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(1) Background: Annual flax (Linum usitatissimum) and many wild relatives possess showy blue flowers and finely textured foliage. To promote the use of blue-flowered flax as ornamentals, an herbaceous perennial flax breeding program was initiated to develop ideotypes and test their effectiveness. The objectives of this study were to (a) compare traits of interest for herbaceous perennials in breeding populations (CF, oilseed) and accessions of annual/perennial species in a common garden; (b) quantify the impact of selection (direct, indirect) for traits of interest; (c) identify top candidate species for continued breeding using the herbaceous perennial flax crop ideotype; (2) Methods: Recorded traits, based on the perennial flax ideotype, included: flower diameter, flowering period, stem length and diameter, plant width and height, summer and winter survival; (3) Results: OS and CF populations had smaller stem diameters, longer flowering periods, larger plant size, more uniform growth, and improved winter survival compared to wild species. Linum austriacum was the top wild species for the CF breeding ideotype but comparable in performance with L. perenne for the herbaceous perennial flax ideotype; (4) Conclusions: The effect of 1–5 yrs. on selection for target/non-target traits in wild species for future R&D is exemplified with selection and release of an herbaceous/garden ornamental perennial flax for the market. [ABSTRACT FROM AUTHOR]