Until the last few years, I didn’t consider pleated skirts. They seemed overly dressy and conservative to me. Maybe it was the fabrication or the office atmosphere they gave me. But I’ve moved to liking them on me. If made correctly (not too poofy at the start of the pleat, near the hip is a no go!), I find them very flattering for my shape. Kind of balancing for my wider shoulders. I mostly wear with boots.

Like many, I’ve got a couple sizes in the closet depending on where my weight is. That may be part of the issue making me feel like I have more than really is worn at a time. So, the black skirts below are an either/or for sizing. I just didn’t see this being a category that I’d have more than one or two of.

I’m in love with the velvet teal skirt and wear it year round. It’s not nearly as shiny IRL. It’s actually become my travel skirt when I travel by car because it’s so soft and comfortable. I was so sad they didn’t carry the same again this year, as I would have duplicated - though in another color. When looking, I saw the last skirt below. Faux leather and washable. Seems to fit what I like. But maybe too hot? It’s hard to know when I can’t feel the fabric before purchasing. I might be better off holding out for something in navy, though that’s generally harder to find.

Sometimes when I find something I like, instead of sticking to the original garment, I buy more, often with diminishing returns. Then if I’m ever over the style, I have to pass on more pieces than I should because I’ve bought too deep in a style. I do think one could argue the teal and black skirts don’t have the same vibe.

What about you? Do you have any rules you set up for yourself, or how do you make your decision about how much of a style you will buy?