Derby Days

17 Apr

by Lauren

So… spring means horse races.  And often times that means you need a fierce dress and fab hat to match.  Unfortunately for me, I will not be able to attend any horse events this spring (which kills me), but alas the legal world calls… Admittedly, that means I have not really been on the look out for cute spring dresses, however there are quite a few that have caught my eye.

This spring, the dress trend is all about pretty florals – I can imagine that Gold Cup & the Kentucky Derby will be full of flower print dresses.  For some, that means you want to avoid & for others that means you want to embrace – so I am trying to show a mix of both.  I have also provided some hat suggestions.  I typically err on the side of the more utilitarian in the hat department – e.g., a sunhat that I will be excited to wear again, over a hat with tons of silk flowers that I will throw to the back of my closet only to be seen upon my next move.  However, for those of you who are going ALL out – I have some fierce options for ya.

*Remember shopbop is 20% off with WEAREFAMILY13 – I am posting this immediately instead of waiting for the AM so you have extra time to consider shopping there! 

Cap Cana


Troubadour Cap Cana Dress

I adore the color, the back, the tiers, the sleeves – this dress is divine & this is probably my # 1 pick.

Jenni Kayne

Jenni Kayne

Okay, its Jenni Kayne so it is going to break the bank, but if you are doing something ultra fancy like box seats at the Kentucky Derby (hi, Jessie) you can probably justify the purchase.  Plus WEAREFAMILY13 gets you 20% off until 4/18 at midnight.  I love this dress, if it were the same price as the one above it (& if sleeveless looked good on me) it would be my # 1.


Halston Heritage

I think this is super chic, and with the right hat, it would be a perfect Derby look.

Malene Birger

Malene Birger

Because of the fabric, this is probably better suited for a more casual field-type affair such as Gold Cup.  A simple fascinator or sunhat would complete this look.

Rachel Zoe

Rachel Zoe

I love the way this dress incorporates the mod trend so elegantly.  This would look fierce with an equally captivating black or white hat.



I am normally not a huge Shoshanna person, because it just doesn’t fit me properly!  But there is no denying the lace + color of this frock are springtime perfection.

Madison Marcus

Madison Marcus

I have it on good authority that this dress is SUPER cute in person.  I love the colors and I love the lace overlay.  It runs a tad big so if you are deciding between sizes, go down.

Red Valentino

Red Valentino

I mean what’s not to love?  Probably only the price point. (it’s also here & here).  This is Derby Perfection Obsession.

Nordstrom has an entire page devoted to derby head attire & it is reasonably priced!  The other site I have happened upon is Hat A Tude, which has beautiful hand-made & unique creations.  Lastly, the Neiman Marcus in Palm Beach had some beautiful fascinators, I have failed to take note of the brand, but if you happen to have an NM in your town, that is also worth a drop by.


I really like this BCBG fascinator, and its only $38 – you could wear this with a dress that is a bit more on the minimalist side, to look ultra ladylike, or you could wear it with a boldly printed dress for a “look at me” punch.  It would look really cool with that Jenni Kayne frock.

White Hat

Of all of the super “Derby” hats, this one caught my eye & held it for over a week. It’s stunning.  This with the lilac Shoshanna, the Troubadour, or the Halston Heritage?  I die.

Bow Hat

For me, I prefer a giant bow over a ton of flowers – this one rocks, IMO.  I think its fiercely chic to hide behind a giant black and white hat with a stately bow.  I want this.  Now. 

I highly recommend browsing for your perfect Derby hat, if you are going all out.  And below, a few of my favorite sun hats for those who are doing Gold Cup or just want to be more understated.

Eric Black and White

Eric Javits

There is 100% classic and will enable you to look chic at the beach or out shopping, for eternity.

Eric Straw

Eric Javits

Where this one lacks in Derby punch, it makes up for it in versatility – tie a scarf around it for gold cup, put a big bow on it, and then remove the flair (or keep it!) for a day at the beach or errands around town.  I love this hat and have been dying to add it to my collection for years.


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