So. That sewing with a plan concept. Let's start with analyzing my recent plan-free sewing:

What I made and I wear:

Black linen Liberty Shirt
Red linen Liberty Shirt
Black linen gored skirt
Pink silk crepe cowl neck top

What I made and don't or rarely wear:

Two white notched-collar blouses
One green notched-collar blouse
Red and white polka dot cowl neck top
Green and white polka dot tunic.

An obvious pattern is the Liberty Shirt versus the notched-collar shirt. The Liberty Shirt is easy to make and feels satisfyingly solid when done. It's terribly comfortable and doesn't need any fussing or rearranging when worn.  It does need pressing, but that's just to smooth it out, rather than fighting with recalcitrant facings and twisted bits.

The notched-collar shirt is more fitted and shorter, so it takes more fussing. It's designed with loose facings; I stitch them down but that always involves a little arguing. I don't like the sleeves with either cuffs or a turned hem. The collar (it's that HotPatterns notched collar) always involved a moment of "will it work?" suspense.

Oh, and the Liberty Shirts are all in pure linen, while none of the notched-collar shirts are.

So it appears that the sensible thing is to make more linen Liberty Shirts, and meanwhile to lengthen the notched-collar shirt, give it sleeve vents like the Liberty Shirt, and audition it in some linen to see if I wear it. I do love the faintly retro feel of that shirt, but apparently not enough to wear it.

Moving on, what I expect to make and likely succeed at:

Black wool/rayon gored skirt
Matching Liberty Shirt
Grass green Liberty Shirt
Chocolate brown gored skirt
Cream linen Liberty Shirt
Amber/pumpkin Liberty Shirt

This seems sort of plannish, in that all of the Liberty Shirts (black, red, black again, green, cream, pumpkin) should go with all of the skirts (black, black again, brown.)

Fun plans with lower odds of success:

Cassis gored skirt  (Cassis, you ask? OK, OK, purple.)
Matching Liberty Shirt with dark cassis silk facings.
Sewing Workshop Haiku Two jacket in a tweedy green cotton flannel with green silk facings
An improved version of the notched-collar shirt pattern, in a pink Japanese cotton with green polka dots

Plannish? The cassis shirt should work with its matching skirt, both black skirts and might play nice with the brown skirt. The cassis skirt... um...yeah. It would probably work with the cream shirt. Maybe the green shirt. It wouldn't actually clash with the black shirt, but I think all that visual weight on top will be weird.

The green jacket should work with all the skirts, but I'm not sure if the shape pairs well with the shape of the Liberty Shirts.

The Japanese cotton shirt has no friends other than maybe the black and brown skirts. I think that it's part of another, so far unplanned, family/capsule.

Hmmmm.

Image: Wikimedia Commons.