Plus Size Preppy Outfits Remix – Part 1

A plus size preppy outfits “remix.” 

Yes, this is the remix [said like Wyclef in No, No, No Pt. 2].

I saw Wyclef live once.  He opened for Mary J. Blige.  It was just him and a guitar.  Good times!

I digress.

So I recently posted some preppy looks (here and here) and decided I needed to post more!

Because preppy styles are currently trending, for those of us rocking preppy style 4-eva, it’s a dream. 

It’s time to take advantage of the trends and stock up on preppy staples.

Plus Size Preppy Outfits Remix

Plus Size Preppy Outfits Remix - Plus size outfits for fall with bright colors and preppy vibes by Alexa Webb.

Life is Short, Wear Stripes

These plus size preppy looks feature a rugby striped sweater in navy.

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I think Melissa does a fantastic job of breaking down this outdated “rule” regarding plus sizes and stripes. 

To see more outfits with this sweater, go here.

And for more outfits with similar stripes go here, here, and here.

Plus Size Flare Jeans

The first five outfit ideas 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 an 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.

Outfit 1 Details

Since I love mixing prints, I topped the striped sweater with an oversized plaid scarf.

This gorgeous Italian scarf is made of wool, alpaca, and mohair.

Bright plaid scarf for preppy outfits by Alexa Webb

Guaranteed to keep you warm and stylish!

You might recognize these New Balance sneakers and trucker hat from my last preppy post.

When I see a good thing, I remix it. 😉

But this time I opted for a Louis Vuitton Pouchette Métis for the bag.

Jewelry

And for jewelry, some gold classics: hoop earrings,  a chunky link bracelet, and a Tory Burch watch.

The hoop earrings featured in this look are made by PAVOI, which I’ve mentioned many times before.

You can find PAVOI on Amazon, and must say the quality is really great for the prices!

I actually own a bunch of PAVOI pieces now.  I started with a couple of these thick gold hoops in the two larger sizes. 

I’m quite impressed. 

You can check out my Amazon store and follow me on Amazon for more of my finds.

Jewelry Care

These are inexpensive plated pieces so you might need to “baby” them for longevity.

Avoid the obvious: showers, pools, spraying your wrist with perfume while wearing them.

Store them in air-tight plastic bags, if possible.  This will keep the plating from damage and tarnishing.

Plus Size Preppy Outfit 1

Plus Size Preppy Outfits - A plus size rugby striped sweater, flare jeans, plaid scarf, and retro sneakers for a preppy sporty anthleisure look. Alexa Webb

Shop the Look

Outfit 2 Details

This second outfit idea is just like the first but I added a navy quilted vest.

Plus Size Preppy Outfit 2 

Plus Size Preppy Outfits - A plus size rugby striped sweater, flare jeans, plaid scarf, and retro sneakers for a preppy sporty anthleisure look. Alexa Webb

Shop the Look

Plus Size Navy Quilted Vest (less $ similar, less $ similar)

Outfit 3 Details

The third outfit is just like the first two but I topped it with a blue wool coat.

Plus Size Preppy Outfit 3 

Plus Size Preppy Outfits - A plus size rugby striped sweater, flare jeans, plaid scarf, blue wool coat, and retro sneakers for a preppy sporty anthleisure look. Alexa Webb

Shop the Look

Plus Size Blue Coat (similar, less $ similar, less $ similar)

Outfit 4 Details

The fourth outfit is like the first three but I finished it with a bright pink wool coat.

Plus Size Preppy Outfit 4

Plus Size Preppy Outfits - A plus size rugby striped sweater, flare jeans, plaid scarf, pink wool coat, and navy retro sneakers for a preppy sporty anthleisure look. Alexa Webb

Shop the Look

Plus Size Pink Coat (similar, less $ similar, less $ similar or here, less $ similar)

Outfit 5 Details

The fifth outfit is the same as the fourth, but I swapped the New Balance sneakers for some pink Vans.

These “Old Skool” Vans are unisex and should accommodate wide width feet.

Plus Size Preppy Outfit 5 

Plus Size Preppy Outfits - A plus size rugby striped sweater, flare jeans, plaid scarf, pink wool coat, and pink Vans retro sneakers for a preppy sporty anthleisure look. Alexa Webb

Shop the Look

Pink Sneakers {unisex/wide width} or here (similar, similar)

Outfit 6 Details

The sixth outfit idea is very similar to the first five.  But instead of sneakers, I opted for some pink flats.

So cute!

And since I’d want to show off these adorable driving flats, I opted for ankle-length demi-boot jeans.

J.Crew Sizing

These demi-boot jeans are from J.Crew.

In case you haven’t heard, J.Crew now has many items in plus sizes up to a size 24 or 3X. 

Their sizing is comparable to Lane Bryant

One thing to note is that some of their pants and jeans come by waist sizing (vanity), so check the size chart below to see which size you are.

JCrew Denim Size Chart

You can find more outfits with these jeans: here and here.

Plus Size Preppy Outfit 6 

Plus Size Preppy Outfits - A plus size rugby striped sweater, cropped demi-boot jeans, plaid scarf, and pink loafers for a preppy look. Alexa Webb

Shop the Look

Plus Size Ankle Demi-Boot Jeans (full-length, less $ similarless $ similar)

Pink Flats (similar, less $ similar, *wide width, *wide width)

*order one full size up for wide width

Plus Size Preppy Outfit 7 

Plus Size Preppy Outfits - A plus size rugby striped sweater, cropped demi-boot jeans, plaid scarf, pink wool coat, and pink loafers for a preppy look. Alexa Webb

More preppiness coming your way so make sure you’ve subscribed to get my new posts delivered to your inbox!

For more outfit inspiration check out my Pinterest boards and my Instagram!  Oh and please “like” my blog on Facebook!

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

11 thoughts on “Plus Size Preppy Outfits Remix – Part 1

    1. Unless there is some issue (like not opening the post in a browser), it should be only one additional click. But, I understand. Hopefully, you’ll decide to subscribe again sometime in the future. Thanks for reading.

      1. Hopefully, you’ll be able to see the main image again soon… I am working on it! 🙂 (I am not tech savvy so I think I’m going to have to hire someone, but it’s in process).

  1. I just wish there were still some low rise jeans. I am 5’3”, I have an average size torso and no waist. As in, my rib cage sits almost directly on my hip bone! Extra high waisted jeans rest somewhere between my armpits and under my nose🤦🏽‍♀️ Add in the fact that I need really thin, stretchy material (fibromyalgia and Autism, yay!)
    I love seeing the outfits you put together, and shopping my closet to see how close I can get 😊

Leave a Reply

Your email address will not be published.

This site uses Akismet to reduce spam. Learn how your comment data is processed.