She Found Style

an attempt to discover my sense of style in one year and learning more about myself than I ever imagined along the way

I’m Not Done Yet: My Skirt Dilemma

Just another photo of me NOT wearing a skirt

Over dinner the other night, I was discussing this blog with my husband.  I was counting the months I’ve been working on this (6) and the number of months I have to go (6) and feeling like where do I go from here and I’m really happy with where I am at right now so what do I do now and where is the challenge?  I may not be hitting the current trend (who cares) but when I get dressed up to go out to dinner with my husband, it’s no longer traumatic for me!  I leave the house feeling put together and confident and beautiful.  The whole point of my blog challenge!

But Mike gave me a look that said, you aren’t done yet missy.  And I gave him a look back that said, what do you mean?

Oh, right.  My skirt dilemma.  I’ve been dragging my feet on this one because I can barely explain it myself.

I love skirts.  They look so cute on people.  The few times I wear a skirt they look pretty cute on me.  But I rarely wear them even though I’d like to wear them more.  So what’s the problem?

It’s almost like a math problem that I just can’t solve.  Skirts have a few more parts to the equation than other looks and I have a hard time wrapping my mind around how to make them work.

Let’s begin.  You have your skirt, you’ll need a shirt and a belt, I’m on the Oregon Coast so add a sweater and a jacket, don’t forget tights and shoes and maybe a pair of socks to go over my tights if it is particularly cold that day.  Are you still with me?  With skirts you have to consider proportion – more math!  The skirt can’t be too long or too poofy.  The belt has to work and the shirt and sweater need to be the right length – not too long or too bulky.  Don’t get me started on jackets and shoes.  Throw in the fact that I’m not even 5′ and now every skirt is basically too long or too poofy. And why don’t we just throw in the fact that I am a true perfectionist – if I can’t do it right the first time, I’m not doing it!

Does this count as a true dilemma to you or is it just me?

Where to even begin?!  I think I’ll start by collecting a few skirt looks I really like, I’ll gather information on proportion and then I’ll start trying to copy some looks.  How does that sound?

How do you tackle challenges?  I could use a little inspiration right now!




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16 thoughts on “I’m Not Done Yet: My Skirt Dilemma

  1. Try a fitted mini over woollen tights and some boots. A good piece of knitwear balances out the look 🙂
    Skirts are fun and look fab with winter fashion!


    I live in Scotland (winter 70% of the year) and it’s one of my favourite looks!
    Good luck!!


  2. I can totally relate to your dilemma and I live in southern California.

    I’m always cold so wearing pants just always seems warmer. I really need to just make or buy more skirts or dresses.

    Cute pant outfit though!

  3. Wow. I have never given skirts this much thought. I tend to tackle challenges by taking one of 2 courses. Either I dive in the deep end or I take baby steps. I think for a dilemma like the skirt issue you can try baby steps if you like. I think starting with a dress is the best way to get used to wearing them and force yourself to make it work. I struggled a long time about how to a mom in a skirt all that bending over that is required seemed like a peep show waiting to happen which was my own personal skirt dilemma. Anyway I started wearing dresses because they are so easy to throw on that the ease of dressing won over my fear of a Marilyn moment at preschool pick up. With a dress you can work out the length and volume and everything without having to also worry about the top half of your outfit so much. Anyway I think a deep end approach may be to just choose a black maxi(or knee length or mini) skirt and try to make it work wearing it everyday for a week. Play with shortening with pins or tape or rolling the top. Play with all the proportions until you find what works.

  4. I am certainly so “fashionista,” but I am a fellow Northwesterner who has found a way to wear skirts comfortably and with a feeling of confidence in these elements! The two pieces that made skirt wearing a reality for me are leggings and cute tall boots. I have short legs too, so I stick with knee length (nothing longer) skirts. I am always pleasantly surprised when I manage to pull off a skirt with leggings, extra tuffs (rain boots) a sweater, and some fantastically large earrings. This is just me though….and as I said: I am no fashionista :o)

    • Erin, I love how practical your advice is and yet totally embodies your lovely style as well. Which is what I’m learning more of these days: it’s less about being a “fashionista” and more about showing that unique style we all have. You do it well. Thanks for stopping by!

  5. I have this same dilemma! My husband has always tried to suggest skirts, but jeans are so much safer to me. I feel comfortable, and I know what I’m doing. I really still have a hard time figuring out an outfit with a skirt and avoiding the frumpy-factor. I think what has helped me is going straight to casual dresses. That way I don’t get obessive about what top to wear, and I usually throw on some boots or flats and a bright colored cardigan. I need to feel comfortable, that’s always the key for me.

    • Char, Thanks for visiting! I love the idea of starting with dresses first. When I hit the thrift stores today, I’ll be looking for them. Dresses do sound like a better starting place. Thanks!

  6. jenn brooks on said:

    You’ve given away the fact that you sew…My suggestion is to find some fabric that you really love. You’ll be able to get away with quilters cotton for this one, poplin, lawn (2 layers so it’s not see through) or any sort of knit . Make yourself a couple of a-line skirts with cotton lycra jersey or french terry yoga waists. Instant gratification since they are SO fast to sew up, flattering, and insanely comfortable. And they will fit you properly. Plus you’ll be able to skip the belt and if the fabric is bold enough, you can let the skirt carry the outfit. You also might want to consider making yourself a maxi skirt or two…I’m 5’1″ and store-bought maxis are a disaster but I’ve made myself some that are the proper length AND are not as fall and I think it works okay…and then I hide fleece leggings underneath. I’m warm and nobody knows.

    • Jenn, Thanks for stopping by! Yes, I am a sewer so I really have no excuse, right?! In fact, I’m in the process of acquiring a dress form which I’m hoping will solve all of my problems. Thanks for all the tips. I love your ideas. Thanks for being a part of the conversation!

  7. I was just thinking about this today! I want to go more towards skirts because…well, I’m heading into my 40’s and I so don’t want to be one of those women who should have quit wearing jeans a few years ago. (And I don’t want to be hanging out in dockers and crepe-soled shoes either. ) But yes, the cold. The proportions… the need for boots and tights and layers and then, after 40….the whole bare leg thing. Sheesh. What I really need to do is head back 150 years where I could be completely covered and the whole thing would be solved. *grin*

    • Tonia! Thanks for swinging by and sharing your perspective. Yes, I’ve often thought of time travel to alleviate my problems too. 🙂 We’ll get this skirt+weather thing figured out – we’ve got to!

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