A New Kind of Prep for Spring 2014

Just don’t tell Muffy. You know she can’t stand anything nouveau.


It’s sort of a running joke that I have a tendency to dress like the type of guys I find myself attracted to — collared shirts under crewneck knits, loafers, blazers, a pocket square. I’m sorry to tell you that I actually wear my sweaters tied around my shoulders, and it’s not in an ironic way at all.


My inspiration stems from a combination of a romanticization of what I imagine my grandfather wore during his pre-war Yale days (I know, I know, Douche Bag Jar) and the uniformed boys of the Dead Poets Society. I look to old photographs of JFK too — his wife got the style accolades but this dude could dress. Surely there are designers known for their “preppy” aesthetic, but until recently, Jil Sander’s 2012 pre-fall collection was the only real fashion that served as my wardrobe’s muse. (Even then, the faux-collegiate “Js” were too obvious for my liking. No offense, Raf. You still rule.)


You can imagine my joy, then, when this Spring 2014 season, hints of a new prep began creeping in. This kind was a bit less obvious when compared to the standard pearls and twinsets. It was a modern take on the old classics, a nod to — but not full out pointing at — that old fashioned idea of a stereotypical WASP.

But it was there: Organic by John Patrick lead the way with his modest hem lengths and buttoned-up shirts. The flats kept it easy, approachable, preppy.

My next spotting was at Creatures of the Wind, where an updated take on a non-white tennis knit was shown over a polo and tucked into a skirt. This skirt, by the way, resembled the type of print typically reserved for wallpapered dining halls of very old-American clubhouses.

Then came a trio of modernized cricket sweaters at Rag & Bone, and at this point my prep-hunting felt a bit like bird watching: I began sitting at every show with a pair of proverbial binoculars (but how Lauren Hutton of me would it have been if I had ACTUAL binoculars), squinting my eyes in the hope of another sighting for prep.

I waited patiently through ’90s reruns, nodded politely at the space age and smiled approvingly at the weird. A case could be made for Karen Walker’s baggy sweaters, or Lacoste’s sportswear or even the bleached khaki at Reed Krakoff, but it wasn’t until Michael Kors that I felt myself perk back up again. His trench coats and trousers were enough to send me on a Pinning frenzy — to which I’ve created a board titled “HOW I WANT TO DRESS RIGHT NOW AND ALWAYS.”


Purists believe that true preppiness delineates a lifestyle, not one’s outfit choice; you’re preppy because you grew up in a coastal New England town and attended boarding school somewhere in Vermont, you learned to ski before you could walk and sailing comes as naturally as breathing. But where many mistake “preppy” as a synonym for rich (which is hard to argue considering it’s deep-rooted in old money) the clothing, you’ll notice, is never ostentatious. It’s always classic, like Organic, and sporty, per Rag & Bone. 

The fun in fashion is that it allows us to be whoever we want. So if your last name doesn’t include the prefix ‘von’ and you grew up in a household closer to Detroit than Greenwich, you can still dress like a boy named Knox, wearing an outfit entirely inspired by the boarding school you didn’t attend — or, you know, Jil Sander resort.

Oh these old shoes, Muffy? Why, they’re Tabitha Simmons for Creatures of the Wind.


Images courtesy of Style.com (runway), Vogue.com (detail) AVForums (Dead Poets Society), and Hamptons Magazine (the shot of all my boyfriends in blazers).

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  • I have always loved this look too. Takes me back to high school in the south. You had to have a Ralph Lauren polo shirt in every color.

  • Amatoria Clothing

    You’re adorable. I actually need more pieces like this. I always end up buying pieces that are “interesting” in some way. Then, when I am trying to pull an outfit together, I have a closet full of prints, textures, interesting shapes… but not enough basics. I guess I always prefer to spend a couple of hundred dollars on something bold than a basic white shirt. It always comes back to bite me in the tailfeather.

  • diane

    I am lusting after those red and white loafers!

  • Oh I love this college preppy style! And I was sooo in love with Robert Sean Leonard when I first saw him in Dead Poet Society!!!

    Mafalda ❤

  • pixiedust8

    Funny. I lived through the Preppy Handbook era at a very preppy school where girls actually wore sweaters with big monograms on the front, collared shirts and pearls.

  • Jackie @ Kleiden drew

    Thing is: You can do so much with a classically constructed piece. In a few years, Reed Krakoff may show fringed khakis or a cable-knit V-neck with a large gaping hole on the shoulder covered by clamshell pieces. Wait, has that already been done? Someone has I’m sure. (Would LOVE to see!)

  • Charlotte

    I think you hit the nail on the head about why the MK collection is so damn appealing: It’s mens prep worn my women and that’s chic as shit.

    I’m also trying to get on my knee sock game this fall and will possibly pull out some of my old polos…

  • I think that my style has been deemed “too preppy” that my dad asked me the other day if I were a Republican. Either way, whether or not Dead Poets Society and everything academic has an effect on my style, I’ll leave up to the stars. I’m a sucker for preppy.

