Search Results: boyfriend to wear

So I'm planning in detail what I should wear when I meet my boyfriend and I honestly can't decide which look I should go for.
I have a good amount of time to decide but I'm still curious what you all think
I like that there's an age gap so I kind of want to embrace my young side, make it even harder for him ya know?

So my boyfriend and I come from pretty different worlds. In HIS family he only has 1 brother, and his family sees each other nearly daily as almost all of them within 30 minutes of each other. So typically no one cleans up their houses when having a visit. And no one dresses nice, even on holidays it's almost like a normal day with extra food. Even on Thanksgiving or Christmas no one sits down and eats together, it's a "eat as you come" deal and no one dresses nice.

My family is very different. I am the second oldest of 12 children. Everywhere we go people look at us, openly stare, and even actively point and count. So our mother has always made sure we dress nicely in public. No clothes with holes, no sweat pants, nothing that even LOOKS old and faded. Even for just a trip to Walmart. And beyond that, our family isn't "close" like hism we're more the type to get together on SOME holidays per year IF even that. One year we might see our grandmother twice, the next, not at all. SO when everyone DOES get together, it's an event. Everyone sits together, everyone dresses to the 9's, we use the good China, etc.

Yet everything we spend a holiday with my family my boyfriend of almost 5 years STILL complains about having to dress nice because "it's just my family". In his mind he couldn't IMAGINE his family judging him for wearing a shirt that has holes in it to Thanksgiving. However in MY family we still think about that time my Uncle's wife wore sweat pants to Thanksgiving 3 years ago and she has already been uninvited to any future holidays or weddings for the offense.

Is it wrong to expect him to dress up a little on holidays at least?