For about as long as I can remember I’ve had a strong interest in clothes, fashion, I use that term loosely in my case, and fashion trends. My first memory ever is the day that my parents came home from the hospital after my mom had just given birth to my sister, Heather. I was 3 at the time. While my parents were gone away to the hospital my grandma had taken me and my older brother Lee shopping and gotten us new matching sneakers. KangaROOS. They were royal blue with two Velcro straps, a bright yellow KangaROOS logo on the side and of course their signature zipper pouch (which I used to put change in, I don’t know why, I was 3 and I felt like I needed to utilize the pouch). I don’t remember the shopping trip but I vividly recall sprinting across the yard to meet my parents when they pulled in the driveway. I was more excited to show them my new shoes than I was to meet my new sibling. Sorry, Heb. I’ve always cared about and been picky about how I dressed, especially so when it comes to footwear. Throughout my 40+ years I’ve paid attention to, participated in and in some cases been victim to numerous fashion trends. It’s still something that interests me to this day and I enjoy seeing some of the trends from my youth come back into style. I saw a teenager the other day that looked like he stepped directly out of the 90’s. Backwards cap, baggy jeans and retro Jordans. He was just missing the Starter pullover. But it got me to thinking of how we dressed back then and inspired me to make this list of The Top Fashion Trends…Of My Lifetime.

20. Birkenstocks and Socks

Ok, maybe this one is just me. Because a Google image search did not produce the results I was looking for. I finally settled for the image above because it was the closest thing I could find to what I’m talking about. I’ve seen a few people around wearing this combination but more often than not it’s younger kids wearing their clogs with Nike socks. That’s not what I’m talking about either. Ya’ll are doing it wrong. I prefer to wear mine with quarter crew socks. Not pulled up tight but not super scrunched up either. This pairing is my current “fashion” obsession. And since Google and today’s youth can’t get it right, I’m claiming it as my own. Jump on the bandwagon at your own risk.

19. White The Game Hats

Back before WWE wrestlers or West Coast rappers adopted the moniker, The Game hats were a thing. These college caps were pretty popular in the late 80’s and early 90’s. The white went with pretty much anything and you could rep your favorite college team or any school in general, it didn’t really matter. But you got extra cool points for having a “Cocks” hat such as the one shown above or an “X-Men” Xavier hat. I had a few of these hats. One was a Georgia Tech cap that said “Buzz” inside the 3 bars. I wore it so often and for so long that the bill was frayed and the white had morphed into a color that can only be described as dirty sweat. Frayed bills and dingy hats were little trends in their own rite, so you could actually get a 3 for 1 with one of these bad boys. Throw a fish hook on the bill and you were really cooking.

18. Jeans Cut at the Bottom

The first of a few jeans entries on the list, I give you jeans cut at the bottom. I first remember this trend gaining traction in the mid 90’s. Maybe we didn’t have boot cut jeans back then, I don’t really know. But I do know that I hated the way most jeans gathered at the bottom on top of my sneakers. To combat this bunching we would cut slits along the seams at the ankles of jeans. Besides achieving the desired result of preventing the pooling, these cuts looked cool. Or I thought so anyway because I took the scissors to virtually every pair of jeans I owned. You had to be careful with this trend however, because if you accidentally stepped on the bottom of your jeans you were at risk of ripping the slit higher up the jeans leg and effectively ruining them. I still see this trend here and there today and some jeans even come pre-cut like this. Some pairs even have zippers or buttons at the bottom to recreate this trend that was on the cutting edge in the 90’s.

17. Sports Jerseys

I’m not exactly sure when we started wearing sports jerseys as our choice of tops. But when we did they were everywhere and we wore them with everything. Jeans, shorts, jean shorts, khakis, sweats. Anything went and any sport was in season. We wore NBA, MLB, NFL and NHL jerseys. You could show allegiance to your favorite team, favorite player or just go with whatever jersey you thought looked the coolest. I had a vast array of sports jerseys. Some that stick out to me were my Pittsburgh Penguins hockey jersey, my Chris Webber Golden State jersey and my Sterling Sharpe #84 Packers jersey that I had customized with “Holley” on the back. But I would have to say that my all-time favorite was my blue alternate Orlando Magic Penny Hardaway jersey. This trend lasted for a pretty long time and I can’t say for sure when it died out. Jerseys came back in a big way when throwbacks became popular in the mid 2000’s but I hardly ever see people wearing jerseys now outside of sporting events.

