Help outfit me for adventurous strolling/timid hiking

I learned the hard way how useful a couple Kleenex can be! (Hadda use my shirt sleeve. Ew.)

I’ve seen plenty of people carrying them on trails of all kind, and they’re just awkward, pick up any wind, and gives you something else that has to be held in hand or stowed somewhere. Umbrellas are great from getting you between buildings or vehicles when you can’t put on full rain gear, but if you are going to be out in inclement weather for any significant amount of time they don’t stop the rain that gets blown sideways by wind, drips down from a backpack, or splashback from the ground. A lightweight rain suit (waterproof pants and a jacket), however, can keep you as dry as you can expect to be.


Yep. And I’d bet they carried it on their next trip, too. Think about that.

It sounds to me like what most people are suggesting is way overkill for the OP’s conditions. For what he’s describing, I would go with:

A pair of jeans (or shorts if it’s hot out)
A flannel shirt (or t-shirt if its hot)
A wide-brimmed hat
Comfortable sneakers and athletic socks
A phone
If it’s below 60 or raining, a light jacket
If the walk’s going to be longer than about an hour or it’s really hot out, a water bottle

And that’s it. I don’t see why anything else would really be necessary. If you want, you can toss in a pocketknife, a granola bar, a fitness tracker, headphones and a music player (assuming your phone isn’t one), and so on, but those are all matters of personal preference.

We’ve actually been helping a friend recently following surgery to regain leg strength. She’s currently not outside for very long walks (working up to increasing distances) but is wearing dark sweat bottoms and simply layers a cotton tee with a sweatshirt under a medium weight winter coat. Seems to work fine.

I mostly agree, though, I’d add a rain jacket and rain pants, if it might be raining. If it’s cooler, add a fleece jacket and wool knit hat or something (and put on the rain jacket if it gets cooler; the windbreaking aspect of the jacket will help a lot). If it’s really cold, add another fleece jacket over the first one, and some gloves or mittens, and wear the rain pants over the jeans for warmth.

If you find yourself getting uncomfortably sweaty, you could switch to a fancy wicking t-shirt, but walking for half an hour in a wet cotton shirt won’t kill you, if you have warm enough other layers.

If you’re planning more than an hour walk and it might rain/snow, then I’d start considering ditching the blue jeans for something that’s not cotton, but that’s really just in case of things going wrong – rain pants should keep your jeans generally dry enough to keep you warm for a couple hours.
If you move up to half-day or all-day hikes in cool conditions (rainy and 50 degrees or less, or under freezing in any conditions) then you need to start thinking a bit more about what you’re wearing, but just for walking an hour, worry about comfortable shoes, a raincoat and pants, and then go for it.