I Tried Dressing "Like A Lady" For a Week

When it comes to my toilette, I am low maintenance to a fault. I don't wash my hair that often, because it gets too dry; I'll choose coconut oil over La Mer any day; I don't know how to contour; I couldn't style my hair if you paid me; I just bought Birkenstocks. If I were a protagonist in a movie, all of this would be effortlessly charming: the Girl Who Just Doesn't Try. But in real life, my attempts at undone quirk often turn me into the Girl Who's Awkwardly Underdressed At Fancy Events. I'll always be more of a thrift store aficionado than a polished businesswoman, but sometimes I gaze at my wardrobe of slouchy jeans and zero hair products and worry: Am I doing this woman thing right?

The word “lady” has changed since the days when it was used to denote a woman of the upper class. It's slangier, now; either a term of respect (“Thank the nice lady for the balloon, honey!”) or one used to demean (“Watch where you're going, lady!”). Its masculine twin, "lord," has fallen out of fashion — Michelle Obama is the First Lady; Barack is not our Lord — though we still use the word “gentleman” in a sort of suave GQ-esque sense. In the United States of America, land of the free and home of the California beach wave, we don't really have “ladies." Still, there comes a time and an age when women are expected to achieve certain adjectives, like "polished" and "appropriate" and "elegant."

I don't care about being a capital-L Lady. But I would like to be ladylike, should the situation require it. Sometimes I wish knotted hair and wrinkled clothes weren't my default. I want to be able to control my own level of ladylike-ness. So I decided to try out the basic tenets of so-called lady-hood for a week, and when I say basic, I mean embarrassingly basic: nice hair, nice makeup, nice clothes. My qualifications were simple: I tried out one ladylike thing a day, and kept the rest of my look in all its messy glory. Maybe someday I'll reach the level where “experimenting with being ladylike” means throwing Mrs. Dalloway-worthy dinner parties and polishing silver, or wearing a bold lip and a bold eye at the same time — but for this slightly rumpled writer, a little red lipstick is cultural hurdle enough.

DAY ONE: RED LIPSTICK

I feel so awkward in lipstick. Oh, I know my insecurities are completely out of proportion with reality. I'm not one of those women whose lush, pillowy mouths are begging for a rich fuchsia, or whatever, but I know on a intellectual level that I look perfectly normal in lipstick. But on an emotional level, I feel like lipstick turns me into some circus freak, like everyone is laughing at me behind their manicured hands. This overreaction may seem ridiculous to the confident reader, but believe me, the cultural baggage and weirdness of makeup runs deep.

So, like Hercules facing the Hydra, I held my breath and went for it, club swinging. My grandma told me never to wear blue-based reds and I always listen to my grandma, so I opted for the loveliest orange-red lipstick from Elizabeth Arden, called Marigold. (In half-exciting, half-depressing news, this is officially the first nice red lipstick I've ever owned.) I carefully filled in the shape of my mouth; I blotted like a pro; I sashayed out of the bathroom to show my boyfriend, who responded, HORROR OF HORRORS, “I'm glad that's not your everyday look.”

Believe me, he tried to take it back once I fell on the floor like I'd just been tasered — “I just mean it's an exciting, unusual look for you...” — but the psychological damage had been done. I hopped on a train to go downtown, weeping all the way. Just kidding, I took a few troubled selfies.

I work in a very casual office once a week, and the trepidation I felt at showing up in lipstick was ridiculous. “AM I A TEENAGE BOY?” I wrote in my notebook. “Why do I feel so insecure at the idea of looking purposefully nice?” I know why, actually; I've written about it before. The whole no-makeup makeup look is safe, because you look like you didn't try, and if you didn't try, who cares if people think you look bad? But once you're obviously trying to look good, you're vulnerable.

No one in the office said anything. I did share a (possibly imaginary) moment of lipstick solidarity with a new hire, whose hair was in glorious disarray and who was wearing a witchy dark maroon on her mouth. I went for coffee, took a few Photobooth selfies on the office Mac, and survived. No public shaming, no public stoning, nothing at all. Who knew? Wearing lipstick is not opening yourself up to scathing sociological criticism. No one cares what shade of red your mouth happens to be that day.

