Leandra and Harling Discuss the Urge to Look Less “Instagrammable”

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“What Would You Wear With This?,” heir to the throne of “Should I Buy This?,” is a monthly conversation between Leandra and Harling about the contents of their online shopping carts and the potential outfits that lie within. Come for the clothes, stay for the feelings.

On Fri, Aug 9, 2019 at 1:36 PM Harling wrote:

Hello! My sleeves are already rolled up, so let me jump right in: I’ve thinking a lot about how, more and more these days, I’m not really getting dressed in outfits. I just pick out individual pieces and put them on and…that’s it. And as a result, I don’t think my “outfits” are very good most of the time, but I kind of like them even more because they’re less Instagram-y? Have you experienced this? I like to think our style brains are cut from the same (terry)cloth, but, separately, am also curious to hear your take on the following items that are currently lingering in my shopping cart, and what you might wear them with:

This top (arguably the perfect nipped-waist, oversized short sleeved button down)
These shorts ($22.99! I don’t think I can resist)
This dress (to be worn with a kerchief around my hair and flip flops on my feet)
These shoes (I won’t buy at full price but I WILL stalk heavily all fall)

On Mon, Aug 12, 2019 at 11:55 AM Leandra wrote:

Yeah, of course it makes sense! I loved those Bottega Veneta square toe sandals with the thong and all the skinny straps when I saw them, but knew that attempting acquisition would never work, both because they’d sell out quickly and because I’d feel like a parody of myself if I ever deigned to wear them. I think we touched upon this when we spoke about trends earlier this month. I referenced an anecdote about a DJ tweeting, “If a blogger has it, I don’t want it.” It’s the same mentality here, just reversed. Actually, I interviewed Chloë Sevigny last week (please remind me that I’ve reached my humble brag quota for the duration of this exchange), and we were talking about style and getting photographed and she asked if I feel pressure to turn UP dressed UP in response to my asking her the same question and I told her that I felt like even though turning UP is kind of true to my constitution, I’m pretty self-conscious about doing it where I know there will be street style photographers. This, btw, is not me complaining about getting photographed, I marvel in the peer-level validation for being considered well-dressed but to this point, I’m also self-conscious about those peers thinking I am crying for attention.

But, you know, as I write this out it occurs to me that turning UP is, like I said, true to my constitution, so I wonder where that self-consciousness is coming from, really. Maybe I’m more self-conscious about being considered the sum of an Instagram account as opposed to a Thinking Woman. Not sure. But now it seems like the more genuine act of living honestly would be to get those Bottega shoes even though I know everyone has them.

I don’t know if this took us too far off course, but the TL;DR is: Yes, I am feeling the same pang of wanting to dress less, let’s say, “impressively” these days. I don’t know how much of it is tethered to returning to my “style roots,” a time before my access to stuff grew disproportionately (to a degree, all of our access has grown given fast fashion) and how much of it is more psychological (see: above). I do know that I hate those Loewe jazz shoes, think you should get that LPA dress, that the shorts from Mango look like they were *actually* designed for you, but that the Celine top you sent already sold out (but would have been perfect w/ the shorts!). Might I suggest venturing into TRR’s men’s section to find a replacement (if you want one)? I got a Dries short sleeve button down for $32 once.

This one’s for you
This one’s for Haley
And I think this one’s for me

To wear with HOTPANTS…which are harder to come by lately, huh. These are the closest I could find:

Overall vibe of this look is a bit tougher than my aesthetic, but I’d probably add pearl studs or a necklace and, like, Belgian shoes or a pair from Stubbs and Wootton.

On Tue, Aug 13, 2019 at 3:29 PM Harling wrote:

A list of urgent thoughts, in order of importance:

1. You can brag about interviewing Chloë Sevigny to me until the cows come home.

2. I’m so glad you hate the Loewe jazz shoes because I’m willing to be dissuaded from even entertaining the idea of dropping that much money on gloves for my feet. Idk why I’m very focused on foot gloves at the moment. These from Hereu (one of my favorite new brands of late) might be a more economical choice.

