Well, my go-to answer here is that if you can’t decide between a few schools then you shouldn’t apply Early Decision. ED is for people with clear first choices. You don’t have one. That’s true even if you are only choosing between two schools; that’s especially true if you are choosing between five. Applying RD will give you the most flexibility of choice.
“Best selection of males” is a pretty weird way to phrase that. It kind of depends on what you’re looking for, but I also don’t think you can stereotype an entire college full of people. At any of the five schools you’re considering you’re likely to find young men that appeal to you and young men that don’t. And there’s also a wide range of attractiveness.
That said, if you know you want to be close to a city, Middlebury and Bowdoin are kind of out - they are both pretty rural. (Bowdoin is close-ish to Portland, ME, but you have to have a car I think and Portland’s not a big city.) New Haven, Boston, and New York aren’t close to Wesleyan but are easily accessible by train. Vassar is a bit closer to NYC, but it’s still about 1.5 hours driving although NYC is accessible by train as well. Tufts is the only one that’s really close to a city.
The rest are found at all five colleges.
I also really agree with @austinmshauri . You sound like you want something really different from your prep school, but in the process you are stereotyping it and most other schools - which is counterintuitive to what you really want. Part of what college is about is learning to think critically, broadly, and with more complexity, so start now: even at a small school with around 2,000 people you will find 2,000 completely different, diverse, interesting people. Even though a school might have an overall ‘vibe’, there will be differences. For example, at Middlebury there are bound to be at least some people who are very much like your prep school classmates (in negative and positive ways), especially given the location and who tends to go there. But there are also probably skateboard kids, people who are “fratty” (whatever that means), hippies and hipsters, conservative Wall-Street-dreamer types…everyone. It’s also not a high school movie where everyone fits in neatly defined boxes. Some of the “hipster” kids are going to be conservative at heart and want to work at banks; some of the “preppy” kids might have a really deep interest in social justice and international affairs; some of the “fratty” kids might be very serious about school work and want a PhD. (I have tons of friends in Greek orgs. You can rarely tell the difference between them and someone who wasn’t, especially by the time they graduate. They’re people…who happen to be a member of an organization that does stuff.)
It’s also kind of interesting that you want something different and yet you are considering a bunch of colleges that are traditionally attended by prep school grads. These five colleges are the kinds of places that are like magnets for upper-class private school graduates - which is not a bad thing at all, just an observation. If you really wanted something completely different, you might consider schools that tend not to attract kids from there - like UF! In all seriousness, do consider New College of Florida. Very small school, very good school, and has a different vibe from the New England/mid-Atlantic small LAC. Also consider some West Coast LACs like Lewis & Clark, University of Puget Sound, Willamette, and Whitman. Or maybe some Midwestern ones like Grinnell or Oberlin.