I have a knee-length red plaid woolen kilt I picked up on a college trip to Scotland almost 20 years ago. I trek it out once a season or so, usually around the holidays, but I like it and am trying to think of ways to get more wear out of it beyond the expected “Going to the Nutcracker” kind of look. Any ideas?
Yes, that skirt deserves to come out more than once a year! However I do understand the issue with looking too holiday, as though you’re wearing a costume, or trying to be Mid Life Crisis Britney. The best way to wear accomplish this is to style it as though it is not a kilt. Steer clear of traditional pairings and add something unexpected and it will look fresh and modern.
Gray will tone down the red and keep it from feeling Christmas-y. While a cashmere crewneck and white button-front is pretty classic, pairing the look with modern black leather ankle boots keeps it current. Hair and makeup can really make this look; keep both relaxed and a bit disheveled. Beachy waves and a bit of kohl will go a long way and look far more modern than polished hair and red lips.
Add a bit of a tough edge to your classic kilt with leather. A black leather jacket and biker boots will be a modern contrast. Unlike the above look, style such an ensemble with very polished hair and face to keep it from looking like a costume; smooth hair with red lips and gently flushed cheeks will look fresh.
A bit of purposeful rumpling will take a look from prep overload to modern cool. A gray tweed blazer with a tailored fit is a great pairing for your kilt; roll the sleeves and maybe pop the collar to keep it from feeling like a uniform. A classic Breton tee is a pattern that will mix nicely with the plaid and also keep it from feeling too much like a uniform. A pair of tall boots with a solid heel will finish the look and keep you warm.