This is not self indulgent, but very insightful and helful. My favorite type of posts. I understand completely your desire to minimalise, too much choice is always overwhelming to me, creating guilt and cluttering my space and my mind. I think you will feel liberated after you purge everything that is creating those negative feelings, and in your heart you probably already know what needs to go.
And I hear you about body image issues too. I put on some weight in the last 5 years, developed some fitting issues along the way (hello muffin top) and had a hard time accepting my new body. And since most of my adult life I was pretty slim and did not have fitting issues, I did not know how to dress anymore. That is how I found YLF actually. But this became a blessing in disguise. Before the weight gain, everything fit me and looked good off the rack. I was buying random cute things but never had anything to wear, and was constantly purging and shopping. Now, shopping is a nightmare, I don't like 90% percent of things I try on, it takes long time and lot of patience to find something that looks decent enough, but as a result my wardrobe is in better shape then when I was slim and could fit and look good in juts about anyhing.
All your goals sounds very good, I agree that shoes needs to be refreshed regularly but I also have hard time letting go of expensive shoes in good condition that are few years old even though I cannot imagine situation when I would reach for them instead of my newer trendier shoes.
And I am also looking for replacement for my everyday top, which is sweater for me. Sometimes it feels too casual but I don't like any of the alternatives. Will follow your search with interest.

Lisa, I'm really glad you took the time to rewrite this. I don't think it's any more self-indulgent than what any of us do here on YLF when we analyze our closets or our styles!

I love your insights and your plan. It kind of makes me want to go downstairs to my holding zone and get rid of everything in it.

I'm in editing mode myself, but right now I'm applying that to other areas of my home as we revamp and renovate some spaces. When I get home from the desert, it will be time to start making my seasonal wardrobe switch, and that will be a good time for more editing. Thanks for the candid thoughts and inspiration!

Lisa, thank you so much for taking the time and trouble to express this (twice). I am so grateful. As Janet says, thank you for the open approach and the inspiration.

Oh, such an excellent read. Very useful to me too. Im still doing my slow- lane edit as opposed to the rapid Konmari sort.
I have been an admirer of your style and outfits , so you must be being a bit hard on yourself, otherwise it means I'm crazy, but then....

I wear pants most work days ( despite loving pencil skirts) because they're warmer and easier for footwear, but I've had some , er, fit changes also.
My big pitfall is to keep buying more pants hoping for some miracle.

Finally I realized I actually had several pairs that worked well with the RIGHT tops-- and footwear that went with them-- and that if I actually wore all the possible combinations I had plenty. I just needed to be more rigorous with outfit creation and not leave things to random morning mix& match rush.
So I vowed not to just buy more new pants. Not a shopping ban- but to relax on too much searching and discouraging order/ return and being tempted to buy some that were really no better than what I have.

The same is true of my skirts-- there are several I can't wear now, and new ones tried didn't quite fit right even sizing up-- but I have several that still work. Again, if I wore them with all of the several different top and shoe options that I know work with each one, I have enough variety.
So there is something about a scarcity feeling that's misleading me to thinking I didn't have enough options, and this got worse when I experienced some shape- shifting and disappointments with how some of my things fit. Whereas really, I had lots of things I wasn't wearing, and while some were not- wearable and needed to be tossed, some were still good fits but I'd forgotten, or had not tried to rework into pretty darn good outfits.

I loved reading this and the responses. Gaylene is correct with her approach - sounds like she has been through a similar experience. I also find it hard with pieces I love or even just like that no longer work for me, or the items that I regret buying that have not been well worn. But I believe you have a genuine desire for a simpler chic wardrobe with less trend driven pieces. I wonder if it is possible to arrange a shopping day or weekend away from your home town where there is more selection, either with a friend or family member.

WRT summer work wardrobe, my approach at the moment for work is to have two pairs of cropped black pants (slightly but not totally different styles), two dress options and one or two more casual looks that work for some occasions that cross over into my other life (I can wear jeans to work and also work from home often). My pants/jeans are mostly on the classic side and are real workhorses - I honestly don't have a lot at all but they are all very well worn (five pairs of jeans, three pairs of black pants, one pair white pants, one pair linen grey pants- the quantity is dead right, although ideally one of the jeans and the white pants would be different styles than they are but I am just accepting it is what it is)

For you I think a couple of simple chic dresses would be fabulous in spring and summer, something fairly simple that can tolerate a leather jacket or chanel style jacket over the top, can be edged up with fab heels or boots. I find dresses an easier fit than pants if buying online, as long as I can get them the right length.

Well done on your process so far:)

This was a great read, both the post and the responses. I am feeling the same urge and I am not very good at being ruthless. I was just telling my husband today that I get frustrated because I put things in the Goodwill pile, then think I need it so I take it out but then don't wear it but it's now back in my closet! Grr! I have to stop doing that! Good for you for tackling this so thoroughly.

