Quest to Cool

Can something be “classically cool?” Maybe.


I finally bit the bullet and satiated a craving that has been unwittingly manifesting since a month before I wrote this bizarre ode to a pair of shoes. Yes, I am talking about the Gucci loafers I’d admittedly rejected for years but have somehow grown to curiously admire, which transpired to portend desire, and here I am.

Now I’m on a mission to do one of two things–if I can do both, I will treat myself to an infant-sized crown to wear at the tip of my head because it recently occurred to me that I really, really want to be Blue Ivy Carter. But I digress.

First,Β I want to make the shoes in question look “cool.” As they stand now, I look down and feel not unlike I am Nantucket bound to meet my angelic realtor of a husband, who has a sailboat, who may or may not catch lobster for me on said sailboat. While we might take out our seafood bibs to nosh on the chewable fuel in open waters, I would take off my shoes to savor their suede glow. “Nice pedicure,” the realtor might tell me. It would be very creepy.

Don’t get me wrong, though–I’m not judging. That life seems beautiful. It just isn’t my life.

Which is where #2 comes in. In trying to make the shoes look cool (which bombastically infers that I am cool), here I propose three different outfits that may seamlessly integrate the shoes into my mode of lifestyle without having to compromise my distaste for lobster, propensity toward denim, leather, the combination of both, and the mere fact that I have never been to Nantucket.

Outfit #1 combines a pair of leather leggings from Topshop with a Blk Denim leather jacket and one white Club Monaco tank top I’ve worn to sleep, exercise, and dine – sometimes all in the same 24 hours – with the somewhat signature Dannijo bracelets of my “look” and, duh, the loafers. It’s not really me, though, until I fall into a squat and begin practicing my kegels.

Yvt8uJ on Make A Gif, Animated Gifs

Ah, that’s better.

Outfit #2 approaches the challenge from a different point of view, instead pairing some of the “classic” pieces emblematic of who I am not but want to be with a mens white blouse from Land’s End and Chloe trousers. The orange lip care of Giorgio Armani’s lip maestro and tribal, gold Pamela Love choker probably speak more accurately to the disconnect.

And finally, in outfit #3, it likely isn’t a Man Repeller post without at least two layers of denim at this point, yes? Here is precisely what I was wearing last week on the day I bought the shoes. It includes ripped Levi’s denim shorts, a Shipley and Halmos dark denim shirt, an Isabel Marant tank top and a selection of jewelry from a combination of: Khai Khai, Eddie Borgo (Forrest Gump ring) and Jennifer Fisher (spine cuff). The outfit that one wears while conceding to purchase an item she thinks she loves is probably more important than we give it credit for. Would I have bought the shoes had I not been wearing denim cut-offs and a bohemian stylet blouse indicative of absolutely nothing the shoes are? I’m not quite sure.

To be fair, though, I’m glad I have them. I think we will be really happy together.

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  • Anna

    I actually LOVE the loafers. Just ordered a pair from Cole Haan. Extra grandmother-ish.

  • CDJ

    I just want to yell, “DON’T JUMP!! YOU CAN LOOK COOL!! THERE’S LEATHER AND DENIM IN YOUR FUTURE, IT GETS BETTER!” to them in the first picture. (them being the loafz)

    • (BAD) Blog About Design

      That was a close one! Thank goodness you commented, we almost lost them! haha.

      Check out the BAD blog…

  • CarolinaG

    I loved it!!!!!!!
    I’m posting looks from Los Angeles and accessories:

  • Nico

    The first look is really amazing, the contrast with loafers is great!


  • Pip

    Oh wow… I LOVE outfit #2 with the loafers! That is the perfect look for those loafers and I have a pair of loafers I hardly ever wear because they just can’t be thrown on with just anything. I love the leather pants with them too though. πŸ™‚ xx Pip

    Easy Outfits by Pip


  • I have loved those loafers for awhile but since I am still saving for balenciaga city bag, I have to wait. I love the outfit 1… leather always works

  • The black outfit is a winner

  • ashleymaciejewski

    The arm party is back!

  • twokidsnyc

    Black on black, white on white, denim on denim. Why do they always work so well?

    • Avery

      these are the questions, aren’t they…

  • My hero.

  • this brings to mind that wise old adage: my fellow repellers, ask not what your shoes can do for you, ask what you can do for your shoes.


  • monkeyshines

    inspiring accessories!


  • You rock Leandra! I love the loafers and the leather jacket!

    Mafalda ❀

  • Paco T.

    You always have the greatest style!!!

  • (BAD) Blog About Design

    I’m loving the jeans on jeans look and leather on leather look. Your quest to cool has been accomplished!

