Starting with OP's considerations, and using a trig theorem,
$$\sum_{k=1}^{n}x_{k}\cos{k}\cdot\sum_{k=1}^{n}x_{k}\sin{k}\le\dfrac{(\sum_{k=1}^{n}x_{k}(\cos{k}+\sin{k}))^2}{4} = \dfrac{(\sum_{k=1}^{n}x_{k}\sin{(k + \pi/4)})^2}{2} $$
Following Dap's comment: since all $x_k > 0$, we can write $\sum_{k=1}^{n}x_{k}\sin{(k + \pi/4)} \le \sum_{k=1}^{n}x_{k}\max\{0,\sin{(k + \pi/4)} \}$ and also $-\sum_{k=1}^{n}x_{k}\sin{(k + \pi/4)} \le - \sum_{k=1}^{n}x_{k}\min\{0,\sin{(k + \pi/4)} \}$. Note both RHS bounds are positive.
Applied to the square we have
$(\sum_{k=1}^{n}x_{k}\sin{(k + \pi/4)})^2 \le (\sum_{k=1}^{n}x_{k}\max\{0,\sin{(k + \pi/4)} \})^2$
and
$(\sum_{k=1}^{n}x_{k}\sin{(k + \pi/4)})^2 = (-\sum_{k=1}^{n}x_{k}\sin{(k + \pi/4)})^2 \le (\sum_{k=1}^{n}x_{k}\min\{0,\sin{(k + \pi/4)} \})^2 $.
Either one of these inequalities is used, depending on whether $\sum_{k=1}^{n}x_{k}\sin{(k + \pi/4)} >0 $ or $<0$.
Applying Cauchy-Schwarz gives
$$
\frac{ (\sum_{k=1}^{n}x_{k}\sin{(k + \pi/4)})^2}{\sum_{k=1}^{n}x_{k}^2} \le \sum_{k=1}^{n} (\max\{0,\sin{(k + \pi/4)} \})^2 \\
= \frac12 \sum_{k=1}^{n} (\sin{(k + \pi/4)} )^2 + \frac12 \sum_{k=1}^{n} |\sin{(k + \pi/4)}| \sin{(k + \pi/4)}
$$
or
$$
\frac{ (\sum_{k=1}^{n}x_{k}\sin{(k + \pi/4)})^2}{\sum_{k=1}^{n}x_{k}^2} \le \sum_{k=1}^{n} (\min\{0,\sin{(k + \pi/4)} \})^2 \\
= \frac12 \sum_{k=1}^{n} (\sin{(k + \pi/4)})^2 - \frac12 \sum_{k=1}^{n} |\sin{(k + \pi/4)}| \sin{(k + \pi/4)}
$$
Note that $S_n = \sum_{k=1}^{n} |\sin{(k + \pi/4)}| \sin{(k + \pi/4)} $ has alternatingly positive and negative value intervals in $n$. Since the sum's argument samples all phase values of the $sin$-function, the sum has expectation value zero, and maximum variance is limited to a value independent of $n$. Indeed, it is bounded analytically by $|S_n|< 1.27$ (** see below). This shows that the splitting of the above sum is a good choice, since $S_n$ measures only the full results' variance, which is bounded, with a value independent of $n$.
Therefore, combining both cases above,
$$
\frac{2 (\sum_{k=1}^{n}x_{k}\sin{(k + \pi/4)})^2}{\sum_{k=1}^{n}x_{k}^2} \le \pm S_n + \sum_{k=1}^{n} (\sin{(k + \pi/4)})^2 \\
= \pm S_n + \frac{n}{2} + \frac{\sin(2)- 2\sin(1) \cos(2 n + 1) }{4 (1-\cos(2) )}
$$
where for the last equation a trig summation was used.
Bounding $\cos(2 n + 1) \ge -1$, and using the above bound $|S_n| < 1.27$, gives
$$
\frac{2 (\sum_{k=1}^{n}x_{k}\sin{(k + \pi/4)})^2}{\sum_{k=1}^{n}x_{k}^2} \le 1.27 + \frac{n}{2} + \frac{\sin(2)+ 2\sin(1) }{4 (1-\cos(2) )} \le \frac{n}{2} +1.73
$$
Applying this to the first line gives
$$\sum_{k=1}^{n}x_{k}\cos{k}\cdot\sum_{k=1}^{n}x_{k}\sin{k}\le
\frac{n + 2 \cdot 1.73}{8} \sum_{k=1}^{n}x_{k}^2= \frac{n + 3.46}{8} \sum_{k=1}^{n}x_{k}^2$$
which is almost what we need.
The required result is obtained when bouding(*) simultaneously $\pm S_n + \frac{\sin(2)- 2\sin(1) \cos(2 n + 1) }{4 (1-\cos(2) )} \le 1.5$, giving
$$\sum_{k=1}^{n}x_{k}\cos{k}\cdot\sum_{k=1}^{n}x_{k}\sin{k}\le
\frac{n + 2 \cdot 1.5}{8} \sum_{k=1}^{n}x_{k}^2= \frac{n + 3}{8} \sum_{k=1}^{n}x_{k}^2$$
which proves the claim. $\qquad \Box$
Remarks:
The above treatment shows that (and how) a bound $\frac{n + c}{8} \sum_{k=1}^{n}x_{k}^2$ can be obtained with some constant $c$. The value $c=3$ could be obtained by computational evaluation of one limit, whereas the looser bound $c = 3.46$ could be obtained analytically. The leading coefficient $ \frac{n}{8} $ could be established in any case.
(*) numerical values of combined bound obtained by computational evaluation.
(**) $|S_n|< 1.27$ is obtained by an analytic bound which is being derived in this post: $|S_n|< 0.149 + \max_{\pm \rho} |\pm \rho + \frac{4}{15 \pi} (\frac{5 \cos(1/2 + \frac{\pi}{4})}{\sin(\frac12)} - \frac{\cos(3/2 + 3 \frac{\pi}{4})}{\sin(\frac32)} )| = M(\phi= \pi/4)$ with $\rho = \frac{8 (2 + 5 \cos(1))}{15 \pi \sin(\frac32)} \simeq 0.8$. This gives $|S_n|< M(\phi= \pi/4) \simeq 0.149 + \max |\pm 0.8 + 0.3135| \le 1.27$.