Dress-Up Wardrobe Update

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I decluttered my closet about a year after retiring early, but kept some of my ‘execu-wardrobe’ for board meetings and special occasions. Then the pandemic hit and I stopped dressing up for much of anything. I just needed to put a collared shirt on over my fleece pajama pants when I was on Zoom.

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Related: FIRE Station FUN – Decluttering Work Clothes

Now I’m finding I need to go shopping for dress clothes again.

I went out-of-town for a board meeting this week and felt like most of the ‘work’ clothes in my closet are looking a bit old. I haven’t worked full-time in 5 years and probably bought most of them 2-3 years before that. That’s 7-8 years old. Some are a bit frayed here & there, or the dress shirts have been through the starchy dry cleaner too many times.

Before my next round of meetings, I think I will get a couple sport coats, 2-3 nice pairs of pants, and a few new button-down shirts. It would be nice to have everything in my ‘dress up’ wardrobe up-to-date before the holidays and other events pop up.

How much of a ‘dress up’ wardrobe do you keep in retirement?

5 thoughts on “Dress-Up Wardrobe Update

  1. Retirement dress needs go in waves. Early on I retained much of my wardrobe out off habit. My consulting work made use of the closet. Then, “neighborhood casual” became my way and I weeded out half of the dress clothes. Next “pandemic comfy” ruled my wear. Now I’ve moved to a 55+ community with dinner at the clubhouse available 4 days a week — collared shirts, blazers, slacks, and shoes preferred. Who cares if some of my stalwart “dressies” have the character of age about them? For certainly the character wearing them has age!

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    1. It looked like you moved … that’s great! That sounds like a fantastic set-up with a clubhouse restaurant. I just need enough new ‘dress clothes’ to look relevant at board meetings & social events.

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  2. I still have all my work wardrobe. Most of my consulting is remote online but when I have a speaking engagement, monitor court civil trials or give a presentation I dress properly. I dress up 15-25 days each year. I do need to update my closet

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    1. 15-25 days a year. I guess that is 1-2x per month. I’m probably about the same for frequency: 3 boards x 4 quarterly meetings / board dinners + special events.


  3. I haven’t retired but I don’t have many nice clothes in my closet. My work doesn’t really require me to where anything fancy since I don’ really need to see clients.

    I have one tailor-made suit I bought ~3 years ago but that was because I was anticipating going to a lot of investor / real estate conferences where first impressions matter. I didn’t make too much out of it though because 1) COVID started not too long after, and 2) it turns out people pay attention to you *more* when you’re dressed like a slob at conferences due to some weird psychology.

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