Twitter isn’t the most forgiving place. Whenever I see some poor soul getting dragged over the proverbial coals on the fickle platform, I ask two questions. Is the dragging warranted? If yes then proceed with popcorn and sit back and enjoy the show. Is it mean-spirited? If so then pour a drink and enjoy the show. Just kidding, I don my keyboard warrior red cape of support and add my two cents.


Last week, legendary music producer Timbaland disrupted our pandemic Friday posting a photo of himself with a caption which read, “Good afternoon, how is your Friday going?” Harmless right? I thought so too however, I first became aware of the post via the ramblings of the Millennial gatekeepers of Twitter.  After falling deeper down the rabbit hole of retweets, I witnessed the digital fashion police targeting the musical meister. Commenters lambasted the “youthful” appearance of the outfit from the man who solidified Justin Timberlake’s solo career and subsequent Black card.


The Offending Outfit


One by one people took pleasure in roasting the icon on the fit, style, and even accusing him of being a middle-aged uncle desperately trying to stay relevant. The backlash was ruthless and I must admit, some of it was downright hilarious. We love you, Timbaland!

Here are a few tweets that caught my eye.






When it comes to style as men mature, the mantra should go big or go home! We must stay wary of the trendy styles of twenty-somethings and if you’re over thirty-five, your style reference should not be someone who had a cell phone in elementary school. Leveling up your wardrobe is about broadening your fashion choices ensuring that your clothes represent who you are today, not who you once were.



The truth is, there is more than enough evidence to support that some men start dressing poorly in their twenties and if that was your story, it may have been all downhill from there. If you went from pagers, to flip phones, to iPhones, your style should have also evolved right along with technology. There are currently so many style influences (Idris Elba) to pull from them that are not only age-appropriate but indicative of the culture in which you identify.




I don’t expect Timothy Mosley aka Timbaland, a guru in the world of Hip-Hop, Pop, and R&B to dress like Mr. Steal your grandmother, but no man should look like he’s trying to recapture a moment that is long gone.  Maybe Timbaland should have given Will Smith or Diddy a call. The fashion faux pas, however, was only one viral misstep for the superstar. I always say to most men of a certain age that the best is yet to come. That includes a bevy of clothes options that are eye-popping and puts even the most discerning millennial to shame.



If you’ve had a few trips around the sun, life has undoubtedly gotten in the way. The journey of Timbaland was no different.  An addiction to pain killers, a divorce, and jaw-dropping and transformative 150lb weight loss are just a few things the music juggernaut had to overcome. I think we can give a pass to the man who gave us iconic albums from the likes of Aaliyah and  Ginuwine.




I’ll close out by defending my fellow Gen X brother and say that regardless of your age, following trends is neither fashion nor style. No one is going to look back twenty years from now and say the comeback dangling earrings younger men are sporting now (an 80’s trend by the way), was classic style. Timbaland however, will always be timeless, and the man who provided my generation, Millennials, and Gen Z, with a hell of a soundtrack to their lives. I bet your Uncle can’t say that.