Working out of town for several days, and tonight is last night before returning home. Decided to go out for dinner, so put on light makeup, lipstick, earrings, blouse, pants, and sandals.
Although I have let my hair grow out, there was no way that anyone would mistake me for anything other than a senior citizen out for dinner, wearing non-gender appropriate clothing and makeup. Gotten to where I don't worry much about what strangers think these days. Wait staff was polite, and called me "sir". Was not offended in the least.
None of the other diners gave me much more than a casual glance, and I had a wonderful dinner, dressed comfortably. No worries about "passing".