I like the idea of challenges, nemosmom. Creativity through constraint works well for me.

I do think a pitfall of arbitrary challenges though is that they can distract me from or conflict with the style that I'm working to express. For example if my goal for fall is to lean into the "Girl on the Moors" moniker and wear lots of teal and plum, etc., then adding "a week of no black" or whatever on top of that just becomes too many moving parts for my brain (or wardrobe). So I think if I try to think up challenges that are specifically designed around the style I'm trying to express, that could actually be super helpful.

I know you are in the same eyes-glazed-over MIHO* boat, so let me know if you want to talk about this further or maybe join me!

*Instead of Mom-on-the-Go, Mom-in-the-Home-Office

ETA: L'Abeille, your process sounds similar to mine except that my working memory is not up to the task of keeping all those variables in my head, least of all at the end of the day while falling asleep!

I like the idea of mini challenges so that you can see what works out of your closet. I liked Angie's dress challenge, and have incorporated some other challenges as fun way to play in my closet: it's pink week! or no denim week! or dress-up to work at home week! I find the weeklong challenge is a short enough time to make it a focus but not a chore, and long enough to think creatively. (It's dress week, but I'm on a plane for 3 hours, what dress do I have that I'd feel comfortable wearing in that situation?)

As Gretchen as others have said, some sort of challenge can be a great place to start. On August 20, I made a list of summer clothes, footwear and accessories that I want to use more before summer is over here in a few weeks. Each day (and often twice or even three times a day, depending on my scedule) I look at that list and, if at all possible, choose one, two or three of these items as a starting point for my outfit.

One of my favourite challenges was one I set for myself several years ago. It was very personal, so you can set it youself based on what you want to do. For example, within a week, I might have said I needed to wear:
A skirt
Long over lean
No black
A button up blouse.
A jacket
A colour

One could "hit" more than one in one day, but it made things more interesting. Not super confining, but stretched my brain a bit.

L'Abeille... have you considered Stylebook? It's free, you could put your new pieces in that and make up "looks" around them in a category of "looks to try" or something.

Thanks Gretchen, The Cat, and ElizabethP. I think challenges are a great idea. I will probably do day by day challenges rather than weekly etc as I think that will facilitate those on-the-fly outfit making skills. I am so grateful for this discussion, it has really gotten my wheels turning!

I do all my outfits for the week at once, based on weather and what I have to do (smart casual, normal work, formal work). Each week I do laundry and hang dry clothes, so about every other week pieces get rotated. Occasionally I do challenges-like frock week, or red and green for Christmas week. Right now I've just been repeating outfits a lot to free up time for outdoorsy stuff

YES! I would love to join in challenges that are specifically designed around the style you (and I) are trying to express!

My process usually starts with "I hate everything in my closet!" and ends with "oh, well, I don't hate this so much today".

Today was one of those days. I put on my James Jeans cargo pocket joggers and a white linen top, but I got sweaty when I went to check the package safe at the front of the property. So I stood in my closet thinking about this one grey shirt I wanted to wear and worked from there. I think I want to move to Canada or Alaska or maybe even the North Pole because I'm sick of all this heat and humidity. If I lived somewhere cold, it would be easy to decide what to wear: all of it, so I don't freeze to death. Just take all the clothes out of the closet and put them on my body. Every single garment, all at once LOL

@cindysmith Yaaas to choosing the least hated today thing!

Cindysmith, lol. Glad you’re back.

I’m less creative than y’all. By the time I factor in size, weather, & how dressy an outfit needs to be, I’m down to a not-very-big handful. First I look at my valet of recently-worn-but-not-ready-to-launder clothes to see if there’s anything there that I haven’t worn around these people recently and that I’m not sick of. After that, magic. Lol. No, not in my closet. I look at the pieces I’ve identified as possibilities and choose whichever appeals to me most at the moment. A lot of my separates have usual suspects for their pairs, and I challenge that only if I have a ton of time on my hands.

Perhaps those who are interested could do a Mon to Fri of looks meeting their style persona. And for those who have several style personalities - maybe a couple of weeks. Putting our best fashion feet forward.

A couple of years ago I did a challenge where I asked the forum to share their patterns- polka dots, florals, plaid etc. it was fun. I also did an art one last year- taking inspiration from some paintings.

