Do You Dress Like A Boomer?

I was asked “Can you provide any advice on how Boomers can look more up-to-date?  I am working with Millennials and Gen Xers.  I want to fit in better and not appear old!”  That’s a great point and very timely!

First, let me say that there is no way to turn back the hands of time.  Boomers will never be 30 again.  Honestly, that’s a blessing.  With all the wisdom gained from experience, you don’t want to go back and learn some of those hard lessons again.  However, even though you can’t be 30, there’s no reason you can’t look younger.  Don’t get me wrong, I’m advocating looking “age appropriately” younger. You know, giving off that young vibe without trying too hard to appear a youngster.

While channel surfing the other day I came across some old footage from comedian Jeff Foxworthy.  I didn’t really know him but I had heard the catchphrase that made him famous.  He’s the guy who did the “you may be a redneck if…” bit.  I went online to check him out and he has some pretty funny stuff.  One was “redneck fashion tips.” That was really funny.  But I digress.

Anyway, picking up on Foxworthy’s bit; I decided to offer up my tips for addressing this Boomer appearance dilemma as Foxworthy would.  So, here goes…you might be dressing like a Boomer if…

1.) You might be dressing like a Boomer if you wear dress shirts untucked

As much as you think this makes you look young, it doesn’t.  Dress shirts have long tails because they are meant to stay inside your pants.  When worn untucked, it looks sloppy and like someone who wants to be cool but has no clue.

If you choose to wear your shirts untucked, buy shirts which are made to be worn untucked.  These shirts tend to have a blocked bottom and they are cut shorter in length.  Also, when wearing shirts untucked, shirts should hit about mid-zipper. If your zipper is covered, the shirt is too long…tuck it!

Some people say an untucked shirt is too short when it hits just below the waist. In my opinion, it’s only too short if it stops above your belt loops.  Of course, when your belly is showing, that’s a sure sign it’s too short.  Use this guide to determine the correct shirt length.

2.) You might be dressing like a Boomer if you only wear collared shirts

If you’re in a relaxed setting, either work or casual, consider taking a break from the collared shirts.  If you are wearing them button-downed, starched, pressed, and tucked, there’s no doubt you’re a Boomer.  Instead, do this…wear some tees.  Now don’t misunderstand.  I’m not talking those that come in the 3-pack.  Those are underwear.  I’m talking tees that are made to be worn as outerwear.  Here’s how you tell the difference.

Tees meant to be worn as outerwear don’t come in a multi-pack.  Also, they have one or more of the following…

  • a chest pocket
  • a graphic design
  • a visible brand logo

Wearing a tee can certainly give a more youthful appearance.  There are also long sleeve and heavier weight options available for winter wear.  So you can wear them year round. If you want to dress it up, wear your tee under a sport coat with jeans or dress slacks.  Go ahead, give it a try!

3.) You might be dressing like a Boomer if you wear “dad” jeans

If you’re asking “what are dad jeans?” that means you’re probably wearing them.  Every time you wear them your co-workers are thinking, “here comes the old man!”  Ditch the dad jeans and pick up a pair of slim or slim straight, dark washed.  If you are blessed with big thighs or carrying around a few extra pounds, then buy Relaxed fit.  No worries.  Just make sure they are dark wash and a more modern fit. Not those you do yard work in.

Want to really step up your casual dress game and blow your co-workers minds, get a pair of white jeans.  Hello white jeans, goodbye Baby Boomer image! These are an immediate image game changer.  For some of you, this may take some guts but take a chance.

If you really want to go for it, forget that stupid “no white after Labor Day” rule!  Wear heavier weight white jeans in the winter.  Just be sure you pair them with darker colors (e.g. black, brown, grey).  Please don’t pair pastel shirts and white jeans in the winter.

