Are you a contrast dresser or uniform style type?

And the world premier of styling my dream shoe

I am a firm believer that your personal style boils down to whatever clothes you wanted to wear from the ages of eight to fourteen, but couldn’t. Then, modernizing them with some styling to reflect the grown-up you, and adding a dash of trends. Simple as that.

It all started in Spring 2024 when I was doing my annual transitional wardrobe inventory. Unsurprisingly, my wardrobe had once again fallen behind as an accurate reflection of my style—most evidently, my shoe collection. I could tell a purchase was brewing. But what?

While staring at the entrails of my half-cleaned closet, it hit me like a lightning bolt: what I needed was a Sunday School Wedge.

And what is a Sunday School Wedge?

Allow me to set the scene—

It’s Sunday. You’re in the tasteful button-down and mini skater skirt combination you’ve had planned for the past six days. You’ve strapped your adolescent legs into some floral, faux leather, or aggressively neon-patterned shoe you scored at Plato’s Closet after an article in Seventeen Magazine promised you your crush would be enamored if you managed to unlock the elusive combination of neon lipstick, a wedge, and confidence.

You have two of these things.

You saunter into Sunday school feeling promiscuous and on top of the world. After the sermon, you’ll probably have pancakes and orange juice at home. This is your runway, and your moment to shine.

That is what the SSW ultimately embodies: the feeling of being both young and old, playful and grown. Just as attached to the fragility of youth as you are deeply grounded in the reality of being an adult.

After a year and a half of failed attempts, I finally found a shoe that had everything I was looking for: the timeless texture of suede, detailing that sets it apart from the crowd, a color that pops at the bottom of the frame and holds its own against the visual weight of the rest of the outfit.

So without further ado, may I present… my Sunday School Wedge.

(I don’t know why I keep capitalizing it—it just feels like a sign of respect.)

Someone mentioned it looks like a “modern princess shoe,” which instantly reminded me of the ballet slippers in Barbie and the 12 Dancing Princesses—one of my favorite on-screen fashion memories. This only strengthens my opening theory and reveals this as another piece I subconsciously secured as an ode to my childhood.

But when a piece like this enters the wardrobe, finding it is only half the battle. The rest comes when it’s sitting in your closet and you’re faced with two choices: to flow with the style of the piece and build an outfit in its designated tone, or go your own way and become a creature of contrast.

To flow with the style of the piece means identifying the way it looks, feels, or what emotions it evokes—and then amplifying that by building an outfit with items that share similar attributes. You’re intensifying the archetype of the outfit and creating a clearly defined character with your clothing.

To be a contrast dresser is to choose your next piece in direct defiance of the original. To build an outfit teetering between textures, styles, or feelings, ultimately giving birth to a complex character—much like yourself.

I believe a healthy wardrobe is full of outfits that achieve both. Some days, you feel less complex than others, and having pieces that pair easily with like-minded items can be a blessing. Other days, you’re much more awake.

I have a rule when I buy a piece of clothing: I spend thirty minutes styling as many outfits as I can with it. This is to avoid the dastardly fate of buying pieces to feed my closet and promptly forgetting they were purchased once they sink into the belly of the beast. It also gives me the opportunity to check in with myself: am I leaning more into dressing for contrast lately, or enjoying the flow of my clothing?

So, here are all of the outfits I made within a thirty-minute timer—and the difference between dressing for contrast or dressing for uniformity:

One of the first words that comes to mind when I look at these shoes is “ballet.” Naturally, this leads to “tutu,” and thus, my very first outfit was born. When I started with these shoes, it became clear very quickly that working with them was going to be a lot easier than styling against them.

This outfit felt complete in that effortless, summer kind of way—like I could get away with the lack of accessorizing if I blamed the heat, relying instead on the shapes of the skirt and top to signal my intentions. Still, it piqued my interest in taking this base somewhere more fall-appropriate...

Another look that stood out to me came immediately after, when I shifted toward intensifying the Y2K essence of the piece. My vintage pink sequined skirt jumped out as an obvious choice, and shortly behind it, my nylon tiger-printed top. Anything that hangs a little low on the collarbone offers the opportunity to block in a fabric with an undershirt, add a little accessorizing, and voilà—we have an outfit.

