Great careers don’t start at your desk.
They start at your closet.
It’s true! What you wear to work determines what co-workers think of you, or don’t. You may want to stand out from the crowd, but in these scary days, when management is selling off loyal employees like so many chipped dishes at a garage sale, a case could be made for blending in.
That case is made in a recent “Ask Vanessa” column in The New York Times. Ali, from Sydney, Australia, asked fashion guru Vanessa Friedman, “Should I dress like my younger co-workers?”
Concerned that she was wearing traditional office garb at lunches, dinners and parties, while her co-workers were dressed in the “jeans, knits and sneakers they wore all day,” Ali was afraid she was advertising herself “as a relic, no matter how well the clothes suit me.”
Vanessa took the question seriously.
“There is a world in which looking old or, more importantly, looking like you are stuck in older ways, becomes a handicap,” she writes. “It suggests you can’t keep up with technological advances.”
No question, dressing like a loser or a Luddite could be a career-ender. On the other hand, “If wearing jeans and sneakers to a work event makes you feel you are faking it, those around you might also get the sense that you are faking it.”
Whether you’re faking it or making it, copying the clothing choices of your younger co-workers will not be easy. If there is a common thread, it’s athleisure, but there are subtle differences. Consider footwear. Gen X is loyal to Vans, but Gen Y insists on Adidas. Gen Z gets their gym wear from Lululemon while Gen Alpha insists on Alo Yoga. (Gen Beta wears diapers, a fashion choice you don’t have to worry about — yet.)
Since I am widely considered to be a fashion influencer, let me influence your wardrobe selection with five bold statements.
No. 1: “I’m chill, dude.”
Take the athleisure look a step further by coming to work in your PJs. A silky nightgown or a fancy lounge set proves you are so confident about your value to the company that you don’t bother getting dressed in the morning. If you’re a remote worker, it’s what you wear anyway, so why not bring all the benefits of working from home to the nightmare that is working at work? Classic long johns show that you affirm traditional values, especially when matched with gum boots and a nightcap.
No. 2: Ready to Fight.
Show you’re ready to fight for whatever hairbrained mission statement that management has dreamed up. Pin an “HR Eagle” ribbon on your quarter-zip to prove you are totally aligned with the latest HR diktats, like the prohibition of personal plants on your desktop or restricting “Bulletstorm” from office computers.
A suit of armor also says you’re ready to do battle, but the clanking of your chain mail and gauntlets could make it difficult to slip out of work early.
No. 3: “That’s right — I’m a star.”
Prove that you’re a top performer by arriving at work in red-carpet finery. Judging by recent photos from the Oscars, the Emmys and the Armenian Music Awards, female nominees are showing more skin with peek-a-boo body parts popping out, front and back. (Male nominees are more likely to be encased in leather and chains, a look not to be recommended unless you are in the IT department.)
No. 4: Show Your Age.
According to “Ask Vanessa,” when choosing what to wear at work, “the best solution may be to lean into your age and the experience that brings.” Let young trendsetters get their fashion cues from “Emily in Paris” and “Euphoria.” You go total “Bridgerton.” That means tailored waistcoats and velvet jackets for men, while women arrive to work in feathered headbands and empire line gowns with chiffon draping. Manipulative evil characters like Cressida Cooper and Jack Featherington may be hated in the world of Bridgerton, but your management will love them.
No. 5: The Naked Truth.
Show you are so excited about getting to work that you don’t waste time getting dressed. You’ll save beaucoup bucks by not shopping and never have to worry about what to wear.
Even better, the shock of seeing you in your birthday suit will so traumatize your managers that their little brains will erase your image altogether, letting you go through the workday totally invisible.
It’s the best fashion advice of all. If they can’t see you, they can’t fire you.
Bob Goldman was an advertising executive at a Fortune 500 company. He offers a virtual shoulder to cry on at
bob@bgplanning.com
Copyright 2026 Creators Syndicate Inc.