Stretching $100

Just don’t rip it — that would blow chunks.


I am on another kick independent of shopping my own closet and making old dresses new that includes spending cold hard cash, no credit line necessary, on clothes. Why? Because when I’m buying something, I really want to feel it. This, of course, will also limit how much I will spend on that which I choose to buy. While I am certainly not above walking into a shop with a wad of cash (if only to confuse bystanders about my vocation of choice), I am also incredibly paranoid. And in a city like New York, a lot of cash + severe paranoia = doors locked, I’m staying at home.

When I was in high school and therefore subsisting on the scant, teetering “salary” my parents would allocate to my social life and beyond, I very strategically delegated exactly 30% of the full dollar amount to weekend activities while the additional 70% went toward a more robust wardrobe. Often after I’d save for weeks and finally accumulate enough capital to buy what was on more than one occasion, the Steve Madden platforms of the season, doling out the singles and tens and sometimes twenties but mostly quarters that would make them mine was much harder than I thought it would have been.

Here I had saved up enough money to make my paltry wallet appear fat and I was going to forgo the liquid assets of my teenage-hood for a measly pair of platform shoes?

Sometimes, hell yeah, but sometimes too, at the brink of acquisition, while standing face to face with the cashier who would strip me of my independence, I zipped my pouch-wallet closed, put it back in my pocket and as I turned around, I would say, “Sorry, never mind.” It always felt good and I never regretted it. (Except like, three or four times.)

When I got older, I wanted a credit card. Those MasterCard commercials were spectacularly enticing, and as evidenced by the American Express ads that looked like Mad Lib pages which would pop up in Fashion Magazines, Beyoncé — and therefore I — were really into plastic spending. The whole process just seemed so much easier than trading dollar bills with bodega owners. Then when I got my first credit card, which came in tandem with opening my own bank account, it was all downhill in the wrong direction.

I’d swipe that seemingly innocent little plastic loan everywhere I deemed fit. A $2 coffee from Lenny’s? Credit card. $6 toilet paper from Duane Reade? Credit card. A cab — any cab — from point A to point B? Sorry, no cash.

And then the bill would come and I would think, what the fuck? When did I buy all this STUFF? Weren’t credit cards supposed to be linked to bank accounts that existed only in the world of Monopoly money thus making my spend not illegal per se but certainly very, very good — too good, obviously, to be true.

This brings me back to my initial point: that when I buy things, I want to know I’m buying them. I want to see the money come out of my wallet and know precisely what I’m doing with it and feel good about it so that when I leave the store, wherever I am, I know the transaction is complete and that it’s been thoughtfully blessed with my own approval. No future what-the-fucks. No crude reality checks about the universe I live in. No swipes that go regretted.

The cash sanction also brings up an interesting game I’ve started playing called Stretching [Insert Dollar Amount Here].


In today’s round, I’ve successfully stretched $100 to afford me a red and black plaid shirt from the mens department at Uniqlo which retailed for $19.90 (the shirt is a men’s small though I am typically prone toward the mediums) and a grey wool mini skirt plus lace inset from Zara, for $39.90.

With the leftover $40.20, I unzipped my childhood pouch wallet, put the money inside, and surmised I’d save it for a rainy day that might require new platforms.

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  • Charlotte

    Not Man Repelling, such a cute and flirty outfit!

    • Raphaëlle Lavielle

      Really? It seems to me that everything is in paring this outfit with trainers. The same shkirt/shirt combo with pointed flats – or worse, ballet flats, yikes – would have been outrageously man getter.

  • I love your new stretching results! Adore the idea, too (can hardly wait for more)!

    Sometimes, just sometimes, I wonder what happened to that feeling … You know: you’re a student and you can name the contents of your wardrobe any day, night and party. And most pieces may have their own special feeling connected to them … lingering and mingling in the wardrobe but only flirting, never fusing, like: o-oh, we are feeling all adulty today, we saw a great exhibition yesterday, it made us think about things, so we want to wear the grey turtleneck today … I can still remember the days when I wanted to charm my much richer adult students at a language school by wearing a dark blue shirt. With tiny white flowers, from a men’s somewhere (we used to simply like each other, it was that simple :-)). I even scrounged some … maternity wear from my friends – lovely, elegant, quite wide blouses, not screaming “I’m pregnant” at all … Anyway: The feeling. When clothes were still all of them connected to special situations or moods, evoking the old ones anytime you put them on … My first Levi’s – my first weight gauge 🙂 …

    Yeah: I like your stretching a lot.

