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.