Last Tuesday I was waiting in line at Blue Bottle coffee. (Okay fine, don’t laugh – their coffee is actually good.) I was wearing, what I thought was appropriately, little. Straight leg jeans from Everlane, a simple white button-up shirt I’ve owned for probably three years, my go-to black loafers, and a navy blazer I’d recently purchased to accommodate the unpredictability that is Chicago weather in October. Nothing fancy.
That sort of outfit you throw together when you’re running late but need to look cute for your actual job. A woman behind me in line struck up conversation –because lines at coffee shops have this effect on people – and remarked, “Oh my gosh, I love your style. You’re always so put together!
How do you pick out your outfits?” I almost choked on my coffee. Listen, I don’t wear dirty clothes.
The jeans had been washed that morning, which was frankly an accomplishment at that point in the day.
The shirt was wrinkled from being stuffed into my work bag the day prior because my office AC was broken and I’d sweated through my regular shirt.
My blazer sported several coffee stains on the sleeve that I was trying desperately to conceal with my purse. But none of that mattered.
Because out loud. There’s this misconception that being put together means you don’t try. That somehow getting dressed each day is a complete afterthought and you just happen to never look stressed, unkempt, or like you just threw clothes at yourself.
There’s this belief that in order to look good you can’t appear to care too much or it ruins the illusion of effortlessness. Newsflash. That’s literally impossible.
I’ve been watching people play this game for years. As both a blogger who writes about fashion and beauty and just a general “person who cares what other people wear” in public. If you compliment someone on their outfit, nine times out of ten it’ll be something they threw together in the morning without a second thought.
The outfits that receive the most praise are always ones that look effortlessly stylish. We compliment people who make it look like getting dressed wasn’t a process. Never do we lavish praise on someone who obviously took hours to construct their look.
I’m sure those people exist, and maybe they look fabulous. But we as a society don’t celebrate them the same way we do Kate wandering slowly around Manhattan in a well fitted pair of jeans and a white tee. We reserve that kind of adoration for people who look like they didn’t try at all.
Which is exhausting and ridiculous. My friend Sarah went to law school with me so she’s been playing this game longer than most. She has to look professional for court all the time, but she’ll swear up and down she just throws together whatever and runs out the door.
And she sort of does! But as she told me drunkenly one night (she always tells me these confessions after a couple glasses of wine), she picks out her entire outfit the night before, irons it, and has backup options if something doesn’t work. “The trick,” she explained, “is always looking messy on purpose.” She’ll wear a crisp blazer but with mussed up hair. Or a tight ponytail with a slightly wrinkled shirt.
It’s never enough to look sloppy or undone but just enough to look like a real person wore it. Like she didn’t put too much thought into it. I’ve found myself eyeing my closet in that same way lately.
The outfits I get compliment on most are almost never the things I put extra thought into. They’re generally my go-to pieces I’ve owned for years that suddenly seem like a new idea when I put them together. It’s usually something fancy paired with something you’d wear every single day.
An old pair of earrings I found at my grandmother’s house with a thrifted tank top. A silk blouse with literally ripped up jeans that still somehow fit like a glove. The key is making sure your fancy doesn’t overpower your daily and your daily doesn’t look too shitty to wear with your fancy.
Like there’s a fine line somewhere where everything has to look intentional, but you can’t appear to have put in the intention. Which is so stupid because in order for everything to look intentional you have to have put in the intention. I bought this camel coloured coat back in December after saving up for months.
It’s probably the fanciest thing in my closet and the most expensive single article of clothing I own. But I can’t wear it with all cute things because then I look like I’m trying. So I wear it with ugly trainers and hole-y jeans.
Or with a five dollar t-shirt from H&M. My expensive coat makes the cheap things look expensive, and wearing cheaper things with my coat makes it feel less insane. My mum does this weird thing where she’ll downplay anything nice she’s wearing.
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Someone compliments her dress and she immediately says something like, “Oh thank you! This old thing? I probably got it at Kohls years ago.” She’ll say that about a brand new shirt I bought her last week.
I swear one of these days I’m going to challenge her on it. Make her actually say “thank you” instead of instantly trying to minimise what she’s wearing. I used to do that too.
Want someone to compliment something about your appearance? Tell them you barely even tried. Make them believe that your shirt is two sizes too big and you’re wearing your boyfriend’s sweatpants because he’s dirty and didn’t want to do laundry.
Acting like you don’t care about your appearance is the ultimate power move against compliments. But here’s the thing. And please feel free to scream at me if you disagree BUT I don’t think that people who “effortlessly” look put together aren’t trying.
I think they’ve just mastered the art of what looks good on them that putting together an outfit doesn’t require thought each morning. They know what flatters their body, what colours suit them, what neckline will draw people’s eyes where they want it to. They’ve done the work.
Take my coworker for example. She is by far one of the most put together people I know. Doesn’t matter the season – her outfits are always on point.
Simple, classic, anything but flashy. I used to think she was naturally born stylish until I realised she wears the same combo of shirts and trousers every other day. Like she has five plain blouse type shirts, two pairs of trousers, and three cardigans.
She found her vibe and she isn’t letting go. That right there isn’t not trying. That’s not trying because she figured out what works and what she loves and now getting dressed is easy.
She doesn’t have to think about it because she’s already done the thinking. I’m working on that for myself now. Purging my closet of anything that either doesn’t work or that I don’t actually wear.
I’m trying to narrow down my outfit combos to ones that I know I love. That I know will fit my lifestyle but also make me feel good and look put together. It’s made picking out outfits in the morning so much easier because I’m basically just remixing different variations of the same thing.
Sound boring? Kind of is. But it’s also made me feel more “me” than trying to constantly be creative with what I wear.
Because when I wear things I love and things I know work for my body it inherently looks better. Which means I get more compliments, not because my clothes are expensive or have cool brand names but because they fit together. I think the secret to looking put together without actually trying is knowing your style so well that you could dress in the dark and it would look like you.
When you’re wearing clothes that suit your body and your personality AND fit your lifestyle, everything becomes easier. Things look nicer because you actually feel nice in them. Of course I still have days where I’ll try on three other shirts before deciding I should’ve just stuck with my original selection.
And I’ll still look in windows to cheque my outfit before leaving the house.
The difference is that I’m no longer ashamed to care about how I look.
If someone asks where I got something or compliments my outfit I say thank you now.
Instead of rushing to explain why that shirt cost five dollars. Don’t get me wrong. Looking amazing takes effort.
It takes time and dedication and energy and yes, money. But there’s nothing wrong with caring about how you present yourself to the world. This whole “trying too hard” mindset we’ve created is just another tool for women (let’s be honest, women mostly) to feel bad about taking up space and wanting to look good.
So maybe effortlessly stylish isn’t about not trying at all. Maybe it’s trying hard enough to know what you love to wear but wearing it with pride instead of shame. Maybe it’s accepting that yes, style does take effort.
But once you put that effort in it allows you to love and accept yourself just a little bit more. Photos by Jessie Andrew Photography
