The issue here is that you should dress like a woman who is out at sunrise. In most cases, that would be a woman out walking her dog or getting some exercise before going to work. This is a bad time to be wearing heels, a miniskirt and excessive jewelry or makeup.
My thought is, the best time and place to go out is where there are crowds. Hiding in plain sight, if you will. So go to the shopping mall at noon or later. Go to the tourist section of town (if there is one) and act like a tourist. Dress like a business woman and go to the business part of town and walk around.
For me (and I have posted this several times), the difficulty is not with being out as a woman, but getting out of my house and neighborhood and getting back in afterwards. So, I underdress and finish dressing in the vehicle. A royal PITA that makes going out dressed almost more trouble than it's worth.