I rarely wear skirts.
Because of this, my confidence is about zero when it comes to creating an outfit based around one. In some ways I feel that skirts and a cute top are a little… well, maybe casual isn’t the right word, but I tend to wear dresses that stand out pretty much anywhere. I am most comfortable in a dress and heels even if I am overdressed for whatever I am doing. I just like to look my best and I think I do when I am wearing a beautiful dress. The dresses I wear are a little more formal (if that’s the right word) compared to the casual dresses I see other girls wear out in the real world.
Please know that when I say I stand out I am not saying I am the prettiest girl in the room, but I am a six foot t-girl in heels. No matter what I wear I am not going to blend into the crowd.
The few times I wear a skirt it’s because I saw an outfit on a mannequin and I thought it looked cute, so I simply bought what it was wearing and wore it. And I am being 10000% serious. I do wear skirts from En Femme because their separates make it very easier to coordinate a cute outfit. But if left to my own devices I am pretty insecure about picking a top to go with a skirt. When I see girls wearing skirts, no matter the outfit, it always looks cute. But when I try something similar my insecurity hits a new level and I usually end up hating how I look. For one thing I can never tell if I should be tucking in a top with a skirt. I mean, I know it depends on the skirt and the top but I still feel pretty lost.
But every once in a while a skirt jumps out at me and I want to wear it. It could be a cute pleated skirt or a leather skirt and I suddenly become obsessed with it. Whenever the weather gets warmer I am drawn to jean skirts. I see girls matching them with simple t-shirts or cute blouses and they always, always look good, even when they are paid with sneakers. The cute/casual/comfy look is just not a look I think I can pull off. Besides, if an outfit doesn’t *need* heels I am zero interest in wearing it, lol.
Out shopping one day I saw a cute top that I thought would look good with a jean skirt. The top was dressy enough that matching the outfit with heels wouldn’t look out of place. So I bought it, along with a jean skirt. It was an outfit that I thought would look cute on any girl, even me. I tried it on when I got home and my confidence crashed. BUT! I expected that. Trying on an outfit in boy mode almost always makes me look terrible. It is a completely different outfit when I am wearing my thigh pads, my breast forms, and have my hair and makeup done. The outfit fit, it worked, and I decided to wear it one my next time out en femme.
My next time out would line up with a photo shoot where I had to review some fishnet stockings. I met up with Shannonlee and we took some pictures outside at a park in a couple of different outfits. Since the jean skirt outfit looked very summery it was a perfect location for it. She took some pictures of this ensemble and before I changed into a dress (yay!) I asked her to take a photo with my phone. I wasn’t thrilled with how I looked, but I knew there’s a world of difference between an iPhone camera and professional equipment. I didn’t let the picture crush my self-esteem (that much) and I moved on with the shoot.
Of all the photos we took that day, I was most curious how this outfit would turn out. I dissect every photo of myself and I look at what I am wearing, my makeup, and whether I look too boyish before I decide if I want to share the picture on my website. If it’s a good picture then I want to show it off, obviously. I clearly like doing that 🙂 but I am also willing to hear feedback on an outfit as to whether or not it works for me. I am often insecure and I admit compliments do a lot to pull me out of a funk if I don’t think I look pretty in a picture. I am shallow and honest enough to admit that getting Likes on a photo I post on Twitter does a lot for my self-esteem.
That being said, here are the photos of the outfit. I think they turned out okay but I am not sure it’s an outfit I will wear again (unless ya’ll think I should, lol).