Style Tips gives you valuable insight on how to rock the season’s biggest trends from some of the fashion industry’s most influential names. 

While their relevance in contemporary fashion has wavered, denim jeans have been a staple in every guy’s wardrobe for over one and half centuries now. Once a pragmatic sartorial option reserved for blue collar professionals, jeans have since transcended into style-forward trademarks for trendy denim specialists such as Acne, Rag & Bone and A.P.C., to regular catwalk cameos for luxury houses like Gucci, Saint Laurent and Balmain, to conceptual creations crafted by avant-minded labels including Vetements, Alyx and OFF-WHITE.

Very few clothing items have undergone such radical transformations throughout the years as denim; from billowing bell-bottoms that swept across ’70s disco clubs, to acid-washed dungarees rocked by ’80s punks, to the ripped jean explosion throughout the ’90s grunge era, all the way to the bedazzled-everything baggy bottom-shakers that assaulted the 2000s, jeans have reinvented themselves more times than pop evangelists David Bowie and Madonna combined.

Of course, not all denim is cut from the same cloth, so to speak. There’s myriad washes, cuts and styles to choose from, so selecting the perfect pair can be challenging to say the least.

To steer you in the right direction, I sat down with Jonathan Cheung, the Head of Design at Levi’s (aka the OG denim brand) to get a low-down on denim’s cultural relevance over the last few decades, what jeans are trending right now and the do’s and don’ts of denim shopping.

Lindsay Armstrong

How do you think certain fits and washes come about during specific eras?

I think fashion in general is a reflection of human society. It’s a sign of the times and how people want to dress or want to express themselves via social, economical, political and sexual identities. So design is a reflection of that and often we create designs to reflect the way people are living and choosing to express themselves.

Men’s skinny jeans and tapered fits, for example, were in part a reflection of sneaker culture and how some guys choose their sneakers and shoes first and then dress accordingly. I think that is part of a drive towards a fit that is skinny around the ankle.

Adam Katz Sinding /

What is it about denim that resonates with youth subcultures and their respective philosophies?

I think denim has grown hand-in-hand with subcultures, which really started post-war with young guys coming back from the war. Denim was first adopted by biker gangs as a symbol of rebellion and then it became associated with more unsavory parts of the population to the point where, in the U.S., certain schools would ban jeans or not recommend them for school wear.

Of course, that was the torch that lit up their popularity and part of it was because jeans are working class. They are affordable and accessible and everyone can get them. There’s no kind of economic exclusion on them. And then you can customize them; you can wear them any way you want and they fit in with many types of subcultures. You can be a rocker, a skate kid, a punk, a tech nerd…it all works. You can be a girl, boy, any gender, any age, any economic demographic and it all works. There’s something super universal about denim which is a part of their longevity and lasting appeal.

Adam Katz Sinding /

Seeing as Levi’s is a heritage brand, what compromises need to be made when collaborating with other brands?

We tend to be very picky when choosing the collaborator. If you are choosy from the beginning, then things tend to work out better as we go along the process. We pick collaborators that have similar values and characters to us. And they are usually or always fans of the brand.

They want to work with Levi’s because they genuinely love and respect the brand, which is super important, and then we try to give them as much liberty and freedom to express themselves because that’s what we want. Their individuality and expression of their character and their identity.

There will be certain parameters that we will give them. For example, if they’re messing with the 501, they will have to use 501 fabric and it will need to be a button fly. Certain rules on branding or the tab have to stay in place in order to protect the identity and legacy of our brand, too.

Adam Katz Sinding

What do you think is the biggest denim trend right now?

First of all, just the general resurgence in denim has been amazing. If you scroll back a couple of years and read the business headline, it was like the denim apocalypse. Denim was on a downward spiral and I think it has finally come back. The resurgence of vintage denim and authenticity is a big reason for the comeback as is this mixing of high and low (a la Vetements).

In a world with so much choice and so much noise, picking something that is authentic and has a true and honest character is best. Obviously the clothing choices you make are a reflection of your own character. Skinny, ripped jeans have been big for a while, but now we are seeing a transition into baggier, more tapered fits.

Lindsay Armstrong

Do you have any specific people or trends in mind that have helped denim’s revival?

Coachella, rappers, this huge shift towards the West Coast and Los Angeles being an incredible fashion influence on everybody. A lot of musicians are blurring the lines between music and fashion and becoming fashion designers themselves, like Kanye. I think that is super important and super relevant.

What’s the first thing you think guys should look for when shopping for denim?

I think they should look for something they are comfortable in. Comfortable as in comfortable in character, not just soft, loose and baggy. I think they should look for a brand and place that they trust. They should start with simple, nothing too elaborate, and try on as many fits and sizes as possible.

Most guys tend to fix on the size they were when they were in their early 20s or teens. They’re like “Oh yeah, I’m a 32.” Sadly, sizes tend change the older you get…

Adam Katz Sinding

What’s a style faux pas?

Generally, I think trying too hard. My general rule of thumb is to be as playful as possible but keep it simple.

What’s your go-to denim?

I would say maybe 300 days in a year I’m wearing some form of 501 jeans. I also love the 505. Today I’m wearing a vintage orange tab biggie 606, which are almost 50 years old themselves. I cant think of many clothing items that get more treasured and expensive with age.

Fashion is notoriously cyclical, but what seems to sustain denim’s relevancy in spite of it all?

I think you have to remain relevant and you have to change. Whilst denim has been the continual thread throughout Levi’s history, I think the fact that being adopted by the youth, which drive generations to change, enables relevancy and by extension longevity.

As Charles Darwin said, “It’s not the strongest that survive but the ones that are most adaptable to change.” So you have to be willing to change but keep your core identity and values as a common thread throughout.

It’s travel season, so make sure you amp up your airport style game with tips from globe-trotting fashion photographers. 

Words by Nico Amarca
Fashion Editor, North America
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