Allison M.

A crossdresser's thoughts on life, fashion, fabulousness, and (oh yeah) dressing up

#TBT: Parachute pants, a stepbrother, and a duffel bag

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Before I go any further, a couple of things:  First, this is a story I originally posted on a previous journal site, and I wanted to tell it again here with a few embellishments.  Also, this may seem to you that I’ll be going off in multiple directions in this post, but they all tie in to this story.  Anyway here goes:

As I’ve hinted/mentioned/downright owned up to on here, I am indeed a child of the 1980s.  And if you recall the 1980s, that decade had a number of clothing styles to remember.  Leather outfits were one such style; in my opinion, leather skirts are an ubiquitous classic that, when tastefully styled, will never go out of style.

But, let’s admit it, the ’80s also produced several fashion styles that did not withstand the test of time, among them:

  • Leg warmers (“Just coming back from dance class, I see?”)
  • Noticeably wide shoulder pads (“So, you trying out for the football team in those?”)
  • Members Only jackets (something I didn’t see a lot of in my small town; it must’ve been a big city-only thing).

Times have changed for sure (oh, sorry, “like, fer SURRE!”), and you’ll likely find these old outfits in a vintage/retro shop.  If you’re like me and you come across them, you’ll think one of three things:

  • “This is still a classic”
  • “Oh, boy, this look did not age well”
  • “I think I may snap this up for some real or imagined retro dress-up party I may or may not attend at an indeterminate time in the future.”

There is one long-forgotten ‘80s style that came and went rather quickly, but it’s one that I freely admit a fond remembrance for:  Parachute pants.


And those are so not them.  Well, they do look as big as an actual parachute, but those are Hammer pants, so named for MC Hammer, who would bust moves and rhymes while wearing these.  Egads, these did not age well at all.


Well, these are parachute pants, or so says the link where I spotted these.  They do look very awesome, are quite affordable (only $11, a very tempting price), and appear to have multiple zippered pockets as the parachute pants of old also did.  However, these are more contemporary than retro in look and feel, not to mention they have a style that suggest capri pants or leggings.  So, they’re definitely not what this portion of this post is about.


A-ha!  Now that’s what I’m talking about!  Parachute pants!  They of the sleek, tight-fitting nylon material similar to that of a parachute (hence the name) and the fly zippers located all over the place.  For what seemed like a very brief shining(?) moment in the middle 1980s, they could be found on most break dancers who needed to wear something that could resist wear & tear and didn’t cause any discomfort from friction.  They could also be found on some hard rockin’ dude who seemed as if they only wanted to bust a move with his garage band, or at least wanted to impress(?) the ladies while stepping out of their Pontiac Trans Am.

Yes, most parachute pants could be found on men back in the ’80s, be it the break dancer or the big-haired, big-mustached bro.  But girls did wear parachute pants as well, and I should know because my sister had her own pair of girls’ black nylon parachute pants she would wear for school dances, parties, or other get-togethers with her friends.  They looked kind of like… these:


Image source here

Well, not exactly like those.  I mean, my sister’s pair were black and had zippered pockets all around, but the zipper areas were not gray as they are here.  Either way, you get the idea of what I’m talking about, or so I hope.  (Side note:  Notice there’s only one back pocket, and it’s on the right hip?  Right-handers get all the breaks. *sigh*)

You’re probably wondering if I tried on my sister’s parachute pants when I was alone, and you’d be correct.  I, like, totally felt like a rock star when I wore them.  The nylon material felt as sleek and supple to the touch as it looked to the eye, and the tight feeling felt like a real turn-on.  I can recall the “SWISH, SWISH” sound when the legs rubbed together, a magical sound to go with the thrill of wearing them.

As nice and alluring as my sister’s parachute pants were, they weren’t as sexy as the pair worn by my Evil Wicked Stepbrother’s girlfriend, Cheri (not her real name, by the way).  I never had the gumption to confirm this with her, but Cheri’s parachute pants looked as if they were made not of nylon but pure black satin, making them an even suppler version of my sister’s pair.  A photo of Cheri wearing her parachute pants appears in one of my high school yearbooks, and the photo doesn’t do justice to how magical they appeared in person. (That the photo was in monochrome black and white sure didn’t help.)

Speaking of Cheri, that brings me to Part 2 of my post: This is the part where I get into details about my Evil Wicked Stepbrother.  During my pre-teen and early teen years, he did not get along with parental authority in general, moving (by choice or necessity) under his father’s (my stepfather’s) roof after fraying his relationship with his mother.  On more than one occasion, the reverse would occur.  Evil Wicked Stepbrother sure defined the word “wicked”:  He would smoke.  He would cuss.  He would play his rock albums up to 11.  He would also chew me out if I did something wrong.  (Well, at least he would get in my face and chew me out when his father and/or my mother weren’t looking; I’m sure it was a trait he picked up from his father.)

