As the 151st Run for the Roses approaches, Vineyard Vines unveils its 2025 Kentucky Derby Collection, blending Southern charm with contemporary flair. Celebrating 15 years as the Official Style of the Kentucky Derby, this collection offers a range of attire for everyone, ensuring you’re race-day ready. Here are some of our favorite looks from the collection.
Our first look is for the woman who loves a statement dress. This Ruffle Tiered Dress is perfect for the Kentucky (or New York) weather, and with a strap heel, it pulls the whole look together. Add this Curl Fascinator to perfect the look.
Our second look is all about sophistication and letting everyone at the Derby know you mean business. The lace pencil skirt paired with flutter sleeve blouse is perfect, and then the Stuart Weitzman Rosie 85MM Leather D’Orsay Pumps add a little bit of spunk that the outfit needs. Add the fascinator from the last look, and voila! Our style editor also suggested Kentucky Derby cashmere crewneck sweater if you want to give a more relaxed look.
The next look is fun and flirty, and will erase all the stress you might have about the bet you made on your horse. This tiered maxi dress paired with this wicker clutch makes for a perfect pair, and the fascinator helps pull everything together for a fancy but easygoing look.
For the men, this look blends classic Southern charm with a playful twist. Toile-printed linen trousers in soft blue and white bring a fresh, whimsical energy, balanced by a crisp white button-down for timeless polish. Finished with brown suede loafers and a matching belt, it’s a standout choice for Derby day festivities — effortlessly stylish, festive, and refined.
If you wanted to go a bit less flashy and more classic, polished, and Derby-ready, this look pairs crisp cream trousers with a light blue and green gingham blazer for a fresh take on traditional Southern style. A white shirt keeps it clean and timeless (and any white shirt would work just as well). Effortlessly sharp and versatile, it’s a winning choice for a day at the races or a festive garden party.
This last look is easy, breezy, and race-day ready. It pairs lightweight linen trousers with a soft two-tone blue button-down for a fresh pop of color. Layered under a classic ivory linen blazer, it brings effortless polish without sacrificing comfort. Perfect for a warm Derby day, this outfit keeps things sharp and breathable — and looks just as good with any crisp white undershirt.
These are just some of the looks you could create with Vineyard Vines’ new Kentucky Derby collection. They have all of your needs for Derby Day and beyond.
Which look is your favorite? Let us know!
XOXO,
Your Fashion Bestie
