Nashville-based fashion stylist and wardrobe consultant Carson Love brings us another fabulous set of tips to ensure your wardrobe reflects your personal style AND the season.

**********

While your calendar might be sprinkled with all kinds of warm-weather events, few spring traditions are more exciting than the horse races! The beautiful horses and pageantry take center stage, but spectator fashion certainly shares the spotlight.

As a personal stylist, I believe a little outfit planning and forethought can go a long way. If you’re lucky enough to attend a race or two this season, I encourage you to get a step ahead on what you’re going to wear. This will ensure you look your best and feel comfortable and confident during the long race day.

With the Kentucky Derby and Nashville’s Iroquois Steeplechase right around the corner, along with many other horse races throughout the South, let’s break down the essential components of a perfect race-day-ready ensemble!

This article contains product affiliate links. We may receive a commission if you make a purchase after clicking on one of these links.

Below, we’ll cover everything from hats to dresses to separates to shoes to bags!

WHAT COMES FIRST: OUTFIT OR HAT?

A client asked me the other day, “Do you find a hat first, or do you start with the dress and then match the hat to it?”

If you have a specific color palette or vision in mind for your headwear and are going the custom-order route, then you can totally start with the hat. However, most of the time, I think it’s best to find an outfit you feel great in and then find the coordinating headwear.

Luckily, fabulous headwear is easy to find, so going custom isn’t a necessity. Here are a few different silhouettes and styles I love to help you along your hat hunt.

Tip: If you’re looking for a hat and can’t find the perfect color, find a neutral hat that fits well and take it to your favorite florist! They can often attach fresh blooms based on your chosen palette.

Brimmed Hats

When looking for hats online, opt for woven or straw materials versus wool so it’s more breathable. More on that later!

Wide-brimmed hat made of woven material, featuring a pale beige crown and a soft pink brim, pictured against a white background.Pin
Eugenia Kim Emmanuelle Packable Wide-Brim Fedora, $195, at Saks Fifth Avenue | Image: Saks Fifth Avenue
Wide-brimmed brown straw hat with a black ribbon and pearl embellishments displayed on a white surface.Pin
BTB Los Angeles Ollie Pearly Straw Fedora, $98, at Neiman Marcus | Image: Neiman Marcus
A wide-brimmed straw sun hat with a white ribbon detail, displayed on a white background.Pin
Eugenia Kim Core Mirabel Straw Sunhat, $495, at Saks Fifth Avenue | Image: Saks Fifth Avenue
Elegant black and white striped hat with a large floral embellishment displayed on a mannequin head against a white background.Pin
Collection 18 Striped Brim Dress Hat, $118, at Dillard’s | Image: Dillard’s

Fascinators & Headbands

Elegant black hat with feather and mesh detailing on a mannequin head.Pin
Collection 18 Multi Net Fascinator, $48, at Dillard’s | Dillard’s
A young woman wearing a white feathered hair accessory and an elegant earring, gazing to the side with a subtle smile.Pin
Gigi Burris Adrienne Band, $380, at Revolve | Image: Revolve
A blue glittery fabric bow attached to a headband, isolated on a white background.Pin
Kentucky Derby Fascinator, $118, at Vineyard Vines | Image: Vineyard Vines
A pink hat with feathers and a white rose.Pin
Kentucky Derby Curl Fascinator, $248, at Vineyard Vines | Image: Vineyard Vines
Yellow headband with intricate sunflower beadwork, perfect for what to wear to horse races, set against a white background.Pin
Wide embellished headband, $48 at e.Allen | Image: e.Allen

PICK YOUR BASE: DRESS, JUMPSUIT, OR SEPARATES

We often think of sweet dresses as the primary outfit of choice for Derby and other horse races, but there is a wide array of options outside of the dress department! Dresses are always a sure bet, but don’t feel like that’s your only option. You might feel more comfortable in a chic jumpsuit or matching separates. (Even a coordinating shorts set was featured in our styled shoot last spring for the races.)

Regardless of which direction you choose, my major tip is to “Know Thy Tailor.” Don’t be discouraged if things don’t fit perfectly off the rack; that’s the nature of mass-manufactured clothing! Instead, factor in tailoring costs as if it’s listed on the price tag so you can have adjustments made to achieve the perfect fit.

