What Would You Wear with This
Leandra and Harling Talk Outfit Repeating and Retail Therapy Alternatives
01.24.20

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 Thu, Jan 9, 2020 at 2:13 PM Harling wrote:

It was tricky for me to figure out if I even had something to say about shopping this month, because I’m not in a particularly shoppy mood post-holidays, which are uniquely conducive to making fun-filled purchases. But I guess my malaise is fitting for a month when our editorial theme is Consumption and its joys and discontents, hmm?

Speaking of joy, that’s something I am in the mood for–small, zippy, satisfying bursts of it at regular intervals–and it wasn’t until someone messaged me on Instagram to inquire what alternatives to retail therapy give me the same kind of thrill that I had a revelation about the competing interests of January in general: consuming less, but feeling more.

It can be such a barren month, both in terms of weather and socialization, which makes feeling in general but particularly feeling Thrilled with a capital T a more challenging thing to access. There are so many things I could rattle off that historically bring me joy–my family, my friendships, Austin, a satisfying project at work, a delicious book–but the spine-tingling quick hit of a purchase is another thing altogether (and, I’ll admit, often a more superficial one). It’s candy! Where do you find your candy outside the realm of shopping, especially if you’re trying to be more conscious about how often you engage in said activity?

On Sun, Jan 12, 2020 at 7:43 PM Leandra wrote:

The thing about retail therapy is that it’s a coping mechanism, right? It feels like a drug—you put it really well by describing it as a “spine-tingling quick hit,” and then again calling it candy. Finding an alternative to it can be a slippery slope if you’re not really conscious of the fact that you’re replacing one plea for escapist behavior with another. Which, btw, there is nothing wrong with—we all have coping mechanisms. We need them to survive! My philosophy is that as long you’re not ruining your own life or anyone else’s, good for fucking you if you have figured out what works to make the banalities of your days/weeks/month/life feel better. Tbh, specifically with retail therapy, for me it is often enough to just mindlessly scroll through new product pages on luxury brand websites. I would do it before I could afford anything, too. Often I see something I like, which reminds me that I have something similar, and that re-inspires me to wear it in a different way. This actually happened recently with a very good looking Toteme tux blazer on Matches. It reminded me that I have a great Isabel Marant one that I bought, also from Matches, while I was pregnant a couple years ago, and I really liked that the sleeve appears cropped, so I thought maybe I’ll tuck and tape the sleeves in and wear it with some black wool trousers.

Obviously the scrolling is like tempting the devil and every so often I’ll end up buying something. Like somehow these ended following me down a rabbit hole of cooking websites when I was trying to find easy breakfast recipes for my kids this AM. I’m not going to get them, but, you know, they’re haunting me.

I haven’t answered your question. Sorry. Candy outside the realm of shopping… it depends! If I’m specifically trying to scratch the fashion itch I take to my closet and start trying on outfits I’ve never worn before with all the clothes I definitely have worn before. That usually gets me going in the same way that getting something new does. If I’m using retail therapy as a pick-me-up to distract me/because I’m sad/because I’m avoiding something, I, tbh, often concede to the therapy, or a glass of wine, or a piece of cake and then feel terrible about it the next day. One good thing about me: I’m not lazy about returning shit, so that happens a good amount.

Not a satisfying answer, huh. What do you do!

Laura Lombardi Necklace

On Tue, Jan 14, 2020 at 6:23 PM Harling wrote:

Remember Polyvore???? In addition to using it to search for stuff when I was in college, I was also a frequent partaker in its collage function, which basically allowed you to paste together different clothes from around the internet onto a white square, paper doll-style without the doll, which would probably be extremely helpful in terms of visualizing what pants (or kilt??) I would hypothetically wear with this sweater/shoe combo:

I definitely get a thrill from outfit idea generation that’s reasonably close to what I get from making an actual purchase, even when the ideas are entirely hypothetical. Since Polyvore doesn’t exist anymore I often take screenshots of things and open them up next to each other on my desktop. It’s not a perfect system, but it scratches the itch to some extent.

Another itch-scratcher: borrowing clothes! I’ve been borrowing stuff from my mom’s closet for years but the satisfaction of doing so didn’t fully crystallize until recently when I messaged Jenny Walton on Instagram about how much I loved a particular sweater she was wearing (which is currently on sale, for those interested) and without skipping a beat she messaged back saying that she was going to leave it with her doorman so I could pick it up and borrow it!! Which I did! I’ve worn it twice, which was indeed thrilling, and also ultimately the perfect amount. I still need to return it (sorry, Jenny!!) but I have a hunch that doing so will feel akin to leaving a party at its peak, or when a show decides to stop airing episodes while it’s still culturally relevant like Fleabag or Broad City. Is this metaphor making sense?? I basically mean that it’s nice to have the opportunity to wear something in the throes of loving it without grappling with the disintegration of that feeling that tends to happen over time, you know?

