I use style app to create virtual outfits then when I have the time I try one out in real life,if it makes the cut l keep it logged otherwise it’s deleted!

I think I have grown more temperature sensitive as I have gotten older. Thus, I check the weather and temperature forecast for the day and for the next few days. Then, I consider my likely activities including walking. Within the context of what I might want and need to wear in the next few days, I choose my OOTD beginning with something I haven’t worn for awhile that I want to wear.

Today was supposed to have a high of 80 degrees but we are also supposed to be starting yet another heat wave. I was also scheduled for a haircut which really limited my choices since the disposable drape is close to useless for keeping out the hair. The slippery fabric of my cropped pants worked well, but my shirt was less successful but not as bad as last month’s denim.

Oh, and in these COVID days I am also guided by what might or might not be a bit snug.

I am using my ( handwritten) clothes tracking lists to plan, more than ever this year. Because I have been trying to wear everything #30 wears I tend to start with the less worn pants. Only 3 work days a week since June so the black 2014 dress pants have been a frequent choice, they have just reached 30 with 18 of their wears being this year. Before I was only using them for evening outings which there have been few of. The 4 non-work days have featured my 2015 NYDJ jeans 14 times
( now at 27, wearing them today) and also 16 wears of the 2019 navy lounge pants. I will wear different pants if those 3 pairs do not suit the tops I want to wear. I am still hankering after silver pants but am waiting until wears are up on these others.
I am also picking from a smaller number of tops- 2 black layering tops, one orange, one olive, one silver, one navy, one peplum, one olive/gold. None of them have 30 wears yet. Again I will wear a more used top if it suits an outfit better.
Plus one dressy top and 2 dresses for the rare dressy event in the past few months.
So I guess I am sort of dressing from a small capsule mostly, of 3 pants and 8 tops, quite often! Surprisingly small.

Though I don’t count wears and never have used that sort of wardrobe management, relying more on an individual item’s condition, age, fit, and usability with other current pieces to determine keep or remove, I have to agree with Jenni that I’ve been using a small capsule approach more than ever. Picking what feels good for the day from a small group of items is working for me.

As summer was an unusually constant combination of weather and activities this year, i. e. hot and staying home, my choices became a predictable cycle of 4-5 pairs of shorts, maybe 8-9 knit sleeveless tops and either sandals or tennis shoes. I might have worn a “dressier” woven sleeveless blouse a time or two. In fact, as I switched out a few things in my closet last week as weather had been changing, my colorful floral blouse and tangerine orange summer cardigan I’d set aside for Easter church still hung unworn. Sad...

This strategy of picking what appeals for the moment, from one of 4-5 pairs of jeans, a shirt or long sleeve tee out of perhaps 8-12 favorites, and a coordinating sweater from my 6-7 daily “stock” pile, appears to be the wave of my future. No activities requiring fancier, festive pieces means I’m simply dressing for comfort, warmth, and to bolster my outlook that I am still me, and today I can do my activities - read, sew, cook, walk, household chores, pay bills, text my daughters, talk on the phone to my mother in law. (Running gear worn for runs, 3 x week.)

At least half, if not 2/3, of my wardrobe is not being worn at all, so no shopping for replacement or enhancement is required, though I’m planning to find some good, warm and weather proof boots so I’m motivated to keep walking outside this winter.

For me, it’s really simple. When I do this, I usually start with a particular piece — either something I just bought, something I am in the mood to wear, or something orphaned that I want to figure out. Then I find pieces in my wardrobe that I think will go with it, and go from there.

This thread is a treasure trove!

For me, I am a rather basic dresser - jeans and sweater most days - so the only strategy I bring into it is always trying to add an "I tried" piece - meaning some non-essential piece that says I did put a bit of thought into it! This could be a traditional "third piece" (i.e. a topper) but is more often than not some necklaces, a scarf, my snakeprint belt - just a little something to prove I tried!

I do exactly what Janet does. Either newest, mood (including weather because I'm moody about weather ) or figuring out the orphan.

If I'm going to play in my closet, I like to look around online for inspiration outfits that have a lot of pieces similar to what I already own. Then I use those as a springboard for putting together new outfits.

Great ideas in this thread! I giggled a little when I saw the word “strategy,” because I wish I was more strategic, but I’m not - my strategy is about comfort and familiarity.
I’m with Donna F. - I check the weather first thing, and generally choose an outfit I can layer this time of year. And I am a uniform dresser, I tend to be in a hurry and rely on combinations that I know will work - i.e. blazer/topper, button-down shirt, jeans, sneakers - on repeat.
I think if I were more strategic, I’d spend more time playing in my closet and getting wear out of more of my clothes by planning new combinations so there’s no guesswork when I’m actually getting dressed. This thread has inspired me to take a little time to do that again.

Oh, and I love Torontogirl’s idea for an “I tried” piece - I’d like to try that!

Much harder now with pandemic, since not many places to go, events, and now, no work days.
As pandemic goes on and essential errands go on, I have come up out of the mire a bit and am making an effort to wear “ outfits “ for most errands.
Because most of these are not super- rushed, I will put something on and then may spend 15 min or so trying a few variations- different shoes, see if different toppers work.
Sometimes I can’t tell if I should feel happy I can find a lot of variations, or sad that most of them will remain in my imaginary life for now, and then later may not fit or appeal to me.