What to wear if you want to look like you know what you're doing with your life even though your shit is spread between so many toilets it seems impossible that it'll ever get together?
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Alternatively, the prompt is: what do I wear when I want to look like I know what I’m doing with my life even though I don’t? One time I heard Barry Diller on a podcast say: “No one knows anything including myself.”
He called it the best advice he could give, which I took it to mean that we’re all just trying to figure shit out. We’re trying to do it all the time.
Some of us are more relentless, or maybe the word is fearless (less self-conscious?) about achieving this state of “figured out” while others among us have a harder time. It’s like, if I don’t realize that none of us know anything, I think that the little I do know isn’t enough, or is enough — embarrassing enough to stop me from trying to figure shit out because god forbid I expose the profound, yet insecure truth that I. don’t. know. anything.
Idk anything!
In the end, the difference btwn us (me and Bar) is not in how much we know, it’s in what we’ll do to bridge the gap of unknown.
Unless it’s not! Another interpretation could be: rules are arbitrary in our personal, adult lives. We all make them up so just do what the fuck you want — make a plan and be courageous (but also open-minded!) about sticking to the script and go!
No?
Here’s the thing about dressing to look like you know what you’re doing with your life even if you don’t: you want to be taken seriously, right? Like you want the people in your purview to not write you off as a flimsy fucker in a jingling bracelet but you also want to exude this energy that says, ~*~give me advice if you have it! Bc I could use some guidance or at a minimum, compassion.~
It’s a combination of “Take me seriously! I know what I want” and also, “Pleeeez help me.” All of it is wrapped in that underlying sense of no one knowing anything, including myself. So you’re wondering if there’s a way for your clothes to say it for you because it’s a mouth full and somewhat contradictory and people don’t seem to want to accept this fact of being human — that we are walking contradictions, so what do you wear to acknowledge it?
In the past, I’d have told you to throw your balls against the walls, like chuck them into several walls.
“Depend on yourself to be the confidence factor. Surprise the hell out of them with your candor, so what if you don’t know what you’re doing with your life? No one knows anything including those people you’re talking to!”
But now I’m not sure that’s the right advice, I think more likely you probably want to wear something simple. By your own terms! Something you feel innately confident in, but which also provokes this vague sense that you’re taking a risk.
On top
My comfort zone is a button-down shirt. Do you know what yours is? Identify it and then think of what could be a low-key deviation from it. A low risk, but still somewhat risky alternative. For this argument, I’m defining risk as an alternative to the comfort zone — vaguely unfamiliar but still familiar enough.
Like this silk crochet top, which has the makings of my comfort zone — a collar, an open neckline, a relatively loose fit. It pairs with bottoms the same way a button-down would (tuck it in, leave it out, the majority of my upper half is covered) but it’s not actually a button-down. And certainly, it’s not as stiff. Indulge in the slinkiness, Leandra. Become one with it. I look like I know what I’m doing with my life and the proof is in the puddles
gathering at my wrists.
Now bottom
I chose a pair of pants that are practical. They’re responsible. They’re quiet but they’re cool. Lightweight enough to wear through the summer even though they cover my legs. Shapely enough in that cool cocoon way that suggests their wearer is thoughtful about how she gets dressed. And they’re a faded shade of navy blue, which makes them a softer color option to wear through a warm season.
The pockets are big enough to harbor my insecurities
OR the various task orders I sign on a daily basis because I am responsible for signing task orders. It’s as if they (the pants) say, “I know how to build a house.” Now whether the onlooker is to believe this house is lifesize, metaphoric or that it is just a lego rendering remains vague but who cares, the pants also ask, “Who wears the pants?” And then they answer, “I do.”
I do!
Part of the key here (though this is less about the vibe you’re going for and more about the rules of tension-dressing) is that the top is delicate — it’s this dainty crochet fabric that is like, “I’m a little flower” (I’m singing this in a dramatic, mocking tone), whereas the pants are the French equivalent of American Carhartts. So you’re like, “I’m a flower” on the one hand and “I build houses” on the other.
