This is the question I ask myself each and every time I leave my house for a destination other than work. Because at all other times, my primary sartorial aim is to roll as deep into pajamas as I can, without making it completely obvious that I'm wearing pajamas in public.
The leggings and yoga pants trend has been a serendipitous boon to my goals. These days, if you're a woman whose legs are coated in plain black fabric of some kind, I've found that it's more or less no questions asked. And if you have a long, tunic-like shirt to cover a reasonable portion of your ass, all the better. Throw on a pair of boots, and you literally look like every Real Housewife of New York who's not actually on Real Housewives of New York.
The tricky part is the bra.
Sadly, I don't have little size A mosquito bites that would be legitimate candidates for going braless. I've got size D-cup knockers that at various points in my reproductive history have ventured further into the alphabet than I even knew possible. It was like Dr. Seuss' whimsical book, "On Beyond Zebra," except for titties.
But that doesn't mean I won't try. I hate wearing a bra and remove it at the first possible opportunity. That's where the layers come in. The trick to getting away without a bra in public is layers of thick clothing and outdoor gear that you're pretty confident you won't be taking off at your destination (e.g. an ice skating rink). That way I don't feel self-conscious about my tore-up titties just out there living the dream, and I don't have to be uncomfortable in a bra.
More often than not, I'll put on the bra though because like, what if something happens--like I get pulled over or someone invites me for coffee and I unexpectedly have to take off my coat or risk being considered extremely weird?
The result is unacceptable.
The hair makes up for it though. Because that's also part of the process. Hair goes under a hat without being brushed. Full stop.
Stick your feet into some wool socks and the aforementioned boots, and you've more or less gone as far as you can go with respect to wearing pajamas in public without anyone realizing it.