Chatham’s Best Clothing Stores Reveal Their Top Fall Fashion Looks

Discover curated, head-to-toe autumn outfits from reader-voted favorites – blending trend, personality and local flair to inspire your wardrobe refresh for the cooler months

Compiled by Hannah Posner

Chatham’s most fashionable shops – named best clothing stores in the county by our readers – showcase their signature fall style with curated, head-to-toe looks that blend trend, personality and plenty of local flair. These outfits highlight a relaxed elegance with a mix of both warm and cool tones. See how each store fashioned an autumn fit – from bold evening ensembles to comfy and cute casual wear – and find inspiration to refresh your wardrobe for the cooler months ahead.

Cozy Chic –

New Horizons Downtown

Embrace cozy season with a soft and effortless look. This ensemble from Kleen on Jasper Mills Qvist features a plush 100% cotton fleece knit sweatshirt, elevated by a floral appliqué that adds a touch of whimsical charm. Paired with deep charcoal, wide-leg pants featuring unique contrast stitching, this outfit offers a polished yet relaxed silhouette. Grounding the look are the iconic Birkenstock Boston Clogs, providing down-to-earth comfort and style. Finishing it all off is a rich vegan oxblood bucket bag designed by Joy Susan, adding a deep, autumnal hue that perfectly embodies fall.

Kleen Flower Applique Sweatshirt, $101
Kleen Wide Leg Pant With Contrast Stitching, $96
Joy Susan Kayleigh Side Pocket Bucket Bag, $78
Birkenstock Boston Big Buckle Clog, $180

Beautifully Boho –

Periwinkle on Chatham

Partners Shelly Joyce and Darlene Culberson bring a feel-good aesthetic to their Siler City shop, and this breezy fall look on Shelly captures it perfectly, creating an ideal balance between comfort and style. Shelly’s colorful handmade jewelry is especially striking when paired with a bold sleeveless red top and a flowing tiered maxi skirt in mocha. Earth-toned accessories and strappy leather sandals complete the ensemble, while Shelly’s vibrant statement necklace adds playful pops of color. Ideal for crisp afternoons and casual gatherings, this outfit blends seasonal warmth with relaxed sophistication.

Zenana Sleeveless Top, $18
Vine & Love Tiered Maxi Skirt, $40
Accidity Rattan Bracelet and Earrings, $24
Hopes Unlimited Upcycled Sari Choker, $22
Handmade Wooden Flower Necklace by Shelly, $24
Handmade Beaded Wrap Bracelet by Shelly, $25
Hopes Unlimited Silver Bangles, $16

Everyday Essentials –

Chatham Outfitters

Take a page out of Chatham Outfitters marketing manager Jennie Harris’ book and show off your favorite outfitter in a comfy sweatshirt paired with super-stretchy organic cotton wide-leg pants – the perfect fit for a cozy fall day. Slip-on suede clogs complete the look, letting you lounge in ease without sacrificing style.

Chatham Outfitters Sueded Fresh Terry Sweatshirt, $48
Toad&Co Earthworks Pant, $100
Birkenstock Boston Suede Clog, $160

This practical, down-to-earth outfit on Chatham Outfitters co-owner and general manager Tyler Harris works for both crisp-weather adventures and relaxed days out. A lightweight, quick-drying nylon-poly long sleeve with snap-button closure provides versatility, while stretchy trail pants and durable waterproof boots complete this outfit, which is ideal for hiking through fall foliage or grabbing lunch with friends. LIVSN pants add peace of mind with a lifetime warranty and repair program, ensuring you’re dressed in quality pieces that are built to last.

Howler Brothers H Bar B Tech Long Sleeve Plaid Button-Down, $119
LIVSN Ecotrek Trail Pants, $139
Oboz Bridger Mid Waterproof Shoes, $200
Kavu Above Standard Hat, $40

Autumnal Allure –

Second Bloom of Chatham

What’s better than a little black dress you can style up and down for any occasion? This stunning Jessy B number modeled on Lisa Padgett gets an autumn upgrade with a structured, textured jacket, a vintage purse and classic black boots. Add faux pearls, and you’ve got a luxe look without breaking the bank.