Taking The Sneaker-&-Dress Look All The Way

Someday when I have children, I’ll tell them of a time when fashion was much more strict. A time when the propriety of wearing white was determined by calendar pages, when red and pink clashed, and when pairing sneakers with dresses was only for the urban commuter (and not really okay even then); a time also known as my childhood. They’ll stare at me wide-eyed, half surprised, half pitying their mother who was bound by the now-extinct rules of fashion; I'll return a grave nod of my head, to show them their pity is just — that those times were just as hard as they sound.

Today, fashion rules are much less absolute. Prints can be mixed, "clashing" is hardly even a concept anymore, and white prevails all year round. We live in an age where anything goes, but that doesn’t mean that everything goes together. Such is the case with sneakers and dresses. Heels are an obvious go-to, and a low profile slip-on is a new interpretation of understated flats, but there's an invisible line somewhere that, when crossed, makes your dress-and-sneakers outfit feel like it belongs on a straphanger from a bygone era. And, I think that line is right around the bigger, softer athletic shoes, but does that make reaching for them a flat-out don't? I thought I just finished telling my future-kids that there are no rules, so maybe it's time for this one to be broken, too.

A short dress and a pair of casual sneakers has become an easy combo to pull off given the variety available, and the fashion world's official go-ahead. We wear sundresses with sporty slides. Our LBDs call for monochrome Keds. But, I wondered what would happen if I took this look to the extreme. Would I be able to pull off wearing an athletic sneaker with a long gown? Or, would I look like I was just trying to get somewhere fancy in a hurry? There was only one way to find out.

For starters, let's unpack the fashion sneaker. This isn't a trend that happened by accident, because we all just stopped giving a damn. (Though, we'll admit our collective prayers were answered by the blaze of runway shows taking athletic shoes seriously.) Karl Lagerfeld sent sneakers down the Chanel couture runway and they sold out in short order (for $4,000 a pair, at that). He had already showed pink-and-white tweed fabrications for fall '14, an especially popular show set in a fictitious luxury grocery store, and paired the shoes with pencil skirts and suits.

When Lagerfeld was asked why he brought the rubber soles back, he said, “If you want to look really ridiculous, you go in stilettos [to] a supermarket.” And, as surprising as practicality is on a runway, he’s right. When you need to get stuff done, sneakers just make sense. When you want to get fancy, or command attention, heels seem to be the default choice — and this is a hanging-on fashion edict I'd like to put away. (With Karl's help, we can do it!)

For my out-there attempt, I chose the New Balance sneaks because they were the bulkiest ones I could find (which also makes them insanely comfortable). The larger the shoe, the harder the style is to pull off, and I wanted to make sure I took this challenge to the limit. I skipped socks to make my not-just-commuting intentions ultra-clear. I used the same line of thinking I call to when picking out accessories: The burnt-orange and yellow tones add some pop, but the dark colorway also keeps the pair slightly toned down. For my dress, I grabbed a longer black-and-cream Tibi one with eyelets and a sheer panel at the bottom, which created movement, and ensured the footwear would be seen.

I can’t say that I felt as elegant as I would have in a killer pair of heels, but I felt something completely different: exponentially more cool. I looked like I was really putting thought and effort into my combinations — and coming up with something unique. I felt like I had tried to solve a fashion puzzle, and was shocked to find that all the pieces fit. The outcome was unexpected; the sneakers an element of surprise.

Some might say that this outfit isn’t practical, that you can’t wear a gown and sneakers everywhere. To that I say, au contraire: sneakers allow you to wear a gown anywhere. They dress it down in a way that lets you get away with a fancier look at a more casual venue. Or, they make a more elegant look come off a little more cool. You might feel this combo is too extreme to wear to a wedding, for example, but I can guarantee that if you went for it, you’d have no problems dancing the night away (and would not be carrying your shoes to the after party). One could argue that sneakers and a dress is too weird for a first date, but I would argue that the person who appreciates your sartorial creativity is one you want to go on a second date with. Maybe you think this outfit is too extravagant to wear to Whole Foods, but I would simply remind you that Karl Lagerfeld said it was okay. Have I assuaged all your fears?

Fashion is meant to be fun. And, simply put, anytime you're taking yourself slightly less seriously, you're likely having more fun — an equation that's all but proven by a cheeky pair of tennis shoes beneath a floor-length gown. For me, the style went beyond diversion and into functionality by allowing me to wear — on any given day — a gown that would otherwise hang around in my closet waiting for my next big invitation. When I pushed the limits of what I thought would work, I was able to access another level of my own wardrobe. And, I have a sneaking suspicion that was the best possible outcome.