“You’re So Square, You Have Corners” – Megan Draper (Mad Men)


I bought my first pair of penny loafers a few months into my first job after college. I was working in a biotech lab when my trusty classic suede Puma sneakers started to look juvenile.

FYI: biotech work is very casual, and especially if you’re an entry level lab slave, you don’t want to wear anything too nice because it’s bound to get splashed with some kind of chemical that will ruin it. So, we all wore the same thing, some combination of jean, sweater, and closed-toe flat.


So I bought a pair of serious shoes…black leather penny loafers. A few months later I felt they were a little too square for 22 year old me, and I rarely wore them after that.


Fast forward quite a few years and now I enjoy dressing a little square. I’m also digging through the dark corners of my closet on the off chance my little black loafers escaped my past Goodwill donation sprees. So far, no luck.


The turquoise ring in these photos was a very special birthday gift from my mom. It’s vintage circa 1865, and I’ve been eyeing it in my mom’s collection for years. I love everything from the gold band with bezel set diamonds, to the bright blue Persian turquoise stone, but especially that a woman loved and wore it during the end of the American Civil War. Was it purchased in happy celebration of the end of the war? Or maybe a gift from her sweetheart, returned safe from the front lines? An engagement ring? It’s these questions that make a piece like this truly special.


:: photos – Mr. AN ::

Outfit details – LOFT shirt (altered) :: Blank NYC jeans :: Banana Republic belt :: Cole Haan loafers (similar) :: Valentino handbag (similar) :: Kate Spade watch (customized) :: Stella & Dot bracelet (c/o) (in silver:: Banana Republic stackable rings :: Vintage ring :: Essie “Ole Caliente” nail color

Join the Conversation


  1. says: steph-zn

    Those loafers are so cute but I absolutely love your vintage ring! I have been on the search for one like that for ages…

    1. Good vintage is so hard to find! All the good ones my mom scored are from the 70’s in Chicago. This ring was in a museum store that used to sell vintage items. I’ve never seen such nice vintage that wasn’t a bazillion dollars these days. =P

  2. says: Cee

    Thank you Kelly, for wearing burgundy items so well. I picked up a dark red sweater recently from H&M and I’m counting down the days until fall ;)

    1. says: Michelle

      I totally agree with digging up old pictures! Awhile back I wanted to do a “re-do” post where people take an old picture of themselves and try to update the look.  If people are interested, I would love to host it on my blog! 

  3. says: sassypetite

    I love your style and thanks for sharing the girlsack tumblr.  Am totally obsessed!  I’ve also been searching my closet for a pair of Bass penny loafers from high school, but I think they went into a donate pile years ago, unfortunately!

  4. says: lainey

    I love your style! Just became a fan :) I’ve noticed you love to have your hair kinda scrunched most of the time? I like that hairstyle, I do it quite often. I think you should also try different things with it just like you do with your clothes…maybe straight or nice loose waves. That would look so elegant. Just a suggestion :) Have a great day!

    1. Thank you! As for my hair, it’s naturally curly, and believe me, I’ve tried different hair styles and styling it curly is really the only one that suits me. My hair is very, horribly, thin and fine, so when it’s straight or even in loose waves, it looks like I have no hair. =P

  5. says: Michele Chic

    That’s a lovely sentiment about your mother’s ring. There’s something special about objects with history.

  6. says: Katherine

    I LOVE penny loafers! Seriously, I love loafers of all kinds. I used to wear them in college and embarrassingly enough one day some of those Jesus Christ Latter Day Saints representatives (who were boys by the way) came up to me to ask where I got mine because they looked really comfortable and they wanted to get some for themselves. LOL. 

  7. says: TOBeautyReviews

    Mr AN is getting so good at taking photos, love it!  That ring is beautiful and I love the potentially romantic story behind it :)  I enjoy dressing “square” too LOL! I feel more comfortable when I’m conservative with a bit of a twist of some sort :)

  8. These photos are so stunning!  I love your penny loafers, but I have to say the turquoise ring is the star in these photos.  I adore turquoise and pieces with history, so your ring is right up my alley.  I actually have one that’s similar-looking, but it was made about 100 years later =).

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