What to Wear Wednesday: Boot Quest ’09 and Holiday Festivities: Special Double Freak Out

This week CKD needs your help (yes, YOU) with a few wardrobe-related quandaries.


1.) Boot Quest ’09 is ON bitches and I am having a hell of a time.  Last year’s mission was accomplished during a visit to DSW and I fear I may need to, once again, drive hours away to find something a.) cute and b.) in my budget. 


Here’s what I’m looking for: flat/low-heeled (around 1″ or so) tall boots that can be worn with jeans tucked in, pulled over, AND, preferably with a dress or skirt.  Apparently this is impossible and I might as well shop for the Holy Grail filled with unicorn tears.  I am down with either black or brown, but was thinking a nice cognac color would be different and still neutral enough to work with my wardrobe.


Have I lost the guys yet?  Yeah, I thought so.  Moving on!


2.) For the last couple of years I have lamented the lack of holiday parties in my life that require some snazziness.  I haven’t worked anywhere with a “real” Christmas party since 2002 or so and I always enjoyed the whole dressing up aspect.  (And also the open bar, but that’s neither here nor there.)  The attire was usually somewhere in the “cocktail/LBD” range and I knew what that meant. 


This year, I am Ed’s +1 to his company shindig and I am at a loss as to what to wear for several reasons.  First off, the party is AT the office after work and I don’t want to show up looking crazy-over-dressed as everyone else hangs out in business casual.  Second, this will be the first time I meet many of his co-workers at the Bay Area office and I want to make a good impression.  Finally, these are a bunch of creative-designer-young-hip-Silicon-Valley types and I don’t want to roll in looking like a total rube.  I am not planning on wearing bib overalls so I guess I’m off to a decent start there.


So, dear harbingers of good taste and fashion, can you help the hopeless?  If so, go for it in the comments, email me photos, or kidnap my clueless ass for some shopping.


3 thoughts on “What to Wear Wednesday: Boot Quest ’09 and Holiday Festivities: Special Double Freak Out

  1. I’m having the same issue. D now works at a place that does a HUGE party (3 floors at the Hilton or the ENTIRE Pac Bell Park is standard). Though I already know many of his co-workers, I still don’t want to look like a slouch. The invite reads: “Cocktail attire suggested or dress to your favorite decade.” So does this mean that I can wear the heels, dress and diamonds, OR jeans, tie dye t-shirt and rainbow headband and call myself someone from the 70’s? WHAT? If only I fit into one of the many 80’s dresses I have. Can’t you see me rolling in there in a short, layered, strapless green dress and crimped hair?

  2. I would pay serious money to see you show up looking like an extra from the prom scene in Pretty in Pink.

    That is a fairly vague dress code, but the cocktail attire at least gives you a hint about what’s appropriate/expected. And I doubt you’d ever look like a slouch, my dear.

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