The Best Way to Dress Is Like Your 5-Year-Old Self

Lindsay Miller
Lindsay Miller

At the risk of sounding like I'm really feeling myself, I've got to tell you: I'm dressing better than ever. I'm, like, on another plane of my own personal style. And, now that I'm 34, age has been the deciding factor when it comes to my revised approach to dressing. But if you think I'm about to regurgitate that boring conventional wisdom that the older we get, the more we just know what we like and what looks good on us, and our fashion sense just gets sharper . . . I'm not. That's because my new fashion philosophy is this: the absolute best way to dress is like your 5-year-old self.

Think about it. By the time we're in kindergarten, most of our basic and most enduring aesthetic tastes have been hardwired into our very mitochondria. (Pause while I google whether DNA is even present in mitochondria. OK. It is.) For me, this means I will always have a soft spot for shoulder pads, teal, leopard print, and terracotta. I was raised in Southwest Texas in the late 1980s, after all. But beyond that, children take a devil-may-care attitude to — and a fierce pride in — getting dressed. It's at that age that we start to discover our own identity. It's at that age when most of us start dressing ourselves in the morning; if not for school, on the weekends, at least. When we're still too young to do much of anything autonomously, style is an easy and obvious way for kids to express their rudimentary sense of self. And they have fun doing it. Coincidentally, while I was on my second draft of this story, a fellow writer tweeted this truism after hanging out with her niece:

the best dressed people on earth are 5 year old girls who get to pick out their own outfits

— Pixie Casey (@pixie_casey) November 9, 2018

Clearly, this is a widely agreed upon fact. So, if we already collectively admire the way 5-year-old girls dress, why not just take it one step further and emulate it? Over the last few months, I've been doing just that. To put this style ethos into practice yourself, just follow these few simple suggestions — because no 5-year-old or evolved, modern woman enjoys following rules.

Instagram user SusieBubble — a longtime stellar example of this fashion ethos.

1) Care About What You Wear — Just Don't Worry About It

Like many of us, I have been galvanized anew by the current political and cultural climate. When it seems like everything is falling apart around us, feeling joy can be defiant. When sexism and racism and anti-LGBTQ+ sentiment seem determined to squelch all the joy out of free expression, expressing ourselves freely becomes more urgent than ever. And you know who's really good at expressing themselves freely and without one iota of shame? Any given 5-year-old, that's who.

This is why I stopped waiting to cut my hair into a platinum pixie, afraid it might read as too aggressive or too unprofessional or too masculine. I no longer fret about misinterpreting the "upscale business casual" dress code on that event invite and just wear whatever feels right. (I haven't been turned away at a door yet!) I'm done obsessing over finding the downright perfect outfit for New Year's Eve, at any level of violence to my bank account, when I can more easily rediscover something I truly love already in my closet.

When getting dressed starts to feel like a hassle or a point of stress, just remember being in pre-k. Channel that thrill you felt when you went to a friend's house and opened the lid to their dress-up box for the very first time: a world of possibility, yours for the making. Clothes should be fun and exciting and freeing, not anxiety producing.

2) Throw Off Gender Conventions

As a little girl, I loved a frilly, feminine tutu moment . . . just as much as I loved wearing my dad's old Cub Scout uniform shirt, which was covered in patches and had a jaunty bandana at the neck.

I'm not saying young kids are immune to our culture's gendered approach to every goddamned thing. But they are less likely to understand the ramifications of bending those gendered rules, which means they're more likely to have fun breaking them. Be more like that and an entire wave of style opportunity will rise to meet you.

For example: I recently met up with my running coach, Blue, who was wearing an insanely cool pair of Nike track pants. "I want those," I said. "I wonder if they come in a women's version." Blue looked at me quizzically for a second. "Who cares?" he said (not in a dick-ish way, but in an actually perplexed way). Emboldened, and also kind of embarrassed at being so basic about the whole thing, I shopped both the men's and women's sections of ASOS that afternoon and uncovered at least three long-sleeved t-shirts I both had to have and never would have uncovered if I hadn't just ignored these silly and divisive categories.

