Oh fun! I tried to adopt a tone like this article take, as it amused me. I would need at least one of each of these pieces to dress, although in practice I have lots of options in each category! And I spend enough time outside that I need seasonally specific fabric or cut options to stay comfortable in my four season climate.
Transseasonal:
The Little Silk Blouse
In a flattering colour, with interesting details, and a style that can be worn on its own or layered and tucked or untucked.
The Long Sleeve Crewneck Cardi
In wool or cotton/silk/linen depending on the season, this opens up layering possibilities and can be worn in several ways.
The Slim/Skinny Trouser
Fabric varying by season, this lets me surrender my waist without looking frumpy. A high rise is most comfortable on me and lets me play with tucking
The Full Skirt
Nipped in at my natural waist, then flaring out and ending somewhere around my knee. Along w a tucked top, this is my most traditionally figure flattering look while letting me add a vintage taste to any outfit. And I love the way a full skirt rustles as I walk.
The Girly Jacket
Its neat tailoring and waist definition lets it pair with full volume bottoms while it can be worn open over slimmer bottoms. It combines menswear tailoring w feminine details like peplums, puffed sleeves, etc. and can evoke 19th century style, unlike the cardigan. Fabric and weight vary by season.
The Sleeveless Fit and Flare Dress
Worn as a sundress in warmer months and layered in the cooler ones, this makes for an easy, flattering outfit with minimal effort.
The Clunky Flat Shoe
Varying by season, frequently sporting laces, and always in leather, these add a grounding, sensible note to my sometime whimsical outfits.
The Hat
Wool in winter, straw in summer, I wear one to protect me from the weather and add an extra dose of whimsy to my look.
Seasonally Specific Additions
The Long Sleeve Knit Top
Both cotton tees and wool sweaters form an important building block to keeping me cosy in cool weather.
The Lined Wool Trouser
Hitting at my natural waist to provide most tucking options, and in a tailored wide leg cut for the ultimate in comfort, these are a go-to on the bitterest winter days.
The Heavy Wool Coat
Keeps me warm even in significantly below freezing temps and lets me feel much more true to my storybook leanings than a puffer ever could.
The Baggy Midthigh Short
Baggy to counteract any sexiness implied by a shorter hemline, these keep me cool in the hotter months.
The Breezy Blouse
In summer fabrics and a cut that stands away from my body, these combine w the shorts for maximum cooling in the summer.