Does It Matter What You Wear When You’re Laid Off and Looking?

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I was looking back on some of Corporette’s early hits the other day and reflecting on how different the world is today. One of the first ones that came to mind was a reader question on what she should wear while laid off and looking. I started wondering: in 2026, does it matter what you wear when you’re laid off and looking? Beyond what you’re wearing — does it matter how you comport yourself, at all?

The original query: a laid off Silicon Valley executive had run into a colleague at the grocery store looking a bit schlubby (outfit above, much of it sourced from her son’s closet), and she was wondering what else she should have been wearing.

My advice at the time: I suggested she burn the scrunchie, then told her she should be wearing jeans, a simple tee, and a blazer.

What I’d say in 2026: I still think jeans and a blazer are a fine look, to be honest, but let’s face it, a lot of people aren’t wearing that these days. What if she had met her colleague at the supermarket and she was wearing a Spanx set? Workout clothes? Literal gardening clothes with dirt on them?

I don’t think any of us would really balk if we saw a colleague wearing that outfit. I still wouldn’t want to see, say, an older man I’d worked with in too-tight, too-short shorts, or someone in a clubbing outfit at 7 AM, but otherwise… it’s hard to imagine.

Then I started thinking about all the other ways we “see” former colleagues now — in online forums and on text messages, as well as shared stomping grounds like a local grocery store. Does any of it matter now? My old advice would have been to not express personal opinions! Certainly not strong ones on religion or politics! For God’s sake don’t be racist or homophobic!

That said… a lot of the former lines in the sand for general comportment have gone out the window thanks to the blowback to cancellation culture.

What are your thoughts, readers — is there anything a former colleague could wear, say or do that would make them unhireable or even undesirable assuming you know the right people and have the right pedigree?

Psst: Fun fact: I had dinner with the original writer, Lisa, a year or two later while in town for a conference and still think of our dinner fondly — and it’s hard to believe any outfit would have turned former coworkers off because she’s just one of those people who genuinely seems smart and funny and eminently capable. She’s still blogging today!