R. David Fohrman in one of his articles on the Aish website from the series called Garden Of Eden comment on this:
The mystery in all this deepens when we ask the question: Are the two
meanings of "arom" -- "naked" and "cunning" -- related conceptually in
any way? Are these apples and elephants, two entirely unrelated ideas,
or is there some essential connection between them?
At first glance, the ideas "naked" and "cunning" don't seem to have
much in common. But on reflection, they do seem related in a curious
way. Mull the terms over -- "Naked and cunning, naked and cunning..."
-- what comes to mind? These words just happen to be opposites of one another.
When someone is naked, unclothed, there is no hiding. That person's
"self" is laid bare for all to see. "What you see is what you get". On
the other hand, when one is cunning -- he is sly and devious; he
"cloaks" his true intentions and hides behind a facade. His true self
is not seen.
Fascinating. The two meanings of arom are mirror images of each other.
. And this just adds another dimension to our question: Why would the
Torah take the same word it uses over and over again to mean "naked",
and then, when describing the snake, twist its meaning to convey the
very opposite idea -- "cunning"?
Could the Torah possibly be suggesting that -- yes, the snake was of
course cunning -- but somehow, he was not just cunning -- but he was
"naked" as well? What could that mean?
AN INNOCENT DECEPTION
Biologically, of course, a snake really is naked: It is a reptile, a
creature that, unlike most other members of the animal kingdom, lacks
fur or hair to cover it. But if we think beyond biology, what would it
mean for the snake to be not just "cunning", but "naked"?
If "naked" is really the opposite of "cunning", then it seems to
follow that the snake had both, opposite, qualities: He possessed both
honesty and stealth. In other words, the snake really is deceptive --
but on another, perhaps deeper, level, he's very straightforward. It
all depends at how you look at him. From one perspective, what he's
saying doesn't really work for Adam and Eve, so his words are
deceptive to them. But from another perspective -- what you see is
what you get. He's just telling it like it is -- from a snake's point
of view, of course.
And other relevant excerpt:
What the snake is really doing, then, is forcing Adam and Eve to
confront what it means for them to be human beings and not beasts. In
the end, the snake really is arom -- in all senses of the word. When
he asks, "even if God said don't eat, so what?" -- he is being
straightforward and honest; "naked", as it were. He was just telling
it like it is: "Here's what it is like to be a snake". On the other
hand, when we look at the snake's words from our point of view, from
the perspective of Adam and Eve -- then, his argument looks cunning
and deceptive, the other meaning of arom. What's right for the snake
is not necessarily right for us. He may walk, he may talk, he may be
smart -- but we are different than he; we hear a voice that is not
relevant to him. When all is said and done, we are not snakes.