HD has made a lot of really good looking bikes over the years, but after all the dust has settled, the Sportster with a 'peanut' tank comes out as best looking bike all-round hands down. Now any bike can be customed to fit the rider's taste and likes, but in general, the sporty has the best overall stance, silhouette, and just plain looks.
My first love of the sporty was in a TV show back in the late 60's called "Then Came Bronson" with Michael Parks. I was a newly wed and when I watched that show I fell in love with the red sportster he and his friend were building together to travel the country with. I swore one day I'd have a red sportster. Well the new bride (I'm talking basically by a couple months) thought it was too dangerous and we didn't have the money anyway. So, I settled for and old home built semi-bobber iron head, British racing green, and leaked oil from everywhere oil could leak. I rode that one for a few months then sold it so she didn't have to worry anymore. I know she was young and worried about her man, but dang, it was my motorcycle and she just didn't understand. Oh well ........................
Anyway it was several years before I had another bike ... there was several Hondas 50, 305, 500, and a 900. Somewhere in between the Hondas I think I remember a 650 Triumph Bonny, a couple Ducatis 350, a 650 Yamaha (bad, bad wreck on this one with the wife), a Roadglide, a Dyna, a Softtail Custom Delux, a Suki VS800, and then the other Sporty. Oh wait, I forgot, in the early 60's I had a brite blue 165 HD Hummer till I ran it off a cliff in a dirt pit. Now that was a real thrill to ride. Like it had square wheels, but I loved it.