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In terms of geography, culture and urban build. I'd say that the Upper South influences the Lower Midwest more than the other way around, but I'm sure there's some back and forth.
Choices are
Kentucky
Tennessee
Arkansas
Oklahoma
Texas
Basically the southern states that border the Midwest, plus Texas which almost touches Kansas.
I would say in order from more Midwestern to least:
Oklahoma
Kentucky
Texas
Arkansas
Tennessee
Oklahoma has a similar climate to most Midwestern locations along and south of I-70 (minus southeastern Oklahoma which does resemble the rest of the South in its climate). Oklahoma is grouped with Kansas, Nebraska, and the Dakotas as part of "Plains Tornado Alley". Also shares a border with Kansas. The part of Missouri that it shares a border with is probably more upper-south and not really that Midwestern.
Kentucky shares borders with IL/IN/OH and is actually part of two Midwestern Metro's (Cincinnati and Evansville) even though those both have some upper-south characteristics as well. Kentucky is on the southern edge of the Corn Belt, but as a native Kentuckian, we are culturally and more geologically/geographically similar to Tennessee, West Virginia, the Ozarks portion of Missouri (which is more upper-south than Midwest) and Arkansas as a whole than we are to Illinois, Indiana, and Ohio. That is not to say that there aren't similarities between Kentucky and the three states above it, but not to the level of the other solidly upper-south states.
Texas has some relationship to the Midwest as the plains and that associated climate reach down into the state. The Texas Panhandle can be grouped with SW Nebraska, West Kansas, and the Oklahoma Panhandle as the area where the Midwest meets the West.
Arkansas and Tennessee have the least relationship to the Midwest. The parts of Missouri and Oklahoma that Arkansas border is pretty solidly upper-south. I would say that Arkansas influences those two states more so than those two states influence Arkansas. Tennessee is a pretty solid upper-south state with some deep-south characteristics in the SW portion of that state.
I've lived in Kentucky, and I've lived in the Midwest. For the most part, Kentucky has more in common with Tennessee than any state north of it. Louisville and the Cincinnati suburbs north of 275 feel more Midwestern than the rest of Kentucky, but that's it. The rest of Kentucky is unmistakably not in the midwest.
Funny -- I lived in Missouri for 65 years and never considered Oklahoma to be a "southern state" so I guess that's my answer. It is a plains state and subject to some influence from Texas, Kansas, and the Ozarks regions of Arkansas and Missouri. It's sort of a place unto itself with the Indian country history and cowboys and Bonnie and Clyde. I never got a real sense of "southern-ness" when I visited there. I'm not certain I would call it Midwestern, either.
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