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Style Guide: Classic Fall Capsule Wardrobe

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Fall is arguably the best style season for preppy people, amiright? This post contains a classic Fall capsule wardrobe for 2020 and beyond, from quilted jackets, to turtleneck sweaters, loafers, peacoats and more. When it comes to Fall, my motto is buy once, wear forever.

I've loved that Fall Americana look for decades, even that before my time -- think Jackie O and Mary Tyler Moore. The Fall-inspired styles they wore in the 1960s and 1970s are still relevant today.

And when I worked at the Gap from 2000-2004, my absolute favorite line of theirs was Fall 2003, which I would still wear today:

Gap Fall 2003 ad
My favorite vintage Fall ad from Gap in 2003

Below you will find everything you need to know about a classic Fall capsule wardrobe, from book pairings (since this is a book pairings blog!) to outfit ideas, specific products, and mood boards.

Book Pairings for a Classic Fall Capsule Wardrobe

First, since this is a book blog, let's talk about the best preppy books to pair with your classic Fall capsule wardrobe.

Classic Style: Hand It Down, Dress It Up, Wear It Out by Kate Schelter

Classic Style is the book that framed how I view my style as a whole as an adult coming into my own and embracing what I love, and what lasts, over trends. I found myself nodding in agreement while reading it, and highlighting passages. It's a book I constantly go back to in my mind when I am deciding whether a purchase is "me" and "for the long run." As a bonus, it's filled with the most beautiful watercolor pictures.

The Official Preppy Handbook by Lisa Birnbach

The Official Preppy Handbook

Published in 1980, The Official Preppy Handbook is a vintage must-read for prepsters. Since it centers around prep school culture, it always reminds me of Fall. It's an extremely detailed and tongue-in-cheek, a nostalgic guide to everything that makes prepsters uniquely themselves, including classic style! I keep a used copy on my shelf. As an aside, it would be the perfect reference for an author writing a book with a preppy 1980s setting.

Classic Fall Capsule Wardrobe Outfit Inspiration

Scroll through the widget below for my curated list of classic Fall outfit inspiration:

Mood Boards for Classic Fall Capsule Wardrobe

Pin the mood boards below for reference for casual and dressy inspiration for your classic Fall capsule wardrobe.

(Shop specific styles you like in the Pinterest widget below.)

Scroll and click through the widget below to shop these specific classic Fall capsule wardrobe products:

Classic Fall Capsule Wardrobe Products

Below, get my specific classic Fall capsule wardrobe recommendations in jackets, tops, sweaters, dresses, skirts, pants, shoes, purses, and accessories.


  • Quilted Barbour jacket - a timeless investment piece you will have for years (or decades) and won't regret. Shop them at Barbour, Nordstrom or Tuckernuck.
  • Vest - I prefer J. Crew Factory for an affordable, but effective quilted option, or a Patagonia sweater vest, which is great for layering or on its own.
  • Peacoat - mine is from Nordstrom but J.Crew Factory has a classic camel option similar to mine this year. It's perfect to throw over anything for warmth and classic style.
  • Blazer - I prefer J.Crew Factory's sweater blazers, which are on my list of all-time favorite things, and J.Crew Factory's wool blazers.

