What do I wear if I want to look professional, be comfortable and still feel cool

One among many possible answers to the most popular question from last week's open thread

Are we human, or are we cucumber?

The question that garnered the most upvotes at last week’s open thread was how to look cool at work. Cool but professional. The majority of the queries suggested the environments you work in are professional, but not super strict, so I was like, oh, what about a suit? Originally, actually, I was like, This prompt is on how to dress appropriately for work in clothes you actually like but why does it seem like doing this is impossible?

Like why do we go to stores we’d never shop at to buy clothes that we’re going to have to spend 70% of our waking time wearing?

A suit is a good place to start if you work in an environment that is quasi-formal, but have the flexibility to expose different shades of your flair because out of the gates you can feign like three different outfit formulas by pulling the pieces apart. (E.g.: ba da bing ba da boom, you’ve got a jacket you can wear solo, you’ve got pants you can wear solo, and then in cahoots, you’ve got, drumroll plssssssss: the suit.)

Part 1

I’ll tell you more about the suit later — but the grey turtleneck in figure A is by Kule. The Dr. Scholl’s style sandals are Roger Vivier. Also look at theseeeee. In figure B the t-shirt is Khaite. For this look, the Kule one — boxy and lightweight, amenable and soft is pretty great too. The thongs (hehe) (still gets me every time) are from Toteme. These do the trick for $88.

I couldn’t decide what I preferred with the whole of the suit.

One time last winter, I wore it with a navy blue half-zip and flat copper boots and felt like a million bucks, so I styled it with a featherweight grey turtleneck first (it seemed kind of similar) and opted for Dr. Scholl’s style sandals (not similar at all) that zing! They also sing, but more impressively, they zing!

We’re at that great inflection point in the weather where it’s not really a season — neither hot nor cold, so you get to decide when the morning rolls around that today you won’t make a decision about the climate because it doesn’t know for itself what it is. Wear a turtleneck with sandals, absolutely, for sure. Why wouldn’t you, you know? But then as I was thinking about it, I was also thinking…

If you’re gonna wear a suit to work, you don’t wanna look like you’re Wearing a Suit to Work, so don’t wear a button-down shirt — try something more comfortable and cool. Turtlenecks are comfortable, but they’re not really cool. You know what is like, a totem of coolness, though?

Ding ding ding! T-shirts.

My preference here is a boxy t-shirt because fitted ones tend to take on an air of formality.

So here — formerly figure B is the main event. I chose a white t-shirt although if I had a plain grey one, I’d actually have gone with that. Lately, I am coming to think that grey t-shirts are the unsung hero of any wardrobe that wishes to taut itself as versatile.

The other thing I’ll say about this t-shirt is that I wear it tucked in, but think it works just as well — might even be better if worn left out. Now, what’s going on with your limbs? Are you allowed to wear flip flops to work *if* they’re also kitten heels? Sometimes my preference with a really simple outfit are shoes just as simple, but still unexpected, then silly ass jewelry because FUN!

These rings are from a small brand I found on Instagram — or actually, really, they found me — Blooming Dreamer, the dolphin is Hola Amor and the microbeads are by none other than the original Roxanne.

You can’t see the ankle bracelets while I’m standing but when I’m rolling around my chair to say hi and talk tech support, you can catch a glimpse of what I’m like on weekends — down to swim, etc.

As far as the arms and my ears:

Figure A is from the turtleneck tango — I’d been wearing this wrist all week, it’s a collection, really, of two necklaces wrapped twice around my wrist (the mushroom being one) and two gold chain bracelets. Eventually, I’ll dismantle how I concoct these appendage-specific libations.

Figure B is from the t-shirt look. The juxtaposition of those discreet but still apparent pearl earrings caught a nice wave on the natural stone bracelet and white heart ring — two different vibes, one same look. The multiplicities, people! Dualityyyyyyy.

Part 2

The shirt: Mango

Now here have the pants worn solo, sin jacket. I’m assuming, again, because so many of your comments suggested that the environments are professional but not super strict — that the desire is more about being taken seriously (no one said this, but when I want to look professional or mature it’s usually because I actually want to be taken seriously), that a denim shirt is pretty fair game. You pair that mother fucker with some open foot shoes (these for $520, these for $390, these at $278, $90 for these, and a Real Real search) and a pearl necklace because it’s de rigeur and then you walk up to the Sliding Doors and you say:

To the left, to the left, the rings are by Brua Jewelry — at right, the yin yang is from Wilhelmina Garcia

What a great movie that was.

I kept my arms empty so that my fingers could star. They’re the ones doing all the typing, after all! This necklace is among the rare few beaded strands I have that is actually supposed to be a choker. Usually, I tie a knot in the back.

Here, by the way, is a group of pics that employ a sweater around the waist or shoulders. In case you keep one @ your chair but never actually use it. Or in case you don’t, but get cold, and keep meaning to bring one. Here’s your chance!

Color of the suit, I should add, doesn’t matter — I have this great beige one, which is actually men’s and had it tailored when I was doing an appearance at the Berluti store in Paris in 2019. I have since modified like, 3 mens suits. That’s dramatic, honestly, it’s only been one.

The trick is to find a jacket that you don’t want to change and then you can do whatever you need for the pants. You know who is especially good at men’s suiting, I find, is J. Crew. This guy in deep sage? “Heaven!” Honestly, though, you can just pick a pair of trousers you have and love n pair them with a jacket of the same or similar color that either you already own or would like to own.

And if you go for a charcoal grey number, you don’t even have to wear a denim shirt. Anything cotton (a la something like this by Polo; non sequitur here but look at THIS), in white or light blue or navy or orange ombre (?) would totally work, too. I also like the ones from The Gap!

Part 3

My final trick isn’t tricky — it’s the blazer as a top, do you think you could wear that to work?

It’s a little impractical because when you sit down you’ll accidentally show your boobs to someone if there is no tank top or bra underneath it, but the risk seems worth it to give a lighter weight silk skirt the chance to be worn, or at least to be bought!

Are you allowed to wear clogs to work? Those would be great too. So would penny loafers. Often people ask which ones I think are best. G.H. Bass Weejuns are pretty good (Oooo…) but they take some time to break in. I’ve also found great ones from Church’s and Tod’s @ The Real Real and I just want you to know, because we’re friends, that my period is over.

More outfit ID q’s or requests? Just ask! Tap reply to this email!

I hope you do something fucking awesome for yourself today.

Signing off yours truly,

Leandra