Oh, and I sure feel you on the body issues. It's been a problem my whole life and not likely to get any better so the sooner I deal with it the better!

Sally - you're onto something with the dress suggestion. Why am I driving myself crazy looking for something that is so hard to find. Dresses are indeed a whole lot easier to wear. I am on a restricted budget - partly by choice, so the lack of great options in my city might just end up serving me well for now

unfrumped - you and I clearly experience some things the same way. Your last paragraph is bang on . I need to calm down and let this happen, not try to chase it...

Robin, Jane, Janet,- thanks for your thoughts.

anchie - wow - you are describing my experience as well. Your comments about hanging on to yet never reaching for expensive older shoes goes for me too, which is why I am determined to winnow my collection WAY down. It's nice to know there is someone else out there experiencing the same dramatic body changes as me. I couldn't complete the trying-on part of my project looking in the mirror - the person in the reflection looked dumpy, tired, out -of-shape and middle-aged . I tried things on without a mirror - that's how bad it's become.

The project is still underway - after 2 days of it I'm emotionally and physically exhausted. I still have at least another day to go through shoes and the rest of my clothes. What a massive undertaking ! I cut my jewellery down by half - and packed up at least 6 clutches and 4 bags I know I'll never use. Tough to do, but there are no benefits to keeping extra stuff!

Lisa, I want you to know that this post gave me the courage to tackle the MOUNTAIN of unfiled papers in my study. I am still not done but I got them all categorized today -- huge win! So thank you.

Suz, you need a Konmari kid to do your filing and office organizing for you. I have one who might take on international consulting jobs this summer after she graduates high school.

Lisa, I'm following all of this with interest. I've winnowed my thoughts down to this: don't settle on a "uniform" look even if it seems like it will make things easy. I think you like trend and variety because of the nature of your work, even though clothes that flatter and fit are your priority at the moment. Assuming all your fantastic jackets still make you happy, I would select 2 updated shoes, 2 pants that are not jeans and 2 tops that are not t-shirts/jersey to carry you through till really hot weather hits. If you have these already in closet, all the better.

Lisa, so much of what you said resonates with me. I spent a lot of time last year purging purging purging. It helped I was able to sell things, and it feels good to have mostly a closet of things I love. I also had a lot of jewelry. I gave/donated a lot of it, and I "fixed" a lot of it, by making some necklaces longer (my neck needed more room) and layered many of them to go together. It was actually fun. But the process took me months, so have patience with yourself!
For the summer, I when I had an office job last year, I wore those pants from J Crew that had an elastic waist and a nice drape. They were comfy, cool and polished and would look good with your shoes. (an example is in my finds)
Body image is so difficult in our culture, and I keep special feel good outfits for "less than days"-- that helps, so I don't worry about it when I'm not feeling great about my body-- there's nothing worse than standing in a tornado of clothes and nothing feels good on.
I know exactly the type of shell you re looking for and why are they so hard to find, especially if you want to wear a bra with it?!?! Who is designing them all with spaghetti straps? A pricey but nice top (I got mine on Ebay) is the Joie "Marcher".

Lisa bravo on what you have achieved. You always look fantastic in your posts. In my mind you are the definition of a beautiful and stylish woman, so please don't be too hard on yourself. Extreme weather is always hard so I hope you have fun dressing up this spring, enjoy those fab shoes.

Lisa, I always enjoy reading your posts...this one, and the wonderful responses really resonates with me. I have been winnowing my wardrobe items by removing even more items that haven't been worn this season...just because it fits, doesn't mean I enjoy wearing it. I have really gravitated toward neutrals this past year.

Also, just went through my bags...have a large pile to bring to Salvation Army...I'm sure many ladies will enjoy them in the future. They were in perfect shape, but too structured for my Eileen Fisher/Elizabeth Suzann clothes.

I have already paired down my shoes/boots/booties to ones that I love, are comfortable to wear and look nice with my choice of clothes.

Now, I just need to update my lingerie...sigh...I HATE bra shopping!!

"the person in the reflection looked dumpy, tired, out -of-shape and middle-aged" Yes, that is the problem isn't it! I still feel like the 30-something me but look in the mirror and am like who is that 50-something person? I also always think you look great but we are hardest on ourselves.

Thanks for posting lisap - some good info here but I haven't time to read everyone's comments quite now. I think a lot of us share many of your sentiments. I need a good deal of casual easy to wash items due to living in the heat for such a good part of the year but I still much prefer having a smaller, more well thought out selection in the closet (hello navy and olive). I wish I were better at judging an item that is right from the start so I could do exact duplication more successfully.

And speaking of too many handbags - I think I"m going to check with my nieces to see if any of them would like one of the ones I seem to be just storing.

