The Fashion Magpie Annapolis

Preppy Summer.

I am going to Annapolis this weekend for a very dear friend’s bachelorette party (I wrote about meeting her here), and we’ll be sailing, shucking crabs, and drinking a lot of rose.  Accordingly, I am leaning towards my preppiest duds.  I don’t wear them as often up here in New York, which feels sleek and trendy and urbane, and so this will be a delightful excuse to return to my teen years.  We’re talking washed out Lacostes, faded Nantucket red chinos cuffed at the ankle, a reckless amount of navy, and striped everything.  Think JFK The Myth — young, vigorous, well-heeled.  (JFK The Reality is a different story altogether.)

Below, my preppy summer wishlist…

Chino Shorts in Old Red (also love these striped, ruffled shorts!)

A Long-Sleeved Polo (I’d order a size up for a roomier fit)

A White Ballcap

A Ruffled White One-Piece — just the right amount of nautical

Supergas in Vintage Blue — with a “they faded on the boat” vibe

A Country Club-Appropriate Wrap Dress in White (also love this — under $80!) with the cutest plaid slides

A Sunhat with a Preppy Twist

White White Jeans: This Poplin Top, an Eyelet Blouse ($65!), or This Ultra-Covetable Tasseled Misa

Striped Manebis (major Chanel vibes; on sale!)

A Beachy Striped Maxi (love the loose fit; have also been wearing this constantly — and this achieves a similar effect)

One-piece wonders: this or this (amen amen amen)

Bonne Nuit

P.S. The preppy makeup look is under-done, just-off-the-boat chic: a dusting of bronzer; a few dabs of dewy, transparent luminizer; a flushed natural-looking lip courtesy of Dior; and a spritz of a beachy scent (this smells insane).  I also love a little body oil on the shoulders/decollete to highlight a light tan.  And of course my two-step mascara routine, which I outlined in full here.  Can’t go anywhere without some dramatic lashes, even post-sail.

P.P.S.  I still get a lot of questions about my iPhone case.

P.P.P.S.  My favorite monogram sources, and a true love story.


  1. Preppy dressing is so nostalgic (to me, at least) and perfect for summer. I find myself leaning towards preppy only in the summer … my style has largely evolved from those days of polos & chinos/Lilly dresses! Still love all of your picks, though.

    I’ve never spent much time in Annapolis but my cousin is getting married there in the early autumn. You’ll have to post some recs!

    1. Agreed — summer is the season for preppy wear for me, too. I’ve always found the “preppy” fall and winter looks a bit too masculine for me — cable-knit sweaters, tweed, etc — and generally prefer the light and airiness of worn-in summer duds.

      Will share what we discover! I’ve been to Annapolis a bunch of times and absolutely have to advocate for Jimmy Cantler’s Crabs if you’re down for the authentic blue crab experience.


  2. Oh dear girlfriend…. I LOVE everything preppy and really loved this post. Of course I am a Charlottesville gal too! I might go with this hat instead. The bow in back is divine. But loved it all.'

    Love your blog! I’m in Naples right now, so thinking of you here too.

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