Fall Preppy Outfits for Women

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57 products
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Rich brown knit top featuring an ivory and navy diamond pattern with fine rust-red lines, crew neckline, long sleeves, and ribbed trim. Relaxed brown knit top with repeating diamond accents in ivory and navy, fine rust-red lines, and ribbed trim along the neckline, cuffs, and hem.
It All Checks Out Brown Multi Argyle Crewneck Sweater Entro
$62.00
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Brown floral strapless midi dress with a pleated bodice, fitted waist and full pleated skirt. Brown floral strapless midi dress with a structured pleated bodice and voluminous midi skirt in motion.
A Reason to Stay Chocolate Brown Multi Floral Cotton Strapless Midi Dress Entro
$98.00
Textured sleeveless top with a contoured fit, waist-defining peplum hem, and distinctive gold-tone neckline hardware for an elevated finish. Textured knit sleeveless top with a structured silhouette, defined waist, and softly flared peplum hem, finished with gold-tone neckline hardware.
Keep Me Linked In Red Knit Peplum Top Entro
$64.00
Red and black plaid fabric creates a bold look on this sleeveless shift dress. Close-up detail of the red and black plaid dress showing the structured standing neckline, split front, and contrasting lines.
Plaid to See You Red & Black Plaid Sleeveless Mini Dress Entro
$69.00
Navy and heather gray striped ribbed knit top with an ivory contrast collar. Navy and gray ribbed knit top highlighting the crisp ivory collar.
Making the Team Navy & Heather Gray Collared Rugby Sweater
$68.00
Crisp cotton striped midi dress featuring a collared neckline, partial button-front placket, cap sleeves, and statement waist ties. Striped cotton midi dress with a tailored silhouette, cap sleeves, collared neckline, and attached side ties forming a waist bow.
Lunch on the Riviera Red Stripe Cotton Midi Dress Entro
$68.00
Lightweight red and navy plaid jacket featuring a structured collar, zip-front closure with snap accents, and oversized patch pockets. Plaid jacket highlighting its zip-front closure, structured collar, and oversized utility pockets.
Season in Session Red & Navy Plaid Cinch Waist Jacket Entro
$82.00
Rich dark wash skinny jeans with a streamlined silhouette and classic five-pocket styling. Dark wash skinny jeans highlighting the smooth waistband and fitted upper silhouette.
Keeping It Sleek Dark Wash Stretch Skinny Jeans Just USA
$64.00
Chocolate brown knit sweater showcasing oversized ivory and heather gray diamonds with vivid blue contrast stitching. Perfectly Preppy Chocolate Brown Multi Argyle Knit Sweater
Perfectly Preppy Chocolate Brown Multi Argyle Knit Sweater Moon River
$102.00
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Dark wash skinny jeans featuring a high-rise waist, tan topstitching, functional pockets, and a zipper button closure. Detailed view of the dark denim showing the sleek skinny-leg construction and contrasting tan topstitching along the seams.
Simply Stated Dark Wash High Waisted Skinny Jeans Just USA
$66.00
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Tall dark brown faux suede boots with pointed toes, fitted knee-high shafts, and covered block heels. Close view of the streamlined pointed toes and smooth faux suede finish on the tall brown boots.
Stepping Out Dark Brown Faux Suede Knee High Boots
$78.00
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Navy and red plaid shirt dress with a collared neckline, puff sleeves, gold-tone buttons, matching waist belt, and tiered mini skirt. Navy and red plaid dress showcasing its collared neckline, gold-tone button front, and softly gathered puff sleeves.
Glad We Made Plans Navy & Red Plaid Cotton Mini Dress Entro
$72.00
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Satin maxi dress layered with a cropped cotton sweater featuring mixed cable-knit detailing. Cropped view of the satin maxi dress and textured sweater showcasing the layered silhouette.
The Perfect Pairing Red Cable Knit Sweater & Satin Maxi Dress Set
$82.00
Soft cotton top highlighting ivory stripes, a contrasting point collar, and the upper portion of its partial button placket. Relaxed cotton striped top featuring a crisp collar, dropped shoulders, and understated embroidered detailing.
FRNCH Rumoi Bordeaux Cotton Polo Shirt FRNCH
$85.00
High-rise jeans showcasing the relaxed straight leg shape and medium wash. Medium wash denim highlighting the high-rise waist and button and zip closure.
Day Dreaming Dark Wash Wide Leg Jeans Just Black
$78.00
Sienna slingback heels showcasing the pointed toe, kitten heel, and gold-tone chain. Glossy sienna pointed-toe heels featuring an oversized gold-tone chain across the vamp.
Chain of Events Sienna Patent Gold Chain Slingback Kitten Heels
$48.00
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Belted cotton-rich dress with gathered shoulders and structured cap sleeves with bag. Moving With Confidence Dark Wash Tiered Denim Midi Dress
Moving With Confidence Dark Wash Tiered Denim Midi Dress Entro
