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SS at the moment. Frustratingly I know going clipless would probably give just the right amount of room, but she's not the most balanced cyclist and I don't think I could deal with the guilt if she stacked it.
I think I'll suggest going back to flats for winter.
BCarley-
That's a wise option :) I think foot retention for commuting / knocking around town isn't that necessary: yes it's nice, power output improved blah blah blah but confidence and happiness (and safety too) are the most important things, way more important than any marginal gains offered by SS foot retention.
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SS at the moment.
In that case, get some nice wide flat pedals and allow her to get the hang of riding a small bike.
youramericanlover
edscoble
Is she fixed or SS? Could convert to flats and SS if she's getting wary of fixed and the toe-overlap, though I realise that's not actually a solution for fixed toe-overlap. I know 'get used to it' is not very helpful (although it is true and I started out very worried about - I'm 5'7 so all my bikes have had noticeable toe-overlap - but over time it's faded into the background issue-wise). Another option is to take off the front mudguard? I know front mudguards are nice to have but some soggy toes might be worth it for more confidence on the road, especially in the dark winter.
TL;DR
If she's fixed, take off the mudguard.
If she's happy to swap to free, ditch the cages and swap to flats and SS cog.
If she's free, ditch the cages.