3. Is the root of this issue we’re talking about really just that relentless documentation via social media, street style, etc., conspires to reduce all who participate to caricatures of ourselves, i.e. flattened, 2D versions, which renders any stylistic choice that perhaps felt original at first-wear suddenly…well…uninspiring, to some extent? Commodified for viewing? Overwrought and overthought? Gross, at times? I thought the solution (or rather, the antidote) to this was to simply wear less color, because color has such strong insta-bait connotations at this point, but a two-week experiment of wearing all black and only black last winter indicated otherwise. Perhaps because I was still documenting it! And thus, another caricature was born. Does any of this make sense? I’m not sure. I’m definitely word vomiting up some very half-baked ideas, but only because I don’t have my finger on the answer quite yet.

4. Since clothes are confusing me, I am basking in the relative comfort of home decor, which I’ve found so much more satisfying than straight-up fashion lately (feels so weird to admit that…). MATCHESFASHION actually has a really fun homeware section. I just bought this pillow because it is basically cake. What do you think of this jugs jug??

5. That sleeveless plaid button-up/denim short combo is very reminiscent of a last-minute lumberjack halloween costume I almost wore in college, but I trust your vision implicitly. I will, however, definitively follow your lead on those Belgian shoes, TYVM. eBay has a ton of good ones:

6. I was doing market for an upcoming shoot and came across this Rachel Comey top, which is seemingly “just another leopard print shirt” but upon closer inspection is actually scratching a very particular itch I wasn’t even aware of. I’m seriously contemplating getting it with a Shopbop gift card that has been sitting in my nightstand for far too long. What would you wear it with? Moussy jeans and… I was going to say kitten heels, but I think these loafers would be a little less expected and therefore BETTER?

On Tue, Aug 13, 2019 at 5:17 PM Leandra wrote:

-Can’t wait to see what that cushion looks like in your crib.
Here is the perpetrator of your attraction to glove flats, but don’t forget, Martiniano was the first!

-Thanks for the eBay link, think I am going to buy those black ones.
Those M.Gemi loafers look a ton like these from Bougeotte. I got them like two years ago, and didn’t wear them at all, and suddenly locked eyes with their toe tips at the end of last winter, like they were a nerdy boy who had come back from camp really hot, and I drank their Kool-Aid and we’ve been dating pretty seriously ever since.

-What itch is that Rachel Comey top scratching??? I think you see something that I don’t, though if I put myself in your shoes (literally, see: these) I can fully envision you wearing it with a pair of shorts like the Mango mens-style swim trunks that you linked in your last email. Or these.

(Or these.)

I always forget about Shopbop. It is still good.

^An outfit that is boring, but that I 10/10 would (likely will, likely have) wear/worn. I’d soup it up with accessories, like pinky rings for all my pinkies (toes not withstanding!) and some chains around my neck and so on and so forth but hey this dovetails nicely with your point #3 about relentless documentation. I get what you’re saying–that maybe dressing more quietly is in pursuit of wanting to look less like a caricature of yourself, to not flatten yourself to a photo that lives in perpetuity, and that if you look less like a caricature, you might be less likely to self-document, to allow the outfit to live on in your mind as a hall-of-famer. But I’m more interested in the fact that you still wanted to document. Why did you want to document?

On Wed, Aug 14, 2019 at 2:32 PM Harling wrote:

I love that outfit you concocted. The only thing I would add is a gold chain belt.

Idk what itch the Rachel Comey top was scratching but my love affair was fickle–now I’m really into this bodysuit or this organza wrap top, maybe with this oyster-colored silk skirt. I’m basically concocting a transitional weather going-out outfit, so let’s round it out with either the aforementioned M.Gemi loafers or these ballet flats.

