We’re welcoming Derby with a warm embrace, and because it’s just a few weeks away, we wanted to make sure everyone is as prepared as possible for Kentucky’s most fashionable events! We all know that Derby week is about the hats, but in recent years, it has become so much more. We wanted to give you the best fashion advice possible, so we solicited the expertise of our beloved stylist Shannon Kessler of Primp Style Lounge, but we also have some very special guest models — Rachel Bell and Kate Smith, a.k.a The Hat Girls! These ladies know Derby fashion inside and out, and they’re ready to help you find the ensemble that reflects your personal style. They even shared with us their expert tips for picking the perfect Derby hat.

We also turned to the fashion gurus at Work the Metal, Liv Boutique and Collections to provide today’s gorgeous Derby looks and the makeup and hair artists at Omagi Salon Spa to bring out these ladies’ natural beauty. Blooms Boutique even provided some truly beautiful Derby-themed floral arrangements. The results of all these floral, fashion and style experts’ work is simply stunning! Enjoy!

The Event: Brunch

Describe it in one word: Sophisticated

What to Wear: Louisvillians love their brunch, and when it comes to Derby week brunch, it’s just another reason to dress to the nines. Brunch will forever be the place where iconic Derby fashion thrives. No matter if you’re headed to the Mayor’s Derby Brunch on the River, eating at one of Louisville’s best restaurants for brunch or if you’ll be feasting at the track during Derby week, a conservative dress with a classic fascinator is the way to go. Here are a two perfectly Derby-esque dresses from Work the Metal with matching fascinators from The Hat Girls.

The Hat Girls‘ styling tip: These fascinators are both nice, small, lightweight options that can be worn with a headband or an elastic string, which is so comfortable, you’ll probably forget you’re wearing it.

Look #1:

What to wear derby edition

On Kate from Work the Metal: Coral dot dress, $67; blush and gold necklace, $19; gold cuff bracelet, $19; gold rectangle earrings, $9

Derby What to Wear

From The Hat Girls: Coral beret with feather spray and pearls, $350

Look #2:

what to wear derby

On Rachel from Work the Metal: Blue dot dress, $67; navy and light blue beaded necklace, $19; gold cuff bracelet, $19; gold circle earrings $9

derby what to wear

From The Hat Girls: Navy & light blue beret with feather spray and pearls, $350

The Event: Thurby

Describe it in one word: Fashion-forward

What to Wear: Fashion-forward clothing is the name of the game when it comes to Thurby. It’s just begun to make its way into the hearts of the locals, and it’s got a hip vibe unmatched by the other days on the track. Shannon chose to put the girls in two rompers from Collections — one with a 1920s fella-in-suspenders vibe, and the other with a whimsical, boho feel — and fascinators from The Hat Girls.

The Hat Girls‘ styling tip: We’ve noticed Thurby is a big day for fascinators. All of our fascinators are on an elastic string or designed to slide on the headband so you can wear them on either side.

Look #1:

derby what to wear

On Kate from Collections: Black and cream romper, $106; black statement earrings, $18

derby what to wear

From The Hat Girls: Black button fascinator with white goose and stripped rooster feathers, $350

RELATED: Kentucky Derby Trivia: Fascinating Secrets & Little-Known Facts

Look #2:

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On Rachel from Collections: Mango romper, $120; feather necklace, $40

derby what to wear

From The Hat Girls: Ivory sinamay fascinator with feather flowers and lady Amherst pheasant feathers, $300 

derby what to wear

These beauties are ready to place some bets!

The Event: Oaks

Describe it in one word: Pink

What to Wear: The girly girl side of us absolutely loves that people choose to don our most beloved color for the sake of breast cancer awareness. We love any chance to wear pink, but the fact that it’s for a great cause makes it so much sweeter. We’re partial to fascinators for Oaks, but if you want to wear the biggest, boldest pink hat you can find, we’ll be cheering you on! Here are the pretty-in-pink styles we chose for Oaks from CollectionsWork the Metal and The Hat Girls.

The Hat Girls‘ styling tip: Our hand-sculpted crinoline fascinators are a great option if the weather calls for rain, as they are 100% waterproof. Also, the growing trend in Europe — and one we love — is to wear them smack dab in the middle of your head, resting forward on your forehead, like the one pictured below.

derby what to wear

Oaks is the day to look pretty in pink in support of breast cancer awareness!

Look #1:

derby what to wear

On Kate from Collections: Pink-and-white embroidered off-the-shoulder dress, $158; cream drop earrings, $32. From The Hat Girls: Pink hand-sculpted crinoline fascinator, $220. From Blooms Boutique: custom Derby floral arrangement, call for pricing

Look #2:

derby what to wear

On Rachel from Collections: Cream v-neck fitted dress, $108; gold chain necklace, $32. From Blooms Boutique: beautiful custom floral arrangement, call for pricing

derby what to wear

From The Hat Girls: Pink cocktail fascinator with navy-and-pink spiky-cut goose feathers, $390

Look #3:

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On Kate from Work the Metal: Multicolored flair dress, $69; gold hoop earrings, $20. From The Hat Girls: Gold hand-sculpted sinamay with coral silk abaca, $450

This is a custom fascinator from The Hat Girls. In their custom appointments, they get to know their client and create a design that will reflect the client’s personality and enhance the dress to complete the look. If they have it already, the client will bring in their dress so the girls can match colors and materials to a T.

Look #4:

derby what to wear

On Rachel from Work the Metal: Pink-and-green dress, $69; From The Hat Girls: Green goose feathers with pink diamond-cut rooster feathers fascinator, $360

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This fun and flirty, lightweight fascinator was custom-made for this dress!

