I say you can get him both styles and you can never have too many beds. I have 3 of the normal squishy beds that Parker loves and 1 covered one that he loves too. He sleeps with me so those more like "his place to kick it" beds or to play in/on/around. Congrats on the puppy.
And with the whole dress thing, I had the same problem when I got Parker. There are million more cuter things to get a girl instead of a boy. So what I decided was the next one I get will be a girl so I can buy all those wonderful dresses and girly stuff! But I wouldn't put him in girl stuff...it's tempting but I wouldn't.