Tis the season for dresses: Part I

Ok so from a serious post to a more lighthearted one.

Whenever spring and summer come around I get so excited to switch my closet around. Winter duds to the back, spring/summer to the front. Then I get to see my sundresses and I get so excited to wear them! This has become especially true as spring in central Va means one thing: Horse Races! Getting dressed up and tailgating all day with your friends is such a blast at the races. There are also a lot of other opportunities to show your preppy side, like going to weekly polo matches, visiting one of the many local vineyards, and attending outdoor concerts (Starry Nights, for instance). I wanted to do a few posts on preparing for these fun events, as they are one of the highlights of the year and begin in just a few weeks!

Attending the horse races in Va is a pastime for the young and old. The big races in this area are the Foxfields steeplechase races (the highlight of the year!), Strawberry Hill in Richmond, Colonial Downs, and Virginia Gold Cup. The college kids love to get dressed up in their skimpy sundresses, cowboy boots and Longchamp bags (of course) and booze all day on their plots. At more refined plots, women wearing are designer dresses, pearls, and enjoying a day of cocktails and mingling (did someone say Mint Juilep?)

Mint Juleps

Here are some pics of my friends and I at Foxfields last year

It’s also a lot of fun to wear a really big ridiculous hat. Here are a few I wore to another event last year 🙂

My distinguished pose

This hat is ridiculously big!! Loved the color and the bow

Starry Nights @ Veritas Vineyard

I thought I’d put together some ideas for getting the “southern preppy look” for the upcoming horse races (believe me, this is a steep learning curve for a girl from Boston!)

1. Dresses from Lilly Pulitzer

Lilly’s bright, colorful, and preppy clothes scream Southern debutante (or maybe a weekend in Charleston. Or the Hamptons/Cape for all you New Englanders). The Official Preppy Handbook states that the Lilly Beach Dress is a must-have item for preppy women (this handbook is a tongue-in-cheek guide to preppy dressing and lifestyle; interestingly enough this book served as inspiration to the founder of J.Crew).

Here are some cute L.P. dresses that I have my eye on. You can find them here:

2. Accessories

Accessories make the whole outfit. From Longchamp bags to big, floppy hats, certain accessories are a must to fit into the derby scene. Here are some that are very popular

*Big hats are a must. You can get a crazy, ridiculous one or for a more modern take, check these out from Nordstroms:








* Deciding what to wear for shoes can be difficult. Many times you’re standing the whole day on grass. If it’s been raining, it could be muddy. You want to make sure you’re comfortable but still fashionable. Flat sandals and Hunter boots are commonly chosen (I’ve had the green Hunters for 4 years and they are amazeballs. They last forever!)

Lilly P sandals

Have 'em. Love 'em!

* Bags: The Longchamp bag is ubiquitous. Although I don’t like to conform that often, I do have 2 Longchamps, a big and small one (big one for my computer and work). If you don’t want to go that route (because everyone and their mom is carrying one), you can find a fun straw bag or preppy tote instead. Here are some options:

Longchamp. I have this color!


Marc by Marc Jacobs Preppy Straw Rosa Tote

Ralph Lauren Canvas Pony Flat Tote

3. The perfect cocktail: Finally, here’s an easy recipe for making Mint Juleps your whole plot can enjoy together. I have measurements listed as “counts”, from when I used to bartend.


  • Bourbon
  • 2 bunches fresh mint
  • Water
  • Simple sugar


At the bottom of each glass, muddle the mint and sugar syrup together (this releases the aroma and flavor). Add ice over mint and sugar. Next pour in the bourbon (3 count) and top with 2 count of water. You can serve an extra sprig of mint at the top. Enjoy!!

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