Fashionable Halloween Costumes You Can Actually Wear Again

In my opinion, this is the best time of the year. The cool, crisp weather is the epitome of sweater weather, the leaves are changing and it’s time for harvest and of course Halloween! I have been a big fan of Halloween since I was a small child, as my extravagant costumes could have told you. As an adult, as much as I still love the holiday, I must admit that I no longer partake in Halloween costumes. I tend to value my comfort (and warmth) ahead of hauling around any components of a costume and spending money on something that I will only wear once. I never want to miss an opportunity to look fabulous and a little bit flashy, so this month I want to focus on fashionable clothing items to wear on Halloween…and then wear again! Take your pick of these Halloween costumes you can wear again.

Halloween Costumes You Can Wear Again

Little Red Riding Hood

If you’re a fan of fairy tales and want to channel a classic character like Little Red Riding Hood, I found this absolutely show stopping Trina Turk Sheath Dress with Cape. You’d be the chicest Hood at the party. Now, cut to almost two months later and you have a fantastic dress to wear to your upscale holiday party without missing a beat. Another thing that I love about this dress (besides the vibrant, candy apple red color) is the cape! On its surface, the cape is a luxe detail that makes the entire dress. But its functionality of keeping you warm in the chilly weather makes it even more worth the investment. Fairy tales aside, regardless of where you wear this dress, you’re sure to feel like a queen.

Disco Diva

I think we’ve all at some point either wanted to be or have been a disco diva; whether it be in real life or on Halloween. I feel like I was born in the wrong decade, as I believe I was meant to be a disco diva in my day-to-day life. In the meantime, I can pretend on Halloween and what better way to represent the 1970s divas than with a ton of sparkle? Enter this French Connection Sequin Sheath Dress which is perfect for a fun night out on Halloween or any other night out during the holiday season. For Halloween, style it with some large platform boots, shimmer make-up and smooth hair (or an afro if you’re a natural like me!).

For an elegant holiday party, keep the shoes elevated with a simple pointed-toe pump and petite feminine clutch. Something like this Jimmy Choo Floral Lace clutch would be perfect!

Audrey Hepburn in Breakfast at Tiffany’s

There is nothing more classic than a little black dress. Outside of the definition of old Hollywood glamour, it always makes me think of the iconic dress worn by Audrey Hepburn in Breakfast at Tiffany’s. The little black dress can be worn year around, and now is a great time to invest in one. This one fits like a glove, is reminiscent of Hepburn’s most memorable look and also can also be worn throughout the rest of the year. This Classic Power Dress by Theory is the perfect Holly Golighty dupe when paired with a strand of statement pearls and a tiara-esque hair barrette.

After the Halloween dust settles, you can wear this with your favorite cardigan or leather jacket, boots, flats or sneakers. It makes a versatile base for any outfit at any time of year.

Dorothy from The Wizard of Oz

If you’re like me, then you love a great shoe and know that the right pair can make or break a look. A fun idea for Halloween is to rock these Prada Crystal Ankle Strap Pumps and you’ll look like Dorothy coming straight from Oz!

Surprisingly, you can wear these out on the town or to a festive holiday party if you keep the rest of the outfit simple; think oversized, flowy silk shirt and black velvet or leather pants. If these babies aren’t necessarily your speed, you can still give off major Dorothy vibes with these J. Reneé Pointy Toe Pumps. Pointy toe pumps are hot right now and the beautiful patent leather red will take you through the holidays and beyond.

Game of Thrones

If you want an excuse to take it a little over the top, I think I’ve found one for you. For all of my Game of Thrones, Viking or cave person fans out there, this La Fiorentina Mixed Fox Fur Poncho will make the perfect topper to your beefed up “Mother of Dragons” Daenerys Targaryen, Viking or cavewoman costume. In all seriousness, at the end of the day, who cares what you wear underneath it? This fur cape will stop anyone in their tracks.

For those who love fur, it’s a great investment piece, can be worn all winter long and can make a beautiful heirloom. I wish that one of my grandmothers would have had this baby hanging in her closet! I also love this cape because it can be worn alone or for added warmth, worn over your coat for a shawl or scarf look. The multi-color fur gives you the versatility to wear it what pretty much anything.

“Non Halloween” Costume Styling Tips

Here are a few additional expert style tips when rocking a non-Halloween, Halloween costume:

1. Keep it elevated. I think for most ladies over 40, running around as half-dressed a “sexy” kitten is not ideal. Choose something sleek, and still sexy (think a bodycon midi length dress or something that shows off your toned arms). That way you play the part during a costume party, but you can take that sexy with you throughout the year.

2. Remember it’s not a one and done mindset! I want to bring home the importance of investing in a good piece that you can incorporate into an easy and creative costume and can still wear in your everyday life. It’s OK to splurge on a great piece if you know you’ll get the wear out of it!

3. You don’t have to love to dress up to get into the Halloween spirit. Choose to wear any of these examples that I’ve highlighted above or guess what….you don’t! I’ve enjoyed plenty of Halloween parties in my regular clothes and had a blast. I love enjoying everyone’s creative ways to express themselves in their costumes as well as loving so many other aspects of the spooky season!

Shop Halloween Costumes You Will Wear Again

Pictured above, clockwise from left to right.

Trina Turk V-Neck Crepe Sheath Dress w/Cape, $268

French Connection Emille Sparkle Long Sleeve Sequin Sheath Dress, $218

Jimmy Choo Emmie Floral Lace Clutch Bag, $875

Theory Classic Power Dress, $355

Prada Crystal Ankle Strap Peep Toe Pump, $1250

 J. Renee ’Maressa’ Pointy Toe Pump, $89.95

La Fiorentina Mixed Fox Fur Oversized Poncho, $1,535

How are you going to dress up Halloween this year?

–Carmen Turner

You may also like to read How to Wear Sneakers When You’re A Grown-Up and How to Look Chic in Camo When You’re Over 40.

This post contains affiliate links which may give us a commission at no additional cost to you.

Are you following Fountain Of 30 on Facebook, Twitter, Instagram and Pinterest? We’ve got lots going on, so join in on the fun! Subscribe to our newsletter here. You don’t want to miss a post and we promise not to bug you to death. Oh and we also started a Facebook Group called Growing Younger for women to discuss everything good and bad about being over 40. And check out Lauren’s #growingyounger Car Confessions on our Facebook page.

Image Layout: Fountain Of 30

Please pin!