Infrared- and collinear-safe (IRC-safe) observables have finite crosssections to each fixed-order in perturbative QCD. Generically, ratios ofIRC-safe observables are themselves not IRC safe and do not have a validfixed-order expansion. Nevertheless, in this paper we present an explicitmethod to calculate the cross section for a ratio observable in perturbativeQCD with the help of resummation. We take the IRC-safe jet angularities as anexample and consider the ratio formed from two angularities with differentangular exponents. While the ratio observable is not IRC safe, it is "Sudakovsafe", meaning that the perturbative Sudakov factor exponentially suppressesthe singular region of phase space. At leading logarithmic (LL) order, thedistribution is finite but has a peculiar expansion in the square root of thestrong coupling constant, a consequence of IRC unsafety. The accuracy of the LLdistribution can be further improved with higher-order resummation andfixed-order matching. Non-perturbative effects can sometimes give rise to orderone changes in the distribution, but at sufficiently high energies Q, Sudakovsafety leads to non-perturbative corrections that scale like a (fractional)power of 1/Q, as is familiar for IRC-safe observables. We demonstrate thatMonte Carlo parton showers give reliable predictions for the ratio observable,and we discuss the prospects for computing other ratio observables using ourmethod.