Depending on what kind of event you’re attending, the climate may also play a major factor in what you wear. I advise sticking with warmer-weather fabrics and steering clear of silks, wools, or other less breathable materials. Here are a few current styles (dresses included!) that offer a beautiful foundation for your race-day look.

Dresses

A woman in a black dress.Pin
Gianna Maxi Shirtdress, $495, at Oak Hall | Image: Oak Hall
Woman posing in blue floral dressPin
Staud Wells Floral Cotton Midi-Dress, $325, at Saks Fifth Avenue | Image: Saks Fifth Avenue
Woman wearing yellow floral dress and heelsPin
Elliatt Indie Floral Puff-Sleeve Midi-Dress, $385, at Saks Fifth Avenue | Image: Saks Fifth Avenue
Woman posing on balcony in smocked blue dressPin
The Tommie Cap-Sleeve Smocked Front-Zip Shirt Dress, $170, at Anthropologie | Image: Anthropologie

Tip: Anthropologie is one of my favorite sources for dresses in petite and plus sizing! 

A woman in a dress holding flowers.Pin
Annabel Sundress, $295, at Sue Sartor | Image: Sue Sartor
Dolce&Gabbana Floral-Print Short-Sleeve Belted Midi ShirtdressPin
Can you believe this belted shirtdress paired with a matching tote bag and wedges? (A gal can dream, can’t she?) For a major splurge, find the dress for $3,245 at Neiman Marcus.| Image: Neiman Marcus

Jumpsuits & Rompers

Woman in white halter split-leg vest jumpsuitPin
Alice + Olivia Robin Halter Split-Leg Vest Jumpsuit, $550, at Neiman Marcus | Image: Neiman Marcus
A woman wearing a light blue jumpsuit.Pin
Black Halo Corrine Jumpsuit, $415, at Shopbop | Image: Shopbop
A woman in a green jumpsuit.Pin
Maylé Vásquez Quisqueya Jumpsuit, $510, at Shopbop | Image: Shopbop
Woman wearing orange belted v-neck romperPin
Hutch Belted V-Neck Romper, $168, at Anthropologie | Image: Anthropologie

Matching Sets

A woman stands smiling in a white and green patterned dress with a crop top and midi skirt, paired with clear heels.Pin
Farm Rio Color Festival Green Blouse, $140, at e.Allen | Image: e.Allen
Woman in colorful embroidered romper and beige sandals posing on a plain background.Pin
Cleobella Jeni Blouse, $168, at e.Allen | Image: e.Allen
A woman in a light blue suit with a sleeveless, belted blazer and matching wide-leg pants, standing against a white background.Pin
French Connection Harrie Halter Neck Waistcoat, $118, at e.Allen | Image: e.Allen
A woman stands smiling in a green lace jumpsuit with a zippered front, paired with light sandals.Pin
Farm Rio Green Guipire Long Sleeve Shirt, $260, at e.Allen | Image: e.Allen
A woman wearing a white tiered skirt and cream top paired with beige strappy heels, standing against a plain background.Pin
Zimmermann Cotton-Blend Rib-Knit Tiered Midi-Skirt, $750, at Saks Fifth Avenue with matching top found here. | Image: Saks Fifth Avenue

THE STAR PLAYER: SHOES!

Your shoe selection for race day is not something to be taken lightly. No matter which race you attend, you’ll probably have to walk on various surfaces, from grassy lawns to cobblestone walkways. As far as I’m concerned, the stilettos can stay home! Bring on the block heels, wedges, or even “flatforms” (flats with a platform base).

Some women opt for a spare pair of flats to wear for the walk into the venue, but even then, your “main” shoes for the day will still be getting some serious wear, so giving them a solid test run before the big day is wise.

When trying on shoes, walk on surfaces other than carpets. Most shoes feel much more comfortable on a rug, which is why most shoe departments are carpeted!

Tip: I also like adding extra support to the pressure points of shoes I’ll be wearing for long hours. This can be preventive and shock-absorbing. Try these reusable pads that I recommend to clients:

Packaging of foot petals ball of foot gel cushions, featuring a pair in a clear plastic bubble on a pink card with product details.Pin
Foot Petals Ball of Foot Cushions, $11.99, on Amazon | Image: Foot Petals

Whether you opt for flats or heels, look for a style with a supportive base and traction on the bottom of the sole. Here are some of my current favorite styles.

