Coco Chanel once famously warned, “there are certain houses one cannot enter without wearing a hat.” A full century later, her dictum feels newly urgent in the week leading up to the Kentucky Derby, when, for one day, the entire nation becomes a “house” to which you simply must arrive with a hat. Thankfully, the Twin Cities is a thriving hub for millinery, where names like Karen Morris, Angie Hall Sandifer, and Celina Kane steadily pave the way for the opulent accessory to thrive—even well past Derby week.
Ahead of a weekend packed with celebrations and watch parties, we rounded up the top Derby dressing trends, where to shop them locally, and the can’t-miss Twin Cities events on May 2—hat contests and all. Consider this your invitation to dress the part.
Louisville Approved
The Kentucky Derby’s style playground rarely departs from tradition: formal attire, spring-inspired hues, and a hat that commands attention. Yet, the institution began publishing an annual style guide in 2024, aiming to extend tradition while inspiring modern interpretations and a renewed sense of creativity. This year’s guide is imagined through the lens of guest stylist Zanna Roberts Rassi, who strikes a balance between bold hues and refined tailoring. Here are a few key takeaways from the Kentucky Derby’s 2026 style guide.
Colors: This year leans into what Rassi calls “Crayola” hues—oversaturated primaries like blue, red, yellow, magenta, and green. Particular standouts include preppy Kelly green and luxurious topaz blue. Unexpected color matching is also emphasized, so don’t be afraid to experiment.
Patterns: While florals remain an annual staple, there’s a renewed focus on texture this year—including 3D floral appliqués and delicate, artful lace. Shimmer and sparkle are also present, but in a more contained, sophisticated manner—perhaps woven into the stitching of a tweed suit or subtly embossed within a dress’s floral detailing. When in doubt, stripes rarely leave the canon of Derby style.
Headwear: True to tradition, fascinators dominate, enhanced with voluminous florals, structured bows, and lush feathers. Red emerges as a standout shade, even when juxtaposed with softer, less saturated hues. For a more restrained take, look to minimalist pillbox hats or skullcaps, great complements to a monochromatic, head-to-toe look.
Accessories: Finishing touches require a delicate balance—as the hat should be the first thing to draw the eye. This year’s guide leans into simple, neutral-driven footwear and minimal jewelry, often incorporating sculptural earrings that echo the shades of hats and dresses. Bags stay small but expressive—no larger than a clutch, but rich in personality, sometimes with subtle equestrian nods. For an elegant finish, consider donning a pair of elbow-length gloves.
Where to Shop
Scarborough Fair: This eccentric shop in Falcon heights carries a treasure trove of hats, headbands, and fascinators by local and national milliners, including Karen Morris Millinery and Cha Cha’s House of Ill Repute. In addition, you’ll find thoughtfully curated clothing geared toward plus-size women and a wealth of whimsical, one-of-a-kind accessories from scarves and ponchos to handmade jewelry, pins, and brooches. Stop in at 1583 Hamline Ave. N., Falcon Heights.
Our Derby Pick: Naughty Knot Derby Fascinator by Cha Cha’s House, $225, scarboroughfairshop.com
Courtesy of Scarborough Fair
Celina Kane: Regarded as one of the Twin Cities most skilled milliners, Celina Kane crafts a diverse range of headwear for the modern woman—from opulent, Derby-ready fascinators and bridal accessories to practical, everyday headbands and gardening hats. Shop Derby offerings online at celina-kane.squarespace.com.
Our Derby Pick: Fusilli, $699 (sale price), celina-kane.squarespace.com
Karen Morris Millinery: For internationally renowned hatmaker Karen Morris, headwear is akin to fine art—each piece a blank canvas that invites the imagination to stretch wide open. Based in Roseville, Morris’ pieces strike a balance between old-world romanticism and modern craftsmanship, with a distinct focus on bespoke and couture hats. Her 2026 Derby collection offers a satisfying mix of bold and bright pastels alongside sharp, classic blacks and whites. Shop Morris’ pieces at Scarborough Fair, The Fitting Room, and her Roseville Studio (1975 Oakcrest Ave. Ste. 5, Roseville).
Our Derby Pick: Couture Downturn Brim Hat, $915, kmhats.com
Angie’s Hats: Based out of Lowertown St. Paul, milliner Angie Hall Sandifer is passionate about preserving the nostalgic art of millinery, designing occasionwear hats for everything from the Kentucky Derby to the Royal Ascot. Over the years, she has mastered the artful balance of Derby-ready design, merging the avant-garde and unexpected with meticulous craftsmanship and elegant refinement. Shop her Derby collection at her St. Paul studio (308 E. Prince St., St. Paul) or online.
Our Derby Pick: Ruby, $225, angieshats.com
Courtesy of Angie's Hats
Sweet Ivy: Sweet Ivy has become Galleria’s got-to for occasionwear that feels accessible yet elevated, with LA- and New York-based labels like Misa, BTB, and Hutch bringing a distinctly coastal-chic flair to its resort-ready spring offerings.
