How Can I Know If It Works Until I've Worn It?

Small and relevant experiments

Organizational theorist Karl Weick coined the phrase “How can I know what I think until I see what I say?” to illustrate his theoretical framework for sensemaking in organizations. Weick’s theoretical perspective emphasises action as a pivotal part of change, strategy and organizational life, with reasoning and motives coming after actions. You do something and then you make sense about it afterwards. In some ways I think this also applies when choosing what to wear.

There are a pleothora of tools we can use when putting together an outfit. In upcoming posts, we will cover The Italian Background, The Pale Base Layer, TPO and others. These are just some selected tools and there are plenty more. But these tools are not answers, they are mere guides. Can you look good in a light blue shirt with a dark navy tie? Absolutely. Can you look silly and out of place in a light blue shirt with a dark navy tie? Absolutely. So then what to do?

For me, the crucial thing is to keep experimenting and trying things out, however small they may be. A lot of tweeks probably won’t be noticed by anyone but yourself, but wearing loafers instead of oxfords or wearing knitwear instead of a shirt are small experiments, a testing of ideas. Let me give you two examples:

Knitted T-Shirt

In this outfit, I am wearing a cream knitted cotton T-shirt (Perro). It would have been more common to wear a regular shirt instead, but I was heading for a day at the office with no meetings and a lot of desk time. I could remove the jacket at the desk and wear just the t-shirt.

The rest of the outfit is pretty standard for work situations: The Jacket-Trouser Uniform. The T-shirt felt like a nice tweek, and I think it worked in this context. It was actually quite nice and felt quite relaxed to wear this t-shirt just with tailored trousers and loafers. The important thing, for me, is that the t-shirt is knitted and with ribbed waist and sleeves. It feels less casual that way. Elegant and relaxed.

Also, I like the contrast of the calf leather tassel loafers (Cavendish by Crockett & Jones) and the knitted t-shirt. Suede loafers would have worked just as well, but I think the dark brown leather creates a little more contrast on the formal-casual scale which works nicely. Replacing the brown shoes with black shoes could also give an interesting effect. Next experiment right there.

Striped Shirt

Here I actually started with the shirt and ended up doing a subtle tweek on the Menswear Uniform - grey trousers and navy jacket. The trousers are actually brownish, but do appear grey - especially in photos. The trousers are a high-twist wool (Cavour) and are a bit more coarse than regular worsted (suit) trousers. Besides the better performance in warm weather, this also gives the advantage of a subtle interest added and not appearing as if a regular worsted suit has been broken up. The same can be said for the hopsack jacket (Trunk).

The obvious choice of shirt would have been a plain white or light blue. Safe choices. But I wanted to try this striped shirt out (pre-owned WW Chan via Drop 93) to see how it worked. I think it worked quite well with the jacket on. The pale grey and pink stripes add just enough subtle interest to the jacket without overdoing it. However, the shirt felt more relevant with the jacket than without. During the day, when I took the jacket off, I actually would have prefered the simplicity of a plain shirt. Lesson learned. Because I tried.