At work last Friday, a group of contemporaries and I were discussing some of the finer fashion moments of the last 25 years. We covered some of the early 80s looks, including neon apparel, parachute pants, and sweatshirts with asymmetrical neck holes, a la Flashdance.
And then I trumped them all: In the late 80s and early 90s, I paraded around in UNDERWEAR. Yes, it’s true, boxer shorts were a staple of my wardrobe for several seasons. Worse? In the winter I paired my boxers with LEGGINGS, presumably to keep me warm.
I didn’t really grasp the concept that boxer shorts were actually underwear because my dad was partial to briefs. Boxers became available in a wide range of patterns and fabrics (plaid flannel, for example) and I was in heaven.
As it transpired, I wasn’t the only one in the group to wear boxers as outwear. Apparently it was a tri-state area phenomenon. I’m not sure if the boxer fashion tentacles stretched farther because none of us grew up further away than Westchester, NY.
From boxer shorts, I moved inexplicably to dressing like a lumberjack from the Pacific Northwest. I place the blame squarely on the shoulders of Kurt Cobain and his ilk. If the aim of that fashion epoch was to look like a man, I reached nirvana on every level.
I was also a victim of my environment (and heritage). Growing up in a town with a larger-than-average Italian population, it was impossible to avoid the cliched New Jersey Guido (gwee-doe) look. To achieve this, we utilized many cans of Aussie Scrunch spray, shirts from a store called Chess King, and Z. Cavaricci pants, which sold for upwards of $70. I vividly recall the day my sister bought her very first pair–she’d been saving for months–and my dad and I accompanied her to the mall for the epic purchase.
I’m sure our discussion about fashion could have stretched into the wee hours of the night, but it was a Friday before a holiday weekend and we were eager to get out of Dodge. Lucky for me, I can continue the discussion right here with you!
Pony up: What fashion faux pas did you embrace with open arms?

The flannel shirt as a an outer shirt. – 90s college
The big bang theory (big hair) – 80s
Shirts with famous people (Marx Bros., James Dean) – 80s
cwg says: ahhh, the big hair. what happened to ’salon selectives’ hairspray? that was my shellac of choice.
I think boxer shorts as outwear was a nationwide epidemic…(my daughters, not “I”)
Huge elephant ear bellbottoms. halter tops. straight as a board hair parted down the middle (guys and girls)
cwg says: connie, you KNOW you were dying to slip on a pair of boxers! is there anything more lovely than a halter top? or a top with smocking? i wore a ton of that stuff in the 70s.
oh my, how much time have you got?
* Lace bottomed leggings
* “skinny” jeans with oversized t-shirts
* honeycomb thermals with plaid skirts and combat boots (still miss those)
* Big Bangs
* Bicycle shorts (with two neon stripes, one color on each leg)
* Ruffles
* I.O.U. sweatshirts (2 for $50 at Merry-go-Round)
* $10 silk shirts
I too loved the boxer thing, they were so comfy and totally matched my black t-shirt collection.
cwg says: merry-go-round!!!! i miss those halcyon days!
Lets see-big hair definitely though I tended towards rocker ala Madonna and metal groupie for a while and hit grunge before I was ever aware of Kurt Cobain.
I wore pink and camoflauge way before it became a thing.
I’m a sucker for sheer blouses still(with appropriate undergarmants these days).
I’d have to say the best was tight rolling my jeans though. I’m pretty short and at last there was a fashionable way to deal with my too long jeans.
cwg says (wistfully) ohhh, the tight-rolled jeans!!!!
Tight-rolled pants! (Or penny-rolled, though I can’t imagine why we called it that.) How did we think this looked good?
I’m sure it looked especially bad on me with my ankles that were twice the size of all of my teeny friends’.
[...] 27, 2009 in General Mischief (Oh CWG, there is nothing that a ten-foot pole couldn’t [...]
What about wearing two pairs of socks, two different colors to match your outfit? Guess jeans. Swatch watches.
Um. Boxers are really comfortable. Are you saying that I shouldn’t be wearing them as the most AWESOME SHORTS EVER?
I’m going to pretend I didn’t actually read this.
Hm. Now that I think about it, my biggest fashion faux excellénce has to be in from elementary school when I wore one black shoe and one white shoe, with one white sock and one black sock (respectively).
I loved that look!
I did the grunge thing like everybody else. It was the nineties. Besides, wearing old ripped jeans was cheaper than buying new jeans.
Then I went through my Versace phase. I tell ya, a pair of jeans with $200+ price tag shouldn’t split right up the buttcrack when I bend over, but they did.
I probably would have tried a bit of drag, but I’ve just never had the body for it.
One time – just once – I played golf in a pair of zebra-striped Zubaz that my sister-in-law gave me. After that they became the world’s largest dust cloth.
