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I see nothing at all wrong in being dressed fashionably – as long as it is appropriate for the function that you are attending and is flattering to the wearer. I am not suggesting that one wear a beaded gown to shul on Saturday morning or a wool suit to a wedding. If you aren’t sure if your clothing is flattering or appropriate, take someone whose opinion you trust with you when you go shopping. I remember a couple of years ago my Rabbi gave a sermon/Dvar Torah about clothing and finery. One of the things I distinctly remember is that he said one should wear their finest clothing for Shabbat. I always dress “up” for Shabbat, but again, I say appropriately. I have accumulated a large collection of Shabbat clothing. Since I don’t attend many weddings or evening functions, my fancy wardrobe is far more limited. But, I do know the difference between daytime and evening wear. I do go to shul every Shabbat “dressed to kill”, but always appropriately.