Happy Monday! I haven’t been this excited about a Monday in a while but not only are the Wildcats playing for the national championship tonight but I’m kicking off a series I’ve been excitedly talking about for weeks.

Last year I started the Derby Dress of the Day series – you know the gist  – picking a dress every day and showing you some options for styling it for race day. This year, I wanted to kick it up a notch. So rather than just share collages, I rounded up a bunch of dresses from some great local boutiques, got a group of friends together, received an amazing delivery of hats from Headcandi  (she’s designed hats for blogger favorite Blaire from Atlantic-Pacific and Luke Bryan and his wife Caroline, just to name a few) and played Derby dress up, all in hopes of helping you get your outfit for the track just right (or just share pretty pictures from Whitney Neal).

So for the next 26 days, you’ll be getting a daily dose of a pretty gal dolled up for Derby. First up is my friend, co-worker and fellow crazy Cats fan Lynsey (wait, is it bad luck that I have her in a red dress today?). Lynsey usually hits up the track for at least Oaks and sometimes Derby and this year is no different. Each year we usually discuss in detail her dress options (mostly me sending her tons of links) so it was fun getting her to try on dresses and then trying to convince her that she “needed” one. This look, styled for a day at the Jockey Club Suites, was my favorite.

Red-Cut Out Dress: Leona ‘Jamie’ Dress
I’m pretty obsessed with the simple, a little sexy, super-chic cut-out on this dress. If you haven’t checked out this Nashville-based designer, you need to now. Locally, Clodhoppers carries some of the collection.
Red, black and feathered fascinator: Headcandi
White & Gold Clutch and Multi-Color Cuff Bracelet: Dandelion Boutique

Photos by Whitney Neal (p.s. – check out her new, gorgeous website.)