4.) You might be dressing like a Boomer if you only wear sneakers when exercising

Back in the day sneakers were for playing sports.  Looking back at those old Chucks, you wonder how anyone who wore them can still walk! Those kicks had no support.  If you think sneakers are still only for exercising, then you’re definitely dressing like a Boomer.  Sneakers can be stylish and comfortable.  They range in style from an athletic look to sleek, almost dress shoes.  It really depends on your workspace and how you pair them; but, certainly, add some sneakers to your business wardrobe.

5.) You might be dressing like a Boomer if you only wear sweatpants when working out

Just like sneakers, sweatpants were limited to the gym or doing laps around the football field.  Not any more!  Again, depending on your work setting or after work environment, rocking some fitted sweatpants with a nice tee or dressier sweater will make your younger co-workers wonder who the new young buck is around the office.

I can’t stress this enough.  You are not wearing a sweat suit to work.  These are fitted sweatpants with one of the outerwear tees we discussed earlier.  To be clear, this tee does not have a Nike swoosh or a Reebok logo.  This is not gym wear.

Read this post for more on this trend called Athleisure.  (But do it later. Stay with me here.)  Here’s an example of the look I’m talking about.

6.) You might be dressing like a Boomer if you only wear black shoes with your blue pants

I love a blue suit!  I think every man should own one and wear it often.  However, want to update your look?  Throw on some brown kicks.  Light brown in the summer and darker brown in the colder months.  This combination will automatically update your look.

Why?  Because most Boomers were taught to wear black shoes with a blue suit.  Don’t get me wrong, black shoes with blue pants will never go out of style.  However, blue and brown is a different look and you’ll be surprised at how much of a difference it will make.

7.) You might be dressing like a Boomer if you won’t give up the shirt and tie

Want to show the young guns you got it going on…trade that tie for a turtleneck.  This not only gives you a more updated look, but it can also hide some of the neck issues associated with aging.  Not to mention the fact that ladies love turtlenecks! I can’t count the number of times women say to me “why don’t guys wear turtlenecks more often?  I love them!”

8.) You might be dressing like a Boomer if you haven’t bought a new suit, sport coat or slacks in the past ten years

Ten years is not a magic number, just use it as a rule of thumb.  Most likely if it’s over ten years old, it has a looser fit and the jacket hangs almost to your knees!  A sure way to look old is to wear old styles.  Modern cut clothes are trimmer, shorter and more form fitting.  A looser fitting suit will not only add weight to your frame, but it also signals “old school.”  Get a newer, trimmer fit suit, sport coat or slacks and you’ll be amazed at how much younger you will look.

9.) You might be dressing like a Boomer if you only wear wide, silk, rep ties

Silk ties have always been classy.  That’s the problem. They have been classy for years.  Break up the pattern.

Rotate some wool and knit ties into your wardrobe.  You’ll still look great but the texture of a different fabric will add new life to your look.

There’s nothing that screams old like a blue suit, white shirt, and red or blue rep tie.  Stop it!  Try something like this instead…


Also, your tie width should be consistent with your lapel width and shirt collar length. Strive to have them all in sync.  When wearing a jacket with a 3.5-inch lapel, don’t wear a 2.5 inch “skinny” tie.  The proportions are out of whack and it will look strange.

10.) You might be dressing like a Boomer if you over accessorize

In order to compensate for feelings of being uncool, some guys overdo it on the accessories.  It’s OK to accessorize, just don’t go overboard. I see lots of guys trying to modernize their look by wearing a pocket square, flower lapel pin, wild socks, and bright ties together. It’s way too much!

Go ahead, add a pocket square.  It will brighten up your outfit and update your look. In fact, add some colorful or patterned socks.  But whatever you do, don’t fall into that lapel flower thing!  I’m not sure who started that but personally, I’m not feeling it.  It’s good to accessorize and add some personality but only one or two statement accessories, at most.

Be careful not to go overboard.  You are a professional, not a peacock.

There you have it!  My self-test for guys who think their appearance is sending the Boomer vibe when they’d like to fit in better with their Gen X and Millennial work associates.

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