I am still chuckling over Gaylene's categories: VER (very expensive regret) and BILT (but I loved this). Perfect!!

Seriously, it can be demoralizing to do an edit and realize there are things there you rarely wore, or wore a lot that no longer fit, or simply hate now and wonder what you were thinking -- but it's fabulous to finish to a closet full of "feels great now" items.

Bravo Lisa, for all your hard work. Thanks to you for writing it all down twice for us, and for all those who have shared their wisdom with us on this thread.

Wow! There is so much good stuff here - both in your original post, Lisa, and followups, and also in the comments and suggestions! Every time I plan to comment myself, I end up spending my available time soaking up all of the newly posted wisdom instead.
I can absolutely envision you rocking a wardrobe of current essentials for clothing with shoes and jewelry as your statements. To my mind that is a very sophisticated and fashionable look, so would seem very appropriate for your line of work, too.
Very glad someone suggested adding some dresses to the mix - that seems like a great option for this look. And of course avoids the dreaded finding-pants-that-fit issue.
I'm curious if you see the same people repeatedly in your work? You have mentioned that you don't mind repeating outfits - could you pick a minimum number of outfits that you need for your out-of-the-house workdays and concentrate on pulling that number together - starting with your existing wardrobe, and then adding what is needed to flesh it out?

I think you are a little bit hard on yourself. But I am always inspired by the unflinching analysis to which you submit yourself. I hope this exercise enables you to find a new, more manageable wardrobe that brings joy and allows you to appreciate all that you have.

Hard on myself? If we are not demanding of ourselves, what's the point? I hold myself up to very high standards, which of course I don't meet, but it's what drives me. To drink.

Thanks for this thread, Lisa. You've hit on SO MANY issues that a lot of us grapple with. And you've generated a wealth of insightful responses. I'll join the chorus and proclaim: not self-indulgent at all!

I feel you on the pants situation: so hard to find presentable warm-weather pants. I think this may be part of the reason why we diversify our shoe collections for the summer months -- because summer pants just aren't very interesting, but the shoes options are, especially compared to the past 6 months of nothing-but-boots. I too have a habit of perceiving pants as a perpetual wardrobe hole. I think I just have to come to terms with the fact that pants are not how I achieve wardrobe variety. Too many fit, comfort, and footwear constraints -- I would need a larger wardrobe, more motivation to make alterations, and a higher tolerance for impracticality, among other things. I have to constantly remind myself that NO ONE will notice if I wear the same pants twice in one week, which is not the case for tops, or skirts for that matter!

La P - I have come to this conclusion. I can find four tops I love to one pair of pants. And truthfully I wash my tops after every wear but pants except for in the height of summer, can often get two or more wears. I do own one pair of statement pants, but I have decided I can get variety in other places:)

Sorry Lisa to hijack your thread!

Not at all - you are both astute with this pants-as-perceived-wardrobe-hole issue. I admittedly haven't attacked my pants yet - in terms of trying them on- because it is such a hassle and so demoralizing. The less I have to see of myself undressed the better. But you're right : a couple of pair of cigarette pants or crops can work for the season until it's too hot to wear pants anyways.

Congrats for attacking the monster, Lisa! Agree with many others including Sal (above) + I so would like to see the black suede sling backs in action cuz am planning a pair for myself, too. As for the 867 pair of GAP jeans-- you and Laura... really made me smile:-)

First, congrats on deciding to review what you have and to making a change! That's awesome! And I hear you with having too much of something. At one point my wardrobe was bursting at the seams and it's taken me years to streamline it. And I also nodded my head about the jeans, because when my weight goes up or down it's the first thing I want to buy too.

I have been wanting to reply to this for a while now, and now I don't know where to start. So maybe I won't, I'll just thank you for starting this thread, and for all that you shared. You have no idea how much of what you said I could relate to.

I also want to thank all of hose who contributed... a LOT of good stuff in this, things to think about, ways to get my own wardrobe edit "unstuck".

I esp want to thank Suz for this:
Seriously, it can be demoralizing to do an edit and realize there are
things there you rarely wore, or wore a lot that no longer fit, or
simply hate now and wonder what you were thinking -- but it's fabulous
to finish to a closet full of "feels great now" items.

I need to read this over and over again. Wow, it happens to others, too? I have SUCH a hard time getting rid of my "mistakes". Such a hard time. It's ridiculous.

Perhaps this is way off base, but would it help to do one of those 333 clothes challenges to really distill what you love to wear? I have not done one myself, but it does sound interesting.

Elizabeth, I liked Suz's comment too - and wish I would hurry up and get there. I'm not finished the project yet - it is taking a lot of time. Mind you, I puttered around and rearranged the bedroom and cleaned out drawers while I was doing it. I still have lots of clothes to go through before the final collection reveals itself