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How to Pick the Perfect Kentucky Derby Outfit

For those loyal readers, or for those reading the past few hours, you can probably tell that I love the Kentucky Derby.  In case you’re planning to attend either the actual event yourself (I’m jealous of you) or if you’re planning to attend a Kentucky Derby celebration closer to home, then I thought it beneficial to share some of my favorite ensemble inspirations to give you a head start!  But first, a few of the rules that I tend to follow:

– It’s typically easiest to pick the hat first, then follow up by picking out your dress

– Go for color!  This is a spring/almost summer event, so I try to avoid black unless I feel like it’s the absolutely perfect outfit

– Be willing to stand out!  The Kentucky Derby is not a time to fit in, so go big

For this year, I have a couple of dress options that I can pick pending the weather.  Though I’ve already purchased a large, white hat that will fit perfectly with our Derby events.  For my inspiration, I’m working off of the following looks:

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Huffington Post




What are you planning to wear for the Derby this year?  Do you have a favorite color to wear for Spring and early Summer events?

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  • Reply stephanyalexandra

    Yessss! I really wish NY was more of a big hat type of place. I would be the happiest girl ever! I really like your posts! I just followed you 🙂 Check out my blog and see if you like it

    April 30, 2015 at 12:55 pm
    • Reply semisweettooth

      Thanks, lady! I’ll check out your blog tonight. 🙂

      April 30, 2015 at 2:38 pm
  • Reply The Two Savings Sisters

    I’m not going to the Kentucky derby but I am going to a couple of British weddings where hats are typically worn. I love all of the above outfits especially the first.

    April 30, 2015 at 1:39 pm
    • Reply semisweettooth

      STOP THE MADNESS! Even my Brit friends are not getting married in England. They’re ruining my style, don’t they know that?! (Ha!) So jealous. I can’t wait to check out your posts to see what fascinators you decide to rock for the big events. 🙂

      April 30, 2015 at 2:40 pm
      • Reply The Two Savings Sisters

        I dont blame them, the weather is horrific here even in the summer. A summer wedding needs a back up plan in case it rains, a field, rain and stilletos don’t mix!

        April 30, 2015 at 3:36 pm
        • Reply semisweettooth

          Haha, valid point. But I figure that’s what makes it so green, right?! 🙂

          April 30, 2015 at 5:04 pm
  • Reply Laura Kate

    I like the top one with spots – v pretty woman! Just need a Richard Gere to top it off 😉

    May 1, 2015 at 6:05 am
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