That's just a small list of items in my Working Girl wardrobe that I hate to wear, but wear them anyway. I pull them out of my closet - from my dresser drawers or off the floor depending on how far I got folding my laundry the last time I did it. I hold the item in front of my face, then up to my body, and think to myself, "It won't be as uncomfortable as last time."
It usually is uncomfortable at first. But then as I start commuting my gray skirt starts to ride up, as it always does, and my black tights start to sag in an awkward way.
If my day's uncomfortable item happens to be shoes, which only happens if WG2 leaves the apartment before me and a pair of her shoes happen to work with my outfit perfectly, I think, "It'll be fine, I'll wear my Uggs on the way to work and just slip these bad boys on when I get to my desk." I convince myself that I won't be on my feet that much. Then by 9:30 my feet are throbbing and I've switched into my go-to black pumps that live in my shoe closet.
Shoes are easy to deal with; you can change into a more comfortable pair or take them off when you're at your desk. But the rest of the outfit, well, you can't exactly take your skirt off in the middle of the day now can you? And it'd be a little obvious if you completely changed your outfit around lunchtime.
When I wear an uncomfortable outfit, I usually deal with it. But there was that one occasion where I had to go to the Gap and purchase a cardigan because I didn't realize that my dress was very low cut. Another day, I barely left my desk because I was wearing leggings with a dress (or should I say shirt?) that hugged my tush a little more than I would have liked it to. At first, I didn't think it was that bad, but it didn't help that one of the men in my office gave me a weird look from the conference room when I first walked into the office that morning.
Then, there was the time I took off my undies. Yes, my underwear.
I wore a red cotton dress from Forever 21 - top quality couture right there. Underneath I had worn a dark green thong. Let's just say I wasn't really thinking that morning. It wasn't until I got to the office and went into the bathroom around 10:30 that I noticed my thong was fully viable through my red dress. I kept it on for a while but my self-consciousness escalated and I eventually went to the bathroom and took it off.
The 'no underwear' thing made me a different kind of uncomfortable, but thankfully the the kind of uncomfortable that none of my coworkers would notice.