Fall is the perfect time to channel your inner prep with classic, polished looks that scream cozy sophistication! Whether you’re going into the office or still working your way through school, these fall-themed preppy outfits blend timeless style with autumn’s warm, crisp energy and bold patterns and textures.
So grab your pumpkin spice latte and get ready to add these Pinterest-worthy fall outfits ideas to your preppy outfit mood board!
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Preppy Outfit Wardrobe Staples to Buy for Fall
To nail the preppy vibe this fall, stock your closet with these timeless pieces and accessories that channel classic, polished style and different outfit combinations. Here’s a bulleted list of must-have wardrobe staples for creating those chic, Ivy League-inspired looks.
- Plaid Pleated Skirt: A mini or midi skirt in fall-toned plaid (think navy, burgundy, or forest green) is a preppy essential. Perfect for pairing with sweaters or blouses for a schoolgirl-chic look.
- Tights and Knee-High Socks: All these outfits with skirts needs some beautiful tights or knee-high socks to complete them!
- Cable-Knit Sweater: Opt for a cozy cream, navy, or pastel cable-knit sweater. It’s ideal for layering over collared shirts or under vests for that classic preppy warmth.
- Oxford Button-Down Shirt: A crisp white or light blue Oxford shirt is a non-negotiable staple. Look for tailored fits to tuck into skirts or trousers for a clean, polished vibe.
- Quilted or Tailored Vests: A monogrammed or plain quilted vest in hunter green, navy, or mustard adds a preppy, outdoorsy touch. Great for layering over shirts or sweaters.
- Tailored Trousers: High-waisted khaki or pleated trousers in neutral tones like beige, charcoal, or olive scream sophistication. Choose a slim or straight cut for versatility.
- Crested or Monogrammed Blazer: A crested blazer is the ultimate wardrobe staple for an instant prep school vibe.
- Mary Jane or Oxford Shoes: Classic leather Mary Janes or Oxfords in black or brown are preppy footwear must-haves. They pair perfectly with skirts, shorts, or trousers.
- Argyle Sweater Vest: A sleeveless argyle vest in fall hues like burgundy or teal adds a scholarly vibe. Layer it over turtlenecks or button-downs for instant prep.
- Corduroy Skirt: A corduroy A-line or midi skirt in caramel, navy, or olive brings texture and warmth to your fall preppy outfits.
- Polo Shirt: A long-sleeve polo in a rich fall color like burnt orange or forest green is sporty yet refined, perfect for pairing with skirts or jeans.
- Loafers or Penny Loafers: Sleek leather loafers in black, brown, or burgundy are a preppy footwear staple, adding polish to any outfit.
- Silk Scarf or Headband: A patterned silk scarf or headband in classic prints like paisley or stripes adds a feminine, preppy flair to your looks.
- Structured Tote Bag: A leather or canvas tote in a neutral color (beige, navy, or black) with clean lines completes your outfit with practical, preppy style.
- Hair Bows and Neck Scarfs: Bows are the uber-feminine touches that will make your outfit look schoolgirl chic in seconds.
- Ivy League Branded Tops and Sweaters: Tops and sweaters with logos from Ivy League schools are the perfect addition to your preppy capsule wardrobe for casual outfits.
These outfit staples are the building blocks for endless preppy fall outfits. Mix and match them to create looks that are cozy, classy, and totally on-trend!
Tip: Want a crash course on how to dress preppy? I suggest you watch the movie “Clueless”. It has the most amazing preppy outfits in it and is one of my most fave movies from the 90’s!
Fall Patterns & Textures To Snatch
Fall is the best season for fashion, in my opinion, because you get to incorporate all kinds of gorgeous patterns and materials for a stunning outfit. Be sure to grab preppy style staples in patterns like houndstooth, stripes, checkers and plaid. In terms of warm fall materials, think wool knits, corduroy, velvet, leather, suede and tweed.
