Have you heard? Fifth&Brannan is hosting a launch event in San Francisco. Want to attend? More details here.

If you’ve been reading this site for any length of time, you’ll know I’m a bit anti-fashion, meaning I’m against going 100% trendy, or following trends to the letter because, well, they pass.

To be more accurate, fashion trends (re)cycle every 20 years or so. Have you noticed?

When I lived at home, my mom always mentioned to me when she saw certain celebrity trends on TV that were familiar to her. It always went something like this:

“When I was younger, we were all doing that! I can’t believe that fashion style is coming back…”

Fashion is cyclical and can look dated after its popularity deflates and until its next refresh. Classic style, on the other hand, stays relevant no matter the year.

jnco jeans vs 70s flares

Case in point: Early- to mid-90s, wide-legged jeans were really trendy in certain circles. Do you remember that? They were huge. And with each year that passed, they became progressively hugererer. This denim company called JNCO had the largest pair of pants I’ve ever seen. They were called the Twin Cannon. The cuffs had a 26″ circumference. wtf? The cuffs covered your whole shoe and you basically looked like you had no feet.

Twenty years prior, in the 70s, flared denim was very popular, mimicking the same silhouette around the ankle.

That’s what I’m talking about when I mention the cyclical nature of fashion. Sure, the pants aren’t EXACTLY the same, but they’re closely related, both trendy, and they’re both… out of style.

Now contrast this with something like the basic fit of the Levi’s 501. How many times has that silhouette changed since the early 1920s? Maybe a little, but not very much. The 501 is a classic because the fit is just right, and it hasn’t changed much in its 90-something year history.

How to avoid being a tragic trend chaser by sticking to classic looks

Classic style, circa late 1960s

This image is from the 1960s (source:Take Ivy*) but could easily be mistaken for a photo taken present day

I’m not completely anti-fashion trend, though I have a couple rules I follow when dabbling in them.

Don’t go full-on trendy

Adopt trendy ideas and elements of popular items, but don’t completely replace your style. When you do that, it looks contrived and unnatural, almost like you’re trying too hard, which you probably are.

Diversify your classic look with trendy elements

So apparently man jewelry is trending a bit the past couple years. Things like manly rings and bracelets and things. I’ve always liked how certain bracelets looked but I could never really find any affordable options before the markets started producing them to capitalize on the trend (perhaps they caught on to Street Etiquette?)

When I found this leather and metal ID bracelet J.Crew put out, I got one, knowing that I’m pretty much indulging in a trend, but that it was okay because I’m just using it to accent my already personal look. This brings me to the next point.

Adopt trends because you love them, not because the cool kids are doing it

This is a big pet peeve of mine. I hate seeing people chase every single fashion trend out there in the hopes of looking more chic or being the envy of their peers. Style is personal, it’s intimate. It should reflect who you are. If you’re chasing trends left and right, what does that say about you and your personal style? Not much.

If you find a particular trend you like, then by all means, adopt it. Kinda like me with the bracelets. My watch gets lonely from time to time, so I wear two or three bracelets because I like how it looks. I’m not doing it for anyone but myself. I’m not doing it because People Magazine told me the new “in” thing is wearing man bracelets. I just do it because I like it, and I make it look good. Simple.

Don’t ever forget your personal style says a lot about you, and trend chasing isn’t doing you any justice.

Learn to spot trends and decide if it’s really you or not

Excessive pants rolling (no matter the occasion) seems to be a trend. I understand if you’re walking along the shore at the beach, but if you’re at the mall? I don’t think that’s necessary. Half-tucked button-up shirt? Kind of a trend. Boat shoes? Classic item gone trendy.

I’m not pointing these things out because they’re good or bad; that’s for you to decide. The point is, figure out if this trend you follow is really you or not. If you’re trying hard to be the cool cuffed-pants guy, but you look doofy doing it, then maybe it’s not really you.

Take a long hard look at the trends you follow and see if you can really pull them off. You might need to start being honest with yourself, or, who knows, maybe you look super sexy and can pull of trend X quite well. If that’s the case, and it meets the rest of the criteria above, well then awesome!

Know what looks good on you

I know a couple heavyset dudes who love rocking the Levi’s 511 denim skinny fit. If you have to buy a skinny fit model in a size 42 waist, maybe you shouldn’t be wearing denim labeled “skinny fit”. This goes along with the whole idea of being honest with yourself. If you want to complement your physique, stuffing yourself into skinny denim isn’t the answer.

