When Are You Willing to Sacrifice Comfort for Style?

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There has always been a balance between comfort and structure in workwear — and it used to be pretty clear when you could get away with prioritizing comfort versus when you needed more structure. Quiet day at the office with no meetings? Pajama pants and flats. Big court appearance? Pantyhose, skirt, and heels.

But… comfort has kind of won, hasn’t it? In 2026, when are you still willing to sacrifice comfort for style?

At this moment in time, I think the pantyhose, skirt, and heels are far less likely to be required. Pull-on pants are everywhere (including reader favorites from Athleta, Nic + Zoe, and Eileen Fisher), flats are more common than ever, and I even vaguely recall a reader discussion where everyone was ready to burn their underwire bras. (No? Just me?)

So here’s the question: When are you still willing to sacrifice comfort for your appearance or the vibe you’re going for? Will you pull out the Spanx for a big day and put on uncomfortable heels for an important event, or is it a resounding “hell no”?

For my own $.02, I am exceedingly reluctant to sacrifice too much comfort. Part of it is because there are so few times that it’s actually called for that I’m almost rusty at them. Walk in heels at my friend’s wedding? I’m more liable to fall. Pull on Spanx for a 12-hour day at an alumni conference? I think I’d be more likely to duck out after the official programming, change into yoga clothes, and then rejoin everyone for drinks at the hotel bar. I will still wear underwire bras, but let’s just say even that is much more of an occasion than it used to be.

Over to you — when are you willing to sacrifice comfort for style? Are there still occasions when you feel that looking polished is worth a little discomfort?