10 Surprising Styles That Date You

Jeans, Sewing and More

Don’t worry, it happened to the best of us. We are all drawn to the allure of fleeting fashion trends from time to time. Maybe the celebrities we respect wear them. Maybe a friend suggested it.  Or maybe you even have other significant powers against you. It seemed to work at the time and no one had any complaints. But then 10 years go by and that mistake still has time in your rotation. You feel comfortable in it and the gaze settles in the blind spot of your way. While that style may have worked at the time, it’s not now and it’s hanging out with you every time you use it.

Being good friends who are here at HSS, we decided to put together a list of 10 styles you’re dating so you can watch them if they’re still in your closet. Listen, we know you have good taste, but sometimes you just need a third-person perspective to show these things. The styles in this post range from the 1980s to the 2010s and we all participate in some of these styles at one time or another, don’t try to pretend we didn’t! Many of them are cyclical modes that have come and gone several times over the past century. So maybe if you stick with some of them, they’ll be back in fashion one day, but for now they’re just dating you.

  1. Washed sour denim – 1980s

Good denim ages beautifully.  This is one of the characteristics of the fabric that has made it so attractive for so long. When you wear jeans or a denim jacket, they develop a patina that is unique to your body shape and what you do with it, this is especially true for raw denim.  In the 1980s, designers began artificially aging denim to accentuate many of its shades and textures with chemicals. Thus, the birth of acid-washed jeans.

The problem with acid wash jeans is that you remove most of the potential to build your own patina. Create the look you set because your jeans are old to you. This didn’t seem to matter to most people in the 1980s because acid-washed jeans were everywhere. Acid washing is also closely related to different settings of the 1980s: high waist, loose hips, tight ankles. Most people who wear acid-washed jeans today probably get them in thrift stores, but you’re sure to find parents who have been holding them since the 1980s. And if you’re in your 40s and 40s, that’s one of those styles you’re dating.

  1. Oversized sewing – 1990s

In the 1984 concert film Stop Making Sense, Talking Heads lead singer David Byrne wore an increasingly larger version of the same gray suit as the show progressed. At the end of the show, his suit was so big that he looked like a boy in his father’s jacket. A decade later, Byrne’s jokes turned out to be prophetic in nature. Sewing in the 1990s became so large that, compared to their counterparts in the 1960s, most men looked like children dressed in adult clothes.

The problem is that the suit that has stuck to your father’s closet during this time can become fashionable again. Like most fashion trends, the greatness of sewing is cyclical.  Designers in the 1990s were inspired by the 1940s. Now the cycle is starting to return as some celebrities, under the influence of professional stylists, begin to wear drastically enlarged sewing. Justin Bieber wore a gray suit, customized, by the way, for a 2022 Grammy that looks so big it could easily be mistaken for a tribute to David Byrne. However, for now, it’s still one of the styles you’re dating.

  1. Cargo shorts and pants – 1990s, 2000s

Cargo bags were added to the hips of U.S. Army uniforms during World War II to help them carry everything they needed on their marches through Europe. This feature eventually surpassed the military surplus in a popular fashion during the 1990s. Cargo pants and shorts are common everywhere, from mall retailers to catwalks. Each brand offers its versionand everyone has at least one pair in their closet.

Ironically, all the extra pocket space is almost never used. For good reason too. Anything placed in your pocket will vibrate as you walk. If it is metal, it will clink. If there is some kind of theft for it, your pants will turn uncomfortably with each step. The pockets were purely aesthetic in most cases, and some never showed buttons on the lapels. Functionally, they are more problematic than they are worth.

This trend was so popular that it lasted until the 2000s. It was only during the great #menswear revolution of the 2000s that freight exchanges vanished. Men decide they no longer need extra carrying capacity in their daily wardrobe, whether they wear it or not. (Perhaps that’s why there’s an increase in stylish bags, bags, and backpacks at the same time.) However, cargo bags never really die, and some brands sometimes reintroduce them with little success. If you look at cargo bags in nature today, you can tell that they are outdated if they are loose, while thin versions are not republished contemporary.


  1. 11″ + Inseam Shorts and Swimwear – Late 1990s, Early 2000s

Looking at the best NBA moments of the late 1990s and early 2000s, you’ll notice two things that stand out from today’s NBA: baggy shorts that go through the knees and defense. WAKAKAK… Basketball players at the time followed the popular trend of long, loose shorts because somewhere in the mid-1990s, shorts headed south and continued. At the turn of the millennium, it is common to see shorts and swimsuits that almost reach the user’s ankles.

Since they were introduced into popular fashion, shorts have a fairly consistent stitching that hits somewhere around the middle thighs to the bottoms. Even when most other garments were expanded in the 1950s and 1980s, the shorts remained roughly the same length. So it’s hard to determine why they grew in the late 1990s, but when they did, they grew rapidly. Some men embraced this trend during its heyday and were constantly stuck with it.

The most famous hanger for oversized shorts is Adam Sandler.  Their streetwear photos are so bad that they’ve taken a cult following almost, somehow, in good. Sandler is a legend with too much money and success to pay attention to fashion trends. All of us ordinary humans had to leave the big shorts back to where they came twenty years ago.

  1. Ed Hardy & Von Belanda – 2000-an

Graphic design by tattoo artist Ed Hardy and motorcycle brand Von Dutch was inevitable in the 2000s. While the two brands don’t have a direct relationship, they will always be connected through a specific aspect of pop culture from that decade. Celebrities such as Christina Aguilera, Paris Hilton, Justin Timberlake and Ashton Kutcher popularized Von Dutch trucker hats and Ed Hardy printed T-shirts. Immediately afterwards, everywhere from high school to nightclubs, they were filled with two brands.