One extra gift this look in particular brought me was the reminder to style white t-shirts under loose fitting summer tank tops as the perfect transitional fall styling choice.

Now lets get into a little contrast dressing-

A slack-jawed button-up sitting above a textured or structured skirt has always been one of my favorite silhouettes. The casual, boyish wrinkling of the shirt overpowering a maximalist pink sequin number was one of my favorite combinations of the day. It struck the perfect balance between two very different feelings: relaxed and punchy. A hidden wooden necklace added an extra layer of texture, tying in with the warm-toned bag on my shoulder and completing the look.

Another contrast I wanted to try was the idea of feminine versus academic. When I started building my next look, I was drawn to my favorite white bubble-hem maxi. It felt too similar in tone to the shoes, so I wanted to hit hard in the opposite direction. I began with the same button-up I had loved before, then added a little pattern mixing with a microscopic-patterned vest. For extra measure, I topped it off with a lightly pinstriped blazer.

An energy I associate with academic is also clumsy—the endearing awkwardness that comes from ignoring the physical self in pursuit of intensifying the mental one. You can thank Milo Thatch from Atlantis, and my own personal first ten years of dressing for life, for that stereotype.

I think contrast dressing is one of the great revealers of self. It makes you question the stereotypes in your head and gives you the opportunity to understand yourself a little better. Why do I think this skirt embodies the word feminine? Why does the “opposite” feel like adding something masculine? Why does academic mean, to me, a jumble of fabrics squished together, while to others it might mean crisp uniforms, clean button-downs, and the scent of stone and rain?

For me, academia is an extremely noble pursuit—and it’s most pleasurable to watch in environments where money isn’t present. True academia is an insatiable desire to understand more, by choice, despite a lack of resources. That kind of character, the one who’s trying to appear professional while being oblivious to the “styling blunders” the upper class of academics might spot, is far more interesting. One truly had their head in a book. The other... not so much.

To me, academic style is pinstripes unknowingly stacked on clashing patterns, navy paired with black because it’s close enough, and more. Essentially, how I dressed for most of my life until I read a fashion book.

Now this is where things started to get sloppy.

Sometimes, when I’m putting together an outfit and nothing is quite landing, I get tunnel vision. Getting dressed shifts from building something that reflects my style to simply getting dressed and getting out the door.

I started with the idea of a little sock styling, adding some stripes to the bottom of the frame, which led me to choose a pair of jeans that would show them off. Jeans I hardly ever wear. The outfit as a whole was fine, but it wasn’t me. And that’s a huge distinction to make when getting dressed.

Did you negotiate your taste for practicality one too many times and land your body in a style you don’t even recognize? It’s quite the slippery slope.

This led me to try swapping the socks for something a little less attention-grabbing: a butter yellow and baby blue pairing—

Which led to the revaluation of the outfit here-

I like it more, but still just not quite right for me. So we scrap it and keep it moving.

Now this is an outfit of true contrast. Suede appears twice, but not matching. Denim is stacked on top of cashmere. Silk is layered over leather. It’s both casual and intentional, oversized and fitted, formal and slouchy. This outfit belongs nowhere—and everywhere—all at once.

And despite all of this, it’s still not my style.

Another reason I love this thirty-minute styling ritual is because it keeps my styling muscles flexible—something that absolutely cannot be achieved if you only get dressed to leave the house. I can fall down the rabbit hole of negotiating fits and styles without the pressure of running out of time or needing to be somewhere. I can build outfits and take the time to realize I don’t actually lovethem for myself—and use that insight to steer me back toward a style that feels more me.

While these shoes can thrive in both contrast and uniform dressing, I had more fun when I was flowing with their style. A pair of shoes like this—so clearly marching to the beat of its own drum—deserves to be listened to. I’m sure there will be times I try to force-feed it its opposites, and we’ll be able to compromise. But for now, I think I’ll just do what the shoe tells me to do.