But it doesn’t always happen, which I’ve become more conscious of as well. I’m trying to pay really close attention to the pieces/outfits that I’m interested in wearing on repeat and never grow tired of. For example, here’s an outfit I’ve been wearing at least every two weeks (sometimes more) over the past few months and I think I’m just getting started:

If I had to analyze why I’ve gravitated toward it so many times, I would say that it’s a) extremely comfortable but still put-together-looking enough for multiple occasions/circumstances and b) is relatively simple but has an element of surprise contrast courtesy of the purple and neon yellow accented sneakers. It’s also a great canvas for a variety of accessories, so I can mix things up that way and keep it feeling FRE$H.

Are there any particular outfits you’ve been wearing on repeat lately?

On Wed, Jan 15, 2020 at 10:38 AM Leandra wrote:

A few things! First: I used Polyvore for the same purpose–it was like my Cher closet. Then I would take screenshots of the outfits I made and upload them to manrepeller.blogspot.com and get wordy and philosophical about why I was pairing a fashion sweater with Nike shorts (because trends are best served by taking them to their genesis), end scene.

Speaking of philosophy, I also agree that sometimes putting the outfit together (even without actually owning it) can scratch the itch. I was listening to the Goop podcast last night and GP interviewed Eckhart Tolle and he was yapping away about ego, and how it’s separate from us (e.g. you or me) in a thought like, I can’t handle myself anymore! and went on to say something to the extent that when you look at something and enjoy it, when it resonates or whatever, it’s ego that comes in and makes you think you need to own it to define yourself. Or something! Anyway, it got me thinking of this dramatic story I wrote about social proprietorship, and also what you’re saying right now. You will probably disagree with this assertion given the anecdote I just shared but the point is: Sometimes I really feel like we have the same brain. Case in point: Your TV show pitch in our content world meeting yesterday.

Speaking in terms of peeks behind the curtain:
1) We should 100% ask Jenny if she wants to be part of our talent collective; can’t think of someone who embodies the fashion ethos of Man Repeller better—she fucking loves getting dressed, has so much fun doing it, is creative about where she gets it/how she makes it, and all of it is so inspiring.
2) We should probably host a clothing swap at the office? The idea hasn’t appealed to me, I think because I was never allowed to borrow my friends’ clothes. My mom didn’t let me, I think it was an insecurity of hers born from her refugee immigrant mentality where she probably felt like it was embarrassing for me to accept handouts. Totally missed the cultural milestone of friends-that-share-clothes, but obviously I did not have that rationale/logic when I was like, 12 years old. Point being: I’m ready to let go!

And now! Do I have any outfits on repeat? Yes! While as a rule I’m pretty sure I have a template and so technically, I wear the same thing every day even though the actual garments are different (I also have a long form musing on this as the real definition of style incoming), in terms of actual outfits
I’ve been wearing this grey Adam Lippes mens henley a lot

Under a cardigan sweater, this one specifically, but this one does the trick

White high waist, straight leg skinny jeans

And a rotating panel of mid heel shoes.

The henley is casual, and makes this great tension when I wear a pearl necklace or gold chain. Or both! And it looks kind of off under the cardigan because why all the buttons, but I like the offness. Then the jeans are like veggies to me, a necessary part of every meal (per the food pyramid) and the shoes–which could even have a pointed toe–catch the sweater and henley without making me feel like a corporate lawyer because no boxy shoulders or blazers here, pal.

There is something to be said about outfit repeating being the new refusal to outfit repeat, no?

Brother Vellies shoes

On Wed, Jan 15, 2020 at 9:49 PM Harling wrote:

Very funny you’re bringing up the old Man Repeller url because LITERALLY JUST LAST NIGHT I had a random hankering to remind myself how the MR website looked in, like, 2012 so I went to the website archive.org and pulled it up! And there was hundo P a Polyvore collage that featured high-top Converse and “skinny-loose pants” (skinny legs, loose crotch–please consider this an official entreaty to revive the coined term henceforth).

Agree completely re: Jenny. She’s one of those people who dresses so timelessly her outfits look like they should be in a coffee table book but also so perfectly of-the-moment that they could be in the feature image of an article about style on zeitgeist dot com. Looking timeless and of your time at the same time is nearly impossible, right?? Which is probably why I can only think of a handful of women who have managed to do it. Another good example of someone who does this regularly is Chloe Sevigny. Let’s put her in the talent collective too, and pay her a commission for the tights + LBD + flower brooch I will inevitably buy if I continue gazing at this photo.

At the very first fashion week event I attended EVER on behalf of Man Repeller, there was a woman there who asserted loudly that she has never, in her entire life, repeated an outfit. I remember this vividly, partly because it was my first ever fashion week event but also because everyone in attendance (myself included) was visibly impressed. It’s interesting to think about that proclamation now, though, because I don’t think it’s something a person would place a premium on achieving, much less brag about, in 2020 (this was 2016).

