A matchy-matchy look is retro in a bad way. It looks gimmicky. That is why I will never recommend it to anyone; however, I have been known to do a few matchy looks for myself and specific others and each time someone says, "I thought you said not to do that, but that looks good!"
The reason I say the general public should not do matchy-matchy looks is because it is too delicate to pull off without a true sense of style and fashion. For many of my clients I am a teacher of fashion. Throughout the shopping process and outfit making, I am telling my clients why we choose one thing and not the other, but I can't quite explain why the rare matchy-matchy look works. It cannot be taught easily. But here is a quick try.
Pictured above it a great example (minus the cheesy earrings and hairdo) of a matchy-matchy look by Jennifer Lopez in Gucci. Why? It's fashion forward and unique, it's chic with clean lines, it's sexy. It is also matching two pieces in a fresh color and not overwhelming us with multiple bold matching pieces. Also, it is not matching a pattern (generally a no-no), it is matching a color and vibe.
Pictured below is not a good example of matchy-matchy by Paris Hilton and Victoria Beckham. They look unimaginative, girlish and costumey. (I shall refer to them as monsters of their respective themes.) So, one rule you can take away from this matchy-matchy lesson is not to match more than two items in an outfit and even then be positive it is timeless or unique.


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