Win, Place, Show Kentucky Oaks Fashion

It's the most wonderful time of the year … Kentucky Derby season!
For lady horseplayers, handicapping your outfit is sometimes just as challenging as picking the winner of the Kentucky Oaks. Are you having difficulty finding that perfect outfit for the first Friday in May? Take a look at these three styles that are sure to be a winning look whether you're live at the races or at a watch party!
Win -

You cannot go wrong with this sophisticated look for Kentucky Oaks day! The black and pink color scheme reminds me of the silks of Oaks contender I'm A Chatterbox. I love the cap sleeves on the dress and its hint of multi-color prints along the neckline because you can pick up any one of those colors to accent in other areas of the ensemble, like the heels that I paired with it. Finish the look off with some exceptional horse bling and you're sure to turn heads at Churchill Downs!
Want the look? Here's where to find it:
Just Cavali stretch-knit mini dress, $198, theoutnet.com; Slingback black multi-color block heels, $40, shopakira.com; ASPCA Tender Voices 1/10ct T.W. Diamond horseshoe pendant necklace, $250, jcpenneys.com; Bling jewelry ravon rose ring, $35, blingjewelry.com; Monsoon Jolie Flower Hatinator, $105, monsoon.co.uk
Place -

This off the shoulder skater dress is perfect for Oaks day because it is fun, floral and flirty. You can dress this look up or down depending on how you accessorize. I chose a mid-height wedge sandal to pair with the dress to keep you comfortable while walking around the track. I love the white clutch because it can also be worn across your body so you have your hands free to cheer on your winning horse. Since the dress has a large pattern, I'd keep it simple with a small hairpiece like the fascinator shown here. Did you see the horse shoe pendant charm from Auburn Jewerly? It is customizable by color and chain length, and also can be worn as a bracelet charm. I own one (and love it!)
Want the look? Here's where to find it:
Ax Paris Floral Print Print Pleated Skater Dress, $82, nelly.com; Mustang Wedge Sandals dunkleblau, $52, zalondo.co.uk; Accessorize zip envelope flap across body bag, $34, accessorize.com; Kate Spade New York beach house bouquet enamel stud earrings, $48, saksfifthavenue.com; Untold Alice fascinator, $37, houseoffraser.co.uk. Racehorse Pendant, $95, auburnjewelry.com
Show -

Beach style is in this year, so why not bring it to the races?! This is my favorite look of the three. I could see this look being worn at one of the several watch parties taking place all over the country from other racetracks and house parties to local establishments. The look also carries nicely into the summer months and could be recycled to other ensemble for a different venue. I choose these great (and affordable) palm leaf printed trousers and white blouse because the colors reminded me of the green and white silks of Oaks contender Stellar Wind. A straw hat and sunglasses will keep you feeling cool in this outfit while walking in the comfort of flip-flops. To make this ensemble even more personal to the event, swing by AlexandAni.com for a Kentucky Derby themed charm bracelet!
Want the look? Here's where to find it:
Lucluc white bad collar long-sleeve blouse, $22, lucluc.com; White palm leaf print cropped trousers, $27, newlook.com; Pink Ice tuxedo jelly flip flops, $20, pinkice.com; Nine West scale checkbook secretary wallet, $40, macys.com; San Diego hat, nordstrom.com; surf sunglasses, $10, target.com; Horseshoe necklace, sophiebysophie.com; Alex and Ani Kentucky Derby charm bracelet, $38, alexandani.com.