Leandra and Harling on Fall Shoe Nirvana and Schleppy Outfits

“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 but stay for the feelings.

On Oct 13, 2019, at 6:11 AM, Harling wrote:

Lately when I think about my shopping philosophy, I’ve been more critical about focusing only on items I feel are “missing” in my wardrobe—every time I think to myself if I had [insert thing here], it would make this whole outfit, I write it down, and tally which items come up the most. I’ve historically had a tendency to impulsively fall in love with something and disregard what would actually be helpful to spend the same amount of money on, i.e. an item that would fill a hole. But I no longer get a spine-tingling thrill simply from making a new purchase. In order to evoke that feeling, the purchase has to be explicitly meaningful—which is different from practical, though connected in some ways.

I’m curious if you identify with any of this.

On Sun, Oct 13, 2019 at 12:42 PM Leandra wrote:

Do you think maybe that behavior is influenced by the way fashion consumption habits are being impacted by the recent era of austerity? Is it dramatic to call the collective push towards “conscious consumption” the era of austerity?

Or do you think you’re kind of growing up and coming into consciousness of the order of consequences, and in doing that, delaying the instant gratification of buying something from inside the myopic silo of “I love it!!!” And thinking more critically (and broadly!) about what actually you need (if anything)?

On Mon, Oct 14, 2019 at 11:26 AM Harling wrote:

I’m not sure we’re living in an era of austerity. I’ve been giving this some thought, and even though streamlining has been on my mind (and yours too, from what I can tell), the apparent injection of it in fashion’s collective consciousness appears to be more of a balancing of the scales than the tipping of them. Because the increased appeal/success of streamlined brands like Khaite, Tory Burch, the new Thakoon, and COS has not come at the expense of the appeal/success of brands that lean in the complete opposite, maximalist direction like Gucci, Christopher John Rogers, or Area. They coexist!

Maybe it’s a good thing because it forces brands to really define what they are. Good for brands, yes. For people, though, I’m not sure. I’m conscious of the fact that my taste is constantly being manipulated by an algorithm. I’m also conscious of the fact that I’m growing up, and I’m sure that has something to do with my craving to dress (and shop) more simply. The outfits I’m excited to wear again and again over the next few weeks consist of these black pants from AYR, this COS cardigan, a white turtleneck, and these New Balance x Reformation sneakers. I’ve mentioned this in prior  conversations, but I’m still struggling with jewelry. Perhaps it is an era of austerity in the way — and yet! I wouldn’t be mad at all if the tooth fairy left this wildly-out-of-my-budget ear cuff underneath my pillow (big news: I’m back into ear cuffs).

On Tue, Oct 15, 2019 at 11:37 AM Leandra wrote:

I actually don’t think maximalism has to necessitate an absence of austerity—the common denominator among the brands you mentioned is a severe level of focus. They seem to reject distraction and in their own ways, commit to essentialism. Obviously denying superfluousness for Gucci or Area is going to look very different from doing that for new Thakoon or like, The Row, but you could still argue they’re both doing it. If I were a more linear thinker and not a victim of distraction, I might dig into how and why but I really want to respond to that ear cuff!!!! Given how many diamonds are on it and the fact that it’s ~the real deal,~ $1,200 seems like a fair price.


I so rarely refer to price points as fair, but I think it’s the best compliment you can give one, no? It doesn’t imply favor or disdain, advantage or disadvantage (e.g. when it’s very cheap, that might not be fair, but it is to the consumer’s advantage), and it enables a bit of objectivity (I’m not coming at that price thinking about whether I can afford it, and therefore whether I think it’s too much or little…I’m evaluating its features).

I don’t know enough about how COS clothes are made to really back this up but the price point appears to be fair there too. I’m rly into this top, feel like it would look great with a white t-neck under and, because I’m insane, some leggings-cum-tights + silly shoes.

I am low-key obsessed with these from Marc Jacobs. They’re kind of a joke, but also seem essential to me?

Meanwhile! I have recently been scouring consignment sites for men’s cardigans to varying degrees of success. Look what I recently found from The RealReal.

Not a cardigan, I know, but a worthwhile vest to pair under a turtleneck with high-waist blue jeans and New York mules.

Also not a cardigan, but see high-waist blue jeans and New York mules here, too.

