First Outing in Full Fem Attire

So I’ve made up my mind… I’m heading out in full fem attire while stuck in my enforced predicament. Here’s the outfit plan: a denim mini-skirt paired with ruffled white underwear, white peep-toe heels with a 3” heel height, and a black figure-hugging V-neck vest top.

The challenge is this: I’ll drive from outside the park into its car park, strip off my clunky masculine clothes to show off the lovely ensemble underneath, then secure those normal garments in a bag. The key for that lock sits on the opposite side of the park. I have to trek all the way across and back (roughly 10 minutes total if you count walking in heels).

I’m thrilled but also nervous about this. I don’t even own any makeup yet, nor do I have all the accessories I want to grab—a handbag stuffed with girly bits, bangles, earrings, a scarf, and a hat come to mind. Right now, I only possess the skirt and heels.

I’m still weighing up several details where your input would be great: Location specifics. Can anyone recommend the best setting for this? There’s a huge park almost directly across from my house. It seems ideal, but I worry my housemates might spot me over there, even though it isn’t in direct view (they have that nosy habit). Driving out of town feels safer to me. Is wearing heels really necessary? - I manage them well indoors, but outdoors for a long distance? Flats might be smarter for a debut… yet I REALLY want the heels. Ugh! And there’s the noise factor; will they draw too much attention?

Are there better predicament options?

Passability check. My shoulders are quite broad and my wig isn’t great. I’ll shave most of my body (arms aren’t hairy enough to worry about), so my legs in a skirt with heels should be my strongest asset. Any other advice or experiences from your first outings?