My ex-wife would occasionally do this as well. If a vacation was approaching she'd buy me a set of shorts "in case I wanted to wear them", or sometimes when we were shopping together she'd point out shorts she thought I'd look good in. She did this despite the fact I always wore Speedos, and knew I enjoyed wearing them. She never suggested or bought new trunks I'd actually have considered wearing.
She didn't like me wearing Speedos and her argument was always that they were "embarrassing" or "too revealing" despite the fact she always wore 2 piece bikinis on vacation. The level of double standards! One of her lines that made me laugh the most was that "other women can check out your package" - yes, and other men can check out your cleavage? What's your point? I once told her that if she expected me to cover up in shorts then I expected her to wear a t-shirt or full body sarong. Of course, she never.
I will say though that these exchanges were non-existent in the 80's and 90's when we were together and Speedos were a little more popular, and both of us had been on our respective swim teams at college so she was more than used to seeing me in Speedos and was okay with it. It was only really post-2000 when fashions changed, and our relationship deteriorated that she started using Speedos as an issue to pick at.
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