Dispersion engineering of optical waveguides is among the most important steps in enabling the realization of Kerr optical frequency combs. A recurring problem is the limited bandwidth in which the nonlinear phase matching condition is satisfied, due to the dispersion of the waveguide. This limitation is particularly stringent in high-index-contrast technologies such as silicon-on-insulator. We propose a general approach to stretch the bandwidth of Kerr frequency combs based on subwavelength engineering of single-mode waveguides with self-adaptive boundaries. The wideband flattened dispersion operation comes from the particular property of the waveguide optical mode that automatically self-adapts its spatial profile at different wavelengths to slightly different effective spatial spans determined by its effective index values. This flattened dispersion relies on the squeezing of small normal-dispersion regions between two anomalous spectral zones, which enables it to achieve two Cherenkov radiation points and substantially broaden the comb, achieving a bandwidth between 2.2 and 3.4 μm wavelength. This strategy opens up a design space for trimming the spectra of Kerr frequency combs using high-index-contrast platforms and can provide benefits to various nonlinear applications in which the manipulation of energy spacing and phase matching are pivotal.