With the holiday shopping season commencing, I have a confession to make. I love shopping for groceries, books and stationary, but shopping for just about anything else is a necessary evil. Shopping for clothes is the worst of those necessary evils for me. There are some things set my geek heart ablaze, but staying current with fashion is not typically one of them. At most, I’m a passive observer because I love reading magazines in the bathtub.

When it’s time to replace something that’s too worn or otherwise FUBAR 1 , I cry a little on the inside. If the piece was a wardrobe staple, sometimes I cry on the outside, too. Not because I have this deep attachment to my articles of clothing, but because it sets off this deeply unsatisfying process for me that usually involves:

  • hours of searching online and offline for some phoenix-like article of clothing
  • a trip to a loud, overly perfumed mall with dismal lighting with the potential of leaving empty-handed
  • finding something I like only to find out it no longer exists in my size anywhere in the known universe or only comes in neon yellow
  • finding something that fits enough for me to then schlep to the tailor (I’m just shy of 4’11” with an athletic build. Off-the-rack is an off-the-wall idea for my body.)

If the procurement of new clothes isn’t a buzzkill enough, then I have to actually get dressed every day 2 . Some of you reading this may love standing in front of your closet mixing and matching to your heart’s delight. I applaud you. That’s not me. My heart’s just not in it. I’m more the type who has always marveled at how other women on business trips or at conferences seem to have 37 fully-accessorized options in a suitcase the size of my backpack 3 .

Considering I’m in the business of helping frazzled women get their shit together and feel less stressed, it was beyond time to deal with my fashion issues. If something’s stressing me out, it’s time to stop messing about. Plus, I’ve been itchy to find a happy medium between spending time and energy on something so perfunctory to me most days and Matilda Kahl’s Why I Wear the Exact Same Thing to Work Every Day act of rebellion since I read it. While it’s taken a few months to layer in some of the simplifications, here are some of the decisions made so far:

My color palette is largely down to 5 colors - black, gray, red, purple and hot pink. Occasionally, there are other accent colors. The whole point was to simplify, not make compliance difficult or dogmatic. Result: More things match other things with less effort and consideration. Plus, shopping got easier. I can visually skip over huge sections in some stores and even some brands that don’t offer my color palette.

When I’m working with clients or doing heavy-thinking work, comfortable clothes are now non-negotiable. My formative “professional work” years were spent wearing a black, brown or navy suit at a client site. It’s taken a while to ditch the belief that a suit is the only way to convey professionalism. Now, “office attire” means black yoga pants, a tee-shirt or Uniqlo HeatTech layer and a sweatshirt or sweater layer. Result: I can take 5-minute exercise breaks to stay energized and focused during the day. Then, I’m 100% focused on the client with whom I’m working or the project on which I’m working instead of my irritating collar and hearing my clothes rip upon stretching.

I leveraged what works for me - namely a simple A-line skirt. When fate brought Krista Gorrell of Teton Tailoring into my life, I asked if she could replicate my favorite, but fading, A-line skirt. Much like the Postal Service recorded Give Up using the USPS, Krista upped my skirt count by 4. I selected the fabric; and she made it happen. It was the most excited I’ve ever been to receive a package of skirts. Check them out!

While this is by no means an exhaustive list, it’s a start. Perhaps, you have another fashion time-saver to share in the comments below.

Yet, I also share this as inspiration. For me, choosing an outfit was a daily activity that felt like a drag. Maybe there’s a part of your getting-up-and-getting-ready routine that feels like a drag to you. If there is, get creative. Because stress in any form is a waste of your time and energy.

Have a relevant tip? Thought of some part of your day that you could simplify? Have a question? Please share them in the comment section below.

Notes: (1) Fucked Up Beyond All Repair (2) Getting dressed is considered optional most Sundays and all snow days. (3) By now, the fact that I mostly use a backpack, instead of a fancy purse, shouldn’t be much of a surprise.