Skirting Around

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).  

Love, Hannah

12 thoughts on “Skirting Around

  1. Hi Hannah. I fully understand that completing a look or an outfit with a skirt is more complicated than with a dress. Coordinating a top just right can be challenging for my girl side. But it gives so much more flexibility. I have broad shoulders which means I can’t find a lot of dresses in my size that fit and still look pretty. Many will actually look rather drab. I am a size 18 and yes I can find that size on-line, but most brick and mortar stores will not carry that size. On the other hand, I find great flexibility in wearing skirts and a cute top. And shopping is much easier.

    Liked by 1 person

  2. I think a great looking jean skirt is difficult to mess up and you most definitely did not mess it up
    I looks very nice.
    I’m a skirt kinda girl myself, dresses while I love them have never looked great on me, but give me a cute skirt, with a pattern or such or yes the casual jean skirt and I’m good to go.


  3. Hannah – you look great – I have two jean skirts (mini and knee) and several tops to go with. I love your simple floral top with distinct shoulders – you go girl!


  4. Well let’s just say that it isn’t the color I would choose for myself, it’s just not me, that being said, I think you look fabulous as always. I’ve said this before & I’ll say it again, I think you’re to hard on yourself. You always portray yourself in a positive matter for girls like us. I love your advice & reviews & I’m always looking forward to your next post. You’re an inspiration for all us girls out here, so stand tall & continue the good fight.



  5. I think you nailed the look. I myself love to wear skirts. Give me a great looking maxi. The fun part for me is trying to coordinate a good looking top.


  6. Nothing wrong with that outfit that I can see! I tend to prefer skirts/tops over dresses (although I do have a few dresses) because you only need to fit 1/2 of you at a time. My rules for skirts/tops: 1} Solid color skirt, solid or patterned top; 2) patterned skirt, solid top; 3) patterned top, solid skirt; 4) If the colors look icky together, don’t do it.


  7. Being 5ft 8in ,I can get away with skirt ,especially ones that just come below my bottom outline. And especially a floaty skirt that blows up to show off my bottom a little.!! But winter will soon be here and longer dresses will come out of my wardrobe.


Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s