Why Is Getting Dressed Between Seasons So Awkward? Leandra & Harling Dissect

shoes and bag still life

“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 Sept 20, 2019 at 12:00 PM Leandra wrote:

Hey! Are you feeling at all like the convos we’ve been having for What Would You Wear With This are a little manufactured and irreflective of our genuine work rapport? Let’s try something else by instead launching this question, which really, I want to know the answer to: What’s on your mind right now as it relates to fashion, or style, or shopping?

On Sept 20, 2019 at 12:03 PM Harling wrote:

Is it a stretch to theorize that the conversation feels manufactured because my outfits are feeling that way right now? Ha. I’m struggling with how to get dressed because I’m jumping ahead to fall….

On Sept 20, 2019 at 12:10 PM Leandra wrote:

Same! I’m always struggling with that this time of year. It’s like… I try to predict exactly what I’m going to want to wear and then start planning into it like I’m an advertising executive trying to get ahead of an upcoming presentation, even though I don’t know what the client wants but I do have an inkling from having worked with them before. So I start road-mapping, but by the time the presentation comes around, the client has explained exactly what they want and the presentation I put together is… useless… I am the client… the presentation is me….

In non-metaphoric terms: I have a habit of buying stuff that I don’t need yet, then by the time I need the stuff, they feel old, or really, they feel like a caricature of what I want to say with my style. So then I get the right thing because the dust has settled and the season is here and I’m certain. This year, I’m trying a new thing where I don’t buy anything. Except these. Maybe.

On Sept 20, 2019 at 12:21 PM Harling wrote:

Yeah, I overcompensate as soon as the season changes, then try to reinvent the wheel with my wardrobe. I put things together that I’ve never worn before without thinking them through, or ruin outfits I loved the first time I wore them by adding stuff that doesn’t need to be there.

On Sept 20, 2019 at 12:25 PM Leandra wrote:


On Sept 20, 2019 at 12:33 PM Harling wrote:

It’s true. I can’t un-see the loafers I recently paired with my long-sleeve vintage Austrian crop top from Imparfaite Paris (similar here) and these pale blue creatures of comfort pants (similar here). That outfit that looked so much better when I wore it with sandals last spring.

On Sept 20, 2019 at 12:45 PM Leandra wrote:

So… call me your wacky woowoo Aunt Sally but I have a theory about what is going on. On the heels of MFW, which Prada owned (I know this is an opinion we share) and you mentioned you loved it because it was trendless (I don’t disagree, but I also think it was mostly just an essentialist version of what it has always been). But broadly speaking, Prada resonated with a much bigger sample size than just the two of us. It is often relevant, but this season, it was really relevant. There’s an essentialist whiff in the air, because culturally speaking, it seems that we’re re-evaluating our relationships to innovation and consumption. And, to bring it back to your wacky and woowoo Aunt Sally, I’d like to guess, with zero context beyond my own mental objects, that this vibe ties back to the stars. I read at the beginning of 2019 that the planet Saturn has relocated to Capricorn and that it’s going to stay there for a little while. Idk how long! And apparently Capricorn is a sign of like, structure and simplicity and quality over quantity. And I really feel like the world is feeling that impact! Or at least my world is. Fashion is the lens I choose to absorb my existence through, and in my lifetime, I haven’t experienced such a profound, macro-level doubling down on essentialism, a trimming of the fat. A reigning in on what’s important and what’s not. Who I am and who I’m not. Locally speaking, it’s hitting me in the closet. And it sounds like it’s hitting you too?

On Sept 20, 2019 at 12:55 PM Harling wrote:

Oh, it’s hitting me. And it’s strange to experience that while confronting a wardrobe full of florals every morning. I just want to wear black trousers with a super fine-gauge knit top and nondescript loafers and maybe a gold clip-on earring. To be clear, I don’t believe in astrology, but I guess I understand your urge to attribute this shift to something seismic and universal because the pull is strong. Sry Aunt Sal.