    Your Friend, Jess

  • Buggy

    Awesome article from a fellow New England Prep!

  • Leandra Medine

    HEY AMELIA. I wore this today -4- U.

  • AshleyOlivia

    Ah! I love preppy. And now I have a question that has been plaguing me
    ever since I acquired a pair of camel penny loafers last Fall… Do you
    wear socks with loafers? I’ve tried wearing them with and without, but I
    can’t make up my mind which is better, and now I just need someone to
    tell me.

    • Amelia Diamond

      I’d say no. The socks-in-loafers thing gets a little Pee Wee Herman for me though I think Leandra has before argued that’s a good thing. It’s personal taste.

      (but sometimes loafers can be really painful before you break them in, so walking around in them in thick socks can help, and someone else told me that if you blowdry your feet with the loafers & socks on (?!??!) it can help stretch them out…

      • AshleyOlivia

        They are the Sahara leather color of Sperry’s Hayden Penny loafers… I love them, and they would be my favorite pair of shoes if I can solve this sock vs. no sock thing! I, too, feel weird wearing socks with them, though I tend to imagine myself more as an old-man-smoking-a-cigar-in-my-study (but not in a good way) than Pee Wee Herman. Yet I also think they look strange when I wear them without socks… something about bare flesh visible with loafers just strikes me as odd. I’m not sure this is a viable concern or just the side effect of visible socks being everywhere on the runaway and in the fashion mags last year. I never felt comfortable in the visible socks look, but I think the aesthetic has messed with my brain so that nothing looks right now.

        I’ll be the first to admit though that my fashion instincts are not impeccable… For some reason, I just discovered last winter that red and brown look beautiful together. I had randomly and inexplicably been functioning under the idea that red and brown never go together, until the Duchess of Cambridge wore the color combination one day and it occurred to me that, hey, it looks great! I’m praying for a similar epiphany in the loafers and socks category.

        By the way, the loafers do pinch a teensy bit, but I’m one that always suffers for my shoes, so I almost don’t notice!


    • Chloe

      What about tights? I have a pair of MK loafers that I wear endlessly with skirts and dresses and stocking’d legs.

  • Michelle

    Hah I find myself sometimes wandering a bit too far into men’s sections, drooling over all the fine-colored shirts and sweaters. Now I just try to balance my preppy masculine choices with edgy feminine pieces.

  • Katie

    Preppy proves perfect. Preppy is life. I live in Scottsdale, AZ – think bleached hair, fake cheek bones and Juicy Couture and that’s my city – but I always try to prep up the desert by tying an obnoxious, corded sweater around my shoulders or clonking around in leather loafers. People don’t get why I have to have a nautical themed day once a week, but if only they could see that I pretend I go to a boarding school fraught with cobblestone and kids boozing with their family’s money. Love live prep.

  • Poulette

    I love the way Europeans, specifically the French & Italians, interpret this look – its the bomb. When I try, because I am pale & blonde, I look like a soccer mom from the suburbs in Illinois. The only way I’ve found is dressing like a little boy …. But then, I look like a boy. What are my options, soccer mom or little boy?

    The saving grace is some killer fushcia lipstick…. It’s what separates me from the boys.

  • This Exquisite World

    There’s just something so appealing about those clean-cut lines…


  • S

    Leandra you are the bomb, I have always loved prep and dressing like a boy (whilst still wearing makeup to assert my gender).

  • Guest

    “I have a tendency to dress like the type of guys I find myself attracted to…” I love loafers, sweater vests, driving, driving caps…

  • Wind-up bird

    “I have a tendency to dress like the type of guys I find myself attracted to…” I love loafers, sweater vests, and snappy hats. How I’ve never made this connection , I’ll never know.

  • Nicole

    I go to an all girls catholic school and I always wanted to know how to turn the preppy look (EVERYONE has the same bag, shoes, sweaters — even when we’re out of school and supposed to be “out of uniform”) and give it an edge with my own unique twist. You’ve definitely have given me inspiration on how to do this and I am so excited that it was on the runway this year!

  • Claire

    You’re hilarious! Brings me back to my days in prep-school.. imagined I was wearing a tie, loafers, and a nicely embroidered blazer… but alas..I was wearing khaki flares from american eagle, nasty sneakers, and my brothers hand-me-down polos. the good life.

    • Amelia Diamond

      haha this was my school uniform too, essentially. oh my god i owned so many pairs of AE khaki flares…

  • Preppy is always approachable – partly because it dates well, is functional and presents immaculately to the sneering on lookers – not like we care what others think, fashion is meant to be self interpretative? But when fashion crowds reinvent it with new pieces its so easy to just go straight back to the basics.

  • Love the super deep V-neck sweater! http://www.lezu.com

  • Margaret Ely

    Amelia, your shit is great.