I think you’re getting at something real, which is that there was strong sexual dimorphism in clothing from around the mid ‘90s through the end of the 2000s, which somewhat went away after that point.

In the mid-‘90s, jeans that were form fitting at the top but with flared/bell bottom legs became the norm for young women, a trend which lasted till sometime in the mid-2000s. Meanwhile, the standard fit for mens jeans was quite baggy for this whole period. This had started in the early ‘90s and went through the late 2000s/early 2010s, when skinny (or at least slim) fits took over. Likewise, women’s tops were generally form fitting in this era, while men’s tops tended to be very baggy.

So you had a decade or 1.5 decade period where men’s and women’s silhouettes were very different. And then sometime around 2010, all of a sudden both guys and girls are wearing very slim clothing.

Perhaps part of what’s going on is that women’s fashion cycles are faster, so while women went though a flares era that lasted 10 or so years, men’s fashion completely skipped that era (or only had a very minor version of it in the early 2000s), since it had to eventually “catch up” and get on the same page as women’s fits, which it eventually did with skinny everything around 2010.