I think I need to start wearing suits to work much more often.
My boss always does, except certain Fridays. I almost never do. Mainly dress pants and shirts with a sweater or vest. He's not at all fussy, after my abdominal hernia surgery I wore loose track pants to keep pressure off the site. And I often wear black athletic shoes like Sketchers.
I think I need to upgrade my image. I work across the street from a Macy's, Nordstrom, and there are various other men's shops close by.
Upgrade or comfort?
= new reply since forum marked as read
Perhaps you could mix comfort with a slightly more dressy image?
Your boss sounds like a cool guy, with a good fashion sense.
Go for whatever look you want! It will be good for your self-esteem, no question on that.
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... when I was visiting, he and my sister threw a "dessert & champagne" party for their longterm
friends who had been in the same MBA program as my BIL. Their most interesting friend had been
'the hippy" of their group (and that was a very relative term). He told me that he often thought the
biggest mistake he had made in his career path was selling his drum kit so that he could complete
his MBA (this was a man who, at that point, was making a fairly healthy 6-figure salary). He once
drummed on Chuck Berry's tour (never met Chuck, who would just show up at the actual gig).
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His first job interview (post-degree), he wore his only suit and his best (say only) nice dress shirt --
which had Porky Pig and Daffy Duck embroidered quite boldly on his lapels. 
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The interview actually spoke to him for a coupla minutes, but stopped abruptly and said, "You
know, due to your attire, I've been assuming you were here for a CREATIVE job. The suit's OK,
but before you go to another interview, invest in an actual dress shirt."
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Years later, he had been passed over for a VP slot several times. One of the senior VP's took
him aside and told him to look around at all the senior execs. "What color are their suits?"
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"Navy-blue or gray, both colors pin-striped."
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"What color are YOUR suits?"
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"Green or brown."
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For the second time in his career, he was told to invest in his wardrobe.
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He doesn't think it was the ONLY nor maybe even the MAIN reason, but that year he was
given a VP position with his agency.
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So, it depends on your circumstances. If it weren't a factor, I wouldn't be averse to wearing
Bermuda shorts and a propellor beanie.
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