With regards to keys, I've got the Gustin Military Key clip. Snap it to my belt buckle and tuck the keys into my back pocket. Works well to keep my jacket pockets free and doesn't create a giant lump.
Merino wool boxer briefs and undershirts were both a nice change.
Prescription sunglasses were a huge change. I don't always wear my contacts and having the prescription sunglasses for driving made a big difference.
An umbrella when the weather forecast indicates the likelyhood of rain. I really value the comfort it provides during rainy commutes, plus when not in use I feel like it makes me look like I have my stuff together (haha).
Another thing I recently did was get contact lenses to almost replace my use of spectacles. For me there are many added benefits.
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Y shirt stays are another small thing. Keeps the dress shirts perfectly tucked all day. 20 bucks well spent.
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Another one: Realizing I should be wearing narrow size shoes after finally getting my feet measured on a Brannock device at Allen Edmonds. Game changer for me