On Sept 20, 2019 at 12:59 PM Leandra wrote:

That looks like a pretty accurate depiction of you! I remember you wearing some permutation of that toward the end of last winter. But what are you wearing right now to scratch the itch?

On Sept 20, 2019 at 1:11 PM Harling wrote:

Glad you asked! I actually landed on a very satisfying-to-wear look last night this dress from COS plus this Barbour jacket plus these loafers.

On Sept 20, 2019 at 1:14 PM Leandra wrote:

Side note: Snickers bars are basically protein bars, right?

On Sept 20, 2019 at 1:16 PM Harling wrote:

For context for the reader, I’m just gonna let them know you have, like, four empty wrappers scattered around your laptop right now, which is directly across from me. So glad you’re getting in your daily recommended dose.

On Sept 20, 2019 at 1:25 PM Leandra wrote:

That outfit you mentioned sounds cute! I’ve been mostly wearing black wash jeans with black or navy sweaters and sandals and then stretching in the way of accessories. I actually find the Repeller earrings much more relevant in the context of a dark winter outfit than I do a lighter fare summer look. But tbh, this transition has reminded me how I have always felt—like it’s not about what you wear so much as it is how you wear it. I’m convinced I could wear the same exact outfit every single day and look different. (As a matter of fact, I challenge myself to try it for a week.) Today, for example, I’m wearing a grey cardigan with light wash denim cut-offs, white socks that hit my shins and a pair of black and white loafers. I wore the same thing on Monday and Tuesday but on Monday I had on my sock shoes, and a big red cashmere scarf over my shoulders. On Tuesday I had on sandals. Today I’m wearing a pearl necklace, a big gold wrap bracelet and a bunch of gold huggies (tiny hoops) in my ears. But, I know what’s coming, so this look feels boooooooooooring. By mid-next month, I’m going for plaid trousers, a rugby, a turquoise necklace, and suede loafers.

That’s one part of me. The other part is going for black wash jeans, silver sandals, a navy blue sweater, and RHINESTONES IN MY EARS. The nuance is that I’m also wearing a white crew neck t-shirt under the sweater because I need something to break up the darkness.

On Sept 20, 2019 at 1:30 PM Harling wrote:

See, idk, to me this transition DOES feel like more about what I’m wearing vs. how I’m styling it. My closet literally does not contain the clothes I want to wear. All my hero pieces feel too feminine and my accessories feel too cute. I basically want to wear the same clothes as those featured on the @hommegirls Instagram account but accented with overtly ladylike (which I consider very different from feminine) accessories–grandmotherly stuff like pearls and tortoiseshell barrettes and soft satin purses.

On Sept 20, 2019 at 1:32 PM Leandra wrote:

What do you think it’s a reaction to? Like is this the-new-you, or the-realized-you that’s always been underneath?

On Sept 20, 2019 at 1:40 PM Harling wrote:

That’s a good question. I think it’s both. It’s been here in that what’s swirling around in my head is largely a composite of outfits my mom and grandmother have worn. But it’s new in that I don’t feel like I’ve repressed it up until now. I just didn’t feel the urge to identify with it in a definitive, singular way. There was too much other stuff I was interested in experimenting with first.

On Sept 20, 2019 at 1:44 PM Leandra wrote:

Makes complete sense, but do you think you can tie your identifying with it to, like, coming to terms with being more like your mom or grandmother than previously you believed yourself to be? Or am I reaching—is this a pure function of how fashion is changing?

On Sept 20, 2019 at 1:49 PM Harling wrote:

It’s definitely a function of how fashion is changing. But even though I’m interested in dressing differently, and know what I like, I’m still stopping short. I don’t quite know how. It’s reminding me of that graduation speech someone gave, where they talk about how your taste evolves faster than your ability to meet it… DO U KNOW WHAT I AM TALKING ABOUT?

On Sept 20, 2019 at 1:51 PM Leandra wrote:

Ira Glass!