I am dying to be wearing dresses and sandals but it is not warm enough so I am on repeat repeat repeat.

cindysmith, ha! I have those days too. That was part of my goal in starting this thread, was to figure out how to minimize them. I do not want to live at the North Pole, however!

FashIntern, interesting, it sounds like you're not the only one who has go-to combinations for certain items.

Sal, I hear you. I'm excited about autumn clothes, although I probably will not really make the switch until late September. We tend to have a nice Indian Summer here in Seattle and I like to milk it since our summers start so late.

nemosmom I'm glad you're excited about a challenge idea! I spent about 10 minutes brainstorming outfit prompts that fit with where I want to go for fall. The idea is that if I don't know what to wear in the morning I just pick a prompt and go from there. Some of them are extremely to fairly general (wear a top I haven't worn yet, wear a short necklace plus a long necklace) and some of them are really specific (combine cornflower blue and teal, build an outfit around my watercolor landscape pendant). I'm not sure how to structure a challenge so that it would be both specific enough to be useful for me and general enough that it would be useful for others. I could maybe think about how to generalize some of those more specific prompts. Oooh, it could be like a writing group but for our closets!!!

"a writing group but for our closets" hah! This is precisely how I ended up at YLF. So many folks who are thoughtful about their outfits *and* their prose.

BTW, I have some gear outfits that combine cornflower blue and turquoise/teal. The "watercolour" effect works better than I anticipated!

I'd be up for a "persona" challenge later in the fall, but not in September. Just too crazy with back-to-school! I did a garçonne/androgynous challenge in October (last year? the year before?) that was really useful and fun.

My daily outfit planning consists of deciding on which pair of jeans/pants/leggings and top/sweater to wear. Dont forget the sneakers and soon to be required steel toe work boots. Lather, rinse, repeat, yawn!! Unfortunately, boring dressing is the norm for working in a production setting.. Maybe I'll do "frocktoberfest" by wearing dresses more often to celebrate my birth month. Hope I don't incur the wrath of the "safety fashion police" at work.

Like many others, I start with the weather and the activity. I usually then choose my top (or dress) and then pants, toppers if needed, footwear, and accessories. I almost always choose my outfits in the morning, unless there’s something really important, such as a performance or job interview. Then I’ll plan the outfit several days in advance.

I'd join a "persona" challenge later in the fall, too.

That would be fun.

It really is hard to describe a "process" based on mood and intuition. I don't know how it really works, to be honest -- it's just what catches my fancy most at that moment and again, it often revolves around a "newer to me" item (might be thrifted or consigned, doesn't have to be brand new...it's just something the feels fresh to me.)

Brainstorming a list of prompts is a great idea for days when you’re feeling stuck! And I love the idea of a writers group challenge for our personas! October? That would allow some time to riff on ideas a bit.

Emotional dresser reporting in. I rarely plan outfits unless there is a specific dress requirement, like today was wear purple at work - so I had preplanned to wear my purple velvet skirt and a purple handbag.

I check on weather and how much walking is required. If lots of walking (as compared to a normal day in the office - that will narrow my footwear choices). As for the rest, it is entirely up to my mood. Usually I will want to wear one item - and that and the general vibe I am going for - will inform the rest. I find a fluid and relaxed approach to dressing works well for me and gives me the opportunity to try different combinations.

I love the idea of a "persona" challenge. It's so hard to stray... heck, I have never even defined my persona properly. But to spend a week or more consciously trying to feel "me" would do me the world of good, both in defining and in my never ending quest to find reasons to purge some pieces.

The travel capsule is the right analogy for how I dress. I have planned outfits for work. 8-10 a season. I rotate unless the weather dictates my shoe choice. This process works for me - takes little precious time and I know I will feel good/ look suitable.
Any creativity I have with respect to clothes happens at the purchasing stage, when I’m putting an outfit together.

