So, I have bought countless socks, most from Wal-Mart and, while they "fit" they also cut into my legs. I wear ankle socks as they're comfy so it's not as bad as it could be but the point is, I can't wear my women's socks because they cut into me and have had to wear the only male clothing I have left, which is, men's socks. However, over time, thanks to wear and tear along with thanks to the work shoes I have to wear (Which are also men's shoes...), slowly one by one, the socks got holes in the bottom of them, big holes might I add and one by one, were thrown away. However, now I am down to just 1 or 2 pairs, 1 if there isn't a pair in the dirties, 2 and only 2 if there is but I believe it's just 1. So, now the last pair, is also about to go on me, at best they'll hold out for 2 more days at work, at best.. so, now I need your help please. This will hopefully help you to determine what size socks I wear. Shoe wise, the only female shoes that have fit my feat so far are, the Catapult size 10 shoes (women's) that I bought at K-Mart. Tbh though, it only had a W on it but no tag to indicate they were in fact women's but I believe them to be women's as their men's shoes had an M on it but also did have a tag stating those were men's shoes unlike the pair I bought which had no tag and a W on them. I also bought some socks from there but, they didn't fit me, can't recall the brand but size wise was probably the same as the following socks. At Wal-Mart I bought, Hanes sizes 6-8, 8-10 & even 10-12 (their largest size), I also bought whatever other name brand socks they had there in their largest size (10-12) but sadly, none have fit my big feet. (Well, not without cutting into me anyway) About the only option I have left is to try to find socks online but, I don't know of any sites that sell them? I hope the size/name brand of socks and the shoes I own helps you to determine what size socks I need because if not, then, I'm basically screwed and will have to give in and buy more men's socks and continue to wear them and I really don't want to have to do that.

Thanks if you're able to help me or for trying if you tried.

EDIT:
After much needed sleep, I remembered my special occasion shoes that are women's shoes. This is the brand and size, hope it helps and I'll edit this into the OP post.

Pierre Dumas Boots size 10 M
Pierre Dumas High Heels size 10 M (I have two pairs in two different colors)

And yet, the women's socks in the brands I bought at Wal-Mart for even 10-12 don't fit me. (Again, that's their largest in store size)

Funny thing about socks, the M on the label turns upside down into a W (and vice versa) a lot!

Haha, just kidding. In the sock department I say comfort and preference over buying the right gender. I will buy what I need when I need it (Men's sport socks to go with my army boots, women's socks for my slip-on shoes). Most people don't even look at socks at all, and when they do, the sock has to be pretty crazy for them to register as more than just "socks", so go with what works best for your comfort that still suits whatever you are wearing.

I wear a size 12 wide in women's shoes and the size 10 to 12 women's socks fit my feet, but just barely. I only buy the ankle socks though, because I don't like the taller ones.

derbyvilleonline.com

Clothes for derby girls! I have gotten some socks here that are super cute and designed to fit a larger girl! (Feet are a womens 11-12)
Good luck!

After much needed sleep, I remembered my special occasion shoes that are women's shoes. This is the brand and size, hope it helps and I'll edit this into the OP post.

Pierre Dumas Boots size 10 M
Pierre Dumas High Heels size 10 M (I have two pairs in two different colors)

And yet, the women's socks in the brands I bought at Wal-Mart for even 10-12 don't fit me. (Again, that's their largest in store size)

When it comes to women's socks, quality matters.  I like to get my socks from SockDreams.com.  They have the best selection of pretty socks in the Universe, their shipping department is awesome, and they do an excellent job of testing out everything they carry, and the descriptions on their website are extremely informative as far as quality, fit, durability, whether a sock is good for thin or thick legs, whether a sock stays up or falls, etc.  Sockdreams.com is the best.  I can honestly say that I've been happy with everything I've purchased from them, and I have never been disappointed with the quality.

Best of luck.

I'll second the recommendation of sockdreams.com

Everything a sock fetishist could want!