Let $\xi=(E,p,B)$ be a line bundle (not nec. orientable). Then the tensor product $\xi\otimes \xi$ is orientable.
I obtain this by choosing $b\in U\cap V$, $U,V$ open in $B$ such that $\phi_U:p^{-1}(U)\longrightarrow U\times \mathbb{K}^n$,$\phi_V:p^{-1}(V)\longrightarrow V\times \mathbb{K}^n$. $(b,x)\in E$. Then $\phi_U(b,x)=(b,u)$, $u\in \mathbb{K}^n$, $\phi_V(b,x)=(b,v)$, $v\in \mathbb{K}^n$. Then $\phi_V\phi_U^{-1}(b,u)=(b,v)$, $v=\lambda(b)u$. Thus for any $(b,x_1\otimes x_2)\in F_b(\xi_1\otimes \xi_2)$, $\phi_V\phi_U^{-1}(b,u_1\otimes u_2)=(b,v_1\otimes v_2)=(b,\lambda(b)u_1\otimes\lambda(b)u_2)=(b,\lambda(b)^2 u_1\otimes u_2)$ hence the transition map is a positive scalar multiple and the tensor product is oriented line bundle.
Is my way correct or not? Is there more clear way to prove this?
In general, let $\xi$ be an arbitrary vector bundle. Is $\xi\otimes\xi$ always orientable? How to prove? I am confused. Thanks.
George's answer is absolutely correct, but here is a more direct argument, which avoids characteristic classes and uses only linear algebra. First of all, each real rank $N$ vector bundle $p:E\to X$ is determined by a cocycle $\xi_{ij}: U_{ij}=U_i\cap U_j\to GL(N, {\mathbb R})$, where $U_k$'s form an open cover of $X$ which trivializes the bundle $p$. (These functions are just the transition maps between different bundle charts.) By definition, the bundle $p$ is orientable if and only if $det(\xi_{ij}(x))>0$ for all $i, j, x\in U_{ij}$. Suppose that we have two vector bundles $E\to X, F\to X$, where $X$ is paracompact; in particular, we can assume that the trivializing covers for both bundles are locally finite. Then, by intersecting their trivializing covers, we can assume that they have a common trivializing cover. It is a straightforward computation to check that if $E, F$ are vector bundles over $X$ with cocycles $(\alpha_{ij})$ and $(\beta_{ij})$ then the cocycle for their tensor product $E\otimes F$ is $$ \gamma_{ij}(x)= \alpha_{ij}(x)\otimes \beta_{ij}(x). $$ Here $\otimes$ is the Kroneker tensor product of matrices, see e.g. here: Tensor product of matrices represents the tensor product of the corresponding linear maps. Observe furthermore, that if $A$ is an $m\times m$ matrix and $B$ is an $n\times n$ matrix then $det(A\otimes B)=(det(A))^n(det(B))^m$, see the same wikipedia page.
Therefore, if $\alpha_{ij}=\beta_{ij}$ as in OP's question, then the determinant of the tensor product is positive. Hence, $E\otimes E$ is orientable. The same applies to George's remark about tensor product of vector bundles of even rank.