Here’s a must-see list of 12 cozy chic and uber preppy fall outfits to elevate your wardrobe this season.
1. Skirt and Knit Sweater with Collared Shirt
Combine a button up collar shirt underneath a sweater for this preppy layered look. Add knee-high socks or decorated tights with boots or Mary Jane shoes for that ultimate preppy charm. This outfit is perfect for crisp fall days and screams “Ivy League casual chic.” A beautifully curated handbag doesn’t hurt this preppy look either!
RELATED READING: Must-Have Old Money Fashion Accessories to Look Rich on a Budget!
- @sarah.naja
2. Button Down Shirt with a Plaid Skirt
Layer a crisp button-down shirt with a plaid trousers or a plaid skirt for a casual but still polished preppy outfit. Add a pair of loafers for a polished, school-inspired vibe.
RELATED READING: 12 FALL STYLES STAPLES FOR YOUR CAPSULE WARDROBE
3. Blazer and Skirt with Booties
Well fitted blazers are a capsule wardrobe staple for any preppy outfit. Find a tailored corduroy, velvet or structured blazer to pair with a skirt for the ultimate fall preppy street outfit.
- @sophia_rosemary
4. Monogrammed Cardigan and Button-Down Shirt
Rock a monogrammed cardigan in a vibrant fall color like burnt orange or deep teal, buttoned up over a crisp cotton button-down shirt. Add loafers and a crossbody bag for a sporty yet classy outfit that’s great for casual fall outings. Bonus: throw on a headband for extra prep points.
RELATED READING: 31 COZY CHIC FALL OUTFIT IDEAS
5. Tailored Vest and Pleated Trousers
Layer a sleeveless vest over a long-sleeve turtleneck in a bold fall color like burgundy, brown or red. Pair with high-waisted pleated trousers in plaid and complete the look with Oxfords and a watch with a leather strap for a scholarly, preppy feel.
- @melodiebanfield
6. Camel-Colored Coat with Bows
Neutral shades and bows are a must for that school-girl preppy outfit look. Add bow details to your hair, as a neck scarf or on your coat to bring out this feminine preppy fall outfit idea.
SHOP PREPPY HAIR BOWS: AMAZON
- @aliaslouiseblog
7. Bow Tie Blouse
A cotton or silky blouse with a bow tie neckline with a tweed midi skirt, plaid trousers, or even jeans is a great way to incorporate some preppy pep into your outfit. Pair with ballet flats and a pearl necklace for a feminine, preppy outfit that’s perfect for fall events or date nights.
For the ultimate prep-school vibe, tie a cable knit sweater around your shoulders to look like you came straight out of Harvard!
8. Cable-Knit Sweater with Plaid Skirt Fall Outfit
Plaid and cable knit sweaters go together in a preppy outfit look like peanut butter and jelly. Mix and match different colored sweaters and plaids for capsule wardrobe staples that will fuel a ton of preppy outfits to come.
- @styledbyvienne
9. Matching Blazer and Skirt Preppy Outfit
This matching blazer and skirt outfit in a checkered pattern is perfect for a party or interview when you want to look extra prepared and coordinated. Finish the look with matching boots and handbag that tie into the outfits colors for the most polished look.
- @inesbombshell
10. Wool Coat with Vest and Skirt
Stay warm but prep-school chic in a long wool coat in neutral shades like gray, camel, brown, black or navy blue.
11. Ivy League School Sweatshirts
Can’t afford Harvard? Me neither, but that shouldn’t stop you from getting this casual preppy fall look; grab some Ivy-league branded polo shirts or sweatshirts to add on top of a skirt or jeans for a cozy casual fall outfit idea.
12. Polo Shirt in Fall Colors and Patterns
Collared polo shirts are going to be a versatile addition to your preppy capsule wardrobe. Grab a few in different fall colors and patterns to wear with trousers, a skirt or jeans for your next preppy chic outfit.
Which fall preppy outfit ideas have you added to your style vision board this season??
