IMO, wool socks are far superior to cotton socks. The primary reason for this is that the wool wicks moisture away from the foot much more efficiently than does cotton; as a result, your feet stay much drier with wool socks than with cotton socks. As an experiment, wear a pair of wool socks one day, and when you take off your shoes and socks at the end of the day, feel your socks and then your feet. My guess is that both will feel dry. The next day, do the same with cotton socks. At the end of the day, both the socks and your feet will feel damp/clammy. The difference between wool and cotton is why, before the rise of miracle fabrics, "technical" gear was made of wool. The variance in wicking is one key difference. A second is that wool retains the majority of its insulating abilities when wet, whereas cotton does not. I only wear wool socks, except for sporting events, when I use high-wicking synthetics. For the price, I think the Gold-Toe Windsor wool socks are a great deal, particularly when they are on sale at department stores, often for around $5.50 or $6.00 a pair; they are very durable and can be machine washed and dried. I buy a bunch of the same color (particularly the reddish-brown), and I don't really have to worry about matching pairs after they've been washed. The reddish-brown goes really well with most brown shoes. (Against standard fashion advice, I tend to match my socks to my shoes rather than to my pants.) Unfortunately, cotton seems to be the preferred sock material these days; my guess is that this is a result of the years of marketing by the cotton industry, and traditional fears about machine washing wool. (Why are virtually all sports socks made of cotton, which is terrible in this application? -- one exception the SmartWool brand.) As such, wool socks in patterns are hard to find, whereas patterned cotton socks are readily available. I also like the Pantherella, Polo Purple Label, Brooks Brothers Merino, Dore-Dore, and Faconnable wool socks that I've run across on sale. Sierra Trading Post often has the Pantherella and sometimes the Dore-Dore socks on sale. Also, cashmere socks are a total extravagence, since the soft cashmere wool wears out really quickly. That being said, I picked up some very fine/thin Silk/Cashmere Dore-Dore's on Sierra a couple of years ago, and they are beautiful, though still pretty fragile.