The Event: The Kentucky Derby

Describe it in one word: Iconic

What to Wear: “What’s the Derby?” Said no one. Ever. It’s where we get the best phrase to describe Kentucky, “The land of fast horses and beautiful women” — and you better not get those two things confused! For the fastest two minutes in sports, it’s time to dress like you’re ready for the Winner’s Circle. With Derby fashion taking a turn to a more modern look in recent years, we wanted to give you some ideas for different options to fit your personality and taste. Shannon chose fashion-forward jumpsuits as well as classic Derby dresses from Collections and Liv Boutique with hats from The Hat Girls. But before we dive in, we need to know: How do you pick your Derby hats?

Tip #1: If you’re getting a custom hat, get your dress first.

What The Hat Girls say: This is a question we get almost every day, and luckily there is no right answer! We would say it’s about 50/50 with our clients, but if you are getting custom hat, we generally recommend getting the dress first. Most women are not getting a custom dress made, so when you get the dress first, that allows us to completely customize the perfect creation for your overall look. Now that we have our shop in Norton Commons, a lot more women are coming in and finding their dream hat and then going to get a dress that will match.

Look #1:

derby what to wear

On Kate from Liv Boutique: Floral fitted dress, $354; gold geometric earrings, $198; chartreuse stone necklace, $2,500. From The Hat Girls: Ivory sinamay hatinator with purple sinamay accents, lavender feather flower and curled stripped quills, $650

derby what to wear

Hatinators are a great option for the woman who wants the illusion of a big hat, but wants to keep it light and comfortable!

Look #2:

derby what to wear

On Rachel from Liv Boutique: Cobalt blue scoop neck dress, $328; red drop earrings, $26; pineapple purse, $298. From The Hat Girls: Red hand-sculpted crinkled crinoline fascinator, $255

Tip #2: The hat should match the overall look.

What The Hat Girls say: We think it is amazing when the hat is perfectly matched to the overall look. We both have a very strong eye when it comes to color matching, and we are both perfectionists! We think this is one of our strongest attributes that will set our custom pieces apart from the rest. When you see our clients at the track, you can tell that she has really put a lot of time and thought into her entire look and gone above and beyond with her headpiece.

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The sun shines bright on our old Kentucky home, and these ladies are ready for the races!

Look #3:

derby what to wear

On Rachel from Collections: Blue-striped jumpsuit, $146. From Liv Boutique: Red drop earrings, $26; red and gold cuff, $325

derby what to wear

From The Hat Girls: Custom red leather roses and curled stripped quills fascinator, $480

RELATED: Ladies, We All Know Derby is All About the Hats!

Look #4:

derby what to wear

On Kate from Collections: White and red floral dress with red lace trim, $165. From Liv Boutique: Red tassel earrings, $84. From The Hat Girls: Custom handmade red oversized ombre feather flower and curled pheasant feathers on floppy white sinamay hat, $650

This beautiful hat was custom-made for this dress! The girls started with a white, floppy, sinamay hat base that flows well with the cut of the dress. They created a red and coral ombre feather flower, set as the focal point, that mimics the floral design of the dress’ fabric. The curled and dyed pheasant feathers were carefully placed to complete the design of the hat.

Tip #3: Understand what goes into custom creations.

What The Hat Girls Say: Our custom hats are one-of-a-kind creations made to match your dress, style and personality to a T. We start with a 30- to 45-minute custom appointment where we get to know the client and what they really like. We spend anywhere from 5 to 30 hours on custom creations, which is why they tend to be a little pricier than what you see in the store. We tell our clients to bring the dress if they have it already and pictures of any accessories they are considering.  We are essentially styling our clients from head to toe in the custom appointment, along with designing the hat, and we discuss what accessories and shoes would go best to complete the look to perfection. Another important thing we ask the client to do before the custom appointment is to look at our website and Pinterest to get inspiration for things they do and don’t like. Seeing what customer doesn’t like helps as much as knowing what they do like.

derby what to wear

Derby roses are red, and Derby jumpsuits are too! These girls look absolutely stunning, we bet you think so too!

Look #5:

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On Kate from Collections: Strapless red jumpsuit, $165; gold chain necklace, $32. From Liv Boutique: Red and gold cuff, $325. From The Hat Girls: Gold abstract turkey feather fascinator, $570

derby what to wear

If you are looking for something different, that will make you stand out, one of The Hat Girls‘ gold feather pieces is sure to set you apart from the crowd.

Look #6:

derby what to wear

On Rachel from Collections: Red one shoulder jumpsuit, $115; black earrings, $18. From The Hat Girls: Ivory sinamay hatinator with black feather design, curled quills and veiling, $520

derby what to wear

This piece is a classic black-and-white look with a dramatic twist. It looks like a hat, but has a shallow crown and therefore is kept on with a headband — making it a hatinator! Like all of The Hat Girls’ fascinators, it slides on the headband, which allows you to wear this piece with an extreme tilt to the side, bringing all the drama, along with the veil.

derby what to wear

These beautiful flowers were made by Blooms Boutique for this shoot! We love that it incorporates Derby roses and a Julep cup.

what to wear derby

With a little sugar, spice and fashion advice, you’re ready to walk into the Winner’s Circle!

THANK YOU! THANK YOU! THANK YOU!

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For more on what’s going on in Louisville, visit our Happenings page. And for more on the local boutiques that provided these styles, visit our SB Guide or download our FREE SB App.