Well, gentle reader (dear kitschen? pookie?), this question happens to be right up my alley! I'm a huge fan of vintage style, and as much as I admire the dedication and gumption of the gals who rock it full-time, I know that a lot of people (myself included) want a way to get that kicky feel without feeling like you're in retro drag.
It can be difficult to find a midway point between vintage and modern fashion. You don't want to go too far and look like you're in costume (if you do, awesome! You don't need these tips and should go read another one of my posts!), but you don't want to look mish-mashed, or quash the great flavor of your old school pieces. Experimentation is definitely key; you can find a way to make them work together.
For this specific case, when you said "high-waisted skirt" and "vintage," this is immediately what came to mind:
And, indeed, it's a very retro silhouette! But the basic idea can totally be rocked modern-style. Pair your high-waisted skirt with pretty blouse just like Ms. Holloway up there does--but pick a fresh modern print, a more updated collar or sleeve. Depending on the fit of the skirt, you may also be able to wear a thick enough blouse over the top to give it a new look. Without the high-waistedness visible, it becomes your average pencil skirt, nicely paired with a button-up and a sweater vest.
Out of the office, a blouse with a keyhole neckline would look sassy and fabulous, and a simple black tank top or a pretty camisole can be effortlessly chic. A high-waisted skirt is definitely a statement piece, and you can make it work with a little trial-and-error and some thought. (And you can always pair it with a sweetheart neckline or a pussybow to go full out pin-up secretary!)
I hope that answered your question, and feel free to ask away with any questions/conundrums/ponderances/queries!