Shopping non-sequitur: Is Sydney-based brand, Matin, on your radar yet? Their stuff is a bit pricey but I’m into a lot of it, especially this chocolate-colored silk caftan dress, these twill pants, and this cotton/silk mini dress.

Another non-sequitur: As I’m making up potential fall outfit ideas in my head, almost all of them involve a pair of superrrrrr light-wash jeans.

Your points about relentless documentation are the perfect distillation of what I think I was trying to get at. Feels so nice 2 b interpreted by u. I think the urge to “capture” is ingrained in me, to some extent, at this point. I’m like Pavlov’s dog, except instead of salivating when confronted with food I reach for my phone camera when confronted with something I find interesting or funny or engaging or beautiful. I’m pretty conflicted about my stance on this impulse, especially because the people I spend the most time with (Austin, my sisters, my close friends from high school and college) don’t share it it in the slightest. They could be staring at the juiciest of summer sunsets at 6 p.m. a.k.a. golden hour and the idea of taking a photo wouldn’t even occur. It’s hilarious and makes me feel like a freak!

But anyways, I think the reason I still felt the urge to document even when I was dressed head to toe in simple, black items, is because capturing that became a narrative in its own right. Maybe that’s the point of what I’m trying to say: A photo of an outfit is no longer just a photo of an outfit in 2019. It’s a story, a headline, a thing to be captioned. And that changes everything, right?

On Fri, Aug 16, 2019 at 3:07 PM Leandra wrote:

But what is behind your impetus then, to share that story or headline or thing to be captioned?

When I track and try to break down how I feel when I’m motivated to share something, it’s usually punctuated by feeling like I’ve broken through something to arrive somewhere new. Example: pairing pants and a top that don’t work at first try-on, then pinning the pants up, loosening the top–whatever it is, to land upon feeling like, FUCK YEAH I LOOK EXACTLY HOW I WANTED TO WHEN I ROADMAPPED MY IDENTITY THIS MORNING. It’s like creative problem-solving in the most reductive way. And honestly, what is more satisfying than looking exactly how you wanted to, of manifesting from brain to body? It’s validation from yourself. To yourself. Obviously, once you set out to share it, you’re asking for validation from a third-party gaze but documentation doesn’t necessitate sharing. I take tons of pics that I never intend to let anyone see, they’re for my own visual record. Is it fair to assume what you’re talking about, really, is sharing?

Also fair to assume: I want that brown caftan. I’d love to wear it with suede loafers, or boots in the fall. Speaking of boots, is your head there yet? I think this is the vibe I’ll be going for.

They are super expensive, but I invite you to consider the vibe (chunky heel and straight shaft) more than anything else.

To pair with vaguely tapered trousers, like these or these:

And a cardigan like-a-this:

Have I already shown you this outfit? I feel like I have. Anyway, there’s a black beanie and pearl stud earrings, too.

On Mon, Aug 19, 2019 at 11:10 AM Harling wrote:

Hmmm. Good question. You’re right, I’m not just talking about documenting, which I often do just for myself, almost as a visual record/diary. Very different from sharing, which by definition includes the third party gaze and/or input. The experience that I’ve arrived somewhere new is definitely part of the impetus to share for me, sometimes. But other times it’s more about interaction that sharing begets. Sometimes I share purely for that purpose, not because what I’m sharing is particularly noteworthy–especially on “Stories” where the stakes are nonexistent. I’m pretty sure Stories are the closest thing we have to old-school circa 2013 blogs nowadays (low stakes hot take), and that’s why they are so satisfying to both partake in and observe.

My head is not anywhere near boots as of yet but it probably should be because last winter I had a boots identity crisis wherein all boots started looking funny/nonsensical to me, like a word you’ve been saying over and over again or staring at on a page for too long. YOU KNOW? I love those from The Row, particularly the subtle chunk aspect. Not sure what my boot vibe is but my general vibe is definitely these Brunello Cucinelli wedges with sheer black tights, a denim mini skirt and this Miu Miu sweater.

