Do you often dress your sims in clothes from the opposite gender?

i've done it once or twice. i'd do it more if 90% of the meshes didn't deform the opposite frame.

Nope. Cuz what would my guy sims wear anyway? XD There's only like a few nice female sweaters that look okay on males but that's about it.

I would more often, but I find most of the clothes on the opposite gender are really awkward and just don't look right. Especially male clothes on the feminine frame; the shirts are too lumpy all over, the pants have like, a really deep dent in the fork, and the shoes make their feet unnaturally thin. It's kind of annoying too, because some pants and shoes have had their gender tags removed completely, so they show up without adjusting the tags, and I get excited to use them and then I'm let down cos they look so bad on :(

No, it's just not something I think about. What's funny is I often where my husband's clothes especially his t-shirts. But I just don't think that way with my Sims? Might have to consider this because a big comfy t-shirt is always a thing in my life.

Sometimes. Not with tops, though. They always look weird when you switch them idk what it is

There are a couple of accessories that I turn the flag off for, but almost never for clothing. If I'm being honest, the work for that gender conversion was done very poorly, and I don't like for my sims' bodies to be deformed in the clothes they wear.

There's some male suit jackets and tie sets that look great on some of my femalre Sims, and Caleb looks hot in the female leather pants.

Never.

I tend to go overboard with the whole clothing settings. I do tend to use more of the male clothes for the women than the womens clothes for the men.

The vast majority of the clothes from the opposite gender deforms Sims to such an extent that I don't like it. If it didn't I would make more use of this feature. The most annoying thing being that the hips and knees of females sink when you put any male clothing on them. With female clothes on male Sims it's the chest area that looks off.
That said, for certain Sims these changes to the body frame might actually work well with their story or personality.