Feeling summer preppy

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How inspiring is this vintage photo of Lauren Hutton, looking all sorts of aces in a denim skirt and simple button-down? You can tell that she knows that the key to preppy dressing—now and always—is to keep your lines clean and minimal. I went searching for pieces that fit that description, and bring them to you here.

A black gingham button down is preppy, for sure, but in a very versatile way: you could wear it with skinny black pants and look completely sophisticated, or dress it down with your most beaten-in jeans.

These wide-leg chinos look ideal for summer, and they’re the perfect khaki hue too.

Regular readers know that my favorite chinos are these Tel Aviv pants from Nili Lotan, which aren’t cheap but which I shell out for because no other chino I’ve ever tried manages to accommodate my not-tiny ass and thighs.

A denim skirt that looks pretty much exactly like the one Ms. Hutton is wearing in above picture.

I’d wear this polo dress with bright, contrasting sandals and maybe an armful of bangles.

Nothing’s preppier than a good striped tee, and this one has some nice touches, like the slightly-longer-than-sleeveless sleeves.

I like an oversized polo shirt like this classic (and very tennis-y) one.

You can’t get much cooler than a seersucker button-down, and this one also comes in a very good pink if that’s more your speed.

Tretorns are pretty classically preppy footwear, and I like the colorful details here.

Espadrilles are also rather preppy footwear, and these are so cute and feminine; here’s a flat pair for those of you who can’t (or won’t) abide heels.

This sweet straw bag gets edgy with the addition of a checkerboard strap.

 

I love how a woven belt can add excitement to any outfit to any old outfit with a touch of color and pattern.

And speaking of color and pattern: this is rather winning.

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21 Thoughts on Feeling summer preppy
    cw
    3 Jun 2021
    7:40am

    I always think I’m not a preppy person and then I look in my closet and I’m totally a preppy person with a few exceptions of bohemian type tops. I’ve had really good luck with J.Crew chinos. Am quite tempted by the wide legged chinos and everyone should have a flat pair of espradrilles and a straw bag. Could we have a post on straw bags? My only complaint with them is I like them lined so things don’t get caught on the straw. Am I alone in this?

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      Candy
      3 Jun 2021
      9:29am

      Totally agree with cw. Yes to lined straw bags for just that reason and yes to chinos from JCrew — even from their JCrew Factory outlet, where I just found a great pair of girlfriend chinos.

      4

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        D.Morgendorffer
        3 Jun 2021
        12:54pm

        CW, I’ve mentioned before my belief in style polarities. So, it’s not strange really to have a preppy/hippie dual identity, especially given that both come from the collegiate mythos. Also, despite their seeming differences, the preppy and the hippie feel the pull of shared core values: enjoying public broadcasting, donating to the Humane Society, appreciating comfortable, cotton skirts, and believing in the usefulness of zippered tote bags.

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          Rae
          3 Jun 2021
          2:37pm

          LOVE this comment. Spot on.

          2

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          cw
          3 Jun 2021
          2:45pm

          Nailed me, D.Morgendorffer!

          2

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            D.Morgendorffer
            3 Jun 2021
            3:05pm

            CW, I clicked on and looked longingly at every single item in this post myself. I sometimes wonder if it would be more efficient if Kim France, Edith Machinist, and Tiffanie Miyashiro of Miyashiro Studio had joint custody of my debit card. Each month they could send me a note informing me of upcoming purchases: “Dear D, This month you will be paying the power bill, getting a button down shirt, and scoring a Japanese vintage art book. Love, US.”

            25

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          Mamavalveeta03
          4 Jun 2021
          1:48am

          ❤️❤️❤️

          2

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          Kim France
          4 Jun 2021
          11:03am

          You really outdid yourself here, D.

          7

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            D.Morgendorffer
            4 Jun 2021
            12:43pm

            Your kind responses made my Friday, thank you!

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    patty
    3 Jun 2021
    10:30am

    Crossbody straw bags act as a grater for cotton tops. So sad.

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    Sheilabird
    3 Jun 2021
    10:39am

    How many needlepoint belts did I make in college for my beaux and my brother- and for free?! Still love seeing them- this whole post is so great. It all speaks to me!

    6

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    Mimi A.
    3 Jun 2021
    11:09am

    The Nili Lotan Tel Aviv pants are marked down in the Cement color, a nice medium gray. Ah, discounts – the gateway drug of lusted-after, pricey clothes.

    5

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    CC
    3 Jun 2021
    11:31am

    Oh I want a Lacoste polo now…

    I don’t have a straw bag but I’ve been super duper into every one of this seller’s bags- not a one yet purchased.

    https://www.etsy.com/shop/ObsidianCraftsKE?ref=simple-shop-header-name&listing_id=573289472

    4

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    Eloise
    3 Jun 2021
    9:11am

    I’d love a straw bag post! I’ve never actually had one – I’m too lazy to swap out my bags seasonally – but the right one might convince me….

    3

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    Sandra
    22 Jun 2021
    6:19pm

    So….after many years of fashion blunders I took the preppy route and love it! This is a great post and I love all the comments. Happy Preppy Summer everyone!

    0

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    Aimee
    3 Jun 2021
    5:10pm

    I can confirm those Alex Mill chinos are every bit as good as they look! Comfortable but extremely flattering and well cut. Trust their size chart, I ordered two sizes and ended up keeping the smaller one.

    3

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    Viajera
    3 Jun 2021
    1:49pm

    I am sized out of both of the things I liked! That means I win. bwaaaa haha haha One was the gobsmacking belt and the other was the gingham, which comes in blue.

    5

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    Liz
    3 Jun 2021
    1:58pm

    I’m definitely more of a fall prep than summer one, since chinos, polos, and pastels look silly on me, but I do love a good summer preppy accessory, like those belts. Kiel James Patrick from RI is my favorite place for preppy rope bracelets, boat shoes, ribbon belts, and things with anchors on them:
    https://kieljamespatrick.com/

    3

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    liz
    3 Jun 2021
    9:30am

    Can I suggest Hat Attack for their wide array of straw bags? Some are very practical.

    3

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Kim France

I was born in Houston, Texas in 1964 and have lived in New York City since 1988. I had a long career in magazines, working at Sassy, Elle, New York, and Spin, and in 2000, I founded Lucky magazine, which I edited for ten years.

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