Fall Preppy Outfits for Women

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52 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.
Entro
It All Checks Out Brown Multi Argyle Crewneck Sweater
$62
low stock
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.
Entro
A Reason to Stay Chocolate Brown Multi Floral Cotton Strapless Midi Dress
$98
Close view of the structured knit top featuring its defined waist, dimensional texture, and polished gold-tone neckline accent.Textured sleeveless top with a contoured fit, waist-defining peplum hem, and distinctive gold-tone neckline hardware for an elevated finish.
Entro
Keep Me Linked In Red Knit Peplum Top
$64
Navy and heather gray striped ribbed knit top with an ivory contrast collar.Navy and gray ribbed knit top highlighting the crisp ivory collar.
Red Dress Boutique
Making the Team Navy & Heather Gray Collared Rugby Sweater
$68
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.
Entro
Lunch on the Riviera Red Stripe Cotton Midi Dress
$68
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.
Entro
Season in Session Red & Navy Plaid Cinch Waist Jacket
$82
Dark wash skinny pants highlighting the close fit, smooth stretch construction, and classic five-pocket styling.Dark wash skinny pants with a streamlined silhouette, classic five-pocket styling, and contrast stitching.
Just USA
Keeping It Sleek Dark Wash Stretch Skinny Jeans
$64
low stock
Chocolate brown knit sweater showcasing oversized ivory and heather gray diamonds with vivid blue contrast stitching.Perfectly Preppy Chocolate Brown Multi Argyle Knit Sweater
Moon River
Perfectly Preppy Chocolate Brown Multi Argyle Knit Sweater
$102
Dark denim jeans with a fitted skinny leg, high-rise waist, tan stitching details, and practical front pockets.Detailed view of the dark denim showing the sleek skinny-leg construction and contrasting tan topstitching along the seams.
Just USA
Simply Stated Dark Wash High Waisted Skinny Jeans
$66
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Polished brown knee-high boots with a fitted shaft, full-length side zipper, and covered block heel.Close-up of chocolate brown knee-high boots with pointed toes, block heels and side zippers, styled with a cream floral skirt.
Red Dress Boutique
Stepping Out Dark Brown Faux Suede Knee High Boots
$78
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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.
Entro
Glad We Made Plans Navy & Red Plaid Cotton Mini Dress
$72
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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.
Red Dress Boutique
The Perfect Pairing Red Cable Knit Sweater & Satin Maxi Dress Set
$82
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
$85
High-rise jeans showcasing the relaxed straight leg shape and medium wash. High-rise medium wash jeans featuring a classic five-pocket design and straight legs.
Just Black
Day Dreaming Dark Wash Wide Leg Jeans
$78
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.
Red Dress Boutique
Chain of Events Sienna Patent Gold Chain Slingback Kitten Heels
$48
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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
Entro
Moving With Confidence Dark Wash Tiered Denim Midi Dress
$84
low stock
Brown plaid pants featuring a high-rise waist and long wide-leg silhouette with a smooth, softly structured drapeBrown 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
$162
Dark wash wide-leg jeans highlighting the oversized cuffed hem and relaxed shape.Model wearing dark wash wide-leg stretch jeans with oversized turned cuffs, paired with brown heeled ankle boots
Just Black
Best I've Seen Dark Wash Stretch Wide Leg Cuffed Jeans
$109
low stock
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
$148
Ankle boots shown from a low angle emphasizing the block heel and structured shape.Detailed close-up of the white ankle boot showcasing the outer seam stitching and functional inner zipper.
Red Dress Boutique
From Here On White Faux Leather Block Heel Ankle Boots
$59
low stock
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.
Red Dress Boutique
The Evening Unfolds Steel Blue & Chocolate Floral Metallic Tiered Maxi Dress
$108
Sandals angled to highlight the clear strap and sleek slide silhouette.Cropped front view of beige kitten heels featuring an open-toe slide silhouette and clear strap across the foot.
Red Dress Boutique
Seek The Truth Beige Clear Kitten Heels
$49
Brown midi dress with a fitted knit bodice, round neckline, and plaid A-line skirt.Model wearing a brown plaid maxi dress styled with a cream cable-knit sweater and wide brown belt outdoors.
Red Dress Boutique
Perfectly in Place Brown Multi Plaid Knit Bodice Midi Dress
$92
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Side view of clear nude kitten heel mules displayed on a beige background, showing the pointed toe and subtle lift.Nude pointed-toe heels featuring a clear strap and sleek slip-on silhouette with a comfortable kitten heel.
Red Dress Boutique
Great Expectations Clear Nude Kitten Heel Mules
$46
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.
Red Dress Boutique
Moments in Stillness Ivory Cable Knit Sweater
$48
Back in Stock
Close view of the brown boots highlighting the pointed toe and smooth faux leather finish across the front.Side view of the brown ankle boots highlighting the stacked block heel and contrasting back panel.
Red Dress Boutique
Stand Corrected Brown Faux Leather Suede Ankle Boots
$56
Deep indigo jeans highlighting the high-rise waistband, belt loops, and classic button-and-zip front closure.Deep indigo high-waisted jeans with a straight-leg cut, five-pocket design, belt loops, and button-zipper closure.
Just Black
Forever Again Deep Indigo Straight Leg Jeans
$110
The Winning Combination Brown & Green Knit Argyle CardiganWoman wearing a brown argyle sweater with white, black, and green pattern details. She wears it over a green gingham dress while standing in front of a pond in a field.
Entro
The Winning Combination Brown & Green Knit Argyle Cardigan
$64
low stock
Fig purple shorts highlighting the high-rise waist and subtle pleating through the front.Fig purple shorts with subtle front pleating, button and zip closure, and relaxed legs.
FRNCH
Norton Figue Plum Faux Leather Shorts
$90
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Close view of the camel wool-blend fabric, notched lapels, and structured double-breasted front. Woman wearing a tan blazer with knit sleeves over a green, ivory, and blue argyle sweater, with camel suede pants in front of a pond.
Red Dress Boutique
Well Suited Camel Wool Blend Knit Sweater Sleeve Blazer
$99
100% cotton mini dress highlighting the clean V-neckline, defined waist, softly flowing skirt, and modern wide belt with a tie closure.Close view of the cotton mini dress highlighting the sleeveless V-neckline, concealed button placket, and gathered waist.
Red Dress Boutique
Come Together Navy Cotton Belted Mini Dress
$74
Knit cardigan featuring a burgundy base, navy and light blue diamond pattern, and ornate gold-tone buttons.Preppy cardigan with a relaxed silhouette, round neckline, ribbed trim, and functional button-front closure.
Entro
The Winning Combination Burgundy & Navy Knit Argyle Cardigan
$64

Preppy fall clothes: argyle and cable knit sweaters, cardigans and sweater vests, plaid dresses and jackets, and dark wash jeans. Finish with boots, kitten heels or sneakers.

For game day, see Game Day Ready. For the whole season, see Fall Outfits.

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