The Ups and Downs of Men’s Fashion in 2020

2020 has been full of highs and lows, and the men’s fashion world hasn’t escaped it. Explore some of the highest and lowest points in 2020 menswear.

The Ups and Downs of Men’s Fashion in 2020
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Fashion trends define not just decades, but the best parts of decades. You know this is true if you’ve ever seen a movie based or made any time before 2010. You know how easy it is to spot the correct period in a period-drama just by looking at the hairstyles, clothes, and other fashion indicators. Unfortunately, certain fashion trends can also define the worst moments that almost seem comical. What this essentially means for the fashion-savvy man is that you really shouldn’t go running after every single trend. Unless of course, you have an unlimited wardrobe budget. Let’s face it. Some trends in 2020 were the highs of 21st Century men’s fashion. Others, not so much.

The 3 Worst Men’s Street Fashion Trends to Leave In 2020

The first thing we need to get straight is that styles and trends are two different things. Yes, they do overlap a lot, but they shouldn’t be thought of as interchangeable. That’s how you end up spending too much on a wardrobe that’s not likely to last long. Rest-easy casual shirts for men like a Phys Ed graphic tee is a great example of style outliving trends. They look good with virtually every outfit and are a versatile piece of clothing to complement statement pieces. But certain trends are nothing more than fads that die out within a few short months. For guys who like to dress up but stay under budget, this can turn out to be a colossal waste of money. If you have been thinking of sticking to these 2020 fashion & Lifestyle trends, we suggest you leave them behind in 2021:

Tie-Dye Men’s Clothing

Tie-Dye clothing has been very visible in 2020. Always hungry for new statement opportunities, people quickly embraced the psychedelic clothing that would have made Jimi Hendrix proud. The problem is, however, tie-dye doesn’t really cut it in every situation. Yes, the world is more open to experimenting, but certain experiments are fated for disaster. But a tie-dye shirt will likely look out of place next year unless you’re on stage in Woodstock.

tie Dye Clothing


Distressed Luxury Footwear

Mens khaki jeans and a pair of well-worn sneakers are a timeless street fashion statement. Skateboarders and grunge tribes have been a part of American street culture for several decades. Maybe that’s what prompted luxury sneaker brands to come out with “old-new” sneakers. Brand new retro-style sneakers that come out of the box looking like they were on someone’s feet for a decade. Many consider this a problematic trend.

On one hand, it tries to pay homage to the street fashion cliques that have immortalized these sneaker styles. At the same time, it fetishizes the worn-down aspect. It is ironic since the people who the trend pays homage to buy these expensive sneakers once and run them into the ground. Sure, you may look tastefully rough around the edges with a brand-new distressed luxury sneaker, but it seems kind of insensitive to people who actually wear the sneakers for years. In any case, my old sneakers from 2010 can give me the same general aura.

Distressed shoes

Retro Cycling Glasses

Okay, we get that retro stuff is cool. No sarcasm, it really is. I love certain aspects of retro fashion, like blocky and looser fits. But when it comes to 90s-inspired sportswear being worn on the streets, it can get dicey. Specifically, retro cycling glasses on the streets in 2020. This is about as fleeting as a trend can be. Why? Just take a look at them. Unless you’re actually doing the part of a lycra-fitted cyclist, you’ll just look tacky. Don’t take the horror into 2021!

retro cycling glasses

The Three Best Men’s Fashion Trends to Keep From 2020

You might think otherwise, but it’s not like I hate trends. In fact, I can prove the opposite. There are several amazing menswear trends in 2020 that deserve to represent the new decade. I, for one, would be happy to see them go the distance. The three best men’s street fashion trends in 2020 that we should hang on to are:

Thick-Soled Formal Shoes

Most sneakers and running shoes of our era look amazing because they have thick soles with larger treads. Often called the commando sole, this often changes how appealing a shoe, and even an entire outfit, can look. And the best part is, formal shoes are catching on. Boots, brogues, and semi-formal shoes are now embracing thicker commando soles. The chunkier look they offer promises a hint of roguish adventure, even in many formal settings.

Thick Sole Shoes


Hard-shell Jackets

Another trend that needs to go forward to 2021 is the mix of technical fabrics, form, and function in American made clothing. In other words, the modern hard-shell jackets designed for outdoor jackets need to stay. These jackets check all the right boxes. They are far warmer and water-resistant than your average windbreaker. They have plenty of convenient pockets and functional accessories. Most importantly, they offer a rugged beauty that just hasn’t been seen in street fashion before.Shell Jackets



Knitwear, when paired with a tailored suit, makes you wonder why nobody tried it before. Provided you choose the right pieces and colors, you can wear suiting and knitwear together in many settings. Knitwear can help you dial-down the formal look the suit exudes, without looking any less classy.



The Ups and Downs of Men’s Fashion in 2020
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Written by Scott Somerville

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