The Best & The Worst: Halloween Through The Years

Happy Halloween, everyone! Today I’ve teamed up with the one and only Kaylin from Stay Blonde Ski Local to bring you all a fun little recap of our favorite (and not so favorite) Halloween memories and costumes from over the years. Kaylin is a hoot and a half and all her answers are hysterical (just like her blog.)

1. What have been your top 3 Halloween costumes:

Easy. 1. Ladybug 2. Olive from Little Miss Sunshine. 3. Pregnant Britney Spears.

Goodness there are so many good ones to choose from, most were from my youth, because let’s all be honest no costume in college is really worth mentioning.  Especially when you’re in a sorority and Halloween is pretty much every weekend.

My favorite, and go to was home sewn pumpkin outfit was stuffed with crumbled bits of news paper and had a hat that tied under the chin.  I wore it in pre-school when it sagged past my knees, and again my junior year of High School when it came to my waist.  Let’s just say we got our money’s worth.

My second favorite would be the T Birds, with custom hand crafted spray painted T-shirts that I made.  I completed the outfit with a fake cigarette made of rolled paper, because I didn’t want to keep a real one behind my ear. It’s the purist in me.

Third is probably when I was a butterfly. Something about having wings makes you feel so magical.  Perhaps I felt a small moment of what tink feels all the time. Also I got to wear four inch power purple heels, and I didn’t look out of place. Clearly I’m the big winner here.

2. Now what your worst Halloween costumes:

Taylor– Anything and everything I wore for Halloween in college. Most specifically this hippy costume. Put some clothes on gross little college girl, you look ratchet. (Just for the record that is my first time every using that word and I’m kinda excited about it. Did I use it correctly?)

The worst costumes included a terrible Britney Spears circa 2001 costume. Think Hit Me Baby One More Time costume gone wrong in all sorts of ways, and me as a college freshman. No pictures necessary.  The real worst was when I dressed up as a drawer liner, and gave myself a full body wax when removing the costume. If only I was joking.

But really this might really be it, a ‘ruler’. Who buys a men’s extra large plain Tee, sews it into a dress, and then makes it into a ruler. This girl.  Seriously so embarrassing.  And probably the most stereotypical college sorority girl with frat boy picture ever.

3. Best Halloween night and why:

The crazy bender I went on back in the early 90s known as Kindergarten Halloween. I was a mouse and was on straight sugar high for probably seven days. The party started in the a.m. at school and didn’t end until long after dusk after I’d hit up all of the rich neighborhoods, just jonesing to get my hands on some of those King Size candy bars- the Butterfingers and Reeses were my drug of choice back then. God those were good times.

I was in Northfield, MN visiting my friend form High School, who went to Carleton. She forgot to mention that October in MN is colder than any winter day in CA, and I froze my little butt off as a Indian. I also took a hour long cab ride by myself with a creepy old man cab driver while hung over, and discovering the newly downloaded piano app on my iPhone. Clearly there are parts of that night that I don’t remember.

4. Naturally we have to talk about the worst night now:

This would have to be the Halloween of 2009 when I was infected with the good ol Swine Flu, also known as H1N1. I’d had the flu for roughly two weeks before I finally decided to go to the doctor a couple of days before Halloween to figure out if it was normal or not to feel as if you’ve been slowly dying for the past fourteen days. As it turns out, it’s not. On the bright side I lost a lot of weight and looked killer in my Halloween costume that year! Because yeah, I still went out obviously.


The worst was probably fourth grade when I decided I wanted to be a bowling ball.   I, along with the help of my Mom, cut two large pieces of cardboard into circles, connected them with duck tape and painted them black with the three finger holes on the front side.  It rained that night and the paint ran. By the end of the night I was wearing two gray soggy pieces of cardboard, that I eventually had to ditch only to reveal my 115 pound 4 foot 2 frame fourth grade frame in all black spandex. It was awesome.

5. How will you be celebrating this evening?

Taylor- Ditto to everything Kaylin says below. Although I might get a little adventurous and take Harlow for a spin around the neighborhood in his jockey costume. We shall see…

I’ll be sitting on my couch probably watching the shows that I missed on Wednesday, and answering the door for the neighbor kids, though we usually don’t have too many.  At some point I’ll have to dress up again, when I’m a Mom and everything, but that’s still years out, so until then I’m enjoying the tranquility of it all.  Clearly I did way too much costuming in college.


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