I had a reader request a post for what I would consider "quintessentially" preppy staples. Since we're heading into fall I picked out a few things inspired straight from the pages of The Official Preppy Handbook.

Loafers | There are many styles and colors available in loafers but you can't beat the classic penny loafer. If you don't have a pair yet, consider picking up a pair in one of the traditional colors of burgundy, black, or brown.
How to style: Use loafers as a replacement for boat shoes during the fall through spring months. Occasionally I'll wear them in the summer but not very often. Loafers are usually worn sockless but if you're pairing them with slacks for work trousers I think trouser socks would be fine. Bass Weejuns are the gold standard and come in around the $100 mark. For those on a tighter budget, consider this Lauren Ralph Lauren pair for under $50.

Boat and Tote Bag | Another absolutely original preppy piece with a mandatory monogram. L.L. Bean and Lands' End both make a good tote although I slightly lean LLB. Lands' End offers more variety including prints and critters.
How to style: The more beat up, the better.

Classic Wool Blazer: This, dear readers, is truly a plus size preppy unicorn. 100% wool, lined, and all the right details. This is probably the preppiest piece on this list. It's from Lands' End so take advantage of their frequent one day sales to grab it at a great price.
How to style: Simply put, with everything for the next decade. You'll then wish you had bought another one.

Blouses of all types |  Wear 'em to work and wear 'em on the weekends. From the true OG OCBD (oxford cotton button down) to the tie neck blouse I showed here, they're worth their weight in gold. I love the colors of this blouse but it also comes in a navy or white.
How to style: Tie neck blouses are one of the hot styles for fall and really, I don't think they really ever do. However, skip the skinny jeans and grab some flares to look on trend and still classic.

Plaid Puffer Vest | If you already have a solid-colored vest, a plaid version is a fun addition to your outerwear wardrobe. It's a nice contrast among the sea of black and navy vests that are everywhere during the fall.
How to style: With a fair isle sweater, corduroys, and near a campfire in the hills.