Derby Style: 3 Race Day Looks + Giveaway

GoldCup CollageIt’s time to break out the flowery dresses, grandiose hats and mix an ice-cold mint julep, because horse racing season is here. Growing up in an equestrian family, I went to my fair share of horse races, frequenting Virginia’s Gold Cup and making a yearly family pilgrimage to Saratoga Springs, New York for the Travers Stakes. As a little girl, I loved going to the races to see the horses of course, but nearly as much I loved to take in the unique fashion that comes with race day. As the years have gone by, the thrill of picking winners and new dresses has only intensified.

This weekend kicks off the Triple Crown with The Kentucky Derby.  But if you aren’t headed to Lexington and are in the DC/VA/MD area then you still have the option to head to Virginia’s Gold Cup on Saturday and look just as fabulous. So whether it’s the Derby, Gold Cup or attending a race-day party, you will need to dress the part and I have a few style tips up my sleeve to ensure that you look hot-to-trot.


If this is your first time attending a horse race, there are a few things you will need to know:  pick the fastest horse, order the strongest drink and wear the biggest hat. Seriously. No matter what horse race you attend, hats are always a thing. Especially at the Kentucky Derby, women are known to plan their entire look around their hat. So don’t be afraid to make a statement with an extravagant hat or an over the top fascinator. Since your crowning jewel is your hat, be sure to tone down your jewelry. No statement necklaces needed with a larger than life head-piece. When it comes to footwear, I usually wear heels but then again, I am not the most practical either! Wedges are a great option as well as pretty flat sandals but if you are going to the Derby and have seats in the grandstands, then don’t be afraid to rock the heels.

Picking out the perfect dress can be a challenge when it comes to prepping for race-day but since I found Rent The Runway it has been an absolute breeze. If you haven’t checked this place out by now, you seriously might be living under a rock. Rent The Runway is website and now store that allows you to choose from thousands of designer dresses that you can rent for a fraction of the price to buy. You can choose from 4 day to 8 day rentals and you can also rent two sizes for the price of one, just to make sure it fits. Perfect for occasions like horse races, weddings, proms, black tie events, the list goes on.

Below are my top race day picks from Rent The Runway, check them out and be sure to scroll to the bottom of this post to learn how you can WIN your very own race-day look for you and two of your closest friends

The Fit and FlareSarah-17Sarah-9

Sarah-21 Sarah-26Sarah-22

Wearing: Dress: Allison Parris – Rent for $40, Heels: c/o Shoe Dazzle (similar here), Earrings: Morra from Ella Rue; Sunglasses: She Inside.

A fit and flare dress like this one, screams Southern Belle and it is the perfect dress to wear to  the Kentucky Derby or Gold Cup. I chose to style this dress with a simple nude heel and a pair of hammered gold earrings for a simple and chic look. The dress makes a statement on its own with its wild print and flirty skirt, so I felt I could keep the rest of the look pretty simple.

The Jumpsuit

Sarah-3 Sarah-7

Wearing- Jumpsuit: BCBG Max Azria– Rent for $65; Hat: Ella Rue; Earrings: Morra from Ella Rue, Bag: Chanel; Heels: Nasty Gal.

If you are looking to make a major style statement, then I suggest wearing a jumpsuit like this one by BCBG Max Azria. I love wearing jumpsuits to events because they are unexpected and super easy to wear. Pair it with a fabulous hat for race-day look that is on point.

The Classic with An Updated HemlineSarah-32Sarah-41 Sarah-31

All photography was taken by Wesley Tan.

Wearing- Dress: Osman– $200 Rental; Hat: Old (similar here); Bag: Chanel; Heels: Shoe Dazzle (similar here); Accessories: Morra from Ella Rue.

I absolutely love this look and think it screams Kentucky Derby. It is uber classy but still flirty and fun with the asymmetrical hemline. I accentuated the faint red stitching in the dress by pairing it with a loud and very horse-race appropriate red hat.

If you still haven’t found your perfect race-day look, no need to worry, just head on over to our Instagram for a chance to WIN a $75 rental and styling appointment at Rent The Runway for you and two of your closest friends! And as for the Derby, my money’s on American Pharaoh. Who will you be rooting for?



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  • Reply
    April 27, 2015 at 8:13 am

    Love the red jumpsuit look. So chic.

  • Reply
    April 28, 2015 at 4:50 pm

    Wedge heels work better at Gold Cup than spikes, since it’s mostly grass.

    • Reply
      Sarah Phillips
      April 28, 2015 at 6:39 pm

      Totally agree Veronica! I usually wear wedges to Gold Cup as well! I might try wearing the spike heels to The Derby if I were sitting in the Grand Stands but I would also bring a back up pair of flats just in case. 🙂

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