I've worn the same thing almost every day for more than 3 years. I love it. The items I wear are either used and upcycled, on sale, or expensive. What matters is quality, sustainability and if I really love the item.
Here are the parts and pieces and why:
White Shirts, Uniqlo: Used to be whenever J.Crew had sales on white shirts I might buy one. Why? I always loved the look of a white shirt. Like the classic "black dress" a white shirt is universal. The downside is how easy they are to utterly wreck. I am always spilling my coffee somehow, so by wearing white, my actions throughout the day are much more considered- and it look nice/they last longer. Last year I was in a Uniqlo to buy socks & underwear when I saw a pile, a literal pile, of white shirts all for 5 dollars each. I bought a bunch. I don't need another white shirt now but when I do, I will try Everlane's.
Purchased in Austin Texas January 2016. Worn them almost every day since. Have had them resoled once by a local cobbler. Still great boots. Love how simple they are. One simple zip and no excess details. Just nice leather and good craftsmanship.
I have been trying all kinds of grey t-shirts over the years. My favorites are always the ones with pockets. Currently I'm on Everlane T's. I like their approach to sustainable manufacturing and transparent pricing. This is a case that I believe paying more for something is well worth it.
Where to begin. Black jeans look good with everything, but they fade. I found a brand that made solid jeans that hold up great. Because they are real denim I've experimented with not washing them for long periods. They don't smell, they still look great, and I they are the only three pants I have bought in about three years. Wear em everyday to work and play.
Simple affordable basics. My drawer is full of identical socks and briefs which makes choosing a pair a breeze. I know a lot of people like different things, but underwear and socks are function not fashion for me, and much like screws, I have found I enjoy these wardrobe 'tools' as standardized as possible.
Outerwear, Second hand shops:
Because so much of my wardrobe is boring and standardized, I use outerwear as a pop of color and expression. Nothing better than used, funky jackets. Example below:
Hope this helps answer any questions you might have, like:
"Does he wear the same thing every day?"
(Yep.)