Here’s the enchilada. The Missoni one is fun, huh? I think I’d wear with like, a patent leather mini skirt, or leather shorts + tights and boots because I’m a knee-high boots person now, waiting diligently and patiently for Toteme to release these in knee-high:

And then I feel like I should get this for Haley for Xmas.

How’s Spain, btw?

On Thu, Oct 17, 2019 at 6:02 PM Harling wrote:

Hmmm, I get what you mean now. I think austerity probably isn’t the right word though. In the context of this era of fashion, it’s not so much an absence of extra-ness as it is an absence of excess. The latter is what I’m trying to trim, because I want a wardrobe that feels solid. Less like the whipped cream topping and more like the brownie, if you know what I mean.

Spain was a whirlwind. I got a sneak peek at Zara’s new collection which actually just came out today and has a ton of good stuff with interesting details. For example, this trench coat, which is double belted so you get the layering effect of wearing two trenches on top of each other without the bulk. This pleated skirt, which looks simple at first when you put it on, but when you move it showcases the contrasting lining underneath. These great black trousers that have subtle side vents. Ooh and this oversized light blue shirt with buttons that run up and down the sleeves. They told me the vibe of the campaign was “refined magpie,” which is incidentally a great Instagram bio if you’re in the market (but also plz never change your current one).

I love that COS top u found!!!!! It was born to be layered over a turtleneck. Except instead of leggings and silly shoes I would wear it with satin pajama pants and a heavy boot.

I feel like your fall/winter 2019 sweater identity is “male chemistry teacher.” Lmk if that’s fair to say. The Missoni one is so good. Not men’s but this one’s a good addition, although slightly more Latin teacher than chemistry teacher methinks.

I just bought two pairs of perfect trousers from The Row sample sale and I need help deciding how to debut them! One pair is a chino material with pleats and the other is a straight leg scuba material situation. Any ideas?

On Thu, Oct 17, 2019 at 9:26 PM Leandra wrote:

Did your chemistry teacher wear leather shorts to school often?

I got great pants from The Row sample sale too! For $140 bucks a pop! I need photos so I can better evaluate how you should wear them, but in the mean time mayyyy I just sayyyyyyyyy: I always forget about Marni, but yes yes a thousand times yes, that cardigan partigan is the tits.

I feel like this top is very Leandra 1.0 and maybe that’s why I’m gravitating toward it but 10/10 would wear with an a-line mini skirt (or black cashmere underwear, tbh) and tights like these, which I was inspired to source after evaluating your Zara links.

Back to the leather shorts thing for a second…I was pretty sure that I would never want to wear shorts with tights again, much less leather ones, but now I think I’m becoming that person? I want to pair them with a chunky sweater (tucked in, or at least fake tucked in because who the hell can fit their chunky sweaters INTO waist lines) and a pair of like, knee-high kitten heel boots. Who am I becoming?

On Fri, Oct 18, 2019 at 11:29 AM Harling wrote:

I think you’re becoming yourself in 2012! A full circle moment.

Hey, Jack Erwin just launched a women’s collection and the loafers look like a chef’s kiss. You know what actually, over the course of this convo I’ve come to realize that shoes are really the main hole in my wardrobe. I never seem to have the right pair to wear with a particular outfit, so I’m thinking ~~~~critically~~~~ about what seems to be consistently missing and I think black suede loafers might be it. Also black or brown knee-high boots (I’m eyeing these and these).

If you could only own 3 pairs of fall/winter shoes, what would they be? Tell me truly.

On Sat, Oct 19, 2019 at 2:55 PM Leandra wrote:

Fall/winter shoes are always a source of annoyance for me and I’ll tell you why: They don’t look good with jeans. Seriously. The best shoes for jeans are sandals—loafers or ballet flats are too basic with straight or skinny-leg jeans (which is what I wear most days). Those kinds of shoes require a pair that is baggier, and that’s fine, but baggy jeans look too schleppy with a long coat, so then I have to change into a short jacket and I don’t have a good one. This from Toteme is pretty nice, but I doubt it’s warm. If I don’t change my jeans so as to keep my long coat on, I have to change my shoes, but I don’t actually know what the right pair of shoes looks like. So far, this new pair by Emme Parsons is the closest I’ve come to fall shoe nirvana. The most basic, boring purchases we make tend also to be the most useful ones. I’d like to make a case for taking the emotionality out of shopping to see what happens.

