Given a permutation $\sigma$ on $n$ elements (i.e. $\sigma \in S_n$), there is a notion of "parity" (or "sign" or "signature") of $\sigma$, which can be defined in several equivalent ways (look here). This produces a homomorphism $S_n \to \{\pm 1\}$.
I've known the various definitions, the proof of their equivalences and the various applications of them for quite a while, and yet something seems missing. I can't convince myself that any of those definitions is really "natural". Of course "natural" is something rather subjective, but for me at least, it is close in meaning to "categorical". For example, a "natural" presentation of the definition (and basic properties) of addition/multiplication of natural numbers, can be achieved by considering the category of finite sets, where these operations are categorical sum/product.
Since $S_n$ is the automorphism group of a set with $n$ elements, I would say that the (horizontal?) categorification of it is the groupoid of all sets with $n$-elements. This is arguably a more "natural" object. Of course, this groupoid is equivalent to $S_n$ so it is just a matter of perspective. Now, we can define the quotient groupoid for which the hom-sets are the two element sets of equivalence classes of isomorphisms, where two are equivalent if there quotient is an even permutation. This is cheating of course. The question is, can we define this quotient in a "natural" way? I find it very surprising that this kind of structure associated with plain finite sets, is so well hidden.
I heard that the K-theory of finite sets encodes some information of this sort. If this is so, I would be very happy to hear more about it.
As a final note, one famous neat application of the notion of parity of a permutation is the proof of the impossibility of the 14-15 puzzle. The proof is beautiful, but it applies group-theory techniques to something which is most naturally viewed as a groupoid. This might be completely unrelated to the main question, but it seems that a more natural/groupoidal definition of parity might be applicable to this situation as well.