In 1972 we were already getting into the bicentennial fervor and I had a pair of red, white and blue striped bell bottoms with the word “VOTE” running repeatedly up and down the blue stripes.
And I will confess that for about six months in high school I did, in fact, own a leisure suit which I probably wore twice.
Now, all of a sudden….I feel so…so…clean!
I recall one outfit I had that consisted of tight black velvet shorts and matching vest top. I paired this of course with a pair of black triple-soled lace-up granny boot shoes. and black stockings. It’s a wonder i made it home alive.
I wore everything that was in so that included the dreaded Flashdance phase (ripped sweats and leg warmers), the Little House on the Prairie phase (prairie shirts with calico skirts) and I don’t know what to call this phase (minis, with gold threaded head bands, roach clips and sometimes gauchos, heck throw some beaded moccasins in there for good measure).
I was a fashion disaster!
Oh yeah, there were also these outfits called “sizzlers” (actually I think they were designed for hookers)
shiny fabric extremely short dress with matching silky “panties” Had to borrow a friends, my mom never bought anything trendy!
Probably the most hideous thing I did as a grown up was my “mommy” jean dress phase…I swear my kids can find pictures and it looks like I only ever wore that stupid jumper WITH little white socks and keds. Darn Curly, I’d rather not remember those fashion disasters!
I’m with plumpdumpling – tight rolled pants, but to trump her, I covered my ankles with white slouch socks. Tight rolled pants and SLOUCH SOCKS!
I thought I looked so cool.
Plus, all the plaid wear in the universe lived in my closet. Damn you Kurt Cobain!
I not ashamed to admit I still rock the “grunge” look every once and a while. I think it’s my favorite fashion trend to date.
I can confirm the boxer fashion tentacles reached as far west as Missouri Valley, IA.
I remember rolling the bottoms of m jeans. You know the trick…fold them over, then roll. The more circulation cut off from your feet, the better it was. And for a while, this was paired with wearing multiple layers (and colors) of socks.
I too did the tight rolled jeans, sometimes even using a pin to make sure they didn’t budge. Big hair was great and how many times did I burn myself with that darn curling iron…
Here’s a sampling of my fashion faux pas:
Velcro running shoes (80s)
Ninja Turtles t-shirt (1988-1990)
The outfits with the matching cotton shirts and shorts that my mom sewed me — The first one was truqoise with geometric patterns (1988), the second was black with neon fishes (1990)
Batman t-shirt (1989-1991) — it was one with the Batman from the comics, not the Batman movie shirts, which had more cache.
Black sweatpants, neon orange t-shirt, neon orange baseball cap (1990)
Black/fluorescent windbreaker (1990-1992)
White high top running shoes (1991-1992)
Hypercolour t-shirt (1992)
A buzz cut in 1993, when these were completely out of style. After I started grade 8 in the fall of 1993, and realized I was the only kid in the whole school with a buzz cut, I decided to grow my hair out, and by 1995 I had straight, shoulder length hair (didn’t look as bad on me, but as a small, skinny guy it got me confused for a girl on multiple occasions). Got my hair cut in a Sgt. Pepper era Beatles cut in 1996, then had my hair long again from 1997-2002 (got me confused for a girl even more times again). Have generally had better hair cuts since 2002.
Very light blue acid washed jeans with a built in drawstring (1993) — Thought these were cool when I bought them in Spring 1993. Realized how out of style these were on the first day of grade 8 in fall ‘93, and got my dad to take me to the mall that night to buy two pairs of stonewashed jeans to wear instead.
Black jeans with giant bleached patches (1995) — I was 15 and on staff at a provincial scouting jamboree. When I had a chance to get into the nearby town to do some laundry, I saw the instructions for adding bleach, and erroniously assumed you were supposed to add it.
Ridiculously oversized black t-shirts (the 90s) — Some of the graphics on them wern’t too bad (Green Day, Nirvana), but some were hideous (Joseph and the Amazing Technicolour Dreamcoat). Don’t think the black colour looked bad, just that they were ridiculously oversized.
Tourist gift shop t-shirts (80s & 90s) — They had city & town names on them, or the names of tourist attractions, and they wern’t ones that had a lot of cache.
Summer camp t-shirts (late 80s, early 90s) — The worst was a hot pink one I got in 1991 — and I’m a guy.
haaaa
i was only born in 1990.
but even today i dress like i shoudve been a teenager then.
rocking the ripped jeans.. often with pyjamma pants under them.
shorts with long johns in the fall and spring..
various band t shirts
more flannel then you can shake a stick at.
shirts with crazy graphics or sayings on them.
ive also been known to sport a flourescent pink backwards painters hat.
and converse. which appear to be more popular then ever.