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I have seen it used in a context that seems to imply they are very incompatible but don't quite understand the meaning of the phrase.

One example is the phrase from the "Polka Dots and Plaid" blog:

Sometimes, you gracefully make polka dots & plaid seem to work together.

Another was a sentence I once saw "Polka Dot seeks Plaid" in personals ad context.

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    Could you please supply the original sentence or any further context which would help disambiguate the meaning?
    – user230
    Commented May 23, 2014 at 1:12
  • @snailplane - done
    – DVK
    Commented May 23, 2014 at 1:19
  • I wanted to answer this, but a good answer here really calls for a picture and I couldn't bear how obnoxious the image search results were D:< Suffice to say, this is a fashion idiom and the two patterns make for a really ugly combination. Commented May 23, 2014 at 1:38
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    @EsotericScreenName I found an image which I think it might not look too bad for you. (In case you might still want to answer this.) Commented May 23, 2014 at 1:58

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It is a traditional fashion rule that polka dots and plaid should never be worn together, because the two patterns clash. In contrast to the idiom like oil and water, it is possible to mix polka dots and plaid, but it is taboo and foolish to do so.

Thanks to Damkerng T for supplying this example image (plaid shirt, polka dot skirt):

blech

The first example states that the listener (you) is so elegant, graceful and chic that they can make even such an unfashionable combination as polka dots and plaid look good.

Regarding the ad, the suggestion here is that the 'polka dot' is someone quirky or unusual (possibly) in search of the same, because they are traditionally thought of as not pairing well with different patterns (e.g. plaid). Alternatively, the polka dot may be searching for their complement - someone who possesses the qualities they lack and vice versa - in order to form a complete or balanced couple, perhaps justified by the trope opposites attract. In the context of a personal ad, one is generally assumed not to be searching for someone who would be a poor match, as the phrasing might suggest. This is a very idiomatic construction with subtle, nuanced meaning which I find quite difficult to describe accurately.

As an aside, for the purpose of understanding the idiom, don't put trust in search results regarding the validity of wearing polka dots and plaid together. It seems that fashion's inscrutable caprice has brought the combination in vogue these days.

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