Rihanna and Leighton Meester looking chic in their heels and socks.

When I think of socks with heels, I instantly think of Dorothy with her ruby red slippers and adorable anklets. I don’t typically think of Paris and Milan runways. However, walking down the streets of Manhattan, I’ve noticed a trend that I felt needed some SHEI discussion: heels with socks.

I’ve seen countless women with fabulous (and I mean fabulous – Dior, Louboutins, Jimmy Choo) heels topped off with ankle socks. The trend, however, is far from new. College Fashion said:

The socks and heels trend is definitely a look that’s been in and out for a while, showing up everywhere from runways to the streets. It was most recently popularized when Burberry Prorsum sent the look down the runway at their 2008 and 2009 shows.

Kelly Osbourne, Alexa Chung, Rihanna, and Leighton Meester [why are you so cute all the time?] have been spotted trotting around Hollywood and NYC in heels and socks. Lucky Magazine’s advice?

When both pieces are black, this combination looks like a chic, streamlined bootie—just be sure the sock is a thin, not bulky weave and that it hits a couple of inches above your ankle.

When asked her opinion on this trend, a friend of mine who works at a couture, clothing company in New York City responded:

I love the style and have been seeing a lot of it at work and that’s typically where I see upcoming trends. I’ve seen bright-colored, floral print socks that come up past the ankle with black, strappy stilettos.

My opinion? I’m always interested in the hot, upcoming trends, but even I don’t think I’m fashion-forward and daring enough to appropriately pull this off. I’d do a bit of research and shopping before walking out of the house wearing this particular look.

Dorothy was so ahead of the times.

Who would have thought that Dorothy would have been ahead of the trend nearly seventy years ago? I always knew that “yellow brick road” was synonymous for “runway.”

[Photos courtesy of InStyle.com & The Guardian (UK)]