Derby Day Inspired Outfits: Hats and Dresses You Actually Can Wear

Tina, here.

Derby. Steeplechase. Triple Crown. It's all coming round the bend. But even if you're not attending the races, there's Mother's Day, graduations, showers, in the mix, too. May is a great time to refresh your dress wardrobe. And maybe, possibly, you could try a hat??

Don't miss our brand-new for Summer, just-released video, How To Buy and Wear A Hat. You can do it! You can wear a hat!

In our May Must-Haves Wardrobe Essentials List, I introduced the concept of a shift dress to you. We've been shopping and have already dressed women in Kentucky and Tennessee, and even California and DC for the upcoming races and May events. The trick is knowing how to buy fewer pieces you can mix and match to get the most wear out of each, and still feel like you're wearing a new outfit each time! You'll need one or two dresses, one or two pairs of shoes, and some accessories. Including maybe that hat?!

Let's start with a couple summer dresses.

This shift dress from Brooks Brothers is an investment. When I was out shopping I stumbled upon it and tried it on (I did not buy it, because surprise, surprise, I have enough dresses in my closet), and it's a great option. I'm 5' 5 1/2" and you can see it hits me right above the knees. It can be hemmed, but there is no hem to let out if you need it longer.

At $398 it's pricey. But here's how I would look at cost per wear: it's navy so you can treat it as a neutral and pair almost any shoes and jacket with it; it will work 3 out of 4 seasons of the year (all but winter), it's a classic tunic-inspired shape that won't date anytime soon. That's the filter I use. Here are some ways you can wear a shift, spring, summer and fall.

One Dress Three Ways


skinny-cta-blog-1

Wedges or flats are a must when you'll be walking through grass.


Pearl Necklace SPECIAL OFFER!

Wear with everything pearls. Gorgeous clasp. You can literally wear this strand of pearls with every outfit featured here. Yes, even the white t-shirt! Single strand 20mm glass pearl necklace. Crystal pave twist closure. Full Length: 16"

Purchase here: $215 $172 with code VAULT20 (YSV Special Offer 20% off)



Derby Hats and More

Let's talk hats. Just try one. It'll be fun. If you're a little uneasy about how to pull one off, watch our video, How To Buy & Wear A Hat, for some little tips that will make all the difference.

Make sure not to wear your derby hat (mine is from Brooks Brothers, but isn't on their website) too far back or too far forward, and you've got to get the crown and rim right. With special events like the Derby, exaggerated styles are totally fine.

Here are a couple new Derby Day outfits with hats. And I gave you some ideas for how to reinvent them this Fall!

Related: Shop Tina's May Must-Haves: Your Perfect Summer Wardrobe Essentials



One word of advice: no jumpsuits or rompers on Derby Day (as if) because you don't want that puddling on the floor of the port-o-potty when you have to deal with that close-to-unbearable sitch. Mkay cupcakes?

Thanks for reading and wear a hat already!

Best,

Tina

New items and ideas for home and wardrobe
Wardrobe and Home Collection
Founder, Tina Adams
Hire a wardrobe consultant