don't have to build some complicated outfit around it.

I'll put on something prettier for an ordinary day because I know I can make it work with the shoes already sitting by the door.

That's the part I didn't expect.

The sneakers didn't make me dress down as much as they gave me permission to wear more of what I already owned.

A floral dress doesn't need a brunch reservation.

A satin skirt doesn't need a dinner reservation.

And a black slip dress doesn't need heels waiting beside it.

Sometimes Tuesday is enough of an occasion.

And if I can look cute, feel like myself and still walk through the parking lot without questioning every decision I've made since leaving the house, I'm calling that a very good outfit.

#EvolvingWomanhood

Healing Workbooks: Visit for Support