Tops / Sweaters

  • Turtlenecks - Turtlenecks are so classic and so cozy. They always look and feel good. My favorite is the washable merino wool turtleneck sweaters from Gap. They offer the coziness of a sweater with the versatility of a washable fabric. Madewell also carries very classic turtlenecks in both cotton and sweater materials.
  • Roll neck sweater - Roll-neck sweaters are a J.Crew staple piece for Fall, going back to the 1980s. I have several of these. They are great for layering.
  • Cable knit sweater - No one does a classic cable knit sweater like Ralph Lauren. No one. But... I do also like L.L. Bean for a more cost-effective option.
  • Boyfriend cardigan - So many women's Fall classic styles are based on men's styles, and boyfriend cardigans are no exception, with their collegiate look. I have struggled to find the perfect one this year, with the perfect Fall tones and large brown buttons. Boden has had my favorite one so far.
  • Oxford shirt - And no one does a classic oxford shirt like Ralph Lauren. They are perfect both on their own and for layering under sweaters and blazers. You can even do chambray or plaid for an extra Fall feel.
  • Rugby shirts - Rugby shirts have a classic Fall look for both men and women, so reminiscent of vintage collegiate wear. I strongly prefer L.L. Bean for these. They are affordable, lightweight for multi-seasonal use, have a pretty chambray trim, and wash well. They just take your average sweatshirt up a notch. I have about 8 of them!
  • Breton tops - Breton tops are striped boatneck tops that are also great for multi-seasonal use and can be layered in the Fall. The boatneck is a touch feminine and stripes are the ultimate print that never goes out of style. Talbots is most well known for this style.

Dresses / Skirts

  • Wool skirt - A simple wool skirt has all the school vibes, and my absolute favorite style is from J.Crew Factory. I have several of these! The stretchy waistband makes them so comfortable and easy to wear.
  • Corduroy skirt - From the 1970s until today, corduroy skirts have such a vintage Americana Fall look. Madewell and Everlane styles are spot on. And I wrote an entire post dedicated to corduroy skirt looks if you want more inspiration.
  • Shirt dress - I love the clean lines of a shirt dress, and a plaid or chambray style is perfect for Fall. Draper James has the best preppy options. Pair with Riding boots for a dressed-up look or casual sneakers for a dressed-down look.
  • Sweater dress - Sweater dresses are so cozy and classic for Fall. I think Madewell and Banana Republic do this look best.


  • Skinny jeans - Clean-lined jeans in a darker wash are a must for Fall! My absolute favorite is the Rag & Bone Cate Ankle Skinny Jeans in "April." They are high-waisted without being too high or tight at the waist, and they glide seamlessly over your hips for a flattering and comfortable feminine fit that hits perfectly at the ankle. They are a blogger favorite for a reason. And -- bonus points -- they generally run a size big.
  • Faux leather leggings - Speaking of flattering pants that are a blogger favorite, Spanx faux leather leggings are also a must. They have great compression and a finish that works for casual wear or going out. I go up a size in these for extra room.
  • Corduroy pants - These are classic Fall Americana at its finest, and when I think of Fall Americana, I think of the Gap and Banana Republic. For a more traditional style, try Land's End.


  • Loafers - Loafers just may be the most classic of all shoes, and my absolute favorite based on style and comfort factor are from Sperry. They bring the comfort of boat shoes to a refined flat.
  • Casual sneakers - Casual sneakers are a must for every season and, for a classic fall look, my all-time favorite shoes, hands down, are Tretorn sneakers.
  • Riding boots - A good brown riding boot is so Fall inspired and lasts forever, and the brand I think of first is the Americana styles of Ralph Lauren.

Purses / Accessories

  • Satchel purse - A brown satchel purse has that Fall collegiate look. I purchased mine at the leather market in Florence, Italy, but I think Coach truly nails this style.
  • Tortoises shell jewelry - The brown shades of tortoiseshell scream Fall and will never go out of style. J.Crew has great options, as does Amazon.
  • Scarf - Lightweight scarves are the perfect accessory for sweater weather. Each Fall, I wear this affordable navy-trimmed leopard print scarf around my neck or in my hair. It's one of my favorite Amazon purchases. Nordstrom is also a go-to for me for a classic Fall plaid scarf.
  • Baseball hat - Fall deserves Fall colored hats! Transition from your Summer baseball cap to one with a classic plaid or tone from J.Crew.

That concludes everything you need to know about a classic Fall capsule wardrobe, from book pairings (since this is a book pairings blog!) to outfit ideas, specific products and mood boards.

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