Ambitious Friday Outfit

I am featuring a complex style challenge: 2 personal challenges plus Debbie's two scarf challenge.  Friday, 12/12/14.

Personal Challenge #1: Wear my black skinny-ish ankle pants with a normal length top to work.

I had felt comfortable wearing them with a longer tunic or cardigan, but could I rock them with, say, a pullover sweater?  They are actual pants -- not leggings -- so this is a totally legit combo but a bit out of my comfort zone.

Personal Challenge #2: Wear black pants tucked into tall cognac boots.  I'm good with wearing brown and black together but I've been a bit boggled at the popularity of black pants with tall brown boots -- almost always, when I see these outfits, I think: Huh, I would wear black boots instead.  But what the hell, you know?  I have a new pair of tall cognac boots I've been wanting to wear.

Two Scarf Challenge: My first stab at this involved pairing two lightweight scarves (black/white cat scarf and black/polka dot scarf) together, but I found the result distinctly meh.  Then I had the idea to combine the polka dot scarf as an accent to a plain black scarf of a normal winter weight and voila!  I used the mint green dots on the scarf to rationalize wearing my new olive green cable knit cotton sweater.

*Olive pullover sweater (Kohls)
Black ankle pants (thrifted, Eileen Fisher)
*Cognac riding boots by Sam Edelman
Black scarf + black polka dot scarf (Target x2)

Verdict:

#1: This is a doable combination with tops that are moderately long or are layered under/over a longer top.  Putting this together proved harder than I initially thought because I had forgotten that the pants are rather loose in the waist and low rise, so there is a tendency for a normal length top to ride up and show my belly circa 2004 (or whenever that was popular).  But this is precisely the situation in which my too-long black T from Target shows its worth.  The black blends into the pants and averts the risk of belly-flashing my coworkers.

#2: The cognac boots looked OK, and I was happy to test them out, but I am a black-on-black girl at heart.  I'll probably not do this combination again.  The inclusion of the orange dots on the black scarf helped justify/rationalize the choice of (orangey) brown boots and made it look a bit intentional, not "I only have brown boots so that's what I wore even though they totally don't go with this outfit."  But I just don't love this kind of high contrast on my legs.  I could, though, more easily see wearing the brown boots with blue jeans or a skirt and tights/leggings in a different color -- blue, burgundy, olive green...but probably not grey or black.

#3:  Muahahahaha, I pwned the 2 scarf challenge here.

Also: Damn, this is a comfy sweater.  I'm glad I also bought a purple one.

True to my "lagging indicator" status, now that I have hesitantly tipped my toe into the skinny-ish pants water, it's time for the skinny silhouette to be replaced at the dominant style.  (Actually, in jeans, boyfriend jeans -- which naturally I do not own -- probably have already eclipsed skinnies.)  Welcome back, wide legs and boot cuts!