What To Wear To The Derby + Chicago Fashion Show

what to wear to derbyOne day each year, folks put on their fancy spring attire and head to the racetrack. Or, for a few minutes, some with otherwise no interest in equine affairs turn to their televisions. Mint juleps are poured, bets are placed, and all eyes are on Louisville, Kentucky, where for over a century 20 of the most beautiful and athletic horses in the world compete in the first of three races that form the Triple Crown. To kick off the festivities this year, we’re inviting sponsors and guests to take part in our Pre-Derby Hat & Tea Luncheon before this year’s Kentucky Derby. This one-of-a-kind event held at Chez Chicago will be hosted by Michelle Relerford, Weekend Anchor for NBC 5 Chicago News and will include several notable speakers.

Kentucky Derby Dress Hats

All are coming together to not only honor the valuable role mothers play in our society as parents and leaders, but also to inspire these independent, beautiful women to reclaim their confidence in both their professional and personal lives. The festivities will also include a Spring Fashion show hosted by Lourdes Duarte, WGN Anchor, to present the latest affordable styles and wardrobes for professional women. And if that weren’t enough, we’re also humbled to be awarding five scholarships to high school and college students who have demonstrated exceptional leadership and academic effort. Both of these features align with our goal of helping women and children believe in themselves, embrace their role in the future, and look good while doing it too. Proceeds from the luncheon will benefit the Daisie Foundation’s ability to serve the community through our ongoing Mother’s Day Initiative. All donations and sponsorships are tax deductible.

Photo credit: Rachel Bires @rach.esq

Lisa Gunderson – Lisa is a PR maven and owns her own business called LMG Chicago. She has her hands in so many fashion related events in the Midwest, that I’m sure you’ve encountered her work before. She is always smiling and is so positive. She’s such a joy to be around! And she always looks fierce! Visit her site at lmgchicago.com.

Tavi Johnson – Tavi is everywhere and she’s one of my favorite Chicagoans-about-town! She makes an appearance at nearly every major Chicago-related event and shares her adventures on her blog Chicago At A Glance. You can find her at chiataglace.com.

Julie Hightower – This lady is a powerhouse! Not only does she host her own beauty and fashion web program, A Better Day With Julie, she is involved with so many philanthropic and charitable events and causes in the city. Julie is spearheading the Mother’s Day Initiative along with the Daisie Foundation. She is truly inspiring and I’m so honored to know her! Check out her website at abetterdaywithjulie.com.

spring dresses

Michelle Laarabi – The flawless face behind the beauty blog Michelle Swoons, Michelle is one of the sweetest, funniest people I’ve met in Chicago! As a beauty guru, she’s always got the lead on the best products and always looks fierce! Visit her at michelleswoons.com.

Cheryl Leahy – I just met Cheryl from All Dressed Up With Nothing To Drink at our photo shoot for this event, and she immediately impressed me with her gorgeous smile and quick laugh. She was so much fun to be around, and she’s a natural in front of the camera! Check out her style tips and fashion advice at alldressedupwithnothingtodrink.com.

Amber McCulloch – She is the plus size blogger behind the Chicago-based fashion blog, Style Plus Curves. Her everyday style is influenced by her girl boss day job and belief in body positivity, size-inclusivity and female empowerment.

Yana Frigelis – Yana is another woman that I’ve just met, and she impressed me with her impeccable style! She is a lifestyle, decor and travel blogger at NoMad Luxuries. Her blog is beautiful and a great source of inspiration for decorating your home! Check her out at nomadluxuries.com.

Aren’t these hats to die for?!? I picked mine up from the August Hat Company. All the other hats are from M2 Boutique and Generation Bliss, both are boutiques based out of Chicago. They have such a great selection of amazing, attention-grabbing hats this spring. Perfect for Derby parties you might be attending or for any Easter services, parades or teas you might be going to!

I’m so honored to be part of this event with so many innovative women that I admire and I hope you’ll join me at this Chicago event to support this great cause. Click here to buy your ticket now! I’ll see you on April 29!


Hey Girl, Hey! I’m Dāsha Guyton, an award winning Lifestyle Blogger and Wardrobe Stylist based in Hyde Park, Chicago. More importantly, I’m a body positive warrior and self-love advocate on a mission to  help you curate experiences and a wardrobe you love. To get to know me and this blog better start here. You can also find my styling advice here on the blog and featured in every issue of Modest Truth Mag. Enough about me, let’s connect on Instagram, Facebook or Twitter.

11 Comments Add yours

  1. sportsanista34 says:

    So pretty!!! Love all the dresses and hats! So colorful and has be in the spirit of all things derby!


    Liked by 1 person

  2. stephienese says:

    You ladies look gorgeous! I need a fabulous hat now 🙂

    Liked by 1 person

  3. Tami @ ThisMomsDelight says:

    I have never been to the derby. Now that I know what to wear, I have no reason for not going.

    Liked by 1 person

  4. Love these photos and how each look is different!

    Xo, Brianne

    Liked by 1 person

  5. Steph says:

    This post is absolutely fabulous! Going to a derby is on my bucket list mostly so I can wear a fun hat.

    @trendyinindy || trendyinindy.com

    Liked by 1 person

  6. All of you looking amazing! This looked like so much fun!

    Amanda || http://www.fortheloveofglitter.com

    Liked by 1 person

  7. Courtney says:

    All of you ladies look amazing!! I’ve always wanted to attend the derby! Any excuse to get dolled up and wear an amazing hat, I’m in!

    Courtney http://www.whatcourtwore.com

    Liked by 1 person

  8. Anna Baun says:

    the Derby is absolutely one of my favorite events of the year! You all look so gorgeous! I love the variety of hats and vibrant florals! XO

    Anna || alilyloveaffair.com

    Liked by 1 person

  9. lauren says:

    so pretty!! love that blue on you 🙂 last year I made a DIY fascinator for derby and it was a hit!
    LMents of Style

    Liked by 1 person

  10. Dressing up to go to the races is so much fun💗! You look fabulous, as always 😍

    Liked by 1 person

    1. Dāsha says:

      IKR, couldn’t turn down a chance to dress up.😀 you’re such a sweetheart 😙

      Liked by 1 person

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