Remember the floral pleated skirt I got a couple weeks back? Well, I spent much of Sunday afternoon trying it on with every possible option in my closet. I’m going to talk through my thought process, what I did and didn’t like, what worked and what didn’t and why…and what the final outcome was.

#1 Skirt with cream v-neck cashmere sweater and chestnut flats. I liked the color combination – the cream with the muted browny-rose shades of the floral on the skirt. But I did not like the proportion of the long sweater over the very long skirt. I lived through the 80s and 90s. I wore the “long tunic over flowy midi/maxi skirt” style and enjoyed it. Then. Now I see it as too 80s, 90s. I do like the way the sweater skims over the elastic waist and belly area. But the proportions are just not good.

#2 So I tried tucking the sweater in. More modern, but…I’m not digging it on me. It took me a lonnnggg time to get relatively comfortable with an elastic waist and my big front belly. I’m much better than I was. But I’m still not crazy about the waistband worn super-high like this. Elastic waists will not stay at my actual waist, because the spot just under my bra is smaller, and movement causes the elastic to slide to the smallest area. Like water seeks the lowest point…elastic seeks the smallest point.

#3 I love the concept of the polka dot tee over the floral skirt, and they have the black tying them together, but…I think the white tee is too white with the dark skirt. It has some very small bits of creamy white in it, but, I think it’s too stark a contrast. I thought the black cardigan might help the situation, but I don’t like the 3-4″ of skirt peeking out from under the cardigan. They’re not even peeking. They’re screaming WE’RE TOO LONG FOR THIS SWEATER!

#4 The 1980s called. They want their secretary back. It’s not that the outfit is that bad. It’s just not me. I thought I’d run with the girly feminine look of the skirt and add a ruffled white top with a pink cardigan. Oh boy. I’m not half the woman this outfit is.

#5 I did wear this in my past life. But that was then…and this is now.

#6 Okay, maybe we’re getting somewhere. Tying the top up allowed it to end about where a crop top would – just long enough to cover the elastic waist and the big belly pooch right below it…but not so long that it had the long over longer proportion I talked about earlier.

#7 I thought the oversized cardigan might help amp up the casual factor and knock back some of the sweetness of the floral skirt. Like a pinch of salt on a chocolate chip cookie (now I want cookies). I do think it does that, but the cream of the cardigan and the white of the tee are not so good together…plus, this chunky knit sweater would be unbearable in the spring. If I ever get to go OUT into the spring.

#8 DINGDINGDINGDINGDINGDING We have a winner! Casual, check! Blue chambray over floral skirt, check! Longer length over high-waisted skirt, check! Casual sneakers, check check! It’s very 90s Elaine Bennis. I loved that look then…and still love it now.

So out of all the looks (and you have to admit, I gave this skirt a good run for its money), I only really liked one. The last one. And I just cannot in good conscience buy a skirt that I will only wear with One Thing. So, it has been returned from whence it came…and I am watching for another skirt that hopefully I will have more luck with.

I liked the skirt. The style, the shape, the colors. And I even could have lived with the high-riding waist (with the right length top over it), but that combined with the very long length…was just not good on me. I’m short. And this skirt just sort of swallowed me up. I did hike it up to around knee length and that was so much better. But right now I just don’t want to spend $$ on an alteration and *I* am not attempting to hem a pleated skirt!

But I hope you liked/got something out of watching my process. I even made a 10-minute video where I talk through each look a little more. You can see it on my IGTV at @fashionschlub at 11am! Also, be sure to take a look at Jodie’s style session of a pleated skirt at @jtouchofstyle !

Be safe, friends!

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