Take this information and put it in one of your big ass pockets as you evaluate where we’re at in this equation: Slight deviation from comfort zone top + practical bottom.
On shoes
Big pants call for small shoes. It’s honestly as simple as that. And small pants tend to call for big shoes. These are cognac suede — my favorite fabric/color combo (particularly with denim) but now that I think about it, I actually believe a satin pair of mules would have better served this look. Hold on, let me try.
Yeah, it’s good! But the above (as in, above it) is not for naught. Both work — and now as far as the dressing equation, we’re at: Slight deviation from comfort zone top + practical bottom + opposite shoes.
Jewelry
Like a punctuation mark, which I know that you know by now. “Serious” jewelry on my digitals and wrists, fun jewelry on my ankle and neck. The other thing I’ll say, btw, about wearing a strand of playful beads (or disks) is that they look more put together when you wear them with “fancy” earrings (like diamond studs — they don’t have to be DRAMATIC diamonds! or pearls, or even just sleek gold mini hoops — my favorite ones are Mejuri; 14k gold and $30 each).
You can reverse this order: gold chain on your neck, lots of beads on your wrists; it’s really the fun jewelry that is going to say, “you’re invited to give me advice,” but the serious stuff counterbalances it — acknowledging that you know what you’re doing even when it seems like you’re walking through life in a blindfold.
Alternatively, you can opt for a different fun accessory altogether — a bag that is like, “I have jokes to tell you, none of them are funny but it would behoove you to laugh anyway,” or a hat that does just as much. I tend to find these glimmers of fun (joy, really) in printed cloth fabrics a la:
Joy hat in figure A — this one is Paul and Joe. I like these ones just as much (maybe more?) for $74.26 (tie dye!), $20 (stiff crochet), $18.59 (Hawaiian floral print) and $13.99 (fruity!)
I think I should expound upon hats. Does that interest you at all? Y/N? The bag is from Gabriel For Sach!
To wrap the equation
Slight deviation from comfort zone top + practical bottom + opposite shoes + combination of fun jewelry and serious jewelry = what to wear when you want to look like you know what you’re doing with your life even when you don’t.
Although now that we’ve come this fart (a typo I won’t correct), I have to say, it’s not that you or we don’t. It’s just that we (we, right?) are still figuring it out — at home, in process.
Stay tuned for next week’s deep dive into how to wear denim cut-offs without feeling like a teenager. And while I still have you: any more requests for this franchise? Let me know by leaving a comment or replying to this e-mail.
Signing off yours truly,
Mortimer
Haven’t read this one yet because I had an idea for a question and didn’t want to forget! What to wear when I’m a Pilates teacher and am SOOOOOOOOOO bored of wearing Lycra all day every day but also need to be able to do Pilates but also really wanna look cool and not like a Pilates teacher....... x
Yes, large trousers give you weight, in the best sense of the word. Jane Birkin in a recent podcast was wearing Carhartts and praising their energy btw. I also find they are the easiest item of clothing to lend a sense of fashion/nonchalance in a work environment that’s more stiff than the contexts you describe.
Shoes though: I totally see your point about not wearing big shoes with big trousers - but what do you do when you have ankles and calves that are not quite as dainty as yours? I often find that I wouldn’t be quite able to pull off the same type of shoes.
The top deviation: can it be a silk shirt, which is more vulnerable than a stiffer fabric? Can the deviation come from pattern in the shirt? Would you in that case wear fun jewellery at all, at the risk of being a bit overloaded?
And one I wanted to ask in your jewellery post and didn’t get a chance: ok good jewellery brands. But what makes a good piece of jewellery. What makes it fun without being tacky or cheap - and this is not always to do with the price tag.
Hats would be interesting to talk about. Especially in relation to face shape. Or where to where them. Can anyone wear them, if properly chosen, or only hat heads (têtes à chapeau)?
I love that you talk about clothes’ attitude. I think it’s what matters most about them (in addition to keeping us warm ;-))