DAY TWO: PROFESSIONAL MAKEUP

Wearing red lipstick for a day should not have sent me into such a state of psychological panic. Cowed and ashamed by my own vulnerability, I decided to get my makeup done by a pro, in order to A) experience the world through a full face of makeup and B) quench any fear of looking ridiculous by continually reassuring myself that this woman knew what she was doing.

I booked an appointment with the lovely Jen Brown, a freelance makeup artist in Chicago who started out in visual arts but found her calling in makeup, because it held all her favorite elements of art: color, sculpture, light. I love makeup artists who treat their job like it's art, because I'm convinced that it's one of the most under-appreciated art forms out there. Jen's studio was beauty heaven: French music playing, soft afternoon light filtering through ivy-covered windows, and all the cream blushes a lady's heart could desire. Sure, my hair wasn't washed, and I was wearing jeans from the thrift store, but what of it? I WAS ABOUT TO HAVE HIGHLIGHTER APPLIED TO MY UPPER BROW BONES!

Jen created two full-face makeup looks that were both minimal and polished — in other words, perfect for my imaginary high-powered job where I wear heels all day. After applying a hydrating primer all over, she ran a concealer with a yellow base down the center of my face (between eyes, bridge of nose, chin) to highlight and cover redness. Then she applied a concealer with pink/salmon undertones to cover up any blue and purple under the eyes.

Next up: cream blush on the apples of the cheeks, fanned out up the cheekbone; highlighter in all the usual places (brown bone, inner eye, above eyebrow, upper cheek bone, and my personal favorite: cupid's bow); lashes curled and mascara-ed; everything set with a translucent powder. Jen mixed about three lipstick colors to create a sheer-ish pink, which she applied over lipliner and set with powder. Then she told me to take my hair down so that she could take a photo (me: “NO!” Jen: “It's not that bad.” Me: “…”):

Look #1

For the second look, she applied navy blue liner along the upper lash line and up towards my brow in a smudgy wing shape, brown eyeliner on the bottom lash line, and a gorgeous nude lip that I, lipstick-phobic as I am, was completely obsessed with: Tarte's lip tint in Grateful.

Look #2

When I left Jen's studio, I decided to take one huge step backwards for feminism and see how my brand new made-up face affected the menfolk. I was curious to see if looking polished and slightly contoured would be some sort of male catnip. (Basically, I just walked down the street and glanced at boys over the top of my sunglasses.) I counted admiring stares from two frat guys, one dude with a mustache, and a hipster bike gang, while I was ignored by a couple of runners and a hot dad. Scientific conclusion: Never rely on hot dads for your sense of self-worth.

Thankfully, the main man in my life did notice, and would not stop telling me that I looked pretty (aw!). As the day wore on, Jen's second makeup look faded into something wonderfully casual, and by the time I was out drinking cocktails with my boyfriend, I felt like the slightly more polished/pretty version of myself that I've always wanted to be able to summon up for elegant drinks and candlelit conversations.

DAY THREE: FANCY KNICKERS

Fashion editors are always giving out tips like, "Wear fancy underwear underneath your normal clothes and you'll feel sexy and confident all day!” Wait, is that just Cosmopolitan? Either way, I decided to try it out, because what's more ladylike than a corset laced so tight you're forced to carry around a vial of smelling salts?

In an effort to do fancy lingerie the modern way, sans smelling salts, I subscribed to a service called [Enclosed], AKA the most magical of mail-order services in the world. Here's how it works: you specify your lingerie preferences and, wonder of wonders, [Enclosed] hand-picks a new pair of “luxury knickers” for you and mails it out every month. I've had pretty underthings before, but I've never had anything that could genuinely be described as luxury, so I signed up for the service with visions of La Perla dancing in my head.

The magic arrived in a little black box, which I pulled open to reveal a mesh bag filled with something netted and black-trimmed, nestled in pale rose petals. The underwear, by Jenna Leigh, was absolutely gorgeous, a sheer boycut neutral wonder that weighed about as much as a breath of wind. I slipped them on, danced around my bedroom like I was in a music video — but, like, a classy music video — and promptly covered them up with jean shorts and took myself out for coffee.

