Support Us Button Widget

Keeneland Fashion Guide: How to dress for the Fall Meet in Lexington

Fall at Keeneland calls for style that’s both chic and practical. Our guide highlights Lexington boutiques and must-have pieces to help you nail the perfect race-day look.

A crowd of people standing and cheering on a horse race at Keeneland in Lexington, KY

Keeneland is a full day of walking and standing — be sure to dress comfortably.

Photo via Keeneland Photo

Whether its your first time or you’re a Keeneland pro, navigating seasonal Keeneland fashion can be tricky — especially in a temperamental Kentucky climate.

We’ve cultivated a guide to a few of our favorite local boutiques with fresh seasonal lineups to have you feeling and looking you’re best for the races.

First things first, take a peek at Kentucky Weather Center, October is starting out warm and dry — at least starting next week.

We should start to feel the crisp autumn air we know and love later in the month, but it’s smart to prepare for anything at Keeneland. You know what that means: layers.

Peacocks & Pearls | 200 Lexington Green Cir. Ste. 170
The boutique has an entire lineup dedicated to Keeneland shopping. All seasonally on theme, the selection is a combination of sweaters + short, midi, and maxi dresses.
Editor Alexis’s pick: This Forest Nights Midi Dress is perfect for a warmer day, but can be elevated with any warm-toned trench coat or a jean jacket for an effortless look.

Ada & Lo | 390 Southland Dr.
This award-winning boutique specializes in simple, classy, and high-end gifts, along with women’s clothing and accessories. They showcase seasonal items daily on social media, keeping the selection fresh and on-trend.
Editor Alexis’s pick: Ada & Lo’s newest dress checks all the early-October boxes — short sleeves, midi length, and a fresh white-and-olive print.

Cotton Patch | 3367 Tates Creek Rd.
Owned by a native Lexingtonian, this premier women’s boutique has been a go-to since 1985. New arrivals hit the racks daily, and the staff is on hand to help you piece together the perfect race-day outfit, from practical tips to thoughtful details.
Editor Alexis’s pick: Cotton Patch recently launched its fall lineup of long-sleeve patterned maxi dresses — versatile pieces that can be dressed up or down to keep up with Lexington’s ever-changing weather.

Let’s talk accessories. Closed-toe shoes are a must for crisp fall days.

Long dresses pair best with block-heel booties or flats for comfort, while shorter midi styles work well with mid-calf boots.

Gold is the dominant metal this season, with bangles, layered necklaces, and statement earrings completing the look alongside classic handbags.

More from LEXtoday
Three Lexington-area residents tested their wits and nerves on Netflix’s global competition. From the casting process to the games themselves, the experience challenged them in unexpected ways.
Got a hot new fling? Hoping to spice things up with your longtime partner? We’re here to help plan your next date in the Horse Capital of the World.
Our favorite dine-in and carry-out options for Thanksgiving dinner in Lexington this year, plus local ingredients.
Over the next 10 days, we’re launching a reader-driven campaign to sustain what we do best.
Potholes happen, but fixing them starts with a simple report. Here’s how to alert the right team and keep Lexington’s streets in better shape.
Explore these dog-friendly places in LEX — from places to eat, drink, shop, exercise, swim, and stay the night with your four-legged friends.
Lace up for a little pre-feast fitness. Local races across Central Kentucky are bringing runners, walkers, and families together to celebrate the season.
Help keep Lexington’s waterways clean by painting a local storm drain with important pollution prevention messaging.
Bookmark this guide for a curated list of events taking place each month that we’re most looking forward to.
Spoiler alert: Traffic isn’t great. We dove into the Texas A&M Transportation Institute’s congestion data so you don’t have to.