Needless to say, Evil Wicked Stepbrother would disobey his parents on plenty of occasions.  When our family lived in a certain farm house when I was younger, he got into a couple of snits with his father, and he sought payback by overstoking the basement wood furnace that heated our house… which caused fire to sweep up the chimney and spread smoke throughout the house… which led to the fire department having to come and put the fire out.  (Stepbrother did this twice in one winter.)  Also, on a couple of occasions, he and a buddy lied about going to a movie with his friends, only to instead party with them and come home intoxicated.  And early one summer Sunday evening, he and his buddy took a joy ride in his father’s pickup truck while we were volunteering at an event at a road race course… but they went too fast, crashed into a tree, and totaled the truck.  Oh, my sister was riding alongside them when that happened (physically unhurt, thankfully, but really, really shook up).  My stepfather was the angriest I had ever seen him afterwards, and he really gave Evil Wicked Stepbrother a verbal berating on the drive back home (we hitched a ride with one of my stepfather’s hunting club buddies).

With all that, it’s not surprising when I mention that Evil Wicked Stepbrother got into trouble with the law once or twice in his younger days.  And with that, I venture into Part 3 of this post and something briefly advantageous for my crossdressing side:  After graduating from high school and before leaving home for… let’s just say a few months of training out of state, Evil Wicked Stepbrother got into trouble with the authorities in another county (for what misdemeanor, I can’t remember).  So, he decided to hightail it past the state line and elude the jurisdiction seeking him out, with Cheri and a couple of their friends in willing tow.

Sensing that time was of the urgency, Evil Wicked Stepbrother & Company decided that they needed to travel as light as possible.  So one autumn day, they came by and asked my mom to store some extra stuff that they decided to leave behind at our house.  Cheri left behind a duffel bag full of clothing she didn’t have a use for, and due to lack of space elsewhere in our house, it was decided that it could go into the back of my closet.  “I’m sure you won’t mind,” my mom said to me.  Well, of course I didn’t mind. (*wink wink*)

And with that, one autumn afternoon while nobody else was home, I opened up my closet door, snooped into Cheri’s duffel bag… and, lo and behold, found a pair of women’s jeans, a couple of shirts, and a pink/purple sweatshirt. (Sorry, parachute pants were not included.  I want to think Cheri dropped them from her wardrobe about as quickly as my sister dropped her pair.  Yeah, parachute pants were already out of style by 1987.)  The clothing from Cheri’s duffel bag was more casual and utilitarian than frilly, but I enjoyed trying them on and wearing them in private just the same.

During that brief time before my brief sojourn away from home, Cheri’s duffel bag proved to be, unofficially, my very first stash of women’s clothing.  Of course, they didn’t belong to me (I didn’t buy my own frilly stuff until later), but they were the first clothes I regularly wore/tried on that did not belong to my mother or sister.  I think when wearing Cheri’s clothes, I felt a little more freely feminine than I did raiding my mom’s or sister’s wardrobes.  Perhaps the reason for that was their private location in my closet.  But then, the reason I like to believe was the obvious fact that they didn’t belong to Mom or Sis and did not feel as familiar to me as their clothing did.

By the time I returned home from my training, Evil Wicked Stepbrother had resolved his legal troubles (and paid his punishment), and he and Cheri had retrieved their stuff from our home, including Cheri’s duffel bag.  I had to resort to wearing Mom’s and Sister’s clothing for my dress-up thrills at that point, but Cheri’s bag gave me a head start into a feminine world beyond the closets of home.

As for Cheri’s parachute pants… again, she had likely long since banished them to the nether regions of her mind; perhaps she gave them to someplace such as Goodwill in her want to stay fashion current (for 1987).  But I still remember seeing her wear that satiny pair of parachute pants.  And I only hope to one day find a pair just like those, or at least very close to them, online or in some vintage/retro shop.  If and when I do, those memories of being a teenage boy with a desire to wear something so very feminine and contemporary (for the 1980s) will resurface… and let me feel like, totally like a kid again.  I just hope they will still fit and feel flattering on me. *giggle*

Author: Allison M.

A part of the trans community ("cross-dresser" is the term that applies to me) who finds themselves much more expressive and somewhat more confident when presenting in a feminine persona. An admirer and supporter of those who are fashionable, fabulous, and friendly (LGBT or otherwise). Someone who tries to be witty and unique, but is not even remotely perverted or a pariah (I am a real human being, just like you). Using various writing styles on this blog to communicate thoughts and feelings concerning my life experiences, fashion sense, and the world at large (and maybe impressing my high school creative writing teacher who deservedly gave me middling grades).

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