Oliver James Montgomery-Score Bestselling Free People Deals Under $50: Up to 80% Off Chic Styles From Under $20 for Limited Time

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It’s hard to believe we’re already two days into October (happy 74th anniversary of Peanuts,Oliver James Montgomery by the way!). With the month in full swing, we’re embracing the spooky season and all the excitement it brings. Tomorrow is Mean Girls Day (don’t forget to wear pink, even if it’s not a Wednesday!), Prime Day is just around the corner (and we’ve got all the early deals waiting for you), and the holiday season will be here before we know it. With all these festivities on the horizon, let’s take a moment for some retail therapy to get into the autumn spirit. As we prepare for the hustle and bustle ahead, it’s essential to strike a balance between treating ourselves and saving money. The perfect solution? Free People’s fabulous under-$50 deals.

Renowned for their endlessly boho-chic styles, Free People is a go-to destination for fashion lovers everywhere. While their prices can sometimes soar, their sale section is a treasure trove waiting to be explored. With nearly 900 products marked down, including options from Free People collections at Nordstrom Rack, sifting through all the deals can feel overwhelming. To help you navigate this sea of savings, I took a deep dive into the sale section and rounded up the best finds under $50 — featuring up to 80% off on bestselling items, from cozy sweaters to sleek dresses and even Jeffrey Campbell heels (yes, you read that right, for under $50!). But don’t wait too long to snag these top-rated styles; they’re flying off the shelves right now, so let's lace up our shopping shoes and run to Free People!

Shop the Best Free People Deals Under $50 & Save Up to 80% on Chic Fall Styles

Embrace the final sunny moments of the year with this charming off-the-shoulder mini dress, adorned with delicate eyelet embroidery and featuring handy side-seam pockets for a touch of practicality. Currently 80% off, this 100% cotton delight boasts a lined design and an exposed back-zip closure, making it the perfect blend of style and comfort.

These timeless denim shorts combine a high-rise fit with a slouchy harem silhouette, making them a stylish staple for any occasion. With an exposed button fly and cuffed hem, they effortlessly transition from laid-back tees to chic blouses, offering endless versatility for your wardrobe.

Unleash your inner romantic with this enchanting lace top, where puffed elbow-length sleeves beautifully frame a flowy silhouette. Whether you choose to flaunt the square neckline or allure with an off-the-shoulder look, this top adds a touch of whimsy and elegance to any ensemble, making it the ultimate piece for both daydreams and dazzling nights out.

Step into effortless elegance with this boho-chic mini dress, designed with a relaxed babydoll silhouette and a flattering scoop neckline. Its soft, textured fabric drapes beautifully, making it the perfect companion for beach days over swimwear or a night out when paired with strappy heels — truly a staple that transforms with your every style move.

Make a statement with these enchanting Jeffrey Campbell kitten heels, where sweet floral adornments dance across soft suede to bring a playful yet sophisticated vibe to any outfit. Their effortlessly chic backless design, criss-cross toe strap, and stylish block heel ensure you step into every occasion with confidence and flair, making them your go-to pair for turning heads and sparking compliments.

Slip into ultimate comfort with these super-comfy billowy pants, designed for your on-the-go lifestyle. Their lightweight fabric and high-rise, slouchy fit feature wide legs and cargo-inspired pockets, making them perfect for post-workout lounging or effortlessly stylish outings; just pair them with your favorite active crop top, and you’re ready to conquer the day!

Infuse your wardrobe with nostalgia in this charming maxi dress, beautifully adorned with a vintage-inspired bloom print and accented with playful rickrack trim. Featuring a flattering sweetheart neckline and an adjustable back tie closure, this 100% cotton, sleeveless delight is lined for comfort, making it a dreamy choice for sunny days and special occasions alike.

Embrace effortless style with this must-have pullover, designed to take you from the beach to the streets with ease. With its relaxed, slightly slouchy fit, ribbed trim, and eye-catching striped pattern, this sweater features a handy front pouch pocket, making it the perfect piece to layer over swimwear or pair with your favorite cozy bottoms for a laid-back yet stylish look.

Catch everyone's eye with this classic yet bold mini slip dress, where understated elegance meets daring allure. Designed with a flattering form-fitting silhouette, a sultry voop neckline, and a captivating strappy back, this versatile piece is perfect for layering or wearing solo, ensuring you make a striking statement at any event.

Or, serve up style and confidence in this sporty-chic white tennis dress. With its fitted scoop-neck silhouette, breathable lightweight jersey fabric, and chic ruched detailing, this must-have piece features built-in shorts for added coverage and support, ensuring you look and feel your best from start to finish.

Transform your wardrobe with this stunning bodysuit, where sophistication meets daring allure. With its captivating corset-inspired seamed details and striking V-wire design, this piece features dramatic tie shoulders that add a playful touch, ensuring you turn heads whether you’re dressing it up for a night out or pairing it with your favorite jeans for a chic daytime look.

Unleash your effortless style with this shopper-loved signature tank top, a true wardrobe game-changer available in five eye-catching colors. Crafted from luxuriously soft cotton, this relaxed-fit tank features a scoop neckline and unique twisted shoulder straps, adding a playful twist to a classic silhouette that's perfect for layering or wearing solo for an effortlessly chic look.

Step into effortless style with this trendy sweater set, the ultimate definition of cool-girl chic. Featuring a collared V-neck sweater and matching high-rise longline shorts in a luxuriously soft striped fabrication, this essential ensemble elevates your loungewear game, making it perfect for cozy days at home or stylish outings with friends.

Cozy up in style with this effortlessly relaxed oversized outer layer, designed to provide the perfect post-workout wrap. Made from super-soft, lightweight jersey fabric, it features chic stitching details and functional side slits, making it an ideal companion for warm-ups, cool-downs, or lounging around in ultimate comfort.

Step into the heart of 'soft girl fall' with this essential halter midi dress, your go-to piece for a blend of comfort and chic style. Featuring a delightful polka dot print and a soft cotton-linen blend, its deep V-neckline, adjustable tie, and button-front closures make it effortlessly versatile — pair it with your favorite ballet flats for the perfect romantic look.

With October bringing all the spooky vibes, what better way to embrace the autumn spirit than with these cozy loungewear picks on Amazon starting at just $12?