The search for reasonable work clothes: My absolute-most-comfortable business casual clothing (and the stuff that didn’t work out)

Do you track how often you wear clothes? I do in Cladwell and I really enjoy it. The app lets me know when I haven’t worn something in 3 months by putting a dot next to it, and it shows me my most worn items. I’ve learned a lot from tracking how many times I wear things, so today I thought I would share my greatest hits and misses from 2019. Here are my best women’s work clothing purchases of the year and what landed in the giveaway pile.

Greatest hits:

Ponte Pants/Wide Leg Pants/Cropped Chinos

Two of these are from Brass and I am not at all surprised that they were my most worn pants this year. In looking for patterns, the obvious answer here is that these are all work appropriate yet they don’t feel like dress pants–they are so comfy. I guess the lesson here is buy comfy low maintenance pants and ditch the rest (this is obvious here, but in the dressing room? Somehow I come out with things that don’t fit both requirements more often than I would like to admit).

The best crew neck tee

It is not surprising to me that the shirt I bought multiples of also made the list–I wore both the black one and the white one 9 times (since August) according to Cladwell. Finding good tee shirts is surprisingly difficult, isn’t it? This one is not sustainably made but it’s really sturdy (the white has no armpit discoloration yet which is a great sign) and unfortunately I haven’t found a better sustainable option yet (I must admit for example that I don’t really like Everlane tees), so these are my current go-to.

Oversized cardigan/Blazer

If there is one thing I’ve learned this year, it’s that I should invest much more in layers than in shirts. I am always cold in my office so a layer is a must. While I have flashier blazers, the oversized fit of my black one from my job market suit is still my favorite. Both of these items are old so I linked to similar things if they’re on your list!

Flats/More Flats/More Flats

If you see me on instagram stories trying on a block heel please come tell me to step away. I teach far away from my office on campus and am no longer interested in hobbling back from my second class of the day. I’ve already raved about all three of these pairs of flats and if I feel I need variety in the future I plan to go back for any of them in different colors instead of trying out a new style that may not be as comfortable.

I have already complained about finding my office style at length, and I think the key is that I kind of want office clothes that look cool. A little oversized, a little casual, just…something that doesn’t give me flashbacks to my high school speech and debate suits. So, lesson learned. Here’s what ended up in the giveaway pile:

  • 3 sweaters (if they aren’t perfect–in sleeve length in particular–I don’t want them)
  • 2 work shirts (one for wrinkling too fast, the other for being an impulse purchase that wasn’t really “me”)
  • 2 tee shirts (see above!)
  • 3 pairs of shoes (for having heels, causing blisters, and otherwise being unwalkable now that I teach in a far away building on campus)

Do you clean out your closet at the end of the year? I really enjoy it! Tomorrow I am doing some sewing/mending and then I’ll be all done!

8 thoughts on “The search for reasonable work clothes: My absolute-most-comfortable business casual clothing (and the stuff that didn’t work out)”

  1. I’m off for Christmas Eve and Christmas so those are my set days to go through my closet! I only started tracking a few months ago, but I’ve got my photos on Instagram to supplement the rest! I love a good clothing year recap – I may post my own. It’s funny that the stuff in your giveaway pile looks like pieces I find myself gravitating towards more now! Thanks for posting!!


  2. I downloaded a wardrobe app because I love the idea of tracking wears, but never got around to entering all my wardrobe items. Did it take you a long time to do that? I go through my closet fairly often to weed, so it’s more of an ongoing thing for me rather than a year-end event.

    A professor friend of mine teaches in 3″ heels! I don’t know how she does it.


    1. Whoa. 3″ heels! That’s a super power. Cladwell made it pretty easy because you select from their images (instead of having to take your own). I update my app when I do a closet clean out, usually while I’m watching TV. I find it soothing 🙂 Also I love putting things in before I buy them to see how many outfits I can make!


  3. This is so great. I love the idea of tracking my clothes but I haven’t been able to find an app that I love yet. I’m Canadian and android so the struggle is real! Also, pointed toe flats are so great because they create the illusion of a heel but your feet don’t suffer!

    Liked by 1 person

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