Halloween is arguably the most exciting holiday as a child. Santa Claus coming down the chimney with tidings of great joy is the tip top of excitement, but there is worry associated with Santa. Have I been good enough? Did he really see me shove a handful of m&m’s into my pocket? HOW MUCH does the man see (???) can keep a child awake at night with worry, but Halloween is the chance to strike out on your own and choose your destiny of early success. It all comes down to the right costume, and your parent’s willingness to indulge your vision.

I think I was in 5^th grade the year I decided that I wanted to really embrace my inner creativity with a costume no one had ever thought of before—ever. I was also a tween, so I had to have something that was a pair, so my best friend in the entire world, Kristen, and I could publicly show our bond. I think we vaguely discussed the idea, but I spent hours thinking about dynamic duo costumes. Brilliance hit with my idea of toothpaste and toothbrush. I would be the toothpaste and Kristen would be the toothbrush. True memory fails me, but at some point Kristen came to her senses and bailed on the idea, while I forged ahead. My mother went to the local movie theater and got a large popcorn tub, which is still on genius level in my estimation. She took a sheet and sewed a toothpaste costume, and I was certain this was the year the town talked about my show stopping costume.

My brothers and I went trick or treating by ourselves. I was the oldest. My middle brother went as Superman. He wore underpants over his costume and rain boots to seal the look, and my youngest brother went as a fluffy bunny, which was a leftover costume from preschool graduation. I remember feeling sorry for him for not wearing a costume with deep emotional connection. Reality hit early. My youngest brother was invited into house after house to show how adorable he was to the other people residing, but not handing out candy. What?? He received extra candy while Superman and I were left waiting on the front steps. As an adult, it all makes sense…

Fall is still my favorite season as a grown up. My oldest son has a display village of “spooky” houses and my youngest is building a haunted house with my husband in our front yard. I love seeing decorations as I drive through town, and the actual night of Halloween still makes my heart pump with excitement seeing the streets packed with avid trick-or-treaters and their hopeful little souls. I see fall as a season of costumes, not just one night. Fall is when texture AND layers AND leather AND boots all go together harmoniously. Fall has the fashion magic. Fall is when I open my closet and am certain that wonderful pieces are in there, and maybe even a magic door like in the Lion, The Witch and the Wardrobe might appear if I dig deeply enough. (Too much?) Fall is the season that I choose to wear a costume every day, and it brings joy to my dormant trick-or-treater soul.

Building my fall costume revolves around a few key pieces. I know that if I have these on the ready, I can costume quickly. My personal preference is texture and shape over print, with the exception of animal print. Is it really Halloween without animal print? Never. Also, fantastic shoes. You can wear the most basic of basics and it will still be fabulous if the shoes express who you are. These are building blocks for my fall costuming. It makes it so much easier when the pieces can mix and match for different occasions of the day.

Let’s start with pant options. I try and think about what I would choose to put in a suitcase for a short trip to decide what is important.

Free People makes an incredible barrel jean, “lucky you mid rise barrel.” I bought the black a year ago and committed fully with the light denim 6 months ago. They are fun and wacky enough to fit the costuming bill. I spent years hiding in dark denim in hope of masking my thighs, but time has taught me to just find a loose jean with a good cut. You can be absolutely boring with everything else you own, but add these jeans and you will look perfect with the cut of the jeans as the stand out. I ordered 1 size smaller than normal.

https://www.freepeople.com/shop/we-the-free-good-luck-mid-rise-barrel-jeans?

The next pair are for the classic girls. These are by Karen Kane, the Brooklyn cropped jeans. They are by far the most comfortable jeans I own, they go with everything and I am regularly asked where I got them. I’m 5’3 and these are perfectly ankle length on me. I easily dress them up or down. Karen Kane jeans are the only jeans I will wear for travel. They also come in a beautiful off white. They will mold to your personal shape with wear.

https://www.karenkane.com/products/brooklyn-cropped-jeans-l82141-black

Next, Maeve by Anthropologie. I have not worn khaki since the 90’s, but I love this one. Again, the barrel shape is the star, but this is an intro to barrel, or a touch of the trend. It’s a good way to test the water without a full commitment.

https://www.anthropologie.com/shop/maeve-curved-cropped-chino-pants?

With your pants being the main story, what do you put on top? This. With everything, for everything. The cut is perfect. Tuck all the way in with the barrel jeans and a studded belt (see below), or front tuck with your black denim to add some slouch to your preppy. Dealer’s choice with the khaki. Roll the sleeves either way. Ralph Lauren makes the perfect button down. If you balk at the price, remember that you can wear it in 20 years too.

How to finish? I saved the best for last. Buy it now. Have it always. I waited for 6 months for this, and I clapped my hands with glee when I picked mine up. Wear it everywhere. Put it over your pajamas and saunter to get your paper. Please wear it to shop for groceries. Picking up your child from indoor, sweaty gym practice? Wear it with heels. Just wear it. It’s costume season, ok?

Also, it’s on a secret sale for a day or 2 more.

https://www.karenkane.com/products/faux-fur-vest-3l09901-stone

(remember the animal print reference? This is it. It takes up less room than your sneakers.)

https://www.karenkane.com/products/side-shirred-midi-mesh-dress-3l12600-tan-w-black

Every costume needs its finishing touches.

Why wear black if red is an option? I will never not wear a western bootie.

https://www.lucchese.com/cdn/shop/files/updated_I6529_Right-2_2048x.jpg?v=1722541074

Fine. You’re right. Sometimes black is essential, and they’re on sale.

https://www.nordstromrack.com/s/vince-kimmy-bootie-women/7465065

Ladylike belts are boring. Wear this with pearls. Keep them guessing. It’s a costume. Here’s one that caught my attention. Also, All Saints. Anytime you’re bored with what you have, All Saints will fix that.

https://www.nordstrom.com/s/7982430?color=001&size=medium

The year of the toothpaste costume was everything childhood should be. The daydreams of what could happen remain with me today. I learned about the possibility of prosperity based on a creative risk, even though I only thought of the reward as candy. It was Halloween magic. It was a costume and for one night, it could be life changing. And really, isn’t that also what fashion is? Isn’t it a chance to try something different and feel fancy free? It’s not serious, but it is a chance to express a sense of self. It can boost your mood or armor you with a bit of physical courage for something that feels daunting. Let a faux fur vest be your costume cape to face the new fall season.

P.S. try “welcome20” at karenkane.com for a discount on your first order.