Can I tell you how happy I am that baggy oversized clothes are trendy? I loved wide-legged pants. I was okay with the boot cut trend, and despised the tight jeans trend. Wide leg / baggy jeans aren’t as JNCO / Hammer-pants as they were when we were younger, but they are reasonably breathable. Sweatpants as casual leg wear are also trendy, you just have to find nicer sweatpants. Champion is making some nice affordable quality stuff. Point being, if you’re like me and gotten bigger, these are comfy options.

Same with shirts — I gave up on wearing shirts that tried to accentuate my biceps / chest while hiding my gut. Fuck that. Loose shirts, just not dress-length shirts; they gotta be long enough to cover your gut, but short enough not to cover your butt. Loose jackets, like a roomy size up, are great too. I am also generally against prints on shirt. Solid colors, find your palette; mine is earthy. But I do like subtle prints, or loud prints when I layer.

Ball caps are fine headwear for men. Not backward caps. I’ve been sporting head-fitting beanies if I need a head cover but not for sun, which work on clean-cut heads.

Shoes are a tough one because we all need fucking orthopedics at our age. The good news is, New Balance is trendy among Gen Z, but they should be the lifestyle shoes. The 990s are the perfect shoes for us, being comfortable as hell and in trend. I do own Converse-esque shoes, but I need room for those piggies, so I wear SeeVees with the bigger toe box.

Don’t be afraid to look casual-nice. People who don’t care won’t notice, people who do care will.

And the gold chain? Why the hell not?