In addition to their contemporary exaggeration, the two brands share a very particular stickiness that defined the popular fashion of the 2000s. Ed Hardy was a tattoo artist who began his career while serving in the United States Navy during World War II. His work had a cult following among tattoo enthusiasts until his estate sold his designs to print on expensive clothing. Von Dutch has a cult following among motorcyclists, starting as a specialty shop in the 1950s, until it was renamed in the 2000s. Even if you’re a tattoo artist riding a custom motorcycle, the two co-opted brands were so playable in the 2000s that they’ll always be associated with the decade’s poor fashion choices.

  1. More than the embroidery of Jean’s back bag – 2000s

Levi’s and Wrangler are the oldest and most famous jeans companies in  the world. Therefore, its distinctive back pocket embroidery is a clear signature of each brand. Levi’s has a curved V-shaped parallel seam line and the Wrangler has a W-shaped parallel seam line. But for a time, there were many denim brands with back pocket embroidery that were not delicate or tasteful.

During the 2000s, the trend of back pocket embroidery became uncontrollable. The jeans section of every department store in America is filled with “signature” embroidery of exaggerated brands. The idea is that all brands want their back pockets to stand out for an arms race to occur that makes jeans pockets more eye-catching and flashier every season. The excessive detail was also not accommodated by the back pocket as the bold seams and embroidery began to take over the entire pair of jeans.

Fortunately, this trend died out after a critical mass was reached somewhere around 2006. Denim brands are aware of and tame their embroidery patterns. Since then, the back pocket design has become as delicate and tasteful as the two denim grandfathers intended. There is even a reactionary impulse from many brands to have no back pocket embroidery at all. This trend is still true for many brands because they choose to place signatures in places that are even wiser than back pockets. But by the 2000s, this was definitely one of the styles you’re dating.

  1. Kaos V-Neck – 2000-an

V-neck T-shirts were created to be worn with collared shirts so you can wear an unbuttoned collar without showing the neckline of the shirt. They still serve that purpose and every man wearing a collared shirt should have multiple V-neck T-shirts. However, there was a short decade in which the V-neck was a popular fad in its own right. This trend turned the V-neck of a basic white T-shirt into every color imaginable, eventually with graphics and prints of all kinds.

Eventually, the ‘V’ itself enlarges, resulting in a ‘deep V’ falling into the middle chest. It also comes in many shapes and molds. The deep V was a staple of early hipster culture, used by baristas and independent rockers. While the standard V-neck T-shirt, often in bold colors and patterns, is the cultural uniform of choice. Luckily, a few years ago, we collectively returned the V-neck T-shirts to the lingerie department where they were.

  1. Fitted dressing shirts – 2010s

The sewing thinned in the late 2000s when the suit returned. The silhouette reflects the 1960s with clean, tight lines. Bespoke dress shirts also became popular, also following the rules of clean line. But some of the men got a little carried away, and the way of adjustment changed to fit. This shirt ended up looking less like a bespoke team and more like a sports team. They also looked very uncomfortable.

This style became popular with gym culture as a way for swollen brooches to show off their hard-earned muscles while still wearing shirts and ties (thankfully, sleeveless shirts and ties never catch). Since stretched fabrics have not yet entered formal attire, these tight shirts are almost always 100% cotton. Limited mobility and unsightly button pulls are common. This trend has largely disappeared,  but you’ll still see it occasionally from a man who goes beyond his shirt or is determined to show off his physique.

  1. Skinny Bond – 2010s

Slim ties first appeared in the 1960s when Italian sewing was adopted by American beatniks and British mods. This style made a comeback in the 1980s with an almost ironic twist. Then, in the 2010s, after suits had their day once again, “skinny” became the standard for a tie once again. The style of the costumes was heavily influenced by the 1960s during this time thanks to designers such as Thom Browne and Tom Ford, as well as the huge popularity of the Mad Men television series.

For many millennial men, thin ties are the only variety available when presented with suits. This is what a link looks like, so it’s just a thin bond that you need to have, right? Then the suit began to move more towards the middle ground. Although millennials know they’ve grown sartoriously when everything is relatively thin, now all those slim ties are the style you’re dating.

  1. Extra narrow neck – 2010s

As a rule, the width of the neck and the width of the tie should coincide, or usually similar, so the trend of the extra-narrow neck and the trend of the thin tie are inextricably linked. The neck has steadily narrowed and widened over the past decade since modern costumes have existed. However, they reached such a narrow width in  the  2010s that they hardly existed in some suits. When your necklace measures a little over 2 inches, you may not have it at all either.

Whenever any style trend goes to extremes, it starts to look silly and thankfully recovers quickly to make it look a little more reasonable. This is what happens with the collar of a suit. Somewhere around 2018, the necklace found a good (and proportional) groove. Today’s costumes were heavily influenced by the 1970s and the extra-wide collar was the defining feature of that era. As the collar continues to widen, the narrow neck left over from a decade ago looks more and more like the style you’re dating.

The problem is that changing suits is a bit more expensive than changing a tie and, as a society, we have a lot of suits with narrow collars to change. There are many details about suits that a good tailor can fix but the width of the neck is not one of them. So, you’ll probably still see worn necklaces for a while because men stick to suits they invested in years ago that would otherwise still fit.

The style you’re dating: the end result

It is said that fashion is fleeting but style is timeless.  The problem is, even for the most elegant men, the two can be hard to distinguish. We all have items in our closets that seem timeless when we buy them, but turn out to be temporary. If you have something on this list, then you should probably let it go. There is no judgment at all. Because we’re just here to tell you as friends, this is the style you’re dating.

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