November brings chilly weather, bonfires and one of our favorite holidays. If you can’t wait to embrace this month and all that it brings to your schedule and wardrobe, you’re in good company. We’re here to give you style tips on what to wear to this month’s Breeders’ Cup, Festival of Trees & Lights, Jim James at The Louisville Palace and, as a special bonus, Thanksgiving!

We’re pretty excited about our gorgeous models, too. We have three amazing and influential Louisville women. Up first is Laurie Wolf — she’s a managing partner of StarLadies Racing, which is an all-female racing partnership that began six years ago. She is also the co-managing partner with her husband in StarLight Racing and is currently on the board of the Backside Learning Center. Up next is Cathy Shircliff! She’s a self-proclaimed horse fanatic who works at Churchill Downs as an event manager, is a member of StarLadies Racing and Hot Pink Stable and is also on the board of the Backside Learning Center and the Kentucky Humane Society. Lastly, we have Allison Myers, the woman behind the extremely popular Instagram account EatLoveLouisville. We got the scoop from this Louisville epicure on where to take out-of-towners to eat when they come into town for Breeder’s Cup or Thanksgiving. Don’t miss her recommendations below!

With the fashion expertise of our stylist Shannon Kessler of Primp Style Lounge, our models are sporting looks from three fabulous Louisville boutiques: 6pm Outlet, Monkee’s and Cordial Lee. We wanted to soak up the beautiful fall weather the best way we knew how, so we took our gracious models to beautiful Foxhollow Farm. Here’s a look at what to wear this November!

What to Wear: November 2018

What to wear november louisville

From left to right: Cathy Shircliff of Churchill Downs, Allison Myers of EatLoveLouisville and Laurie Wolf of StarLight Racing and StarLadies Racing

The Event: Breeders’ Cup

  • November 2 & 3, 2018
  • Times vary depending on day and activity.
  • General admission starts at $20.
  • Churchill Downs
  • For more info, visit breederscup.com.

Hold your horses, Louisville, it’s time to place your bets for the Breeders’ Cup. This annual event is a Louisville classic, and this year, it’s being held right in our backyard at Churchill Downs. Much like the Derby (just with fewer hats), locals and out-of-towners head to The Downs to witness the fastest, and richest, two minutes in sports. Allison of EatLoveLouisville gave us her top recommendations for places to take out-of-towners to maximize their Louisville culinary experience: For a relaxed vibe, she recommends Feast BBQ and Royals Hot Chicken; for brunch, Butchertown Grocery and Wild Eggs; for fine dining, Jack Fry’s, Jeff Ruby and Seviche; and her wildcard picks are Napa River Grill, Mussel & Burger Bar and Grind Burger Kitchen.

What to wear + Shannon’s style tips: Fall is in the air and that means chilly temps have us begging for all the cute outerwear. When dressing for the track, keep in mind the fabric of your dress needs to be warm, and remember that you can always accessorize with a great jacket. Keep warm and fashionable in fabrics like tweed, velvet and wool blends. Check out these four great looks from Monkee’s and 6pm Outlet.

Look #1:

what to wear louisville november

On Cathy from Monkee’s: Tweed dress, $215, and matching jacket with necktie, $350; black clutch, $175 | From 6pm Outlet: Tan front-zipper booties, $180

Look #2:

what to wear louisville november

On Laurie from Monkee’s: Pink-and-black tweed dress, $215; black bell-sleeve jacket, $220; gold drop earrings, $55 | From 6pm Outlet: Black pumps, $60

RELATED: A Local’s Guide to Louisville

Look #3:

what to wear november louisville

On Allison from Monkee’s: Red dress, $278; black ruffle-edged wrap, $98; gold cuff, $210

what to wear november louisville

From Monkee’s: Black drop earrings, $88

Look #4:

what to wear louisville november

On Cathy from Monkee’s: Camel jacket with faux fur sleeves, $190; leopard print clutch, $225

what to wear louisville november

From Monkee’s: Rust-colored strapless jumpsuit, $126; double chain gold necklace, $36 | From 6pm Outlet: Camel front-zipper booties, $180

The Event: Festival of Trees & Lights

  • November 9-11, 2018
  • Times vary depending on event.
  • Tickets start at $6.
  • Louisville Slugger Field
  • For more info, visit nortonchildrens.com.

The 29th annual Festival of Trees & Lights at Louisville Slugger Field is where hundreds of volunteers design and decorate Christmas trees, wreaths and handcrafted holiday items, all of which are for sale to raise funds for Norton Children’s Hospital. Grab a decorated ornament or another fun holiday item at this annual event to commemorate this special way to give back. This beautiful and awe-inspiring event is great for the whole family and sure to be one the kids will enjoy and remember, especially when they see that decorated holiday item around the house!