It’s incredible how much the pendulum has swung toward sustainability consciousness since then, and how much that swing has shaped not only how we talk about style but also what we’re choosing to wear day to day. The gratification of coming up with an outfit so good that you want to wear it on repeat is the thing to brag about now, and how neat is that? Neat not only because it’s an approach to getting dressed that doesn’t rely on accumulating more stuff, but also because it necessitates a much greater level of thoughtfulness toward what you want your clothes to say about you if the thing they’re saying is going to be said again and again and again. And that’s probably contributing to why fashion’s overarching mood is feeling more streamlined right now, because there’s a much more nuanced spectrum of things that a pair of perfectly neutral gray trousers can say vs. an aquamarine polka dot dress which is shouting one thing and one thing only (however both certainly have their merits, depending on the/your vibe).

I’m fully rambling now, but here’s a related question: How do you drum up inspiration from the wardrobe you already have on days when you’re feeling un-creative?

P.S. I’ll share a brain w/ u any day of the week Leandroid Cohen. Especially if it means we can make a TV show and/or timeshare this outfit from Dries:

On Thu, Jan 16, 2020 at 2:24 PM Leandra wrote:

Oh but there is a difference between repeating an outfit and repeating an item! I don’t think I necessarily repeat outfits so much as I do routinely wear the same things in different ways. I wonder if that’s how she meant it. It seems to be at the core of what you’re getting at as well, and to me, that’s real style. It’s like how the best cooks can walk into a fridge full of nothing and whip up a fabulicious meal.

Per your q on how I drum up inspo to get dressed when I’m not feeling creative: I know I’ve said this before, but I actually do keep a note in my phone with outfit ideas, which I add to every time I get a good idea. There’s no real method or rhythm to when these ideas come to me (example: this morning I wrote “Suede fringe jacket as top with khaki trousers + grey collarless peacoat over and black Adidas sneakers” while I was brushing my teeth) but I do defer to the note when I’m feeling uninspired. Of course what often ends up happening is the outfits in the notes no longer inspire me, so I stand in front of the closet and change the line of questioning. Instead of: “What should I wear to make me feel great today?” I ask: “What in here will make me feel the most comfortable?” i.e. “What can I put on that I will be able to forget about the second I’m wearing it (in a good way!)?” So I end up pulling for a pair of high waist jeans with a cardigan and a t-shirt under, or some other kind of knit and then pull out a pair of flat boots if it’s cold and I have to walk far, or slingbacks if it’s not and depending on the shoes, I go ham on the accessories. Not real ham, but they become the point of interest, you know? As I’m typing this all out it’s occurring to me that the real answer to your question is: When I’m not feeling inspired, I focus less on my clothing and more on what I wear my clothing with. Rings on my pinkies, threaded bracelets on one wrist, something dramatic and gold on the other. Maybe a charm bracelet? I’m a big fan of the summer bead mid-winter and lately, I’m all about pearl buttons, but for my ears. What do you do?

And finally, did you know that my brothers call me Leandroid because I am like a “hemorrhoid to their lives: incredibly uncomfortable, but necessary to deal with, and you never regret it once you do” (I added the last part…).

On Thu, Jan 16, 2020 at 5:53 PM Harling wrote:

My “trick” (if I can even call it that) is scrolling through my camera roll to remind myself of past outfits, which I’ve found is useful in dislodging ideas for new ones. At this point my phone is basically an inventory of my wardrobe. The perks of being vain!

I actually did it just this morning when I was standing naked in front of my closet beseeching it to tell me what to wear and it refused to cough up the answer, so out came my phone and I found a photo of myself from last spring wearing this Ralph Lauren sweater with white jeans, a white frilly collar, and black sandals.

See All 4

It was definitely too spring-y of an outfit to fully recreate for this time of year, but it reminded me of how good the sweater is, and how good it looks when paired with a combination of preppy and sporty things. I decided to wear it with gray wool slacks and New Balance sneakers and if I do say so myself it’s a very satisfying combo.

See All 2

Speaking of satisfying I’m feeling the urge to recap some of the points we’ve touched upon in this convo because I think there are some nicely toasted chicken nuggets worth calling out…

Alternatives to retail therapy that provide the same kind of thrill:

1. Mindlessly scrolling through new product pages on luxury brand websites in hopes of seeing something that you already own a similar version of, thus re-invigorating you to wear it again– maybe even in a totally different way.
2. Standing in front of your closet trying on outfits you’ve never worn before with all the clothes you’ve definitely worn before.
3. Collaging looks on your computer with screen shots, like paper dolls without the doll (or the paper for that matter).
4. Borrowing clothes from friends, family members, and sometimes people you DM enthusiastically on Instagram.

Thrill-Inducing Retail Therapy Alternatives

Strategies for re-upping your creative juices when you’re not feeling inspired by your wardrobe:

1. Writing down outfit ideas in your Notes app whenever they come to you, and referencing it accordingly

2. Asking yourself, “What in here will make me feel the most comfortable?” (instead of “What should I wear to make me feel great today?”)

3. Scroll through past outfits you’ve documented on your phone camera roll

The end! Except I also need to say that while I appreciate your brothers’ interpretation of the nickname Leandroid, I’m partial to mine: an alternative smartphone that is slightly too big for most jean pockets and buzzes every time a size 6 Manolo Blahnik sandal hits The RealReal.

Photos by Alexis Jesup of Colors Collective. Prop Styling by Rose Kennedy.

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