What is My Super Specific Search?

Follow my search for a hyper-specific item in pursuit of a certain look. I show you which styles I gravitate towards, the emotions they elicit, and where they can be found. All ending with which items I will take a chance on, and which ones I won’t. Use my search to streamline your own.

Plaid skirts with large, colorful checks, not Pioneer Woman-y and also not vintage 40s goodie-two-shoes.

What does that even mean?

Screen-Shot-2020-05-26-at-10.08.47-PM-8 AceJig_016_1366.1366x2048-6 Plaid-Wool-Mulberry-20191021201233-6
Plaid-Wool-Mulberry-20191021201235-7 large_rosie-assoulin-plaid-plaid-silk-blend-wide-leg-pants-3 Screen-Shot-2020-05-26-at-10.18.22-PM-3
Screen-Shot-2020-05-26-at-10.19.22-PM-2 il_794xN.2278883718_pk8r-2 Screen-Shot-2020-05-26-at-10.26.55-PM-2
AceJig_009_1366.1366x2048-2 3d92f84ef746e4dc44bb6b4105dd1e5e-5 P00305350_b1-2

Desired feelings when wearing this item are...

Items I am trying so far. All the descriptions below have links, FYI.

Nice pattern and different silhouette but too expensive for a print and style I have seen often. Also, the fit seems to be tight, similar to pencil skirts, and that feels dated. Vivienne Westwood (Matches Fashion), $242
This color is everything; so bright and vibrant. The tiered lower half, flared bottom, and puffed sleeves can get bohemian very quickly. I would like to try this and wear an oversized, off-white or orange, knit turtleneck over the dress to make it look like a skirt. For Love & Lemons (Urban Outfitters), $245
There is a point at which bright color plaid becomes too clown-like to carry off with irony. This dress is that point for me. And this price is my rent for more than two months. Gucci (Matches Fashion), $5,500
I know these are pants but I felt the wide-leg silhouette gets after the draping and space I was seeking in a skirt. Looking at my inspiration grid above, it seems many of the images I feel avoid "Pioneer Woman" territory are pastel plaids and unique silhouettes out of a conventional material. Wilroy Traveller on Thrilling Vintage, $88 
This is an awesome take on plaid, practically psychedelic. I can image this skirt with any boxy crop top. You can even wear it on a beach vacation. Saloni on The RealReal, $136
I found this vintage set on Etsy that comes with a skirt, shorts, and a top all in the same pattern. I love the full commitment to the plaid as a way to avoid looking safe with the print. The listing says it is 80's style, which is not the 40's, so it satisfies all parts of the criteria. I may experiment with the top style if I kept this set, since the high neckline is too passé for my liking. ReloveVintageParis on Etsy, $49.41
I am a sucker for matched sets so I really want to try this. The loose shorts are kind of like a skirt and it is the only shorter silhouette that satisfies my search term and I actually like. The print makes you look like a picnic blanket and I didn't realized this was a lifelong dream until now. The Fifth / BNKR, $69.95

Other keywords that proved useful in this search...