Keeneland Fall Stars Fashion for Any Budget

Keeneland Race Course is nestled in the rolling hills just outside of Lexington, Ky. alongside farms where some of the most legendary horses in the world grew up. When the autumn racing season kicks off, Thoroughbred fans the world over turn their attention to this beautiful racetrack, whose signature event is the Fall Stars weekend. From October 2-4, there will be seven stakes races called Win and You’re In events; that means the victor in each of those tests will earn a berth to the Breeders’ Cup World Championships on Oct. 30-31.
With fall in full swing and top-notch horse racing to celebrate, we put together three outfits for any budget for Fall Stars weekend at Keeneland. Win will be the most expensive, with Place (horse racing’s term for second place) as the mid-range ensemble and Show (Thoroughbred-speak for third) as the most affordable look.
WIN

15FallStarsWin by penelopemiller featuring gold jewelry
This $170 Karen Millen frock is a perfect dress to anchor a fall wardrobe: it can get you to the races, work, a date, or pretty much anywhere else. For Keeneland, I paired it with a great pair of knee-high boots ($199, Brooks Brothers) and this sumptuous $215 coat from Mango. The mock-croc purse is $221 from Diane Von Furstenberg and the fascinator is $33 from NYfashion101 on Amazon. Complete the look with these beautiful Lucite earrings for $60 from Alexis Bittar, a chain bangle ($195, Halcyon Days) and a killer pair of sunnies ($98, Chloé) and you have a race day-ready look for $1,191 – and with some carefully placed bets, you can win that all back on the right horse!
PLACE

15FallStarsPlace by penelopemiller featuring zara skirts
A collegiate cool look is perfect for fall, and since patchwork was all over the runways for Autumn 2015, I chose this $70 leather mini from Zara. Then I added an opaque pair of tights ($11, H&M) and these outstanding spectator pumps for $72 from Unique Vintage.  The Daily Look handbag is only $72, but it looks reminds me of a Furla bag that would be 10-times that price. Bows were also a trend on runways this season, so this $54 blouse from Mango incorporates that detail without going over the top. A $47 pea coat from H&M is perfect if the weather gets chilly, and to accessorize I finished the look with a $23 boyfriend watch from Wet Seal, a subtle pair of chevron earrings for $15 by Leslie Danzis, and a pair of Malbec-and-gold sunglasses for $25 from Loft. All together, this ensemble will run you $389.
SHOW

15FallStarsShow by penelopemiller featuring a blue dress
I may have to order this navy dress for $16 from YesStyle – the print is actually kitties, and therefore the dress needs to be adopted into a new home. One in my closet, specifically. The dress also comes with the belt, so it’s a steal of a deal; I added a pair of taupe knee-high boots for $28 by Olsenboye and a beautiful navy Le Rêve croc bag for only $48. A scarf is always a good bet in the fall, and this ecru infinity version is just $16 from Old Navy. I’ve been dying to use these Susan Shaw horse head earrings ($14) in a set for such a long time – I think they’re so incredibly chic. The burgundy faux-leather jacket is a mere $21 from Plumsika, and I finished off the look with a wool hat from H&M for $31. All together, our show look is just $174 from top to toe, which should leave you plenty of money for some bourbon and betting!
No matter what you wear to the races, just remember to have a great time and cheer on your favorite horses as they continue down the road to the Breeders’ Cup World Championships!