“Nobody tells this to people who are beginners, I wish someone told me. All of us who do creative work, we get into it because we have good taste. But there is this gap. For the first couple years you make stuff, it’s just not that good. It’s trying to be good, it has potential, but it’s not. But your taste, the thing that got you into the game, is still killer. And your taste is why your work disappoints you. A lot of people never get past this phase, they quit. Most people I know who do interesting, creative work went through years of this. We know our work doesn’t have this special thing that we want it to have. We all go through this. And if you are just starting out or you are still in this phase, you gotta know it’s normal and the most important thing you can do is do a lot of work. Put yourself on a deadline so that every week you will finish one story. It is only by going through a volume of work that you will close that gap, and your work will be as good as your ambitions. And I took longer to figure out how to do this than anyone I’ve ever met. It’s gonna take a while. It’s normal to take a while. You’ve just gotta fight your way through.”

On Sept 20, 2019 at 2:00 PM Harling wrote:


On Sept 20, 2019 at 2:12 PM Leandra wrote:

But actually, I challenge the notion that the only way to break through the bad taste is to continue making. It is one part of it, no question, but I can’t articulate how valuable it can be to find a mentor or role model, or, really, any model to whom you can aspire. I’m not talking within the context of how to dress, but it seems related because how you dress is reflective of your taste, and your taste informs your style, and your style, you know, is an expression of you, so! Getting your taste where you want it to go is more than just trial and error, it’s trial and output and feedback and error, then more feedback, then modeling, then trial again. But you need this feedback to be coming from someone who you trust, from someone who has a taste level that satisfies a rank you know you’re capable of reaching.

Do you ever feel that way with your clothes? Getting dressed on the heels of fashion week used to be so easy. For weeks, I would just roll into my closet and make these looks and feel like I nailed it every single day. I look back now and realize that’s because I was coming down from a month’s worth of inspiration from venerated members of the fashion establishment—the unlikely but powerfully good style holders that you rarely see in photos but never miss when you’re at a show. To Ira’s point, I saw the good taste, and because of my own taste, or my own pursuit of taste was able to pinpoint exactly what appealed to me and it helped crystallize my own sense of style.

You know, I’ve been thinking a lot about interdependence in my own life, and maybe this is going to take us on a tangent, but I think it’s a relevant one because when we talk about meeting the expectations of our taste levels, we can’t do that in a silo of oneness. It requires a level of trust, and faith, and interdependence on an influence that is bigger than us to help shape the mold. This is not the same as copying the influence! But it is a framework.

On Sept 20, 2019 at 2:21 PM Harling wrote:

I see what you’re saying, but I also think the evolution of personal style is a bit of an outlier because any feedback you’re getting is purely indirect. There’s no third party person who is dissecting your outfit choices in the morning, or annotating them with red ink. It’s only you, and your interpretation of the things you’re seeing and absorbing day in and day out.

There is undoubtedly an influence that is bigger than you that shapes what you desire to wear, but at the end of the day, your perception of that influence is yours alone. And I think that’s where I get overwhelmed, because even though the digital era has allowed personal style to take so many shapes, it’s also made it more difficult to stop throwing spaghetti at the wall and feel like you can wait a beat to see what’s sticking—to really and truly hone in on what speaks to you and why. It takes patience and a great deal of intention. Two things I’m trying to keep in mind right now, especially when it comes to getting dressed, but also in my life more generally. Because it’s so easy to get swept up in the temporary thrill of instant gratification. 

On Sept 20, 2019 at 2:22 PM Leandra wrote:

It sounds like you’re ready to take the time to break out of the cycle of trial and error and really dig your feet into the shoes of your style. Sometimes we forget that just because you’re ready doesn’t mean you’re actually there yet. But if you can appreciate that this stage, like any other, isn’t permanent, it can actually be fun to see yourself on the precipice of change without trying to change it for lack of a more efficient word. I guess this is what they mean when they say: “Trust the process.”

But to your final point, Harling Ross, ah, the thrill of instant gratification! What would you wear with these?

Feature graphic by Dasha Faires.

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This byline is used for stories that involved several Repeller team members, and company announcements.

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