Here are some sources on matching colors to you skin tone or 'season.'
http://en.wikipedia.org/wiki/Flattering_colors
http://www.kinowear.com/blog/category/color/

Now, I don't have a traditional season, so I was wondering if anybody who knows what someone who has flush cheeks, doesn't tan easily, but has dark hair and dark eyes. I know that means I'm clear, but I'm neither warm nor cold since my hair/eyes contradict my skin.

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and I think... I think too much

I'd say it's a light skin tone: so avoid bright colours (purple, red, yellow and orange). On the season scales I think you are Summer cool and muted; it says avoid blacks-don't, black is so versatile. If I was you if your in clothes shop, try the clothes on to judge if they clash with your skin or not.

Cool beans. Do you think this would be a good DHV? Either an opportunity to IOD/Neg if the colors don't match, or an IOI if they do. It could be a thread on its own, and set up for a time bridge since I actually enjoy shopping.

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and I think... I think too much

There defineately some flexibility. As a DHV story you could maybe have something like: "when I was younger an Auntie bought me a pink shirt with yellow stripes, it matched nothing (and yeah it was disgusting to look at)...and from then on I became more fashion conscious and learnt abou colour matching etc" - maybe there's a better routine.

A good conversation topic might be pointing out other people whose clothes clash and discussing it with the HB (it maybe a DLV though if it looks like you're making fun too much).

Pointing out her clashes could be a good neg but you'd need to know the colours well to make it convincing. Also use "I read an artcle in..." then go into the routine.

It's also a good excuse/opener to chat-up the female clothes store assistant(s).

Idk... some of the descriptions are pretty vague. I like the kinowear one, that'll be helpful.