Morning walks

In my effort to take off some weight and improve my health, I have been walking 5 miles during the early morning hours 5 days a week. I leave before sunrise, and get home just as it's getting light.
I have a nice selection of running skirts that I usually wear while working out inside. I recently purchased a new skirt (skort) that is extremely comfortable, and feels great on my legs while walking. I would love to wear this on my morning walk, however I have a few reservations....I walk in my home neighborhood, and I often pass people on my daily route, and there are a few cars driving by me. I am only out to my wife and a friend, so I really don't want to be "exposed", so to speak. I have a bad ankle, so I walk with a very distinct limp. That, combined with all the security cameras everywhere, makes me very hesitant to go for it. These days, many would say "if it makes you happy, go for it....I fear the ones that would be at the opposite end of the spectrum....the last thing I need is to see a picture on social media of "the guy walking in a skirt". I have worn capris under shorts when it's a bit cooler. and black leggings when it's really chilly.
I love the comfort of the running skirt, the way it feels on my smoothly shaved legs, and it's cooler than wearing shorts. I wish that more men would realize how comfortable skirts can be.

I (and others) have said it many times, if you want to be seen as a woman, you have to dress and do what a woman would do. Also, you have to not do what a woman would not do.

A woman would not usually go for a walk alone in the dark. If you dress as a woman and walk alone in the dark, you will attract attention, not only from ordinary citizens, but possibly from the police. It's a bad idea, regardless of what you are wearing.

If you want to walk outside as a woman, wait until it's light out. Go somewhere that's not secluded.

I'm of the opinion if the potential negative consequences of being seen outweigh what the positive effects would be, don't do it. When I have the opportunity to go for an evening stroll I wear a dress, hosiery and a wedge and all the proper undergarments. I don't walk in my neighborhood. I walk in a distant neighborhood and time of day when office workers would be coming home from work or grocery shopping. Although the local grocery stores are open 24/7 you will not find women walking alone at 2:00 AM. IMHO, apprehension, whether realistic or not, will be a killer of the experience.

I walk everyday at one of two nearby parks or at the Mall.

I wear shorts, skorts skirts, bra w/forms
women's tank tops, tee shirts.

A little make-up, wig and glasses.
or sunglasses.

Mostly women walking. They always greet me with a friendly. "Hello or Good morning"

Most people won't even notice. Those that do won't care. I spent a lot of years worrying about things that I was the only one they bothered. Only three options, go for it, walk in a different area, or keep doing what you are currently doing.

I used to walk 5 nights a week 10-11:30. 1/3 my of my route was A well lighted linear park,almost no one out and constantly checking surroundings, 1/3 on a sidewalk on a busy one way street,walking facing 35 mph traffic, to fast to notice anything but a woman walking, and 1/3 along a brightly illuminated riverfront boardwalk that had younger people out walking, this section was the most stimulating for me. I was always properly dressed from feminine sneakers, for flight, skirt or tight jeans, attractive top, forms, hair and makeup done with a touch of jewelry. Head up and tits pointed to the sky, until I had to pass someone closeup then I got engrossed in my phone. Yes I'm a chicken but I was getting better. This area is not close to where I live and the chance of being seen or recognized by someone that would know me was very almost nonexistent. You have to consider risk reward and then decide. I loved it especially when I passed a lamp post a watched my shadow of my skirt swishing from side to side.

I too am a morning walker just like to collect my thoughts for the day while getting my miles in for the day so I dont have to be on the elliptical or treadmill as long at night as I aim for 10 miles a day between the two. I starting mixing in skorts last year. If you stick to black, blue, or grey I've maybe had one or two people I think noticed. Also I keep my distance as people appreciate that with Covid, then if someone is approaching i carry my large water bottle over it to try and shade the skirt effect. I usually wear adidas ones so the stripes make them look a lot like mens gym shorts. Or a sweat towel and tuck it into the waistband like a quarterback does in football seems to work for me after hundreds of walks no one has laughed or commented about it. Just my two cents.

If it was meant to be (caught by someone) it will most likely happen anyway. You're increasing your exposure a bit but the truth is that people judge on first glance. If they see you in a quick passing what will be the first thing they see? If they see a skirt...they judge you are a woman. They don't care after having made the first judgement, their attention goes elsewhere.

Good for you for improving your health by walking!
I run regularly and have thought about a running skirt and jog bra, but I?m not out. So I get by wearing panties and if it?s cool enough for a jacket, a bra too.

I have recently been hiking in a kilt. That?s close enough to men?s wear to not give me away.

Find one (1) cis woman in your neighborhood or city who goes for solo walks in the dark and then I'll tell you if it's a good idea to wear a walking skirt.

Walk in the sunlight, get some vitamin D inta ya...

AND IT'S SAFER.

I live in a suburban community with very little crime, and I am far from defenseless. One of the nice things things about a running skort is that there are shorts underneath. A quick pull and tuck, and the skirt looks like shorts.
Anyhow, I went for it this morning, and it felt great. I'm not out to look like a woman, I just want to wear what's comfortable.