It’s my belief that most men who struggle with what to wear is that they simply don’t know any better, and since they don’t know, they choose to not participate at all. They go with whatever worked in college or whatever their kids are wearing. This often gets played off as, “I don’t care what people think” or “I don’t care about fashion” or “I just want to be comfortable”, but when you boil it down, they do care. Honestly if there wasn’t any care, we’d all just walk around in pajamas. There’s zero sacrifice in comfort with dressing age appropriate.
Logo t-shirts and baggy cargo shorts from the store your 16 year-old shops at are not appropriate for the 40-something. At this point in my life, I’m not trying to hang on to my youth so much that I’m “that guy” who’s obviously trying way too hard to be young & hip. There’s plenty of ways to look fresh, cool and dare I say, ‘trendy’ without going backwards.
When we choose our attire for the day we’re trying to look, at the very least, presentable. Most men have a notion that caring about their appearance or attire is only for women. The fashion industry may lean heavily towards women’s wear, but don’t think for a second that giving a rats-ass about your appearance is only for women.
It’s only as complicated as you want it to be. The first step is to just pay attention. You know what looks good (and what doesn’t) when you see it. Pay attention to both. The simplest step is next time you’re at the mall, look at mannequins in the stores. They’re typically styled pretty well with what’s new. One suggestion however… look around. If the staff and patrons in the store are 20 years younger than you and the music is too loud, you’re shopping at the wrong store. You might want to try Banana Republic first.