I think the classic striped or patterned tee in a thicker, more structured cotton is a great staple. Agree with PPs this is a good way to get started -- comfortable but also polished and easy to clean.
But rather than pairing with skinny jeans, which I find too constricting for WFH and also too hot for DC summers, I wear these tees:
- Tucked into draped, high waist black pants, usually in some kind of stretch knit or poly so that it doesn't wrinkle easier and drapes nicely. Add a pair of Vejas or similar flat sneakers and this is an easy, casual look that still looks very pulled together.
- Tucked into a full or a-line midi skirt and paired with flat slide sandals or a little wedge. Really feminine and comfortable and great for mid-summer if you get a nice, light airy skirt from Uniqlo, H&M, or similar. You can go go monochromatic or have fun with prints.
- Nicer knit leggings (NOT athletic leggings). If you don't like the bulk of the other looks, invest in a couple pairs of dressier leggings. I used to see these called "Pixie pants" sometimes. J Crew does them well, but I have a decent pair from Old Navy that I am sure was cheap and has lasted 5+ years. Get them in black and navy and you can wear with tees, button downs, even dresses if you nail the proportions. Wear with low profile flats or sneakers.
- Linen pants. I have several pairs of slightly cropped, wide leg, elastic waist linen pants that I got from some random Amazon Brandon for like $20 each. They are super light weight, easy to care for, very comfortable in the summer. I can wear them with tees tucked or untucked, and they are totally comfortable for WFH but close enough to "real" pants to wear for errands, kids pick up, etc. They aren't a sexy option but they are perfectly serviceable, and come July, I'll be living in them.
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