Languages are known to differ in how many orderings of major constituents are grammatical, as well as how interchangeable these orders are, a property often referred to as flexibility. Due to a variety of factors, including methodological barriers, flexibility is often underdescribed or treated as categorically, with languages being placed into heterogenous bins such as “free” or “rigid”. This paper advocates for starting from the premise that languages differ in degree and not kind when it comes to flexibility, presents a novel method for measuring flexibility in constituent order (via acceptability judgment experiments), and applies this approach to two languages which are known to differ in flexibility: English (Experiment 1) and Malayalam (Experiment 2). Flexibility is operationally defined as the difference in acceptability between canonical and non-canonical orders. Experiment 1 demonstrates that acceptability experiments can distinguish between canonical (svo), non-canonical (osv), and ungrammatical orders in English. For Malayalam, in which all orders of subject, object, and verb are grammatical and attested, verb-final orders group together and are most acceptable, followed by verb-medial and then verb-initial orders; this provides an initial picture of non-verb-final orders, which have been under-theorized in this language. Finally, a qualitative comparison of each language’s constituent order profile (a plot of the acceptability of each order in a language) serves as proof-of-concept that this measure allows for meaningful comparison across languages. This approach serves to en-rich typological descriptions of constituent order across languages, and it opens up opportunities for testing hypotheses about the source (s) of flexibility.