You’ve definitely already shown me a version of that outfit which is just as thrilling as it is admirable because it means you’ve really drilled down on your fall persona and it’s only mid-August. Meanwhile, I’m still spinning my wheels over yellow jacquard pants.

On Mon, Aug 19, 2019 at 12:35 PM Leandra wrote:

That Miu Miu sweater has been in my wishlist since Julyyyyyyyyyyyyyyyyyyyyyyyyyyyyyy. Sometimes wishlisting a thing is enough to make me feel like I own it, and tbh, you and I both probably have enough lace Peter Pan collars to approximate the sweater with a men’s v-neck from like, J.Crew or something. You also probably have the mini skirt already, definitely have the tights, just established you can make the sweater and do you remember the Hannah MacGibbon collection for Chloe that awarded the world with these?

Bet you can find a consignment pair for much, much cheaper.

So what I love most about the outfit you made is that you kind of already own it. Also, even though I don’t know you outside the context of work, I feel like you’d have picked out the same thing for the first day of school like, ten years ago. What is that?

Before you answer, one more thing: Congratulations! What you actually aspire to do when you’re sharing is, you know, share. Which is so different from showing, and I think it’s only when the impetus of posting gets a little cloudy and doesn’t feel as explicitly about sharing as it does about showing that you get kind of self-conscious. Right? Maybe not, I am very good at projecting. How did we get here? Didn’t this convo start as like, a love letter to rejecting capital-O-outfits and just throwing shit on?

On Tue, Aug 20, 2019 at 11:14 AM Harling wrote:

I have enough lace Peter Pan collars to decorate the coastline of California, so you are correct. Funnily enough, because I have an encyclopedic memory for most outfits, I only remember one first-day-of-school outfit and it was the first day of ninth grade when I was attending a new school and I wore an Abercrombie gray corduroy skirt with a ribbon belt and a pale pink Lacoste polo tucked in. Oh, and Rainbow flip flops! Frankly I had much better inaugural school outfits 20 years ago versus 10, when my mom was still in charge of picking them out.


I’ve attached one for evidence and would like to recreate the adult-sized version pronto with the following elements:

I’ve absolutely shared things for the sake of showing on occasion and you’re right, it does feel noticeably ickier. How DID we get here?? All roads lead back to Instagram, I guess, especially when we start out by talking about photographing outfits. Let me take you on a full-circle journey and lob you an outfit that is not at all attention-grabbing which is exactly is why I like it:

The shoes, I will leave up to you/fate.

On Tue, Aug 20, 2019 at 1:58 PM Leandra wrote:

Harling! That picture! That look. I wish in your approximation the Miu Miu flatforms were just flat, no form.

I like this game, and now want to see your hair bow and raise you a Dalmation purse. This is not a first day of school outfit, but it is a Sunday brunch look before brunch was Brunch with a capital B. Wouldn’t wear it again today, it feels almost too much like a complete runway look (Chloe!), which is not to say I don’t love those clothes but is to say I’ve never really been a full look kind of girl. Someone already thought of putting it together! My work is to pick it apart, discard what doesn’t serve me and keep/enhance what does! It’s not so different from therapy in that way. As far as your final look, how’s about a clog?

And for my final look:

Self-Portrait is doing knitwear, I like the cocoon sleeve so much, recently got these Nike shorts and have been wearing them like mad, would add a metallic strappy sandal, or perhaps an encrusted block heel (these are expensive, I know! It’s for vibe!) and to that, the overall persona reads: What to wear when you’re trying to accommodate multiple temperatures but also, “Chalet resident on Dancing With the Stars with a Nike Running Pro.”

Before I sign off, I promise you this, fisherman sandals are next. Gnt.

Photographed by Louisiana Mei Gelpi featuring Anissa Kermiche vase and Martiniano shoes via

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