What to wear + Shannon’s style tips: Think “holiday comfort” when you peruse the attractions at this year’s Festival of Lights. Look for dresses with some stretch that allow you to easily walk around and admire the sights. You can’t go wrong with a great pair of leggings and a chic poncho. Here are three gorgeous looks from Cordial Lee, Monkee’s and 6pm Outlet.

Look #1:

what to wear louisville november

On Allison from Monkee’s: Sand-colored cashmere poncho with tassels, $196; bronze faux leather leggings, $98

what to wear louisville november

From Monkee’s: Gold statement necklace, $45; brown-and-gold earrings, $58

Look #2:

what to wear louisville november

On Laurie from Cordial Lee: Red ruffled bell-sleeve dress, $34.95; black feather necklace, $28.95 | From Monkee’s: Leopard print clutch, $225 | From 6pm Outlet: Nude pumps, $50

Look #3:

what to wear louisville november

On Cathy from Monkee’s: Suede hunter green dress, $94; navy and green bell-sleeve jacket, $225 | From 6pm Outlet: Camel knee-high boots, $100

what to wear louisville november

From Monkee’s: Indie green leather earrings, $58

what to wear louisville november

From Monkee’s: Black clutch, $175

The Event: Jim James at The Louisville Palace

  • November 21, 2018
  • 8 p.m.
  • Tickets start at $39.50.
  • The Louisville Palace
  • For more info, visit ticketmaster.com.

Louisville native and St. X grad, Jim James of My Morning Jacket, is coming home to Louisville for the last stop on his acoustic tour. He’s pairing up with longtime friend and drummer Dave Givan to make this homecoming even sweeter. Get ready to rock it out with this local Louisvillian and international star at the Louisville Palace on November 21, 2018.

What to wear + Shannon’s style tips: When jamming out to your favorite singer, opt for what makes you feel your best. Whether you crave a great pair of denim and your favorite booties or you want to channel your inner rock goddess with a black dress and over-the-knee boots; let your style take center stage! Here are three perfect looks from Cordial Lee, Monkee’s and 6pm Outlet.

Look #1:

what to wear louisville november

On Allison from 6pm Outlet: Black keyhole long sleeve dress, $64; black over-the-knee boots, $399 | From Cordial Lee: Gemstone statement necklace, $22.95

Look #2:

On Laurie from Monkee’s: Toffee jacket, $150; ripped skinny jeans, $179; gold studded hoop earrings, $55 | From 6pm Outlet: Black booties, $80; black-and-gold sunglasses, $94; designer black bag, $550

what to wear louisville november

We love the gorgeous detailing on the back of this toffee jacket!

Look #3:

what to wear louisville november

On Kathy from Cordial Lee: Thermal black button-up top, $32.95; ripped skinny jeans, $38.95 | From 6pm Outlet: Cardigan duster, $230; black lace-up booties, $199

what to wear louisville november

From Cordial Lee: Fringe gold hoop earrings, $13.95; Studio Botanica necklace, $21.50

RELATED: 3 Simple Fall Recipes + 1 Cocktail From Harvest Chefs

The Event: Thanksgiving

  • November 22, 2018
  • Taking place in homes, hotels, stadiums, restaurants and just about anywhere people like to gather on this annual holiday
  • Be sure to check out our Thanksgiving Day Takeout article to make the holiday prep a little easier!

What to wear: Some Thanksgiving gatherings are casual, some are more dressy and others are a mix of “anything goes.” At SB, we like to look fashion-forward no matter what the occasion, so here are three great looks to rock on Turkey Day that also have a little room for an extra helping and a full belly! These are from 6pm Outlet and Monkee’s.

Look #1:

what to wear louisville november

On Allison from Monkee’s: Bell-sleeve dress, $230; black clutch, $175 | From 6pm Outlet: Black over-the-knee boots, $399

what to wear louisville november

From 6pm Outlet: Black-and-gold sunglasses, $94 | From Monkee’s: Black-and-white hoops with cranberry ball detail, $58

Look #2:

what to wear louisville november

On Laurie from Monkee’s: Red-and-black floral dress, $198; red-and-camel reversible wrap, $174 | From 6pm Outlet: Black block-heel pumps, $60

Look #3:

what to wear louisville november

On Cathy from Monkee’s: Paisley top, $118; cranberry velvet blazer, $188; leather skirt, $180 | From 6pm Outlet: Black lace-up booties, $199

what to wear louisville november

Our amazing stylist, Shannon Kessler, always makes our models look and feel amazing!

THANK YOU! THANK YOU! THANK YOU!

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For more on what’s going on in Louisville, visit our Happenings page. And for more on the local boutiques that provided these styles, visit our SB Guide or download our FREE SB App.