When I mentioned this challenge last Friday, I didn’t realize it would take me an actual week to get to it… or that it would be such a freakin’… challenge. (I know - it says it right there, in the title. Still caught me off-guard.)

I started with a strong workhorse sweater - short sleeves, silk blend, goes with just about everything = slam dunk. Then I harnessed it to a skirt I bought last week, for a film shoot: a skirt I’ve worn once, as a different person, with a different life from mine.

From there, things got crazy, and there were ideas flying all over the place. Ideas that included a pith helmet, one of those Swiss mountaineer hats (like Chevy Chase wore in “European Vacation”), and some unintended 80’s throwbacks.

What I’ve learned:

Start with the tried-and-true favorites first.

It’s okay to have an outfit formula (turns out, mine involves higher heels 90% of the time)

When stepping outside the normal outfit formula… just try one idea at a time. Not all of the ideas at once.

Here are some that I liked, that I will revisit and tweak, once the temps drop (it was 82F this afternoon). #8 was my favorite, but #4 Film Noir Murderess was the most fun.

#1 Basic Outfit + Patent Leather
#2 Added a hat
#3 Swapped shoes and added a jacket
#4 Swapped hats and everything turned into an “80s-does-40s” Film Noir
#5 Vaguely Equestrian.
#6 Swapped Hats + Boots
#7 Swapped back to the green hat
#8 Trying to emulate a Ralph Lauren-type layered look (this was my favorite)
#9-10 Hats that didn’t make it into final lewks.
#11 Vintage Tiny Aigner Purse That The Gods of Thrifting Bestowed Upon Me Yesterday
#12 Closeup on the details from #8