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Sounds like black toe which is usually caused by poor fitting boots. You should take them to a boot fitter. They may be able to modify your boots with five irons or footbeds.

You really only have two general sole types, either sticky rubber or vibram. What I think may be more important to you is the footbed. If you don't already have orthodicts you should look at Superfeet or Sole footbeds. They will support your feet, increase your ankle support and generally make...

Remember very few feet fit perfectly in winter hiking boots without a little modification. I added volumn adjustment shims, superfeet, and a stronger boot lace. Now they fit like a glove. Hope you like yours.

The best winter hiker I've seen this year is Garmont's Momentum Snow. For the money ($140) it's 400grams of insulation, Gortex, and wicked light. Great in Micro Spikes or snow shoes and can be used with flexible strap on crampons.