Maybe to find your "spark" for outfit creation you could analyze what is interesting in this process for you. Is it the trill of working out a new item into many outfits? Or maybe including one item in as many outfits as possible? Or expressing a mood or a position with your appearance? Or maybe how to make dressing for repeating activities more exciting? Variety?
Reading your post and replies maybe just finding the time for outfit assembly is the challenge for you and you could try finding ways to improve this. For the traditional way of putting outfits together I also don’t have time. Mornings are busy and my brain is on autopilot so if I don’t have clothes prepared from the evening before it’s very hard for me to decide what to wear. Evenings are even harder - kids want attention to the very last minute so no way pulling out clothes, trying what works and deciding. What I do however and what allows me to have currently planned outfits until mid November (that's because I want to make myself wear more of what's in my closet and hold my new purchases for a while) is using an app for my wardrobe and outfit creation and planning. Use Stylebook, have tried others before this one, but they weren't as good. Every time I purchase new clothing or shoes, I put it in the app (either stock photo from the retailer or in rare cases just photo I've taken of the item) so it contains all my clothing items, sports gear, shoes, most scarves, hats, bags/purses and some of the jewelry. When I have a bit of free time because everything is in my phone it's very easy to just open the app and compose new outfits. Sometimes I'm inspired by something I have seen or have an idea, or look at previously worn outfits and want to wear them in an updated way. Have lots of saved outfits so even without new ideas could look at the forecast and plan in the Stylebook calendar few outfit options for the week ahead. Then when the day comes I just pull what I had planned out of the closet or adjust if the weather or my mood had changed.
To me deciding and planning this way is extremely more helpful and easier because I can do it during some quiet time when I’m not stressed and could clearly decide what I want to wear.

Without realizing all this had been written, I raised some similar questions today about emotional and intuitive style choices, vs, analytical choices as they relate to signature style. One might consider these two poles a dialectic with a continuum between them. Dialectical thinking seems to apply to numerous elements of style and fashion and as I read everyone’s responses, it’s clear that it applies to the way we plan our daily outfits. Reasoned advanced planning sits at one extreme and spontaneous, at the moment choice at the other; it’s basically Yin and Yang. Challenges can shake things up a bit and make us see new ways of doing something and push us either further towards an extreme or more towards a middle ground, depending on their construction. As an advanced outfit planner looking for a challenge, one might try a day of spontaneous outfit creation, for example. (I can hear all the planners groaning! )

There were many other dialectics I read in this post, but the elements of outfit construction, interest vs boredom; safety vs danger; personal vs generic(?), colors vs neutrals, dresses vs trousers, for example make for great challenges. The more I think about it, working through some challenges also will help someone pinpoint their “persona”. The idea of a persona challenge intrigues me because a persona is made up of multiple complex elements. It can be hard to define concretely. If you start to break things down a bit, I think it helps.....or maybe not....it depends on where you fall on the continuum!

When I purchase new items, get inspired by one of Angie's or other forum members outfits, or see an ad, blogger, or pinterest outfit, I like to see if I can use the inspiration to help me play in my closet to find new outfits. I record these with photos which I keep on my computer in my Photo app. I've also been taking an outfit photo every day and repeat the ones I like. I look at these photos for options and what appeals to me each morning after looking out the window to see what the weather is like, and checking the calendar to see what's happening. If I try to put an outfit together emotionally, it most often fails because the proportions are wrong, there's too much going on, etc. It may be that my eclectic tastes have made my wardrobe a bit challenging.

Thank you again everyone for your thoughtful replies to this thread! My apologies for taking so long to get back to it -- I had a major work deadline that coincided with my daughter's first day of school. Yikes!

Thank you especially to Dreika for your very thoughtful comments. I think you and I are very similar in lacking time/being pulled in multiple directions both in the morning and at night. I also have trouble putting aside a chunk of time on the weekends for this. I'm laughing at myself a little bit because my I realized my response to the situation was "well I'll just learn this whole OTHER skill" rather than "how about if I get a tiny bit better at self care?"

Also thanks to Staysfit for introducing the concept of the dialectic, which I do see applies here, and now see at work all over the forum now that you mentioned it!

I am glad to hear that so many folks are interested in a style prompt/possibly persona related challenge. I will make a note on my calendar in a couple of weeks to post a list of prompts and invite others to add prompts and join in the challenge. I will probably begin this in late September since the fall equinox is my informal "switch to fall dressing" point. Additionally I would like to build a little bit of momentum before I head off to my annual super-stressful work conference in mid-October. I hear others saying that they would prefer to start in October and that's fine! I think this will be a very loose, come-when-you-can sort of challenge. Looking forward to it!