This post may contain affiliate links. Please read our disclosure policy for more information.

From the time I was a kid, I looked forward to Back to School shopping.  Picking out which puppy folder and which Sanrio pen I wanted brought me maybe a little too much joy.  I had just as much fun shopping Modcloth for some outfit inspiration for teachers that are too cool for school.

Too Cool for School: Back to School Teacher Fashion

Flavor Fusion Collared Sleeveless Top in Apple

Keep cool in this sheer, swingy tank with a fun beaded apple embroidery on the collar.  There’s a cute back keyhole on this pomegrante chiffon shirt.  An apple for the teacher?  Try two instead!

Hell Bunny Ain’t That the Fruit? A-Line Skirt in Apples

POCKETS!  Stash your stickers or detention slips in these hidden pockets on the high-waisted cotton midi skirt.  With illustrated apples and blossoms, you’ll be picking this one for sure.

Short-Sleeved Peter Pan Collar Top in Pink

Apples not really your thing? This sheer blouse is berry cute!  Loving the Peter Pan collar that makes me not want to grow up.

Charter School Cardigan in Honey

Preppy and professional, this 3/4 sleeve cardigan comes in all your school colors plus some pretty cute stripes!  It’ll help you keep your cool when classroom discipline goes out the window.

Heart and Solar System A-Line Dress

Science teachers, this dress is out of this world.  This A-line cotton dress features a notched neckline, a stellar print, and POCKETS! I know, I already freaked out about pockets.  But they’re my favorite feature in a dress.

Dashing Darling A-Line Dress in Succulents

No teaching puns here, but this succulent print doesn’t, well, succ.  I just couldn’t help it when I saw this fun print that’ll make you feel like you’re on a desert vacation, even when you’re in study hall.

Novel Tee T-Shirt in Prince

Ever seen an elephant inside a boa constrictor?  Then this shirt’s for you!  Maybe a little casual to wear to school with jeans, so add a super cute skirt and heels.

All Eyes on Unique A-Line Dress in Science

The angles on this mathematical print are all acute.  Swear it.  Rock the geometry in a super adorable black and white dress.

Sugarhill Boutique Dino What You Mean Button-Up Top

Your parent/teacher conferences will be dino-mite in this super cute dinosaur print button up!

Library Love Striped Cardigan

Book it over to nab this cardigan perfect for anyone — the school librarian or the prom queen.

Pencil Me In Leather Flat

Write on!  These pencil-inspired flats are the perfect way to pencil yourself into a great school year.

Style is now in session! Teachers get 25% off $100+ purchases at ModCloth I can’t guarantee having super cute outfits will make the school year better.  But I’m fairly certain when you’d give your look an A+, the day follows suit!

This post contains affiliate links.  All thoughts and opinions are my own.

Dapper Day is a day to wear your best, vintage-inspired duds to the Happiest Place on Earth.  The stylish celebration is coupled with a themed shopping expo held at the Disneyland Hotel.  Buy unique clothing and accessories, check out live entertainment, and maybe even learn a few steps yourself.

But the official Dapper Day just doesn’t come around enough for my taste.  I adore Disney every day of the year.  So I collected some vintage-inspired dresses that serve as an adorable part of your wardrobe, plus give way to some cute Disneybounding possibilities. Disneybounding is a fun fashion trend that allows wearer to wear non-costume clothing while still paying homage to favorite characters.  Each of these dresses is inspired by the Disney princesses I adore.

Vintage-Inspired Dresses for Disneybouding

Rapunzel

The lost princess has found an adorable lavender dress!  Rapunzel would adore this sweet springtime dress.  After braiding your hair, add some faux flowers for a look all the residents of Corona would love.

Belle

Waltz around the Disneyland Resort in a Belle-inspired yellow dress.  Make sure the Beast brings you some red rose accessories to finish off the look.

Ariel

Rule the sea in this lovely blue dress.  Swim away from Ariel in her purple bikini and pay homage to her time on land.  Add seashell accessories and something sparkly as the sea.

Aurora

Make it pink for Aurora, even if Merryweather wants it blue.  This dress is so lovely you’ll not want to sleep in.

Cinderella

Cinderella is always the belle of the ball.  This polka dot retro inspired dress will make sure you are too. Glass slippers are a must.  Bonus points for getting birds to help dress you.

Tiana

No need to chase down frogs.  This green dress will bring the princes to you.  It’s perfect for a spring day in the park or a summer picnic.

Not really a costume, these vintage-inspired dresses are perfect for Disneybounding every day of the year.  I adore the sweet styling, perfect for warmer weather at the parks.

Who will you Disneybound as?