Win, Place, Show Fashion for the Kentucky Derby

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When people think "Kentucky Derby," big hats are among the first things that come to mind. Unfortunately Polyvore doesn’t have an extensive collection to choose from for this post, but there are so many stunning hats out there begging to be worn for the Run For the Roses.
With that being said, here are five somewhat untraditional Derby looks that I would love to wear. The most important things about dressing for the Derby are in fact very simple – make sure it fits right (who cares what size it is or isn’t), make sure it’s appropriate for the occasion (bathing suits are for the water), make sure it’s comfortable  (it’s a long day) and most importantly, make sure you feel confident and love what you’re wearing (you’re going to make memories you’ll cherish for years to come so don’t let a bad outfit get in your way).
SHOW

Show by Victoria Garofalo 
Perhaps I’m a bit (A TON) romper crazy, but hear me out – they’re summery chic, feminine and you don’t have to worry about finding a top that matches your skirt, pants, shorts – glorious! Going to the restroom can make them a little high-maintenance, but that's why gals go in pairs - help a sista out! Because I love ‘romps’ so much I couldn’t pick just one of these Miss Selfridge pieces for this blog – basically the same problem I have picking my Derby horse, I‘m a fan of a handful but know come the first Saturday in May I’ll have to commit to one outfit and one Derby horse. Nude shoes are the way to go with these, but make the “heels or flats” decision based on where you’ll be sitting (or standing) all day.  If you're in the infield or just want to have some fun, the red rose flower crown is simple and makes a statement, or you can go for a floral organza fascinator. Grab a clutch for your essentials or if you end up carrying around a billion things (racing form, Derby glass, souvenirs, etc.) grab a Longchamp – they’ve never let me down. Toss on some fun jewelry, don’t forget your sunnies and giddy up!
PLACE

Place by Victoria Garofalo 
With a figure-complementing banded waist, this Black Label Evan-Picone swing dress is perfect for Derby day. It's classy, comfortable for an all day event, has pops of fun yellow color, oh and it's currently on sale! The red rose earrings are a subtle nod at the historic Kentucky Derby flower and add the perfect touch of theme without being tacky. Kendra Scott’s stackable midi rings are a dainty addition to your hands and the black "Irene" fascinator has just the right amount of flowers and feathers and will sit perfectly on your head with the help of an elastic band you can tuck underneath your hair. You can’t go wrong with the black Ralph Lauren clutch or Calvin Klein ankle strap sandals and, per usual, sunglasses are always a must. 
WIN

Win by Victoria Garofalo
I absolutely adore this 1960s Oscar De La Renta embellished brocade cocktail dress and wish it lived in my closet. It’s for sale and in my size and if I hit any big bets on the Derby this may have to be purchased. The metallic gold, ring chain artwork perfectly compliments the dark tangerine and the floral embellishments. Keep it simple with a solid navy clutch, equestrian motif studs from One Kings Lane and gold leather ankle strap heels. As for headwear, do something simple and navy or have Christine Moore make you one. She is my go-to gal for all things headwear and her creations are gorgeous; she’ll make a one to perfectly compliment any outfit.
What are you planning on wearing to Kentucky Derby 141?