The only time I go out like a slob is if I'm doing work around my property and I'm in my old work clothes. Since I likely have my truck fired up to do some of that work and it needs to be driven, I'll toss my garbage and recyclables in the back and haul them to the drop-off center without changing first. I'll swing by Lowes and/or Walmart like that but [usually] not other places.
Beyond trying to be presentable and not make others uncomfortable, I don't give the subject much thought. This was also the case back when teaching or speaking to large groups.
I think that is the key! How I use to dress for a women's fitness class that was mostly younger fit women, would differ from how I dressed for a senior women's class where most were there to lose weight. I think that is a good self-conscious.
Looks great to me. I like a shorter cut because it allows some height to hair that is thinning. But you look like you have plenty.
If I’m out in public, I almost always try to present an agreeable image. I don’t care much about fashion though. I still wear cargo pants because I can carry phone, wallet, keys, spare glasses, pocket knife, change and not have anything on my belt or in my back pockets (bum back). They just make sense for me. Around the house, it’s bare feet and sweats.