Gotta walk before you run

Like many are saying, pick options that are low impact, a walk at night and on a Sunday when activity is dead will help. Go to a donut shop and enjoy a coffee and just sit there and enjoy the experience. Most people will come and go and be too interested in getting in and leaving.
Pick supportive locations if you feel a need to ease into it.
Wearing a dress in a woman's fashion store would be logical, and only females will be there routinely.
Then again, the reverse might hold true, going to a hard ware store will mean fewer females who will not be easy to fool will be fewer.
Either way, picking the time of day is key. Going out precisely at dinner time on a slow day means the streets will be a lot more quiet.
But you are suffering the same problem I deal with. I am over critical. Likely seeing things that are not there. Presuming everyone I pass will even give a damn. Picturing people laughing that hadn't even noticed me at all.
And besides, I find myself all the time looking at cis females and thinking to myself, 'does she even own a damned mirror?'. You might be looked at as a women and still looked at negatively in some cases. We women are a very judgmental lot