Plus Size Preppy Fall Outfits

Two plus size preppy fall outfits because reasons.

I mean, I know preppy is trending, but when is preppy not on point?

I’m having flashbacks of my youth and loving it!

Plus Size Preppy Fall Outfits

Plus Size Preppy Fall Outfits. These plus size outfits feature flared jeans and rugby stripes. Finish with a puffer vest or plaid jacket, sneakers, and a baseball cap. Alexa Webb

Plus Size Flare Jeans

Both outfits feature these plus size flare jeans from Abercrombie & Fitch.

I love that flares are back.  I am only 5’4″ and I will always rock a flare!

These dark wash flares come in 2 fits and three lengths.

The “Curve Love” fit has additional 2″ through the hip and thigh to help eliminate waist gap. 

Curve Love is a good choice for pear shapes.

Plus Size Ultra High Rise Flare Jeans Sizing

As I said, these flare jeans come from Abercrombie & Fitch.

Go here to read about Abercrombie’s fatphobic history if you’re interested in this controversial brand’s attempt at redemption.

A&F now offers select items in sizes up to a size 24, or a size 37 in their jeans.

The sizing is similar to J.Crew in that their jeans come by waist sizing (vanity), so check the size chart below to see which size you are.

Abercrombie Size Chart

I haven’t tried any of their jeans because they don’t make my size. 

But, go here for a review and more sizing information.

Life is Short, Wear Stripes

The first plus size preppy look features a rugby striped sweater in navy over the flares.

But, if you’re unsure about stripes, please read this post “Are horizontal stripes REALLY making you look fat?,” written by Melissa at Suger Coat It

She explains, “No, horizontal stripes won’t make you look fat. Only being fat makes you look fat.  And you know what, that’s okay.”

I think Melissa does a fantastic job of breaking down this outdated “rule” regarding plus sizes and stripes. 

Outfit 1 Details

By now you know I love mixing prints, so I had to top the striped sweater with this adorable plaid coat.

The plaid of the coat has a bit of kelly green, so I opted for this Gucci crossbody bag in bright green that I love!

Even without the coat, this green bag will work.

See this post for more outfit ideas with a bright green bag.

For sneakers, I went with some retro classic New Balance sneakers in navy.

They also come in wide width!

Make it sporty with a baseball cap or even a trucker hat like this one.

If a team is not your thing, opt for a vintage navy cap without a logo.

And of course, classic Ray-Ban aviators make a great choice.

Plus Size Preppy Fall Outfit 1

Plus Size Preppy Fall Outfits. These plus size outfits feature flared jeans and rugby stripes. Finish with a plaid jacket, sneakers, and a baseball cap. Alexa Webb

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Outfit 2 Details

This second outfit is just as preppy as the first with a green and navy rugby striped cashmere sweater.

It’s topped with a quilted vest in a rusty cinnamon brown color.

Again, I had to [as always] add a bougie bag.  

My favorite Saint Laurent bag (I have it in black), the Lou, in brown suede.  So chic!

But, any brown or tan crossbody bag would look great!

I kept the sneakers and accessories the same as those in Look 1.

Plus Size Preppy Fall Outfit 2

Plus Size Preppy Fall Outfits. These plus size outfits feature flared jeans and rugby stripes. Finish with a puffer vest, sneakers, and a baseball cap. Alexa Webb

Shop the Look

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Disclosure: This post may contain affiliate links, which means if you click on or purchase through certain links, I may receive a small commission.

7 thoughts on “Plus Size Preppy Fall Outfits

  1. The green rugby sweater by JCrew is very chic! I just wish it didn’t cost so much and wasn’t cropped. Love this outfit with flare jeans, jean hat and the shoes!

    1. I saw an exact replica of this top in store at Wal Mart yesterday! Check it out! I think Wal Mart has a lot of JCrew replicas and sometimes I swear if you check them up close they might actually be the exact same piece.

  2. Love these! I have a Old Navy blue and green sweater identical to this one , so I had to buy the blue and white sweater! I was preppy in High School and I still love the look today!

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