Recent Attire & Potential Clothing Challenge

So I know that I've mentioned this but I'm seriously getting to the point where I am pretty much wearing the same items....and I'm actually okay with it. Part of it is because of the weather (no more open toe shoes and skinny jeans are amazing for Oregon rainy season in order to avoid that soaked ankle look) and part of it is because I have less clothes that fit these days since I've gotten fitter (hence why I've tried to maintain the same size for the last 6 years!!). I've been contemplating challenging myself to a 30 clothing item challenge for 30 days...and while I'm probably already doing this, I'm just not there quite yet. :) However I might go through my closets and just create one section full of the stuff that I'm actually wearing these days. Too bad running clothes aren't acceptable everywhere!

I have pulled some older items out of the closet recently, but I've also realized that I like to re-use one of the same items back-to-back frequently, only further showing me that really I just need to complete the challenge anyway :)

Monday happy hr & Tuesday errands:

Black cami (Target) under gray floral patterned top (old Penney's); yellow cardi (Target); skinny jeans (old Walmart); black leather boots (Penney's)

Tuesday teaching:

Same outfit but with thrifted black pants

And I love the above outfit cause it screams "Portland" to me! :)

Wednesday teaching: 

Same yellow cardi (Target); burgandy dress (old Walmart); brown tights/belt/flats, wool hooded coat (old Target)

Tuesday teaching: 

Argyle sweater (Penney's), work-weight denim skirt (Target), ruffled gray suede boots

Wednesday teaching: 

same boots, burgandy skirt (Kohl's), gray button down, black cami, black belt, long black cardi (Old Navy)

Family trip & happy hr in SE: 

Skinny jeans; gray suede flats (Kmart); shirt (Penney's); old blue cardi (Target)

Church: 

Mint shirt (recent Target); gray skirt (Target); same long cardi; black tights (YEARS old & Freddies); black suede flats (Kmart); black belt (from a diff outfit)

Based on these outfits alone I can already start to compile a list of items for my challenge:

Long black chunky cardigan

Wool hooded coat

Black leather boots

Black belt

Yellow cardigan

Black cami/white cami

Black trousers (only ones that fit me currently)

Skinny jeans

Mint green shirt

And being me, I'd HAVE to have at least three dresses, three more shirts, leggings, two pairs of flats, the black cardi, at least 1-2 sweaters, and at least 2-4 skirts.....hmmm I'm well on my way to designing a challenge... :)

It'd definitely make dressing easier...and I'd have less to worry about packing on any trips!

Accessories don't count do they? :)

But uh running and outdoor gear doesn't count....

What would you choose if you had to whittle down your wardrobe? Are there items you couldn't live without? Suggestions for what to include or items you think I could do without?