10 Cute Winter Outfits Inspired By Pepper Ann Characters

I’ll be honest with you guys… I’ve never watched much of Pepper Ann. But I could always tell that, from what I did watch, it was a show I would have been into. Plus, that theme song constantly manages to stuck in my head. I think you know what I’m talking about.

Pepper Ann characters make for some pretty great winter outfit ideas because the characters are all in high school… and they all wear super casual, comfy outfits. With some warmer touches added in, these looks are perfect for any student in the winter. You can wear this stuff anywhere, but really, these looks are great for school. Here are 10 cute winter outfits inspired by Pepper Ann characters – don’t forget to click on the pictures for more info on the clothing featured.


Pepper Ann

pepper ann

This could not be more casual and comfy! The polka-dot scarf and fun color combinations keep this look fresh instead of bummy.



Pairing a more stylish top with super casual, lime green sneakers is unexpected, but this look really works.


nicky pepper ann

Keep a skirt outfit warm with a scarf, knee socks and a cozy sweater.


trinket pepper ann

Sparkly gold shoes keep this look from being too prim and proper. In the warmer weather, all you have to do is ditch the cardigan and tights.


moose pepper ann

To keep this green and red look from being too Christmast-y, add a brown, grandpa-style sweater and comfy sneakers.

Lydia Pearson

lydia pepper ann

A neon striped shirt makes even the dreariest days more bright. Keep the look colorful with purple accessories.


craig pepper ann

You can’t go wrong with a bright shirt, ripped jeans, classic boots and a chic scarf. You just can’t!


cissy pepper ann

This outfit would actually be perfect on Valentine’s Day, but it really works any day of the year. To keep it from being too “in-your-face,” add a lighter scarf and white bag.

Aunt Janie

aunt janie pepper ann

Who said you can’t wear neon in the wintertime? Adding a white sweater keeps it toned down.

Principal Hickey

principal hickey pepper ann

A white tee looks good with any kind of jeans, but make this cozier by adding an oversized sweater.

Which of these looks is your favorite? Which Pepper Ann character is your favorite? Who do you want to see looks inspired by? Tell me in the comments!

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  • Nancy Arrigo

    Pepper Ann herself is my favorite

  • Nancy Arrigo

    I like the Pepper Ann outfit

  • Lissa

    Love the Craig outfit! I’m actually thinking about recreating it… 🙂

  • Jillian

    My favorites are Pepper Ann, Nicky, & Trinket.