ETA to note to shopping update is included as separate response down thread.

I have gained so much from anchie's posts, which has encouraged me to share my recent assessments in case it helps others, too. I am over half way to my weight loss goal, having recently lost over 40 lbs, corresponding from a size drop of Petite 16/18 to Petite 12/14 and the lowest weight I've been in over 8 years! This means that I can often find clothes in stores, rather than shopping nearly exclusively online. I still have a long way to go, but I'm feeling more energetic and strong and excited about how clothing fits me now. My husband has also dropped from a large to a medium and one pant size. Together we've decided to prioritize updating both our wardrobes for this intermediate size to help keep us inspired on this journey, even though most things I buy for this fall/winter will not fit me next year. Some upcoming travels have been instead changed to staycations to find room in our budgets for this update.

It is very important to me to wear excellent fitting clothing even in the midst of body changes. I am working too hard on weight loss to have poor fitting clothes add visual weight and I receive a very big confidence boost from perfect fitting clothing. I am in my early 40s and a recently tenured scientist. I typically dress business casual with mix and match, rather than matching suits. I love floral prints, asymmetry and interesting necklaces and shoes. I keep my clothing fairly simple and unadorned. 

I'm aiming to keep a very tight focused capsule and have worked at identifying my minimum needs and trying to withstand temptation to expand beyond it. My palette for new purchases this season is navy/dark denim, burgundy, rust, and a bit of cream. As you may notice below, I wear Burgundy as it was a neutral and can quite happily go head to toe Burgundy. Many of my tops and cardigans still fit well. I bought everything on sale and all but the newly purchased skirts are from the petite lines. Note that I'm a Canadian living in the US so many of my previous purchases have been from trips to visit my family in Canada. The rest of this is long and likely only helpful to me, but it is nice to document it. I reevaluate frequently and take out of rotation any piece that is ill fitting.

Bottoms. Completely refreshed. 
Navy ankle pants (Ann Taylor)
Straight, undistressed dark straight leg jeans (Talbots)
Medium wash, undistressed boyfriend jeans (Jill)
Navy pencil skirt (Ann Taylor)
Navy floral flared skirt with Japanese flowers (Ann Taylor)
Burgundy paisley skirt (Talbots)
Grey dress pants (Lord & Taylor, Raphaella)
[Still in rotation are some previous wardrobe pieces, but they won't fit for long: bootcut dark wash jeans, grey dress pants, and black stretch straight leg dress pants]
GAP: I need one more pair of dress pants, but I'll do without until the next size change. 

Dresses. Mix of new and previous.
Navy sheath dress (Ann Taylor)
Navy floral sheath dress (previous purchase from a trip to Canada, had tailored to fit current weight as it's a favorite)
Burgundy/purple/indigo sweater dress, 3/4 sleeves (previous Canada purchase that still fits well)
Burgundy/rust long sleeve drapey dress (bespoke dress from an Iceland boutique bought in August. It's drapey-ness handles weight changes well, but I will have this tailored with additional weight loss as it has straight seams)
GAP: None, but I note that well fitting sheath dresses are a staple for my work and with a cardigan or other topper is a FFBO for me.

Toppers. Two new purchases. I grab one of these every day.
Dark denim jacket (Gap)
Burgundy waterfall cardigan (White House Black Market)
Pine green faux leather jacket (from Ann Taylor several years ago)
Bronze faux leather jacket (from Canadian store purchased >10 years ago, it's starting to be too big)
Purple blazer (previous purchase, was too tight but now fitting)
Black blaze (previous purchase, was too tight but now fitting)
Navy long cardigan (Spring purchase at Canadian store)
Many asymmetric/waterfall cardigans in variety of colors from previous purchases still work (navy, aqua, rust, teal, black)
GAP: I was happy that most of my toppers are still working or now fit as this is an essential. I'll continue to focus on cardigans over blazers for my style goals. I would like to add a Moto jacket, but given the good shape that this part is in, I will put that on hold for now.

Tops. I think this is about to be where I need to put more thought into. Many of my previous purchases are still fitting because the tops had stretch, but another 5-10 pounds loss and this section will likely be a disaster. I recently bought three sleeveless shells (ivory, purple, Burgundy) to go under my toppers and two long-sleeve lightweight sweaters (Burgundy - J.Jill, dark rust - Ann Taylor). I'm not finding anything that inspiring in the stores right now, too many details and large sleeves, or shapeless tops, where I prefer body skimming v-necks and scoop necks. GAP: Will slowly refresh this as interesting tops are identified and others are removed from rotation because of ill fit.

Bras: I have refreshed this twice so far. I am large chested and a poor fitting bra can give me back pain, so I pay a lot of attention here. I've gone down a band size, then very recently a cup size. Each refresh includes two everyday bras and a sports bra.

Shoes. Fortunately this hasn't been impacted by weight loss and my previous purchases are still in heavy rotation. I did buy a new pair of Burgundy Chelsea boots and a pair of Burgundy block heel pumps this season. GAP: My tall boots are gaping at the calf, but I will work with my existing dark brown pair for this season and wait to replace next fall. Too expensive to buy for just this season.

Outerwear. I recently bought a hooded, knee-length, fleece-lined burgundy rain coat at Marks & Spencers during work travel. This will be my go-to outerwear for our mild winter. On the coldest days I will use previously bought jackets that are too big. GAP: I'll wait and refresh my winter outerwear for next winter. 

Evaluating my wardrobe, my feelings about it and fit has been extremely helpful in focusing my shopping priority list.