16. Umbro Shorts

Ah yes, the original hoochie daddy shorts, Umbros. These shorts stood out by using the less is more approach. During the same time period that Michigan basketball’s fabled Fab Five was pushing the boundaries of baggy shorts, Umbros chose to go in a drastically different direction. I was actually a fan of both styles and that duality of shorts went a long way towards me discovering that one’s personal style didn’t have to be tied down to a specific look. Umbros were made for you to showcase your nice stems and if you were in on this trend then you definitely weren’t clueless.

15. The Bowl Cut

The bowl cut was a men’s hairstyle that was popular in the late 80’s and early 90’s. The direct opposite of the mullet, it consisted of leaving the hair long on top but shaving it lower down and all the way around. It got its name because, well, it looked like someone put a bowl on your head and then cut your hair. Apparently we thought the mushroom shaped mop top looked cool. Don’t get me wrong, it did actually look good on some people. Unfortunately, I was not one of those people and looking back at photos of myself with the bowl cut is an unpleasant, yet humorous experience. This is one trend that I’m glad didn’t make a comeback.

14. Bucket Hats

Perhaps bucket hats grew in popularity as a direct remedy to the aforementioned bowl cuts. Because around the same time I started seeing less bowl cuts I started seeing more bucket hats. I owned a few of these myself but the bucket hat I most fondly remember was the brown one that my cousin Micah wore. A lot. He wore it so much that it basically became a part of him. Sadly, Micah passed away back in 2006, but I can still picture him with his trademark long hair sticking out from under the brown bucket hat. And it makes me smile.

13. Duck Head Shorts

Next we have the Crayola box of khaki shorts, Duck Heads. These shorts came in a wide variety of colors, mostly pastels. They were a fixture of my middle school wardrobe. Duck Heads were mostly paired up with polo shirts or graphic tees. Bonus points if you combined them with the white tee with the Duck Head logo. These shorts caught on in a major way for a few years but died out pretty quickly as I don’t recall many kids wearing them during my high school years.

12. Braided Belts

Of course we had to have something to hold those Duck Heads up and braided leather belts are what we decided on. We wore these belts when we dressed casual or when we dressed up. They were versatile and stylish. The trick to these belts was getting the right length. Because for some reason we used to loop the extra belt after the buckle back into itself and let it dangle down instead of just going with a normal length belt and running it back through the belt loop of our pants. I don’t know why we did this but it was the only acceptable way to wear them. If you went too short or too long with the excess belt you were at high risk of being ridiculed by your friends.

11. Windbreaker Sets

Next up we have a trend that personified the bright and neon fueled decade of the 80’s, windbreaker sets. It was like the aerobics gear of the time stepped out of the studio and into the streets. These suits were loud. Both visually, with the eye-catching color combos and literally, because of the way they swished when you walked in them. Windbreaker sets were cool, comfortable, cozy and functional. Despite all of that, I don’t expect a comeback from this trend. The only place I’ve seen them in recent years is at decades parties, where they are generally worn in jest.

10. Reebok Pumps

The revolutionary Reebok Pump debuted in November of 1989. These sneakers featured an internal inflation system that provided a custom fit. Alongside the release of The Pump, Reebok launched an ad campaign with Dominique Wilkins and young skateboarding phenom Jessee Roach. The ads did their job as these shoes caught on like wildfire and were virtual must-haves. I got the pair pictured above as my “back-to-school” shoes before I started 5th grade. I was beyond stoked to walk in for the first day of school with my new pair of Pumps on my feet. Although these sneakers were already wildly popular, Dee Brown launched them to a whole new level when he pumped his pair up before performing the winning dunk in the 1991 NBA Slam Dunk Contest. Later that same year Reebok released Shaquille O’Neal’s first signature sneaker, The Shaq 1s, and pumps were once again propelled to new heights. I was a huge fan of these sneakers and solely wore Pumps for several years until Deon Sanders helped break their hold on me with Nike’s release of his first signature shoe, The Diamond Turfs.

9. Flannel Shirts

I’m under the school of thought that flannel never really goes out of style. But back in the 90’s its popularity was at an all-time high. Coinciding with the grunge movement hailing from the Pacific Northwest, flannel took off in a big way. The front men for rock bands were at the forefront, fueling flannel’s fashion fire. But it wasn’t just the rocker who were rocking the flannels, just take a look at a few rap videos from that time period and you will see what I mean. Flannel shirts were versatile in that you could wear them in a few different ways. Buttoned up, over a tee shirt or you could even tie them around your waist by the arms and still pull off a nice fit. I see them make little comebacks every few years but never to the extent that they were worn back then.

