I haven't seen 50 in a loooong while, but I almost always walk in tights/leggings when the weather is cool be cause they are so comfortable. I add a pair of fleece or waterproof over-pants when it's cold or wet. Who cares what the neighbors think? If I feel self-conscious, I just flash back to some of the attire one might see in Walmart or the grocery store.

As for shoes/clogs - mine vary greatly with the season. I'm currently using low-top hikers with a semi-flexible sole and add crampons when needed. I just change the thickness of socks to suit the weather. In summer I wear well-cushioned softer-soled shoes - my arthritic feet object to anything too firm. The softer shoes just wear out more quickly - I go through 2-3 pairs a year, then for a season they become garden/mud shoes before I toss them. I tried walking in my lace-up fleece-lined waterproof boots, but even adding orthotics my feet & legs protested after a mile.

The best accessory I have now is the hand-crocheted 100% alpaca hat from my daughter. So soft, it never itches like the wool ones, and it sheds water wonderfully so I can walk in sleet or snow. Thinking of asking for an alpaca neck gaiter to match...
Sue

@Erinmfs I’m so glad you got yourself outfitted for walking! And you walk to the grocery! Good for you. I’m trying to get myself back to walking but the snow and ice makes it difficult. Be sure to let us know how the new outfit does!