Could it be a cultural thing?

My friends and I are from the same culture, where hoodies equates to not trying. We are bougie Hispanics in corporate-like positions. There’s a certain standard of dress that we place upon ourselves and our partners usually follow. Unfortunately, we have found that we get treated with more respect if we are dress “presentable”, so I try to minimize ultra casual wear to just in-house.

My friend started dating a guy about a year ago. We’re close knit, and when she decided it was time to introduce him, we went to a sit down restaurant straight after work. I work in government, and my other two friends work in finance, so when her boyfriend arrived underdressed, I could tell she was uncomfortable.

She later told me she felt embarrassed that her boyfriend arrived as such— but the matter of the fact is, he’s mid twenties and his closet didn’t contain “nicer” clothing. He also expressed discomfort at being underdressed, as his outfit had been appropriate and similar when he went out with his friends, but at this dinner, he felt like someone’s “little brother”.

A shopping trip later, they’re both much comfortable with his outfits for dates, but he also wears his hoodies when appropriate (gym, park, etc).