A woman wearing beige, knotted sandals and white, eyelet trousers on a beige background.Pin
Hadley Leather Bow Flat Sandal, $250, at Oak Hall | Image: Oak Hall
Pair of beige crochet platform sandals with chunky heels on a white background.Pin
Dolce Vita Ladin, $160, at e.Allen | Image: e.Allen
A lime green slide sandal with a thick strap on a soft peach background.Pin
Maeve Buckle Slide Sandals, $130, at Anthropologie | Image: Anthropologie
Pink and white checkered women's slingback heel with a bow on the toe and a gold buckle.Pin
Larroude Block Heel, on sale for $180 (reg. $300), at Revolve | Image: Revolve
A beige prada platform sandal with a chunky heel, thick strap over the toe, and a buckle-fastened ankle strap, isolated on a white background.Pin
If you want a high-end pair of shoes, these Prada Quilted Nappa Leather Platform Sandals would be great for $1,220, at Saks Fifth Avenue – but, if it’s raining, remember that shoes can be ruined | Image: Saks Fifth Avenue
A person wearing brown, lace-up espadrille platform shoes, shown from the knees down against a white background.Pin
Castaner Tinita Espadrilles, $280, at Shopbop | Image: Shopbop
A person wearing blue cropped jeans and brown open-toe wedge sandals, standing on a white surface.Pin
Veronica Beard Ellen Wedge Sandals, $350, at Shopbop | Image: Shopbop

A THOUGHTFUL HANDBAG

Always double-check the handbag guidelines at the venue you’ll be visiting (they may have changed in the last couple of years!). They may have specific size criteria or even require a “stadium-friendly” bag, such as one that can be seen through.

Also, consider the length of the purse strap. Do you want a clutch that you can set down and leave on a table or a shorter strap that can hang on your arm? Would you prefer a crossbody strap so you can be totally hands-free?

Whatever shape or size suits you, your handbag can add the perfect polishing touch to your overall look! I recommend choosing an accent color from your outfit’s pattern or palette.

Stadium Bags

Transparent handbag embellished with golden studs and a chain strap, against a white background.Pin
Jackie Clear Handbag, $68, at Oak Hall | Image: Oak Hall
A transparent staud handbag with a brown leather strap and trim, featuring a square structure and a visible inner pouch.Pin
STAUD Stadium Mini Shirley Bag, $295, at Shopbop | Image: Shopbop

Clutches

A woman in a blue embroidered dress holding a rectangular wicker clutch with a large pearl clasp.Pin
Pamela Munson Natural The Petite Pearl, $395, at Tuckernuck | Image: Tuckernuck
White woven handbag with a lattice design and a looped handle, displayed on a light gray background.Pin
Top-Handle Rattan Bali Bag, $88, at Anthropologie | Image: Anthropologie
Woman holding a white yves saint laurent clutch, wearing a beige belted dress with puffed sleeves and button details.Pin
Saint Laurent Uptown Clutch, $595, at Bloomingdale’s | Image: Bloomingdale’s

Crossbody Bags

Woman in a beige dress holding a stylish mint green and white striped handbag with pearl detail.Pin
Kentucky Derby Small Drawstring Crossbody, $278, at Radley London | Image: Radley London
White crocodile-embossed shoulder bag with a golden clasp and a designer label on the front.Pin
DeMellier Small Vancouver Leather Crossbody Bag, $525, at Saks Fifth Avenue | Image: Saks Fifth Avenue
A gucci beige leather handbag with a bamboo handle and a gold-tone gg logo on the front.Pin
If you’re up for the splurge, this Diana Mini Tote Bag will draw ALL the eyes on race day! Find it for $3,300, at Gucci | Image: Gucci

Here’s to a fashionable race season!

***********

Looking for more fashion inspiration? Here are a few of the trends we can’t wait to try out this season.

Your StyleBlueprint AI Companion

Carson Love
About the Author
Carson Love

Carson Love is a Nashville fashion stylist and wardrobe consultant who helps clients find their own unique style and encourages them to be unapologetically authentic.