Our Derby Pick: Willow Linen Shirt and Vincent Linen Pant in Francesca Print (worn as a set), $230 and $255, shopsweetivy.com
Courtesy of sweet Ivy
Serge + Jane: A steady Edina staple, Serge + Jane’s spring offerings bring a colroful assortment of breezy linen maxi dresses and chic coordinated sets—including a stunning deep-red linen dress from Farm Rio, with 3D floral detailing that practically begs to be paired with a matching fascinator.
Our Derby Pick: Farm Rio 3D Euroflax Premium Linen Maxi Dress, $380, sergeandjane.com
Melly: Think transportive prints, sophisticated tailoring, and a touch of country club polish—Melly delivers a head-to-toe take on Palm Beach chic, with a strong lineup of Lilly Pulitzer picks alongside labels like Elizabeth James, Farm Rio, and Marie Oliver. In short, it’s a Derby Day one-stop-shop.
Our Derby Pick: Lilly Pulitzer Tiernan Maxi Dress, $348, mellyonline.com
Mille: Since opening at the Galleria in October, Mille has quickly become a destination for vacation-ready dressing, with racks of romantic silhouettes and feminine detailing. The shop’s spring arrivals are a natural fit for Derby Day, laced with a touch of Western romanticism that nods to the wildness of equestrianism.
Our Derby Pick: Mara Dress in Peony Taffeta, $200 (sale), shopmille.com
MartinPatrick3: As one of the Twin Cities premier destinations for luxury and designer apparel, MartinPatrick3 assumes an annual involvement in Derby festivities—this year partnering with Sip N Bloom for its “Race for the Roses” watch party at The Boardwalk, showing looks on the runway alongside Sweet Ivy and Karen Morris Millinery. Explore its spring offerings from luxury brands like Ganni, Cara Cara, and Alémais, and more.
Our Derby Pick: Alemais Sidi Mini Dress, martinpatrick3.com
Requisite: Requisite’s thoughtfully curated North Loop treasure trove is brimming with eccentric spring hues and prints, including bright, preppy plaids and relaxed, coastal-inspired linens. Plus, a diverse selection of race-day-ready footwear, jewelry, and finishing-touch accessories—think silk scarves, chic sunnies, and statement bags.
Our Derby Pick: Rosie Top and Alice Mini Skirt By Lousie (worn as a set), $328 and $198, shoprequisite.com
Courtesy of Requisite
Events
Sip N Bloom’s Run for the Roses
When: May 2, 3:30- 7 p.m.
Where: Boardwalk Kitchen & Bar (1125 Shenandoah Drive, Shakopee)
What: Join Sip N Bloom for an immersive Kentucky Derby watch party and runway experience that melds fashion, floral design, and race-day pageantry—with Derby-winning Jockey Mark Irving on-site to share insider insight ahead of the race. The mini runway show will feature Derby-inspired looks from brands including Sweety Ivy, MartinPatrick3, Karen Morris Millinery, Requisite, and more. Tickets are currently sold out, but a small run of general admission spots will be released day-of around 4 p.m. Patio vibes and full restaurant access will still be open at Boardwalk (weather-permitting).
Minnesota’s Derby Party at Canterbury Park
When: Doors open at 8 a.m. for gamblers, 12 p.m. for partygoers
Where: Canterbury Park (1100 Canterbury Road S., Shakopee)
What: Celebrate the Kentucky Derby at Minnesota’s own iconic racetrack—Canterbury Park opens its doors at 8 a.m. on May 2 for a full day of festivities, complete with Maker’s Mark sampling, DJ tunes, best-dressed style contests, speciality cocktails, and a live Derby race viewing party.
Courtesy of Canterbury Park
Eighth Annual Kentucky Derby Twin Cities Party
When: May 2, 2-7 p.m.
Where: Forepaugh’s Restaurant (276 Exchange St. S., St. Paul)
What: The longest running Twin Cities Derby party returns this Saturday, this time bringing its watch party and style showcase to Forepaugh’s Bar & Restaurant’s historic mansion in St. Paul. Begin your evening with a strut down the red carpet, before enjoying a bubbles bar, specialty mint julep menu, complimentary bites, a best-dressed contest with cash prizes, and a thrilling live race projection.
Courtesy of Forepaugh's
Derby Day at the University Club
When: May 2, 2-6 p.m.
Where: The University Club of St. Paul (420 Summit Ave., St. Paul)
What: Join St. Paul’s historic University Club for Roses, Races & Revelry, a sophisticated Derby watch party filled with bourbon, bubbles, Southern-inspired bites, a live brass band, and best-dressed and best hat contests. The ticketed event is open to non-members.
Kentucky Derby Party at Graze Food Hall by Travail
When: May 2, 3-6 p.m.
Where: Graze Food Hall by Travail (520 N. 4th S., Minneapolis)
What: Celebrate Derby Day at one of Minneapolis’ most dynamic dining spaces—Graze Food Hall by Travail. The event promises plenty of Southern charm, with a rock hall concert series, mini horse petting zoo from This Old Horse, fascinator hat making, Maker’s Mark specials, food, games, prizes, and more. It all culminates in a live viewing party of the most exciting two minutes in sports.
