How I Dress on My Day Off: Comfort, Style, and Convenience

My days off are all about unwinding and comfort. Sometimes, it's a simple day where all I need is loose shirts and sweatpants because I don't have to worry about feeling cold or finding something to wear. Other days, I can step out in jeans, comfortable trousers, or even a casual skirt when I have errands to run or a casual walk planned.

There are days when I step it up a notch and dress in a blazer, smart shirt, and chinos, paired with professional Oxford shoes. For formal meetings, a well-tailored suit often completes the look. However, I rarely buy new clothes because I spend a lot of time looking for interesting second-hand items.

Comfort Comes First

I dress for the weather and comfort. One of my must-haves is comfortable shoes/boots that suit the weather. I almost always wear socks, and I prefer materials like wool, nylon, silk, and cotton. I love layering to keep warm or cool as needed.

On a day off, I might wear comfortable loungewear such as soft jersey trousers and a casual, cozy T-shirt or a jogging top. Layers are key to staying comfortable, whether I'm going out or staying in. I frequently wear the same thing for a few days to save time and avoid getting my clothes dirty.

Why I Choose Comfortable Outfits

On a casual day off, I prefer to wear jeans, a hoodie, and athletic shoes or boots. These choices allow me to run errands without feeling the need for a cocktail dress and stilettos. Clothing that is too fancy can detract from the day's purpose, which is to rest and relax.

Former fashion consultant Clinton and Stacy from What Not to Wear? would disapprove of my choices, but running errands does not require such formal attire. Comfort is key, and on days when appearances matter less, I prefer to dress for practicality and ease.

My Style Inspirations

If I were to share a snapshot of my day off, it would be in the spirit of Bill Cunningham, a NYT videographer who captured people in their natural attire. His videos, often found on YouTube, highlight how individuals choose their styles and look their best. I would love for Bill to take my picture because of the thought I put into my outfit.

I dress for comfort and for the weather, ensuring I am neither too warm nor too cold. My shoe collection is vast, reaching out to styles that are suitable for various weather conditions. Socks are always a part of my daily attire, and I rarely buy new clothes due to the abundance of interesting second-hand options. I also enjoy wearing hats made of wool, nylon, silk, and cotton, layered appropriately.

I want to be polished but not overly showy. I aim to look good, but I do not want to elicit excessive attention. People often say I look eccentric, and in an effort to be noticeable without standing out too much, I try to tone it down slightly. I seek a balance between being myself and maintaining a certain level of style and professional appearance.

My signature self-care practice is to stay comfortable and put thought into how I appear. On a good day, I might be spotted in a choice that makes me feel confident and ready to face the world, with all the layers and comfort that make up my day off outfit.