Polka dots

What is more whimsical than the polka dot? A dress that might otherwise be viewed as overly fancy will immediately be rendered more casual if it’s made from a dotted fabric. On the flip side, something overly simplistic, such as a tee-shirt and jeans will become pleasantly playful if that tee is polka-dotted. A man in a polka-dotted tie will be seen as more friendly than a man wearing a stripe, or god forbid, a solid. Deploy a tiny, barely perceptible, dot for an upscale look, and go larger for a more daytime affair. The larger the dot, the more whimsical the look, right up to the point where you’re wearing a big red nose and floppy shoes, and absolutely killing it as you do so.

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Plaid

Unless you’re wearing a kilt and playing the bagpipes, participating in the Highland Games, or are otherwise actively Scottish, you risk invoking a slight schoolgirl connotation when wearing plaid in skirt form. This is not necessarily a bad thing, however, as plaid is also professional and entirely work-wear appropriate. Plaids involving red risks being too traditional, or too lumberjacky, but purple plaid is appealingly modern. You will be perceived as conservative yet kicky, which is the right balance to strike whether you’re in staff meetings, in your cubicle, or plotting revenge against those who’ve wronged you.

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