I didn’t answer your question though…if I could only own 3 pairs of fall/winter shoes, what would they be?

These, no question. I don’t know why I like them so much, maybe I am blinded by the price tag. I guess I’d wear them with long skirts, dresses, sweatpants and high-waist jeans. (And per the last way, short jackets only!) Something akin to these to wear with long pants and short things + tights. And then it seems redundant to have another flat (like a pair of Mary Janes) and the Emme Parsons loafers so it’s a toss-up. Either would be worn with baggy pants and sweat pants, Mary Janes would be good for straight-leg or skinny jeans too. And actually might pair better with mini skirts. Hmmmmm.

This is weird and hard, though, because I do feel like there is a big hole here that would be accommodated by like, these. I guess my first pick I am actually least likely to wear so I have to kill my favorites. Ugh, WHY DO YOU DO THIS TO ME, HILLARY?

On Mon, Oct 21, 2019 at 11:54 AM Harling wrote:

That Emme Parsons pair is a full dream. I just did a deep dive to see if I could find some comparable lower-priced suede loafers in a similar silhouette and came across these from Aquatalia which look pretty great. I think their appeal lies in the high rise(?) or is the correct term “upper”? and now I understand why I felt the urge to abscond with the black velvet slippers Austin bought to wear to our wedding. Slippers are it right now, huh.

Those boots from The Row. Oof. I’ve been analyzing why I think they’re so good and I’m pretty sure it’s because the chunky sole gives them an element of edge but the fact that it doesn’t have those little visible grooves that most chunky soles makes them sleeker. Am I overthinking? Honestly not sure at this point but in my fantasies, I’d wear them with this $60 skirt in dark brown from the Uniqlo x JW Anderson collab (which is really good btw) and this jacket.

I like the white puff-sleeved blouse you’re wearing today. Wish I could tap for credits.

On Mon, Oct 21, 2019 at 12:48 PM Leandra wrote:

Thanks! It’s Fabiana Pigna. I actually feel too normal today. Like the actual outfit is right—puff sleeve button-down with black t-neck underneath plus navy blue skinny pants and New Balance sneakers, but it’s missing the quirk. Like a turquoise necklace, or a sash that reads “best clumsy” around my chest. I guess it doesn’t have to say “best clumsy” but I do think whatever it says should not make sense.

Hey, do you use the word abscond regularly? Like in informal conversation? Also, I almost bought this skirt from JW Anderson/Uniqlo off the window mannequin this weekend. I think I’d probably wear the navy one more often tho. I have such a complex about knee-length skirts from going to Yeshiva day school but this one is good enough, methinks, to power through the hang-up. Your outfit for The Row boots, btw, is really good. That jacket link led me to this one, which is not styled well but makes such a good case for light jacket weather. Imagine it with a counter fringe skirt and like, this bag, for example. Funky!

What are your thoughts on Bermuda shorts with knee-high boots? I think as long as they’re not too long to be mistaken for culottes, there is potential, and now that I look at these ones again, I actually think they’re  too long. In searching for a better-shaped pair, I came across these trousers. They are like, the perfect silhouette and length, but do you think they’ll make me look like a kid wearing her dad’s clothes with a winter coat?

What is the solution for outfits that get ruined by coats, but are still warm? I wish someone would invent a turtleneck that is also a cropped down jacket.

On Tue, Oct 22, 2019 at 12:06 PM Harling wrote:

Is “best clumsy” a reference I should know about?

In addition to addressing what comes after the balaclava–a pressing Q–we also need to do a story about how to look warm but not schleppy this winter. Narrow tightrope to walk, that one. I don’t think Bermuda shorts and knee-high boots are for me, but I’ll take those trousers and ordain the marriage to a turtleneck that is also a cropped down coat. Plus white sneakers because I’m a sneaker person now!

Speaking of I do use the word abscond regularly. Like these shoes, it’s too fun to save for special occasions only.

Photography by Cody Guilfoyle, Prop Styling by Sara Schipani  ; Photo featuring Marc Jacobs shoes and Mango bag.

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