Maybe they really like the trend of skinny jeans, who knows. The thing is, the trend doesn’t like them, and maybe it’s something they haven’t realized yet. Dress for your body type and you’ll always look your best.

There you go, a couple guidelines on how not to look like a complete trend chaser, while at the same time, staying true to yourself and finding a classic style you can personalize and make your own.

Thoughts? Questions? Leave them in the comments below.

Oh, and RSVP to our Fifth&Brannan Launch Event in San Francisco!


*Find Take Ivy here (affiliate link)

PUBLISHED April 28, 2011


Barron is the Founding Editor of Effortless Gent and the Cladright Association. He's from San Francisco but currently living in New York. Connect with him on Twitter, Facebook, Instagram, or Tumblr.



  • Brandon

    Loved this article, it definitely fits my philosophy of style. The JNCO’s were a throwback! Everyone, including myself, wore those in high school. I used to make fun of kids back then for wearing pants that were tighter than JNCOs, but looking back they were probably much better dressed than I was.

    I am still mind-boggled by the skinny jeans trend (I am talking about the guys basically wearing denim leggings). who actually likes how skinny jeans looks besides other men wearing skinny jeans? In my experience, both women and men-not-wearing-skinny-jeans find them ridiculous.

    • Anonymous

      Brandon, if you were a hipster, you would have gotten the welcome pack, which includes an indoctrination tonic, allowing you to appreciate skinny jeans and unkempt hair.

      • http://effortlessgent.com Barron

        Is the ‘indoctrination tonic’ a can of pbr?

        sorry. stereotyping.

    • http://effortlessgent.com Barron

      Hey Brandon,

      Admittedly, I had a pair too. Not sure if that’s a good thing to admit on here, but hey I keep it real. I’m not much of a fan of the skinny jeans either. I do like a good pair of well-fitting denim, but jeggings? That makes me nervous. Glad we’re on the same boat.

  • Glen

    What if “classic style” is becoming a trend? This is my biggest fear, like what happened to boat shoes. Then how will we be able to differentiate between the well-dressed and the hipsters?

    I rocked JNCOs in middle school. I remember buying a pair because the girl I had a crush on embarrassed me by telling the whole class I wore “butt-tight” pants. I bet she’s married to a guy who wears skinny jeans…

    • http://effortlessgent.com Barron

      I thought about that. The thing is, it will always be a classic, so when that trend of being classic fades, and the trend jumpers hop onto something else, the folks who’ve always had that classic style will always be there.

      Crazy word play.

      Boat shoes are a good example. They’ve trended a lot the past several years, but when the markets move on to something else, boat shoes will still be a classic, because they were born out of purpose and the people who were meant to use them will still be using them (meaning, people on a boat).

      • Maxman

        I live in MA (New England) and boat shoes are a classic that EVERYONE wears regardless of if you are on a “boat”. This def is a trend in other areas, but in New England, i think boat shoes are as american as apple pie, lol. Great post by the way. I am by no means adnishing your comment, just assing a caveat. 

        • http://effortlessgent.com Barron

          Yep, makes sense. Didn’t mean that ONLY people on boats will be wearing deck shoes, but you get what I’m saying. :)

  • Retropian

    great post, especially since you mention my own pet peeves: rolled up pant legs and the half tucked shirt. Both come off as way too contrived. I mean unless one is on the beach or a dock don’t roll, and either leave the shirt untucked or not, but don’t tuck in one half (eye roll here). LOL. You are always spot on Barron!

    • http://effortlessgent.com Barron

      Haha, I’m glad to know I’m not the only one that questions these style choices. I never got into the pant rolling though it seems the whole world is doing it. Then again, I think I had my own variation in 2nd grade. I think back then it was called pegging? Anyway, I digress.

      Thanks for the comment :)

  • http://twitter.com/Dr_greens bt

    You lost all creditability when you posted a pic of  the 60s that “could be people today” except that they  look like skinny jean wearing losers. I would beat up all those kids and take their lunch money.

    Fucking pansies. You dress like girls or hipsters, or idk what.

  • http://twitter.com/iamdalea Dale Allen

    I loved this! You pretty much reiterated things I have been preaching for years! Be your own person and know what works for you. I see everyone wearing skinny jeans but they are NOT for me, I simply don’t like how they look or fit. I prefer my pants a little more roomy not too big but with some room. I am big on dressing timelessly and adapting trends that I like and which work for me!