FI -- Ah, the world is ALWAYS changing. And regardless of where the "push" wording came from, it's an interesting concept to ponder. Of course we all have our preferences for how we would most like to "evolve" our style -- some people really don't want to challenge themselves with conscious efforts to steer their style into a new territory, and others do. There are times I feel less like pushing myself, and others when I'm more open. Just like anything else in life. It's not a judgment on people who feel either way. I do have to say I've always been glad I've pushed myself a little, even when I decide I started down a path I don't want to continue on -- at least I know and at least I tried.

As for "pushing yourself to fit your style to external factors..." I'm thinking back to when I had to adapt my style for a job situation, and even that kind of push I saw as a (mostly) fun challenge. How do I wear something professional for X environment while still feeling true to myself? LisaP did that with having to wear black at her fitness center job. Forum members like MsMary do it with their colorful approaches to business attire. Perhaps it's because I have worked in creative fields for decades, but I *like* the challenge of working my creativity into some external parameters or limits: what are we trying to say or convey with this design or this outfit? Even though I resented the dress codes I endured at some jobs many, many years ago, I'm glad I had to learn how to navigate those and still express myself through style.

Janet, those are great responses to external conditions—much more positive than many.

FI, I learned a long time ago that approaching an externally-imposed limitation as a creative challenge makes me much happier than seeing it as an impossibility to be resented.

Janet, that’s wisdom that applies far beyond sartorial limits.
I’m new enough to the idea of style as creativity that I don’t often apply ideas from other parts of life to it (yet).

Sterling, I'm waving at you as we pass. My wardrobe was much too light-hearted (unsure of fun) for my present needs. Of course our styles will be different, but maybe if I describe the elements of my clothes, you can find something adaptable.

1) Color. I think I remember you saying your wardrobe is a sea of black and navy? Light-hearted colors might be your version of pinks (fuchsia!), yellows, reds, greens, brights or even some pastels, all which can be worn with your neutrals! Find that fuchsia! (If you do pre-owned, you can search by color and size on ebay)

2) Prints. Florals, gingham, polka dots, all read light-hearted to me. (I know not everyone is a print person. But my wardrobe has at times looked like a garden--leaving me with all prints and thus nothing to wear.) The green floral pencil skirt Angie featured today is an example of what I would find as light-hearted.

3) Silhouette--perhaps more flow and/or swish? Kind of the opposite of a strongly tailored style.

4) Details such as trimmings, lace, embroidery (can even be tonal for lower contrast).

5) Sandals and pink polished toenails.

Anyway, just some ideas from a formerly light-hearted person.
I'm very excited for you, and I hope you keep us updated on your changes...or even if you decide things are fine as they are.

FashIntern, FWIW, I didn’t use the word “push” in my post actually! You misread that, perhaps? I haven’t changed a thing in the post either - to clarify things if that helps.

Ophelia -- Thank you so much for taking the time to guide me toward a more light-hearted, fun wardrobe. Adding colors to coordinate with my sea of black/navy and floral prints will be my first step forward. I had not thought to search through eBay for fuchsia if I can't find it currently in retail. What a brilliant idea.

I am excited about this new phase of wardrobe building. Early 2019 was devoted to building a solid foundation. I can take that foundation and now freely add in color and floral prints! YAY ME!

I get to shop NAS tomorrow too! Pretty excited.

Best wishes to all that commented on this thread. I found the conversation fascinating .... and once again I personally benefited from the combined strength and wisdom of the YLF Forum.

Hope you're having a GREAT time picking florals at NAS today! I even "unhid" the NAS threads to peek...no report yet. Hopefully you're still shopping.
Quick thought I had last night--fuchsia may be more likely to show up in winter clothes than fall, which are sometimes warmer toned and more muted hued.