Three Cute Halloween Costumes

Joules Women’s Harbour Shirt (sold out but similar HERE) and Joules Men’s Harbour Shirt c/o (sold out but similar HERE) / Gap High-Rise Jeans (sold out but similar HERE) / Sperry Loafers (sold out but similar HERE) Also have and love the camel suede version! / J.Crew Beret (sold out but similar HERE) / Men’s Mime Accessories / Women’s Mime Accessories / Red Suspenders / Mitch’s Dark Jeans (sold out but similar HERE) / Mitch’s Polo Sneakers (sold out but similar HERE) / Face Paint (Crayons seem small but it’s more than enough!)

I have no words. 😂

Actually, yes I do.

Mitch: “You’re just not cut out to be a mime.”
Kelly: “Was it something I said?”
Mitch: “Yes.”
Hahaha!

Yesterday morning, I shot an Instagram project for Joules, and I laughed so hard once I had the chance to cull the photos.

The whole thing was so much fun, but it was also such the challenge, as Chicago public school teachers were currently on their fifth date of striking (and Lucy hasn’t come off the daycare waiting list yet).

So at the moment, we’re just trying our best to get by over here. 😜 For this collaboration, it meant shooting while we were trying to feed the girls breakfast and directing a crew of movers up the stairs and into the right room with a new bed. And fielding phone calls from Home Depot because the tile guys never showed up to install the backsplash. As well as rescheduling a downtown meeting because it just wasn’t in the cards. (Any other moms out there constantly overestimating how much you can do in a day? GUILTY.) Oh, and our camera also refused to pair itself to our new phones. So that made for some fun tripod adventures. 🙈

Three Cute Preppy Halloween Costumes

But WE DID IT. And we laughed so much throughout the whole thing. In all seriousness, though, we’re *speechless* (😉) about how many costumes we can get out of our classic striped Joules Harbour Tops! Favorite photo is #2, where “Mitch the Criminal” looks thrilled and I’m clearly like “omgomgomg are we going to get caught what are the repercussions for something of this nature how many years in prison MAYBE WE SHOULD GIVE IT BACK.” 😂 Then again, I also really love the mime pics in which Mitch’s white face paint is all over his outfit. Though I did get it all over my inside of my beret… so I guess I *really can’t talk.* (See what I did there? 😉)

The point of this little photo series was to show how many costumes you can get out of just one classic and super preppy shirt… and I have to say that I was pretty amazed by the results of the challenge! We simply used pants and shoes we already owned, and then bought a few costume-specific accessories for each “look” via Amazon, each of which cost no more than $15. (Side note: How did people parent and do Halloween before Amazon? I’ll never know…)

Anyway, it was such a quick, easy and painless way to tackle Halloween costumes… and if you’re at a loss as to what to “be,” consider some of these looks!

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Above are my favorite products from the shoot as well as the accessories for each costume, which we found via Amazon. Again, would love to know what you’re planning for Oct. 31!

Preppy Bank Robber

How adorable is this couples costume? The best part about this costume is just how simple it is to put together. With minimal accessories (gloves, eye-mask, and money bags), you can throw this costume together at the last minute, without sacrificing style.

Preppy bank robbers Halloween Costumes

Joules Women’s Harbour Shirt (sold out but similar HERE) and Joules Men’s Harbour Shirt c/o (sold out but similar HERE) / Spanx Faux Leather Leggings / Sperry Loafers (sold out but similar HERE) Also have and love the camel suede version! / Mitch’s Dark Jeans (sold out but similar HERE) / Mitch’s Polo Sneakers (sold out but similar HERE) / Bank Robber Accessories (sold out but similar HERE)

Preppy Sailor

Honestly, there is nothing preppier than dressing as a sailor for Halloween. And this was probably one of our most favorite costumes to wear. While it’s not the classic navy blue, the black and white stripes still get the job done. The colors, the accessories, and the props all work together to create a oh-so charming costume. Perfect for any Halloween party – small or large.

Preppy Sailor Halloween Costumes

Joules Women’s Harbour Shirt (sold out but similar HERE) and Joules Men’s Harbour Shirt c/o (sold out but similar HERE) / Gap High-Rise Jeans (sold out but similar HERE) / Tuckernuck Red Ballet Flats (sold out but similar HERE) / Women’s Sailor Accessories / Men’s Sailor Accessories / Mitch’s Light-Colored Jeans (sold out but similar HERE) / Mitch’s Polo Sneakers (sold out but similar HERE) / Kelly’s Sunglasses

Preppy Mime

This one is for those of you that enjoy getting a little extra creative. With the little cutest neck scarfs and some totally adorable berets, it doesn’t get much preppier than this. And the suspenders? *Chefs kiss* Oh, and don’t forget the face paint. If you want your Halloween make-up to last all night, opt for waterproof face paints.

mime Halloween Costumes

Joules Women’s Harbour Shirt (sold out but similar HERE) and Joules Men’s Harbour Shirt c/o (sold out but similar HERE) / Gap High-Rise Jeans (sold out but similar HERE) / Sperry Loafers (sold out but similar HERE) Also have and love the camel suede version! / J.Crew Beret (sold out but similar HERE) / Men’s Mime Accessories / Women’s Mime Accessories / Red Suspenders / Mitch’s Dark Jeans (sold out but similar HERE) / Mitch’s Polo Sneakers (sold out but similar HERE) / Face Paint (Crayons seem small but it’s more than enough!)

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What are your favorite cute Halloween costume ideas?

We love hearing from you all, so feel free to drop your favorite cute and preppy Halloween costume ideas below! Trick or treat!

With this blog, we hope we inspired your next Halloween couples costume. But, what about the kiddos? If you’re in need of a little children’s costume inspiration, check out some of our favorite kid’s costume ideas over the years!

We’ve done Little Orphan Annie, Mickey Mouse, Madeline, and The Little Mermaid.