I managed to prove the $\longrightarrow$ part, but I'm not entirely sure how to prove the second part. I can assume by contradiction that the total order $(X, \leq)$ is not a well-order, which means there is an infinite monotonically-decreasing sequence, but how do I arrive to a contradiction? Can I show there exists an initial segment which is not determined by any element in $X$?
Would appreciate any help or hints.
By "determined by an element" I presume you mean "is the set of elements $<$ some fixed element." If this is the case, then: suppose $a_1>a_2> . . .$ is a descending sequence. Is there an initial segment of $X$ corresponding, in some way, to this sequence? Why is this initial segment not determined by an element?
EDIT: As a further hint (and based on the comments below), think about, say, $X=$negative integers. Then:
Is $X$ well-ordered?
What is an initial segment of $X$ not "determined by" any element?
How does that initial segment relate to the descending sequence $-1>-2>-3>...$?
Then, same question with $Y=$negative integers and $-\infty$:
What is an initial segment of $Y$ not "determined by" any element?
How does that initial segment relate to the descending sequence $-1>-2>-3> . . .$?
Hopefully this helps.