    Check out the BAD blog…

  • Hedwig

    Loafers are the best, specifically TODS loafers *cue salivation*. They are THE most comfiest things once you break them in, unlike leather pants, or in your case leggings, which are always chafe chafe chafe chafe chafe

  • Magda

    @Leandra: Where is that half-moon necklace from? It’s perfect!

    • babybulle

      KhaiKhai, her brother owns the line! πŸ™‚

      • Leandra Medine

        You’re good–but that necklace is actually Mark Henry (which is my parents line) Ha.

  • fashcollections

    I love this and I feel like you must have known I would love this even though you don’t know me.

  • Andrew

    Love the first outfit, if not only for the fact that it’s the most unrealistic for summer, a trait that makes for the best outfits.

  • s

    the boat scenario and those shoes just works so well haha. well done!


  • Crystal

    You killed the first look with the black leather but I’m loving the third look too because I just cant resist a good Canadian tuxedo! You make me wish I never consigned my mother’s pair of Gucci loafers…But I would never be able to wear them anyway she wore a size 6 πŸ™ Anyway! I believe you have conquered said quest!

    • Leandra Medine


  • gaby

    Where is the half moon necklace from??

  • Yin

    I love the loafers! They are so vintage yet chic! Although I do prefer heels any time, loafers are always a great addition to any fashion addict’s closet!

  • mary sue

    You wear them well. Way make this “old” shoe look really fresh. very inspirational!

  • Caroline

    LOVE the first outfit. I’m definitely starting to crave fall clothes, as much as I keep telling myself it’s still summer… but that look reminds me of why I love dressing for fall so much!

  • Yuka
  • Maricruz L. Armenta

    Love the loafers! and you always look super cool, also I really like they way you styled look number #1 with the Dannijo’s bracelets xx

  • Carola Disiot

    ahahah funny gift!!! love this look!!!


    Read my last post on Purses in the Kitchen! // Facebook // Bloglovin

  • Oliver Lips

    Those looks are totally awesome! Especially No. 1 + 2!

  • Naomi R Tallin

    I don’t know if I think those loafers embody ‘cool’ but I can definitly get on board with those bracelets!

  • Maria InΓͺs Ribeiro

    love the loafers!

  • kirbybee

    Can I just say I’m glad you finally succumbed and bought the loafers. Not least because I can take it as a sign that my increasing appreciation for my parents/grandparents past sartorial choices is not only ok, but in fact now cool.
    And of course my personal favourite is the double denim, just like my Mum does.

  • Lily Carls

    Does topshop still sell the leather pants from outfit 1? They are amaze

  • LA Shoegirl

    Girl, you got some good f’ing style! Werkit!

  • Jenn

    outfit #2 is my fave!!


  • Those loafers are beautiful!! Love the soft color. πŸ™‚ Btw, the all black leather outfit is too cool! The all white outfit is just so beautiful! Love it!

  • miamarg

    Ok. I wasn’t going to go there with the loafers, but I’m sold.

  • mressentialist

    I’m into these loafers big time. Granny proves she’s practical I guess?

  • Kirby

    So effortlessly cool! Each outfit is more perfect than the last.

  • Dana

    you’re starting to look a lot more “normal” and a lot less “MR”

  • Yu Yu Chan

    Pick a favorite? Nah.. cos I love all three outfits in you, which is totally you!

  • ASparklyHanger

    To be honest, I didn’t love the loafers at first, then outfit 1 looked kinda cool and I started thinking they had potential. But outfit 2 blew me away and now I’m totally sold on them!

  • stephaniesstyleblog

    those shoes are amazing!
    xx Stephanie (

  • Alissa from ChicPeek

    I absolutely love all these outfits! Not sure about the shoes for myself but they look lovely on you! I love the accessorizing, great details and a great touch!

  • Ariana Estrello

    LOVE THEM ALL! Especially the kegels. However, today as I was contemplating about what to wear to my southeastern county fair & rodeo I asked myself, “What is a girl supposed to wear if I’m on my “Quest to Cool” to a county fair? P.S. Leandra, I think you should do a piece on what a small town girl (with the heart of a man repeller) should wear to her local county fair and rodeo.

    • Leandra Medine

      Can I suggest high waist, loose fit denim cut-offs with a matching denim shirt and booties? Seems apropos.

  • Style Revival

    As with all loafers, it’s completely about how you style ’em and you’ve done a bang up job nice one!

  • Leah Myers

    Just bought a pair for $100 at a second hand store. This post definitely gave me the “ok” to buy!

  • Rosie

    “I wear your grandads clothes, I look incredible” Im all for those loafers!