3) Approach Getting Dressed as a Chance to Play Dress Up

My friend Olivia is an expert at applying this maxim. On any given day, she may be channeling a wealthy New England widow who's waiting for her cabana boy to bring her a G-and-T or a pottery teacher in Sedona who's running late to her aerobics class. And she will declare as much when you meet her for lunch. (As you can imagine, the associated outfits are fabulous.)

I'm not saying your sense of style should be put on or fake, by any means — Olivia's never is. I am saying this approach makes putting together an outfit infinitely more fun, successful, and innately childlike. For example, when I was in kindergarten, I won a contest to greet Miss Teen USA at the airport in my hometown of El Paso. I vividly remember the story in the local newspaper about my illustrious honor, which featured a photo of the teen beauty queen coasting down the street on a skateboard in high-waisted, acid-washed shorts and a pair of white leather cowboy boots, her shellacked bangs immovable in the wind. In that moment, I knew she was the f*cking coolest. Kelly Kapowski's bangs paled in comparison. Debbie Gibson could never.

Not long after, I was shopping with my mom at Mervyn's when I came across a pair of pink cowboy boots, replete with not just a leather tassel but a f*cking glitter-festooned lightning bolt on each side. In hindsight, it's obvious that my style icons drew me to them: there was that teen beauty queen, but also the cartoon rock star I idolized, Jem, and the chic women in cowboy boots and saran-wrap tight jeans who populated my mom's social circle. When I wore those powder-pink boots, I stood taller — literally, because the boots had a half-inch heel, but also because I became a character: someone mostly me, just with a little extra something.

Photo courtesy the author — pictured at center with her little sister Courtney and a kindergarten friend.

4) Wear All the Things You Love at Once Even If They Don't "Match"

When I was 5, you might see me affix several star-shaped, glitter sticker earrings to each lobe, buckle on a neon-trimmed fanny pack, smack a NKOTB slap bracelet on my wrist, and pull on a pair of aggressively ruffled socks — all while I was still in my underwear. (That's me in the center of the picture above, inexplicably wearing a visor indoors, multiple shades of hot pink, and an extremely loud pair of spandex pants — shorts? shants? — that I wish I still owned today.

Those pink glitter cowboy boots I mentioned? One of my preferred ways to wear them was with black spandex bike shorts and a huge t-shirt shirt emblazoned with a pink, airbrushed leopard. And you better believe I cinched that swath of extra fabric with a hot-pink, plastic t-shirt clip. I wasn't obsessing over piling on status symbols so a street style photographer would validate my outfit. I was just wearing all the stuff I deeply loved at once because I deeply loved it.

To really embrace this part of the dress-like-a-5-year-old ethos, channel that same spirit of unhinged sartorial clutter in your adult life. Are these vintage lucite dangle earrings with this leopard-print Clare V. waist bag and that pair of marabou-fringed mules I bought on Amazon for $29 too much? Most likely they are, which is why they are just right.

5) Check Your Materialism

As a 5-year-old, I had no concern for, or even awareness of, clothing brands. (It didn't take long for a burgeoning awareness of Sassoon, Hypercolor, and Esprit to change that, sadly.) I just gravitated to colors, prints, shapes, and details I liked. And I certainly didn't have a gigantic closet full of clothing options to choose from. I was a kid! If I liked something, I wore it all the damn time and found ways to wear it as part of as many outfits as possible.

As an adult who loves fashion, letting go of an obsession with designer logos and the consumerist desire to buy more clothes than I can even possibly wear isn't easy. But there are myriad advantages to trying. It is great for your financial health, helps you let go of the desire to impress others, and helps hone your signature style. Case in point: the purple windbreaker I'm wearing in the top photo is something I throw on multiple times a week because I love it so much. I wear it with dresses, with cute workout clothes, with jeans and t-shirts. You can even style it as a skirt — I kid you not. It's recognizably me, and I've more than gotten my money's worth out of it.

While following this new motto has served me well, I think it should be obvious by now that I still dress like a grown woman with a closet full of grown woman clothes. I'm not proposing trying to squeeze into t-shirts from the kids' section, sporting actual NKOTB and Muppet Babies paraphernalia, or wearing Velcro sneakers — actually, maybe I am suggesting you try that last one. I am suggesting we embrace our deepest sartorial desires, rediscover the carefree approach to clothes we took as kids, and own the hell out of our one-of-a-kind, all-our-own personal style. Won't you join me?