Plus Size Preppy Resort Wear

Heading someplace warm and need some plus size preppy resort wear? 

Or maybe you live in a warm climate and are just looking for some wardrobe updates?

Either way, this post is for you!

One look is for day and the other for the night.

Oh, by the way, make sure you check out Part 2 and Part 3.

Plus Size Preppy Resort Wear with a plus size orange top, white capri denim jeans, gold clutch, and gold sandals by Alexa Webb. The perfect vacation outfits! Alexa Webb

Base Outfit Details

Both looks feature the same “base.”  A bright orange top with a pleated peplum hem with white capri skinny jeans.

Unfortunately, there are not a lot of plus size white jeans on the market right now.

But, I was able to find some good ones, including the Spanx jeans that I highly recommend, especially if you are tall or petite.

Look 1 Details

Even though Look 1 is meant for the daytime, I chose some stunning statement earrings in hot pink.

Hot Pink Pom Pom Statement Earrings for Preppy Plus Size Resort Wear - Alexa Webb

But make sure you check out my less expensive alternatives bw

And a coordinating pink straw clutch.

Plus, some oversized tortoise sunglasses, trendy coin necklaces, and a thick gold link bracelet.

I have this bracelet from Uncommon James and love it!

For shoes, I chose some flat and comfortable Tory Burch Miller Cloud sandals.

Miller Sandals

If you watch my Instagram stories, you know that I purchased the Miller Cloud sandals (or here) and they fit my wide feet!

I typically wear a 7.5W, but I got the 7.5 and they fit me perfectly.  

But also, you may have heard that Tory Burch is also offering the classic Miller in “extended width” in select colors. 

If you’ve got wide feet let me hear ya say “Hell yeah!”


And even the same orange-y coral lip, specifically the “Corail Marrakech” from YSL

I layered it over a lip stain (one of my favorite ways to wear these).

As I’ve said, the Yves Saint Laurent Rouge Volupté Shine Oil-in-Stick Lipsticks (or here) are my favorite lipsticks. 

I readily admit they are bougie AF and totally break the budget.  But they are amazing!

They’re 65% oil and feel amazing on the lips!  Not to mention they smell fantastic. 

Plus, the packaging is so gorgeous that I actually bought a lipstick holder, like this one and this one to display them.

And I just can’t say enough great things about them!

The closest lippies I have found at more reasonable prices are L’Oreal’s Colour Riche Shine Lipstick and Sephora’s Rouge Lacquer Lipsticks

While both are similar, they aren’t even close to the decadence of the YSL ones.

Pro tip: Layer a lip stain like Clarins’ Water Lip Stain or  Benetint (or here) under the YSL for longer-lasting color.

Plus Size Preppy Resort Wear – Day

Plus Size Preppy Resort Wear with a plus size orange top, white capri denim jeans, pink straw clutch, and sandals by Alexa Webb. The perfect vacation outfit!

Shop the Look

Look 2 Details

This second look is for nights so I added some accessories that are a little “extra,” like these statement crystal earrings.

I added a gold Lilly Pulitzer clutch with a gold bamboo handle and some gold Lilly rattan wedge sandals.

And I added a Victoria Emerson gold cuff bracelet that I also own.

I know you likely heard me talk about my love for VE bracelets in my Instagram stories.

They’re so easy to put on with magnetic clasps.

Plus, they have long extenders so should fit even large wrists.

Plus Size Preppy Resort Wear – Night

Plus Size Preppy Resort Wear with a plus size orange top, white capri denim jeans, gold clutch, and gold sandals by Alexa Webb. The perfect vacation outfit!

Shop the Look

And make sure to check out Part 2 and Part 3.

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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.

6 thoughts on “Plus Size Preppy Resort Wear

  1. Happy New Year Alexa! These are such refreshing juicy colored outfits. l love orange and pink together, and the flirty peplum is a flattering cut on my short-waisted apple shape. I’m lucky enough to already have white boyfriend jeans ( I need full length for my lipedema legs) and a pink clutch purse, those pink earrings are wild! Can’t wait for sandal weather, dreaming of summer! ???☀️

  2. I love that orange top!!! and with those hot pink earrings!!!! You by far have the greatest sense of color combinations I have ever seen!

    1. Oh, thank you!!! I have a bit of a color obsession and oddly an excellent color memory (yes, that’s a thing! LOL).
      I also must give credit to my college art professor. I remember the day we learned about color theory. I really thought it was pointless. Silly me! ?
      It is one of my most utilized bodies of knowledge I learned in college! I feel like I use color theory daily.

      In case you haven’t read them, check out:
      Color Theory for Fashionistas – Part 1
      Color Theory for Fashionistas – Part 2
      and these videos:
      Color Theory
      Print Mixing

  3. Alexa,

    I am hopelessly unfashionable and had largely given up on wearing anything but v-necks and jeans until I found you. What I needed in my life was a personal shopper- someone that could style me from head to toe with a plus-size figure in mind. I loathe shopping in retail stores (besides Torrid which is a new find for me!) and I can’t afford an actual personal shopper that is also trying to sell me expensive clothes. Instead, I found your blog posts with cute styles and links to the items you style along with cheaper options. I’ve learned a lot from you and now, once a month, I treat myself to an outfit inspired by you, including accessories that up until now really just included a pair of flip flops. I feel like a new person. I’m wearing things I never thought I could (hello pleather pants!) and I’m beginning to embrace my curves. You deserve a lot of credit and I thank you for helping me even though you didn’t know you were.

    1. Hi Libby!
      Oh my, this is such a lovely comment. I am SO glad to hear you’re feeling so great and rockin’ pleather!!! Honestly, that is exactly why I do what I do. My goal has always been to help people look their best, which as we well know, helps us feel our best! Thank you so much for sharing! ❤

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