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Potential high-ROI purchase: lots of the same decent, cheap socks. I've saved several minutes per week of pairing socks by getting two packs of these. 12 pairs will set you back $30-$34, depending on size (plus shipping if applicable); they're listed in Wirecutter's "best no-show socks" (even though they do show while wearing most sneakers; aren't all socks "no-show" socks if you posit a tall enough shoe?).
(Of course, this is less useful if you're fine with wearing mismatched socks anyway. But I think the asymmetry looks slightly bad and it sends a weakly bad signal re: conscientiousness, so I try to avoid it.)
I've been doing this for about 10 years. This January I needed to get some new socks but my brand was discontinued so I decided to buy a few different brands and compare them. I will take this opportunity to write a public sock review.
I second the socks-as-sets move.
The other advantage is getting on-avetage more functional socks at the cost of visual variety.
IMO an important criteria for a sock is its odor resistance. This seems to vary wildly between socks of similar price and quality. Some have antimicrobial treatments that last a very long time, others do not. And it's often not advertised. Reviews rarely include this information.
I don't have a better solution than buying one pair or set before expanding to a whole set. This also lets you choose socks.that feel good to wear.