This is probably rambling and might not make any sense. But ... deep breaths ... here goes.

How do you learn/know/discover that a new-to-you silhouette is a good fit? Does the process necessarily include missteps, including financial ones? Is there a way to learn these things without making mistakes? I’d like to think I’m not just looking for short cuts, but rather that a) I’m risk averse b) I dislike making mistakes c) I want to do things the right way. This seems especially difficult as slow-and-steady weight loss has me in a constantly changing body, so I’m not even all that familiar with its actuality.

I’m thinking a minimal capsule-esque wardrobe is the ideal (I don’t think I’ll ever want a large wardrobe), but at the same time, I keep wanting to branch into new things, silhouettes I haven’t ever worn, or ones that I’m not sure will be flattering on my current body. But multiple silhouettes in a as small as possible temporary wardrobe gets complicated, and I like simple.

Example: I’ve never worn skinny jeans. Or leggings. First, I’ve fully embrace boot cuts (and flares, when they’re around). I’ve always liked wide-legged trousers, too, although I don’t have any right now. I like how boot cuts and flares balance out my proportions, and I like the movement, too. But with all today's tops styles being so fluid and oversized (ack, '80s!), since I’m not terribly comfortable with volume over volume, I’m back to the possibility of skinnies. And then I see Jenn mentioning her new burgundy skinnies, which as she loses weight will transition to “girlfriend jeans,” and since I’m also losing weight, that relative longevity makes sense. Or do I continue to ignore/buck the trends (something I’m perfectly fine with) and continue highlighting my smallest point with more fitted shirts and stick to wider pants?

Example 2: Jersey skirts. It’s the fabric that makes the most sense for a less expensive skirt, particularly given my desire to ban all synthetics from my life. But will it be too clingy over my pear hips? And does the shape of the skirt make a difference, or is the material just a no-go?

I know trying on some pieces is a way to get more information, but will it be enough information to actually make a good decision? Time to go try on (and contemplate) is limited with a little one, as are choices, locally.

I do, however, admit that I’m impatient. I want to be there, already. I think I’ve done a lot of the mental work, of figuring out where I want to go, but I’m having trouble either figuring out what should come next, or actually taking that step.

It’s hard to bring a wardrobe up to snuff while really not want to spend much money on pieces that (if everything continues as it has the past 6+ months) I won’t be able to wear more than one season, if that long. Is it even possible? Or should I just shove all these thoughts and feelings down again and focus on the rest of life — the weight loss, the family, etc. — until I’m in a more stable place, size wise?