8. Converse All-Stars

A fitting follow-up to the aforementioned flannel, Converse All-Stars, share a lot of similarities with those shirts. They are both timeless trends that are always stylish. Chuck Taylors could also be worn in a multitude of ways with many different outfits. And flannels and Converse were both staples of rock stars and rappers alike. All-Stars are absolutely timeless and I’ve owned many pairs throughout the years. When I was in grade school fun colorful Chucks were in. By the time I hit middle school the classic black pair were en vogue. Then when I was in high school the All-Star lows were a thing. Although the iterations may change, the fashion statement made by these classic kicks always remains the same.

7. Nike Sandals with White Socks

Ok, looking back now, the combo of Nike sandals and white socks might have been a little fashion faux pas. But back in the day we rocked these religiously. I remember this trend first gaining traction towards the end of my freshman year of high school, which would have been around 1995. There were two particular models of Nike sandals that I recall being the main suspects, the Beo Beo and the Air Deschutz. Personally I had a pair of the Air Deschutz IIs complete with the yellow bumper pad on the back ankle strap. I wore them all the time back then, always pairing them with a pair of white tube socks, pushed down a little to get that perfect scrunch effect.

6. Baggy Jeans

Kids these days may be in their bags, but back in the late 90’s and early 2000’s we were in our baggy jeans. Heavily influenced by hip-hop culture, this trend of tent-like trousers had teens of the time in a trance. Baggy jeans also had a little staying power as it would be several years before normal sized pants regained their grip. I was a big fan of these jeans back then and adhered to the creed of the baggier the better. I’ve seen baggy jeans make a slight return recently, mostly being worn by younger women.

5. Grey New Balance

Grey New Balances started to catch on a little in the early 2000s. They were a nice alternative to the popular running shoes of the time that tended to be more flashy and vibrant. Before New Balance the only grey shoes I can remember at all were the Wal-Mart, two-strap, grandpa shoes (a trend we also latched onto and for some reason we called them Pastor Troys). The neutral grey color meant you could really wear these shoes with any outfit and still look cool. These were my sneakers of choice for a few years and even nowadays I pick up a fresh pair every few years as grey New Balances have stood the test of time and remain stylish to this day.

4. The North Face Fleeces

These The North Face jackets had the outer garment game in an absolute choke hold for a few years in the 2010s. These jackets were available in both mens and womens and if you attended an outdoor gathering back then during the fall or winter, I would wager that 75% or so of people in attendance had this jacket on. Black and grey were the most common choices, but The North Face produced these in a lot of different colors and all of them worked well. These were around for a couple of winters before they eventually lost popularity and got placed in nostalgia’s closet.

3. Clarks Wallabees

At around the same time that we were wrapping up in North Face fleeces our kicks of choice were undoubtedly Clarks Wallabees. These moccasin style shoes with the thick rubber sole (which have taken more ankles than prime Allen Iverson over the years) were different from most footwear options at the time. The suede camel color pictured above were the first ones that I remember people wearing but before long the brand branched out and we started see in Wallabees in a wide variety of materials and colors. These shoes have stood the test of time as I still see them often today and still have a few pairs in my personal rotation as well.

2. Starter Pullover Jackets

The halls of my high school looked like a Starter supply store back in the mid 90’s thanks to these iconic pullovers. They were available for all the major North American sports league teams as well as for most college teams. They featured a traditional kangaroo hoodie pouch with an additional zipper pocket on the front with a hood and large team logo on the back. Much like the sports jerseys we sported at the time, you could rep your favorite team or just go with whatever jacket you thought looked the coolest. We also paired these pullovers with the team matching Starter snap backs for an added level of coolness.

1. Ripped Jeans

Back in the day ripped jeans were just a badge of honor from going hard on the playground. But somewhere along the line we started distressing our jeans as a fashion statement. This trend took off a little in the 80’s then really started tearing it up in the 90’s with the grunge movement. At first it was just holes in the knees of jeans but this evolved to tears and frayed spots all over. Back then we had to do it ourselves and I remember taking a pair of scissors to dozens of pairs of denims, trying to get the perfect look. Nowadays as this trend lives on you can buy pre-distressed jeans directly off the rack. I’ve been a big fan of this trend since it first started and still enjoy the look of a pair of ripped pants to this day. I’ve stuck with it through all its iterations although at my advanced age I now prefer a more subtle rippage as opposed to the huge holes I leaned towards in the past. To me ripped jeans are a style statement that have withstood the test of time throughout the years and that’s why they’re The Top Fashion Trend…Of My Liftime.