Did I walk like Marilyn Monroe and order coffee with the confidence of Greta Garbo? Not especially, since the secret about nice underwear is this: They're well-made, so you forget you have them on. This is a good thing, since thinking about your underthings all day long sounds absolutely exhausting. I wore my [Enclosed] pair during a day spent almost entirely alone, and the best part of my day was slipping into leggings and a thrift-store t-shirt and reading on the couch. Just me and my casual clothes and my expensive lingerie. Just because. Just because I'm worth it. Whoops, now I'm in a L'Oreal ad. But really, I think this may have been the most effortlessly ladylike day of them all, because the whole concept was fancy, subtle, and all about keeping your own lovely secrets close to your chest.

DAY FOUR: A DRY BAR BLOWOUT

If red lipstick is my Moby Dick, blown-out hair is my albatross. (Out-of-place references to classic English literature? That I can handle.) So I made an appointment at Blowtique, Chicago's very first dry bar, in order to conquer my inner Ancient Mariner. Danielle, the lead stylist, told me that Blowtique has a large percentage of repeat customers: Women who come in once a week for a professional blowdry, dry shampoo between washes like their life depends on it, and have more or less forgotten how to wash their hair themselves. At $35 for a blowout, never washing your hair again isn't the most unachievable dream in the world; it's basically the equivalent of buying a latte every day for a week.

Danielle prepped my hair with a cocktail of Kérastase's blow dry gel and heat protectant, then began to work her magic with a blow dryer and round brushes. “Women don't want the curling iron anymore, now that they've seen how natural hair can look when it's just dried with brushes,” she told me. My blowout took about 30 minutes, and Danielle assured me I could keep the look going for days by pulling hair back in “orange segment” shapes, spraying dry shampoo on the roots, and massaging it in. She also told me the psychological secret to attempting a blowout at home: start drying the back of your hair. “When people start at the front, they get too lazy to finish the back,” she said. I know I do.

I was giving a short story reading that night — I'd planned the blowout accordingly — and having my hair already done made the nerve-wracking process of waiting for my turn to go onstage so much easier. Usually, before any sort of performance, I constantly run to the bathroom to make sure I haven't accidentally morphed into an ogre — a nervous habit that's stayed with me since middle school — but that night, I knew I could relax and focus on my performance, because my hair was dried and styled and out of my hands. Sometimes money and a talented professional can buy peace of mind.

DAY FIVE: REALLY NICE CLOTHES

I own my fair share of cocktail dresses, dangly earrings, and heels, but they're all a little grungy — well-worn vintage pieces and Forever 21 holdouts instead of, well, whatever ladies buy. I've always envied wardrobes where every piece is clearly quality; you know, the type of simple clothing that clearly cost real money and is going to last its lucky owner for the rest of his or her life.

So I decided to dress nicely for a day. No more Birkenstocks. No more thrift store jeans. I wanted an outfit that would look appropriate and polished anywhere — the office, a cocktail party, a spontaneous '70s dance party on a cruise ship. I still love a good Nirvana-worthy grunge look and I'll always be prone to the hippie layers of Mary-Kate/Ashley/Free People, but today, I resolved to be polished. (I still didn't do my hair.)

The preppy-cool brand Slater Zorn sent over their Court Dress, whose quality was immediately evident. It fit perfectly, the fabric was thick and assuring, and it just looked like an outfit. You know? There was no need to accessorize it into appropriateness, or disguise its uneven hemline with a devil-may-care attitude. I paired it with my beloved leopard-print kitten heels from Madewell (here's a similar pair), and a gorgeous floral-and-leather watch from Olivia Burton, which may very well be the most ladylike thing of them all. Who wears a watch these days? Answer: Women who have places to go.

I didn't have anywhere particularly ladylike to go that day, but it didn't matter. Working at my desk felt more purposeful. Talking on the phone felt like an event. Drinking coffee felt elegant. I felt — not ladylike, exactly, but pulled-together, polished, like a woman whose appearance was under control and, because of that, wonderfully secondary to the work she was doing.

Maybe everyone else already knew this, but oh, I get it: Putting effort into your appearance isn't really about your appearance. It's about freeing your mind, ridding yourself of whatever weird lingering insecurities you have when your hair is messy. It's about letting yourself forget all about something as shallow as your appearance, so you can have a fantastic day, whether you're drinking coffee on the couch or — manicure gleaming — just hanging out with the ladies.