$84.00
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Satin hair scarf featuring an intricate vintage hardware print with chains, buckles, straps, and clasps in warm neutral tones. Decorative chain links and buckle details create a sophisticated look on this silky satin hair scarf.
Linked in Style Ivory & Black Vintage Hardware Print Satin Scarf
$26.00
Brown plaid pants featuring a high-rise waist and long wide-leg silhouette with a smooth, softly structured drape Brown plaid pants highlighting the high-rise waistband and flowing wide-leg silhouette with a touch of comfortable stretch.
Astrid Mitchel Brown Plaid High Rise Wide Leg Pants Astrid
$162.00
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Deep navy ribbed knit top showcasing its fitted silhouette and full fold-over turtleneck. Astrid Wilco Navy Essential Sleeveless Turtleneck Top
Astrid Wilco Navy Essential Sleeveless Turtleneck Top Astrid
$68.00
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Ivory ribbed knit top highlighting the fitted silhouette and high fold-over neckline. Close-up of the ivory ribbed knit showing the fold-over turtleneck texture.
Astrid Wilco Ivory Essential Sleeveless Turtleneck Top Astrid
$68.00
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Dark wash wide-leg jeans with subtle fading and oversized turned cuffs. Dark wash wide-leg jeans highlighting the oversized cuffed hem and relaxed shape.
Best I've Seen Dark Wash Stretch Wide Leg Cuffed Jeans Just Black
$109.00
Blue, navy, and ivory plaid jacket showcasing its oversized notched lapels and cropped boxy shape. Close-up detail of the blue, navy, and ivory plaid jacket highlighting the softly brushed fabric and oversized notched lapel.
Astrid Stevie Blue Plaid Flannel Jacket Astrid
$148.00
Detailed close-up of the white ankle boot showcasing the outer seam stitching and functional inner zipper. Cropped view of white ankle boots highlighting the pointed toe shape and smooth leather finish.
From Here On White Faux Leather Block Heel Ankle Boots
$59.00
Metallic steel blue and chocolate floral dress with a plunging V-neck bodice, empire waist, and cascading tiered skirt. Close-up detail of the metallic steel blue and chocolate floral dress showing its shimmery plissé texture and plunging V-neckline.
The Evening Unfolds Steel Blue & Chocolate Floral Metallic Tiered Maxi Dress
$108.00
Cropped front view of beige kitten heels featuring an open-toe slide silhouette and clear strap across the foot. Sandals angled to highlight the clear strap and sleek slide silhouette.
Seek The Truth Beige Clear Kitten Heels
$49.00
Brown knit dress with a fitted bodice, classic round neckline, and three-quarter sleeves. Close-up detail of the brown knit dress showing its classic round neckline and soft knit texture.
Perfectly in Place Brown Multi Plaid Knit Bodice Midi Dress
$92.00
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Close-up of nude kitten heel mules emphasizing the clear strap, pointed toe, and smooth nude finish. Side view of clear nude kitten heel mules displayed on a beige background, showing the pointed toe and subtle lift.
Great Expectations Clear Nude Kitten Heel Mules
$46.00
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Ivory pullover sweater with a classic cable knit design, crew neckline, long sleeves, and relaxed fit. Close-up detail of the ivory sweater showing its textured cable knit design and soft knit construction.
All the While Ivory Cable Knit Crewneck Pullover Sweater
$48.00
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Smooth canvas-feel coat with a button front, chocolate brown corduroy collar, coordinating tie belt, and side pockets. Detail of the coordinating tie belt and smooth canvas-feel fabric on the coat.
The Scenic Way Olive Belted Trench Coat Moon River
$150.00
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Angled view of the boots showcasing the inner side zipper closure and streamlined profile. Close view of the brown boots highlighting the pointed toe and smooth faux leather finish across the front.
Stand Corrected Brown Faux Leather Suede Ankle Boots
$56.00
Deep indigo jeans highlighting the high-rise waistband, belt loops, and classic button-and-zip front closure. Dark blue denim detail showcasing the traditional five-pocket design and smooth structured construction.
Forever Again Deep Indigo Straight Leg Jeans Just Black
$110.00

Plaid, argyle, rugby stripes, tailored layers and preppy fall outfits with a modern twist. The British Prep 101 Collection brings classic collegiate style into the season with polished pieces that feel fresh, effortless, and easy to wear. Discover preppy dresses, cozy sweaters, classic skirts, and versatile tops perfect for creating put-together fall looks.

Complete your outfit with structured jackets, seasonal boots, loafers, and statement accessories for an effortlessly preppy finish. From crisp fall days and weekend plans to everyday outings, these timeless-meets-trendy styles make it easy to bring a polished, preppy feel to your fall wardrobe.

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