10 Plus Size Preppy Clothing Brands to Know

Preppy clothes are so hard to find if you are over a size 14! 

Sadly, Lily Pulitzer, which is the preppy gal’s uniform with its iconic Palm Beach style, tops out at a size 20. 

And worse, most of Lily Pulitzer’s collection stops at an XL (16/18). 

And both Southern Tide and Kate Spade only go to a size 16. 

But fret not, today’s post offers ten plus size preppy clothing brands you should know!

These 10 brands will help you get that preppy look! 

Not all of these brands are completely preppy or even obviously preppy at first glance, but you can certainly find some great pieces.  Trust me!

10 Plus Size Preppy Brands to Know - Plus Size Fashion for Women - Alexa Webb

10 Plus Size Preppy Clothing Brands to Know

In alphabetical order…

Crown & Ivy

An oversight in my original list of 10, this is technically number 11, Crown & Ivy at Belk, is an amazing collection of plus size preppy clothing at some great price points!

Draper James

Reese Witherspoon’s clothing line, Draper James, might not be the first brand that comes to mind when you think “preppy.”

But the collection, with its classic Southern-style, has some great pieces for the plus size fashionista. 

Lots of chambray, seersucker, and gingham!

Free Assembly

One of Walmart’s new private label brands, you can shop the budget friendly collection at Walmart.

J.CrewJ.Crew Factory

An obvious go-to!  As I said in my 7 Plus Size Brands to Know post, J.Crew and J.Crew Factory both now offer select pieces in sizes up to size 24 or 3X. The swimwear selection is very good. 

Unfortunately, not everything is available in plus sizes. [eye roll] 

So the easiest way to shop their site is to filter items by size. 

And be aware that their pants and jeans are sized by vanity waist sizing.  See the size chart below.

J.Crew Size Chart


L.L.Bean offers a lot of great staple pieces in plus sizes, up to a size 24. 

While not an obvious choice for preppy clothing and more likely where you might go for iconic duck boots, which also come in wide width, L.L.Bean is not one to miss!

Lands’ End

Lands’ End has been my favorite source for plus size preppy clothing for a long time! 

They have basics, classics, and practically everything you need, including plus size swimwear, plus size belts, and wide width shoes.

Lauren Ralph Lauren

Lauren Ralph Lauren is an obvious choice for plus size preppy clothing. 

A personal favorite for their classic and timeless pieces that are nice quality, especially if you can catch them on sale.  You can find Lauren Ralph Lauren at ralphlauren.com and at many retailers, including Macy’s and Zappos.

MICHAEL Michael Kors

While the MICHAEL Michael Kors collection is undoubtedly classic American sportswear, a portion are what would I consider to be “preppy.” 

You can find MICHAEL Michael Kors at Macy’s, Belk, Dillard’s, and Zappos.

Sail to Sable

Sophisticated resort wear in sizes up to XXXL or 22.


Talbots is another great plus size preppy clothing brand as it offers both casual clothes and professional wear, with everything in between. 

Lots of plaid, gingham, chambray and stripes, what more could you ask for?  I think the quality is also great for their prices.

Vineyard Vines

Vineyard Vines actually inspired this post when I found out they now offer plus sizes. 

The ultra-preppy brand, known for its nautical theme, whale logo, bow-ties, and playful belts, now offers select items up to a size 24. Here’s the size chart, which is helpful for pants.

They are one of the more pricey brands in this list, but I can’t speak to their quality as I have yet to try them.

If you’d like to also see a list of go-to preppy brands for accessories and shoes, please let me know in the comments below.

10 Plus Size Preppy Brands to Know - Alexa Webb - Plus SIze Fashion for Women

10 Plus Size Preppy Clothing Brands to Know

10 Plus Size Preppy Brands - Alexa Webb

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

37 thoughts on “10 Plus Size Preppy Clothing Brands to Know

  1. These are great. I was wondering if you had ever looked at Belk’s Crown and Ivy brand? It is a distinctly southern preppy style.

  2. I love all of these brands except J. Crew. I have found that their tops are not long enough for me. I have a larger tummy and a “jelly roll” that needs camouflaging. Land’s End seems to be an excellent substitute for J. Crew tops when they are suggested.

  3. I have read that many store that carry Plus-sized clothing are going or have gone out of business, such as Catherine’s , Lane Bryant and now Dress Barn Woman. We are going to be forced to go to the dept. stores with high prices or back and forth with mail order. What will we do???

  4. Thank you so much for this list! Some I knew and shop at often, but quite a few I’d never heard of before! I’m excited to explore and see what they have. I was curious to know why you said you almost left Gibson off of your list.

    1. Hi Michele,
      Thanks! I almost left off Gibson just because I wouldn’t say their whole line is preppy. And they do a lot of blogger collaborations, which sometimes means they have different styles. It’s just a less obvious choice.

  5. Bless your soul! Thank you for this! Vineyard Vines is amazing quality. The stuff lasts forever. Also, you can always pull Lilly in in cute accessories!

  6. I would love to
    See the list for shoes and accessories. Great list, some I’ve heard of and some I haven’t. Thank you

  7. This is a great list! It includes brands I’ve not heard of before, which is fun! I would also add Loft. I get SOOOOO many things there and they often go up to size 26W. Plus, you can always find a sale. I find RL and JCrew not true to size, but it could just be my body. Thanks for putting this together!

    1. What is your go-to shop for longer tops? My middle is my biggest area and want my shirts to cover as well. Typically I buy tunics but sometimes those can make me look really short (5’4″)

  8. Yes. yes. yes, your post is so on time. Looking for fresh new options. So would love post on the new scarf look tops/dresses. Also need source for plus modern boxy, edgy looks. Thanks.

  9. Thank you SO SO much! I have the hardest time finding plus size preppy and that’s totally what I prefer. I am so excited! Love your blog. Thanks for all your hard work. Xoxo

  10. This is a super list! It’s really difficult to find sassy and preppy clothes for my size. Now I know where to go on my next shopping spree. Thanks a ton!

  11. i have been searching for plus a size madras dress or skirt, and a pink or blue seersucker dress for ages. any ideas? I’m usually a plus size 18, but cotton tends to be very restrictive, so I’d probably size up to a plus size 20.

  12. Another less obviously preppy (+ budget friendly) store is Old Navy. They are fairly size inclusive and I have gotten all the preppy essentials (gingham, nautical, plaid) as well as more funky tie-dye, etc. from ON and been really happy.

  13. What about Preppy winter? Just want some ideas but.. spring and summer is mostly what I see.. we are going to Wisconsin . Thanks.

  14. I’ve been SUPER happy with Vineyard Vines…. their dreamcloth is to DIE for!!! Sizing seems spot on for me!! Can’t wait to see what preppy ideas you come up with next!!! xxoo

  15. Just found you. Am an ‘Old School’ Prepster (unfortunately grown bigger over the decades) and appreciate the links to vendors within attractive, traditional, preppy clothing. Please continue to provide the latest info and links to any and all classic preppy apparel!

Leave a Reply

Your email address will not be published. Required fields are marked *

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