I'm going to start a series of posts about what the hell to wear with your kilt. There are many great resources out there for traditional kilt wearers including instruction, rules, images, and often long rants about how people wear their kilts incorrectly. Here's a fairly clear example with some photos: hintsandthings.co.uk There are plenty more out there if you need more detailed instruction.
If you're like me though, and you just want to put on a kilt to go have a beer, have dinner, or go to Home Depot, then you may be harder pressed for good information. I'm not going to list rules, or do's and don'ts. I am going to tell you what's worked for me and what hasn't. There are times I walk out of the house saying, "Yeah, this feels great!" and there are times when I'm out and I think, "man, what the hell was I thinking?"
So for this introduction I'll start with the best piece of advice I know: fit your kilt into your own personal style rather than trying to fit your style into the kilt. This is important, because if you don't wear what's comfortable to you then you're just not very likely to put the kilt on and walk out of the house. If it feels like a costume to you, you'll never be really comfortable.
Here's an example. Say you live in Brooklyn, you're a sound mixer at a recording studio, and you hang out on the lower east side of Manhattan (when you're not in Brooklyn knocking back pints of Six Point). If you put on a full tartan and a bow tie you're going to feel silly.
So, instead, pick up a denim kilt from Howie at 21st Century, or if you have the inclination go for a black pinstripe. Put on that big belt that you normally wear with your jeans, and throw on your Chuck Taylors. Pull on a soft tee-shirt, a hoodie, and maybe a sports coat and scarf depending on the weather. Put on your gigantic sunglasses, and you're done: hipster in a kilt. You're still you, but you're 40% cooler.
If you normally wear LL Bean, then go for a Utilikilt Workman with a big wool sweater and thick wool socks and work boots. You'll still feel like you, and you'll be wearing a great kilt.
If you're a college professor, then check out the tweed selection at USA Kilts. Get a matching jacket if you're Ivy League with tenure, and wear it with a button down and a tie. Black shoes and kilt hose will finish it off fine. If you want to feel fancy get matching flashes.
So that's my advice: work your kilt into your wardrobe as it is. I'll try to post some photos of what I'm comfortable in and if you have pictures of yourself in what you're most comfortable with send them in and I'll post them.
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