Plus Size Preppy Holiday Outfits

Two plus size preppy holiday outfit ideas with a blazer and Mom jeans.  As I’ve said many times, I love mixing classic and preppy pieces with updated items.  I believe that this juxtaposition is what makes style interesting. 

Plus, mixing in trends keeps you from looking uppity and old.

Plus Size Preppy Holiday Outfits

Plus Size Preppy Holiday Outfits with black blazer, white button down or velvet camisole, plaid flats, and Mom jeans - Alexa Webb #plussize #alexawebb

Mom Jeans

And as I’ve said, mom jeans are back!  Remember those?  Just watch some of the early seasons of Friends to see the classic 90s straight leg, light wash, ankle-length denim trend.

Personally, I like them distressed for a more “updated” look because I actually wore them the first time they were popular.  And I wouldn’t want anyone to think I have been rocking them ever since!  So somehow, in my mind, the distressing helps with that.

Despite their popularity, not surprisingly, they are hard to find in plus sizes.  Good American can’t seem to keep them in stock and Asos also has some limitations.  But, I found some at American Eagle, which in case you didn’t know, now offers sizes up to a 24.

A Case for Distressing

For this look, I chose distressed Mom jeans.  I hear a lot, like “a lot” a lot, of complaints about “hole-y jeans.”  And I can understand wanting to look polished and age-appropriate, I do!

But, in some cases, the distressing helps keep things from looking too “stuffy.”  Remember, that “biddy-factor” I talked about when wearing tweed?  The same applies to conservative ensembles.

Because the rest of the outfit is so classic, one trendy piece like distressed jeans, will make you look cool rather than “too old” or “too much.”  Trust me! 

As long as you don’t have much skin showing through any holes, you’re totally appropriate.  I swear!

Outfit Details

You just can’t get more classic and classy than a black blazer and a white button-down.  Except maybe tartan plaid flats.  And this look has all three!

Side note: if you’d prefer a heel, these come in the same tartan plaid.

As for accessories, I added a little bit of glamour for the holidays.  Dramatic red crystal earrings plus a bright red clutch make this outfit festive!

Finish the look with a bold red lip.  If you’re looking for a transfer-proof red that won’t dry out your lips, try this one in “Red Velvet.”

Plus Size Preppy Holiday Outfits – Look 1

Plus Size Preppy Holiday Outfits with black blazer, white button down, plaid flats, and Mom jeans for Christmas - Alexa Webb #plussize #alexawebb

Shop the Look

For the second look, I swapped out the white button-down for a black velvet and lace camisole.  The cami dresses things up just a bit.  

If you need a strapless bra, I always recommend this one.

Plus Size Preppy Holiday Outfits – Look 2

Plus Size Preppy Holiday Outfits with black blazer, velvet camisole, plaid flats, and Mom jeans for Christmas - Alexa Webb #plussize #alexawebb

Shop the Look

Plus Size Velvet Camisole (similar, similar)

More Plus Size Holiday Outfits

Go here, here, here, here, and here for more plus size holiday outfits.

Plus Size Christmas Outfit - Plus Size Red Sweater, Jeans, Plaid Flats - Plus Size Fashion for Women - alexawebb.com #plussize #alexawebb

Plus Size Holiday Outfits with Skinny Jeans, Red Sweater, Green Striped Top, Plaid Scarf, Red Flats - Alexa Webb #plussize #alexawebb

Plus Size Holiday Outfits - Black sequin skirt, Leopard Sweater, white button-down, plaid scarf, green coat, and red flats - Alexa Webb

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Disclosure: This post is not sponsored but contains affiliate links, which means if you click on or purchase through certain links, I may receive a small commission.

2 thoughts on “Plus Size Preppy Holiday Outfits

  1. Hi Alexa,
    I so love the way you style. Looks so effortless!
    I especially like you holiday looks. They are holiday without kitsch.

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