Wardrobe Simplification

I’ve managed to pare my wardrobe down quite a bit by using two questions: do I want to keep this; will I actually ever enjoy wearing this? Amazingly, I got rid of the vast majority of clothes I own just by asking myself those two questions. My initial pass through my clothes was simply asking myself: do I own a better version of this / would I like to own a better version of this? If I owned something better, I gave away the other, and if I wanted something better, I put that back on the shelf as a possible reward to myself for getting my clothing under control.

With fewer items, I’ve found that I have settled into a pretty consistent routine with what I wear. But more than that, there’s a lot less stress around my clothing. I am always wearing stuff I like, and stuff I want to wear. Here’s the routine I’ve fallen into.

Standard Work Clothing

I didn’t think I had a set wardrobe I put on for the average day, but then I realized that I most certainly do.

If all I have on the schedule for the day is working (I work at home) my dress is typically:

I’ve found this to be an exceedingly comfortable set of clothes. And without even realizing it, it’s what I pick more often than not. It also works well if I want to dash out of the house to grab some food or get the kids from the bus. Overall, this is the core of what I wear everyday.

Standard Day Clothing (Out of House)

As with the last, this seemed to work itself out without much conscious thought.

  • Outlier Futureworks (sandstorm, which is basically khaki), or Slim Dungarees
  • Outlier Ultrafine Tee or Wool & Prince button down shirt (temperature dependent)
  • Outlier Socks
  • Allbirds Runners
  • I might add layers on this if the weather is cooler, from sweaters or jackets

I wear the Futureworks when it’s warmer than 70° and switch over to Slim Dungarees as the weather cools, but otherwise I’ve been pretty happy with this setup. It’s comfortable, presentable, and did I mention comfortable? With really cool weather, I’ll wear my Strong Dungarees. Though my tops stay the same, I add layers to stay warm.

Standard Evening Clothing (Out of House)

Typically, I want my evening clothing to be a little nicer, because if I am out in the evenings it means I am kid free for a change. So here’s what I’ve standardized on:

  • Outlier Slim Dungarees (either Dark Indigo, or Charcoal)
  • Wool & Prince Button Down or like dress shirt
  • Darn Tough Socks
  • Clarks Desert Boots
  • Blazer/Sportcoat (Currently either the Bluffworks Grammercy or the Taylor Stitch Telegraph)

This should last me well into the cool season, with the addition of a jacket. I like how the Slim Dungarees dress up pretty easily, yet remain comfortable at all times. I’ll likely trade the blazers for warmer layers in colder weather.


Since picking up the OG Climbers from Outlier, they are my go to pant anytime I can wear them. They look extremely casual, but have replaced all my warm-up or sweat pants. I wear them every evening and every morning before I get dressed for the day. In a pinch, they work just fine out of the house, but they look the most technical of all my pants. Typically I pair this with a cotton t-shirt I still have loads of.

Still Looking For

There’s only two things I still feel I need to round out my wardrobe:

  1. Dressier Pants: In the warmer months my Futureworks filled this need fine, but now a khaki pair of pants isn’t great. While I have a suit, I’d like to get something in between and suit pant and my Slim Dungarees. I’m not sure where I will end up on this one.
  2. White dress shirt: There are not many good options. I have looked at everything out there for a replacement for my standard white dress shirt, for wearing with a suit, and I’ve yet to find one I am willing to pull the trigger on.


In addition to all of the above, I’ve switched all my socks to merino and all my underwear out to the ExOfficio Give-n-Go boxers. I only wear cotton t-shirts at night, and I’ve donated half the cotton t-shirts I had. So when doing laundry, the only clothes which ever need to be folded out of the family pile are my boxers and a few t-shirts. Which is rather comical to me. I mean, my clothes never look or smell dirty, and yet I hardly wash them in comparison to all the other clothing in this house.

I was mostly worried about lack of variety in my clothing over a long period of time, but thus far, it has not been an issue at all. In fact, I feel like I don’t rotate through the few clothing options I have enough as it is.

I didn’t list my Ministry of Supply Apollo polo shirts above, because my Lavender shirt came out of the wash a few weeks back with odd discoloration, so I donated it. This leaves me with just a medium gray, which I don’t wear often. I hope to find different options for these next spring, but am waiting until then.

I have cut down on all my duplicates, but kept both the Dark Indigo and Charcoal Slim Dungarees. They are both so very close in color, in that they are both the same level of darkness. I bought the Dark Indigo first as people said it was closest to “denim” however I find that not to be true and still might part with them (my wife likes them, and says I should keep them). I really do like the Charcoal color though, and it’s a winner for me.

I am now in the hard part of this experiment. I truly have almost all I need, and anything I buy now is not because I need it in any way, but rather because I want it. So can I resist? I don’t know, but I want to try. Additionally, I still have a standard pair of jeans, and have yet to bring my self to get rid of them, but truthfully I cannot remember the last time I wore them.

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Wardrobe Simplification