Loving all your comments and questions...make me really test my thinking! I want to respond to everyone, so I'll break it up so I don't lose it all in a crash.

Una, you said you "aspire to look as dressy as your [my] comfy looks". Which set do you consider my "comfy looks"? When I was working, I would have called the casual slide my comfy looks. Now that my slightly dressy looks are less buttoned up, I find them even more comfy than the casual looks.

Thanks, Jeanie. The power of the WIW pic is amazing! Just keep plugging along at it daily.

Rachylou, that's an interesting question. I think Sterling really captured the essence of it, but I'll add a couple thoughts that sort of collided into making this comfortably dressy formula. First, now that I'm not getting dressed for work, I was concerned that I was slipping into the "why bother...I don't have anything going on today anyway" schlump. I'm 51, so the thought of spending the next 40 years looking like I'd given up was horrifying. Second, I've mentioned my stepmom before...she always looks fantastic...dressier than most, always put together. For years, her simple little formula has somehow eluded me. I wanted to make it harder than it was because it seemed so unattainable. A few weeks ago, we were standing in her new closet. Off to the left were the serious dress up items. The next section to the right was hanging pants...knit and side zip only. The next section had a top and bottom row. The top row as all lower hip length sweaters. The bottom row was all lower hip length button front woven tunics/shirts. She waved her hand toward the sweater row and said, "Fall and Winter I wear something from that row with a pair of slim pants." Then onto the lower row, "Spring and Summer, I wear one of those tops with a pair of slim pants." That's when it finally hit me that it really is that easy.

Sterling...you are so inside my head, it's scary! I definitely feel better about everything when I'm put together/finished. "Intentional" and "finished" really need to be my mantras until this is an ingrained habit;-).

Carla, I think your mini refreshes in Spring and Fall were brilliant. I started the YLF journey back when I thought I had at least 3 more years of working, so although I needed a total overhaul, I did buy more than I really needed, given that my working life was shorter than expected. Your way sounds much smarter!

Sally, Helen11, CocoC...thanks!

Elizabeth, I did see your Summer cottage posts right about the time, this was all starting to percolate for me. I was purging my closet by moving the meh stuff to the "beach capsule". It finally struck me that I would soon be living at the beach permanently and had basically built an incredibly meh wardrobe for this new adventure! How ridiculous is that?

Posting before I have in internet blip...

I like this post by AmidPrivilege:
http://amidprivilege.com/2014/.....etirement/
I think it's about taking an outfit from "humming along" to "rev the motor"- for me that's often the addition of a scarf, necklace, nicer shoes (ballet flats instead of sneakers), maybe a nice cardigan or jacket. I was in NYC this past week and found that scarves really took my jeans + cotton striped top up a notch.

Continuing...

Approprio, I love your thoughts about the cultural influence. When I was growing up we dressed up for the theater, church, flying, dinner out, entertaining guests, etc. Somewhere in the past 5 decades, people seem to have stopped dressing up for these things. For me, dressing up (at least a bit) brings back a bit of the "specialness" (ok, not sure if that one's a word) and the respect for the specialness. Does that make any sense at all?

Unfrumped, I so thought that the blazer/Emmanuelle Alt look needed to be mine. Except...I really can't tolerate layers, particularly anthing that constricts my arms and shoulders. It was a dismal failure for me, but I will always admire any outfit involving a blazer:-)

Sterling...forgot to answer your pant question. In the earlier pics, I am wearing a pair of Chico's satiny stretch pants. They're about 5-6 years old and have seen a ton of wear because they are the only non-zip fly-trouser I owned. When I purged all of my trouser-style pants this Summer, I added the EF washable crepe ankle pants in black (worn 6x so far), the EF mid-weight slim knit pants from NAS in both black (worn 3x so far) and gray, a pair of temperate weather woven stretchy side zip pants in black (worn 2x so far), and finally heavier weight ponte pants in black and gray. I feel like this assortment can take me anywhere I want to go:-)

Ginger, thank you. "Intentionality" is my new favorite word, even if I didn't get to make it up;-)

Jenn, you are right! This really is a priority shift for me, but one that feels so much more me than the sloppy/who cares shift. I do think that intentionality can/will become a habit. Like any habit creation, I'll just have to be intentional about becoming intentional until I can unintentionally remain intentional:-).

Aww...thanks, Angie!

Smittie, you are so right about the simplicity. I have this frustrating habit of overthinking and insisting that things must be more complicated than they look, otherwise everyone would be doing it. Turns out the "secret formula" isn't so secret!

JAileen, thanks! Your standards made me chuckle! I wasn't even asking myself whether something needed ironing, and I'm quite sure that at least a few times, my only questions was, "is this clean enough?"

Sadie...exactly! Thanks for the intro to the Amid Privilege blog. That post definitely tracks the continuum for me.

Fascinating analysis, Carter. I so admire how carefully you think. You may have felt that September was a wasted month, but it sounds as if it might have been your most important month yet in terms of this style renovation.

It seems as if -- with some thanks to stylish step-mom-- you have found your "uniform" for this new phase of life. All these outfits look fantastic and could take you most places very comfortably and with panache. It looks to me as if they're actually all quite similar in terms of level of "dressiness" (I'd call all of them smart casual) -- but the "comfortably dressy" ones more often have sleeved tops (or dresses). Plus your amazing silver pendant.

I definitely had to rejig my work-at-home style, which had become so sloppy or gear-oriented that it basically didn't count as "style" at all. My mantra was: As comfortable as gear, but stylish enough to go out on the street. I've been largely successful in that aim and most days get dressed properly in clothes that don't embarrass me if someone comes to the door. Having said that, I am sitting here writing this...in my gear.

I've really enjoyed this thread Carter. I don't have anything to add as everyone has put it so eloquently, but suffice to say I'm coming back to re-read many times. I have slipped somewhat into 'why bother' territory lately and also lost my fashion interest a bit so this is all very helpful to me. Thank you!

This just about sums it up, doesn't it. Does for me! With a big chuckle added for good measure.

I'll just have to be intentional about becoming intentional until I can unintentionally remain intentional:-).