  • Rebecca

    Great post; thanks for considering your readers on a budget!

  • Aww I love your shirt! Good thing we finally have access to Uniqlo in France, I’m off to their site!

    Mafalda ❤

  • Morgan

    YES! More of these posts please! I love your style but 99% of the time, cannot afford it 🙁

  • Girl, I was literally looking at that skirt like 5 minutes ago as if my legs could survive this winter alone. Also, curious, how do you tuck in your shirt perfectly? I always look like a hobo with oversized/mens shirts.

  • Ahbee

    Leandra, what size do you usually buy your shirts in from Uniqlo? I like the loose fit of your plaid shirt.

    • it’s from men’s, according to my coworker who used to work for uniqlo

    • Leandra Medine

      Hey! This one is a small and yes – it is mens. I don;’t think I’ve actually ever purchased anything womens from that hub.

  • Selena Aponte

    Love this, so smart and desperately needed. Although this may be the first task at hand in which I feel like we (the audience) could possibly challenge you to, this could make for an interesting dynamic. I can’t wait to see what you come up with next.

    P.S slide 4 is just heavenly

  • Yay, do this more often!

  • Amelia Diamond

    I am always feeling like Amilli0naire. Badum-cha! Here all night, folks!

  • Brie

    i find myself saying “never mind” about clothes far more often now than i used to. i’m not rich by any means but i do love fashion. i love clothes, shoes, bags, jewelry, tights, socks, anything really. so, i have a LOT of stuff. like, too much for my tiny apt. when i go shopping, whether it be online or in store, unless i find something i don’t already have or don’t love with all my soul, i leave empty handed. which is almost as big a rush than when i do find something and buy it! there’s always an exception though. for me, it’s white blouses, i’m not sure i’ll ever stop purchasing them.

  • Rafaela Capetillo

    Awesome look for under $100 – especially for broke/stylish girls like me :))

  • claudia

    Love the skirt, is gorgeous! Great look!

  • CDJ

    It’s all about the Benjamin(s), baby.

  • Kelly Hughes

    This is a great post. When you’re into fashion this can be sooo….hard…

    But this outfit? Sorry. It should repel every man, woman, and child. It kind of looks like she lost the top half of her outfit the night before and borrowed her boyfriends shirt to make the walk of shame across campus (complimented perfectly by the lank bedhead.) And running shoes with black socks is never a good idea unless you’re my Dad and you’re cutting the grass. Actually, not even then.

  • Love this! Gonna make my dolla bills stretch like Gumby.

  • Oh, Uniqlo…you bastion of flannel shirts and cozy sweaters.

    I would spend so much more than $100 there…however, I don’t have to.

    And that, my dears, is the best deal of all. 🙂

  • Jessica Rose

    Cute outfit…when you have great pins….you can get away with even wearing a tea towel as a skirt!! X
    Make that the feature of you next post pretty please….;))

  • Elizabeth

    Great article Leandra! I too play this game of Stretching [Insert Dollar Amount Here]. I try to see if I can wear [XX] outfit [XX] different ways by buying accessories with [Insert CASH Amount Here]. I have had a few WTF moments with the credit card too!

  • Love it, but I would be freezing my hot dog legs!

  • Kelly

    Does The Row handbag go into the equation -_-

  • Tatiana

    I dont get how someone would buy a 2800 sholder bag from the row, honestly

    • Guest

      I doubt she actually paid for it..

      • Leandra Medine

        Hey friends – I bought it from a sample sale at a very lucrative 85% off.

  • WildOceanAir

    I have this skirt! Rather, the tapeworm. The straight line is not favored me anything. But I have good news. In Spain is 22, 95 E.

