October officially arrives this weekend — it’s the most wonderFALL time of the year, and we’re ready to celebrate! With art-forward festivals, food-centric jubilees and pink parties supporting Breast Cancer Awareness Month, Louisville’s social calendar is jam-packed with can’t-miss events, and we’re here to alleviate that ever-present worry of what to wear.

With fabulous garments and shoes from Work the Metal and 6pm Outlet, along with expert styling by Shannon Kessler of Primp Style Lounge, we’ve created nine show-stopping ensembles that will have you looking and feeling your best throughout the month’s festivities. Today, yoga blogger Paloma Thacker of Her Bendy Life and fellow yoga instructor Brittany Swan model looks ideal for three upcoming events: St. James Court Art Show, the Taste of Louisville and Pink Prom. So, enjoy October and look tres chic while you’re at it. Happy fall!

The Event: St. James Court Art Show

  • October 6-8, 2017
  • Friday & Saturday, 10 a.m. to 6 p.m.; Sunday 10 a.m. to 5 p.m.
  • Admission is free.
  • For more information, visit stjamescourtartshow.com.

The first weekend of October means the St. James Court Art Show is back! Celebrating its 61st year of artistic exploration, this weekend-long festival will feature over 750 artists from all across North America, right in the heart of Old Louisville. The autumn tradition brings in thousands of visitors and is by far Louisville’s most creative way to ring in October. In addition to showcasing some of the country’s finest art, the St. James Court Art Show awards over $50,000 in college scholarships to metro Louisville high school seniors each year, so it’s not just “art for art’s sake”!

What to Wear? “This is the perfect time to embrace the fall fashion you missed all summer long,” says stylist Shannon Kessler. “Comfortable shoes and a great bag are a must, as you will spend hours walking the streets discovering the local treasures offered at the St. James Court Art Show.” Shannon’s looks embrace comfort, style and, of course, festive colors and creative pairings. The fashion mavens at Work the Metal and 6pm Outlet show us how to dress up the look with a wide-brimmed hat, statement necklace or show-stopping earrings. SB TIP: Opt for these black boots from 6pm Outlet to ensure rain won’t stop you from enjoying the event!

Look #1:

On Paloma, from Work the Metal: Maroon shirt with black tassel fringe, $36; black pant, $24; black hat, $24; metal-adorned forest green bracelet, $16

Paloma wears a head-turning statement necklace with an oversized medallion pendant, $36, from Work the Metal.

Look #2:

On Brittany, from Work the Metal: Floral dress in burnt sienna, $44; olive peep-toe booties, $28; chocolate wide-brimmed hat, $18; leather bracelet, $12

We love the subtlety of Brittany’s bronze-colored feather earrings with gold architectural base, $9, from Work the Metal.

Look #3:

On Paloma: Black choker tee with lace-up front, $22; jeans, $24; and Dusty Rose jacket, $24, from Work the Metal | Nude heel, $60, from 6pm Outlet

From Work the Metal: pink feather earrings, $10

RELATED: The Fall 2017 Fashion Trends Report

Toss your rain boots in the car, so that no showers will rain on your parade! Grab a pair of sleek black rain boots, like these Tory Burch tall black boots, $117.50, from 6pm Outlet.

The Event: Taste of Louisville

Calling all foodies! From traditional to eclectic, this year’s Taste of Louisville will feature the finest of Louisville’s restaurants and chefs. Bites from over 50 local restaurants, delicious brews, a vast assortment of fine wine and spirits aplenty will make this an unforgettable culinary experience. And, since the event benefits Home of the Innocents and Jill’s Wish of Louisville, this year’s Taste of Louisville will leave both your stomach and heart full.

What to Wear? “Sampling the best food of Louisville requires just the right look. A cute choker dress makes it easy to keep your style chic and effortless,” says Shannon. “And a cross-body bag is a great option so you can keep your hands free while juggling plates of delicious food.” This event is all about looking polished while maintaining comfort and rocking on-trend styles. With help from Work the Metal and 6pm Outlet, we suggest an easy, yet standout top like this ruffled, burgundy number with distressed jeans in a unique, grey tone. Breezy cocktail dresses with interesting neck lines and fall-friendly colors are also a fantastic way to dress up for the event without being over the top. 

Look #1:

On Brittany, from Work the Metal: Wine-colored top with floral embroidered accents and ruffled sleeves, $35; elastic-waisted gray distressed jean, $35; green leather bracelet, $39; camel-colored leather backpack, $69

From 6pm Outlet: Dusty Rose sunglasses, $92.50

From Work the Metal: leopard print flats with black pom-poms, $22

Look #2:

On Paloma: Dusty Rose printed choker dress, $34, and feather earrings, $9, from Work the Metal | Nude heel, $60, from 6pm Outlet

These ladies make a fashionable pair!

Look #3:

On Brittany: Dusty Rose choker dress, $69, and gold heel, $120, from 6pm Outlet | Clutch, $28, from Work the Metal

RELATED: Age-Appropriate Style, Chic Travel Bags & Jewelry Box Basics: Ask Megan

Stay chic while you enjoy the Taste of Louisville!

The Event: The Pink Prom

  • October 20, 2017
  • Event begins at 8 p.m.
  • Tickets start at $35.
  • For more information, visit thepinkprom.com.

October is Breast Cancer Awareness Month, and there’s no better way to support the cause and spread awareness while enjoying a night on the town than the 6th Annual Pink Prom. This year’s event will feature live acoustic performances by Justin Fursetenfeld of Blue October and David Shaw and Zach Feinberg of The Revivalists at the Mellwood Arts Center. Additionally, named “One of the Top Charity Events” and “Best Live Entertainment in the City of Louisville,” Pink Prom is the perfect way to finish off this festive month!

What to Wear? Fashion for this event comes right from the title — pink, pink, pink! “With events like Pink Prom on the schedule this month, make sure you have the right level of pink in your wardrobe. Whether you want to rock full-on hot pink, a subtle suggestion in a soft shade or a pop of pretty pink in an earring, the hue will be in heavy rotation this month,” says Shannon. Although you won’t be turned down at the Pink Prom door if not wearing pink, we’ve teamed up with Work the Metal and 6pm Outlet to create three fun looks in the girly shade. Blush-toned sequins or magenta gowns in a classic and conservative style make for the perfect elegant evening wear. Or get creative by adding a pop of pink to your little black dress with bright shoes and funky earrings. 

Look #1:

On Paloma, from Work the Metal: Rose-gold sequined long gown, $89

Those smiles shine brighter than the sparkles!

Look #2:

On Brittany: Black dress with ruffle sleeves, $44, and pink feather earrings, $10, from Work the Metal | Nine West hot pink strappy heel, $44.50, from 6pm Outlet

These ladies are ready to walk down the pink carpet in support of Breast Cancer Awareness Month.

Look #3:

On Brittany, from 6pm Outlet: Hot pink cocktail dress, $1,065, and Nine West hot pink strappy heel, $44.50

Don’t be afraid to pair different shades of pink!

Have a happy October!

Thank you to Christine Mueller of Christine Mueller Photography for the fabulous photos!

And thank you to our stylist Shannon Kessler of Primp Style Lounge for sharing her expertise and styling our models, Paloma Thacker of Her Bendy Life and Brittany Swan. 

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For more on the boutiques that provided these style suggestions, visit our SB Guide or download our FREE SB App.