  • I have to admit that this isn’t my favorite style on you… but I’d love to see some more Leandra style stretchin’ (a whole new sport, watch out for the Olympics!) and I love the sneakers.

  • Chelsea J

    After searching high and low for an hour for the trainers in burgundy, Amazon finally came through!! Note to all who want to purchase– they are men’s sizing and run small (I’m a true 8.5 (w) and ordered a 7.5(m)).

    Fantastic post, per usual!

  • Anna

    Of course combined with a $2000+ handbag…

    • Savannah

      She got the bag from the row’s recent sample sale, which makes its significantly less than its original retail value. It’s still pricey, but the main focus of the post is on the clothes and not so much on the accessories.

      • Leandra Medine

        ’tis true!

  • Savannah

    You look much cooler when you flip half your hair to the other side, opposed to when you have a middle part and each side is equally distributed.

  • Natalia Osvaldová

    Thank you, Great post!! :)) Make me laugh!

  • byjacquelineho

    more of these please! I love it 🙂

  • Bonnie Meyers Cohen

    But you paired it with a bag from the Row…that’s cheating! 😉

  • zoe_whip

    Please, please more of these type posts for us regular people…

  • TEXcarolyn

    Hey no fair accessorizing the cheapo outfit with a $$$$ 2800.00 bag!!

  • Sage

    Actually love this outfit. I can relate to the stretching of funds, too….

  • Dervla

    love this post

  • olivia

    love the plaid shirt!

  • Qlaffa Nastazia

    Very thoughtful & well analyzed regarding your growth of shopping process; And a good point on having second thoughts while we buy. Not a huge fan anymore of well known designers, paying with a garment along their studio’s rent. Respectful pieces with a lot of work worth the spend. But also additional street fashion pieces are Life-Savers. Everyday life needs a blend_

  • jaclyn

    I love it! I am actually pulling a look similar, almost identical to this! Thanks sugar for the inspo!

    check my blog:

  • Stacey Freeman

    What brand is the purse in the pictures? I see the ROW bag in the slide show below, but wondering about the bag you are holding?

  • Mary Boersma

    Yay for plaid. I’ve been on the hunt for something similar!

  • Mary Boersma

    oh, and technically this outfit isn’t $100. nice try though. hee hee.

  • lynne

    buy the sneakers on best prices there!

  • Amy

    check out we LOvE your stylezz 🙂

  • the coattail effect

    I definitely know the evil of the plastic #brokecollegekidproblems


  • N

    plaid shirts are distinctly man-repelling. My bf LOATHES them. I love them. and I really like this outfit, with one caveat: my legs are too muscular for trainers + skirt. it would look awkward in an “I’m-only-wearing-these-so-i-can-walk-to-the-gym-after-work” way. I’d wear the socks with oxfords, moccasins, or maybe pointy grey or white loafers/flats(?). otherwise, brava.

  • Eden

    This article hits home on SO many fucking levels. Although, i would say that it does take one to truly experience that “what the fuck?” moment whilst coming face-to-face with the credit card bill to appreciate the act of stretching a dollar.

    Also, it’s not often the impulse shopper that has the wardrobe that one would kill for. it’s ussually the smart savvy shopper that takes time to ponder over every piece of item that ends up having that classic wardrobe thats relevant year after year while still being in-style!

  • The 109 Block

    I love the outfit, and in fact, the skirt is in my “shopping” list for a couple of weeks!

  • JustSayin’

    i like how you omit the nearly 3K spent on the purse. that always makes a $100 outfit look better ; )

  • Dee

    Love this post. Comes at a very good time, as I’m rethinking my experiences regarding online shopping versus real-time shopping. I like the immediate satisfaction, and the knowing of how much money I have left in my wallet. I think I’ll be doing more real-time shopping now, despite how convenient and completely effortless online shopping appears to be.

  • Monika Jones

    Love this look. The skirt is really cute.

  • Rae

    Plaid perfection! Could I be anymore excited about menswear flannel shirts! Uniqlo- I’m about to hump your ass!