How to Dress for Outsidelands

I went to Ousidelands with Mai from, and she’s doing a whole series on festival fashion if you want to check out what people were wearing. (That’s one of her photos above.)

Mai and I were talking about how San Francisco weather requires a very particular style of dress for outdoor events. It’s colder here than people expect, and that’s true year round. Layering is key, especially for women. A few tips for balancing sanity with style:

Plan your outfit around sane shoes. You want flats with a closed toe. If you wear sandals your feet will get filthy, you won’t be able to dance in crowds without getting stomped, and in the evening it will get cold enough that you won’t be able to feel your toes. We’re not even going to discuss the idiocy of wearing heels in the dirt. Your smartest option? Boots.

Layer on top. The crowd shields you from wind, so you’ll be okay in something sleeveless if you’re dancing, but you’ll mostly need long sleeves — sweater, blazer, whatever. If you’re sensitive to cold (I’m looking at you Los Angles), you might want two thin layers on top of your tank.

Accessorize for warmth. You’ll want a hat or scarf after dark. Invest in a cotton, knit or silk scarf, something lightweight to maximize your bag-footprint to warmth ratio.

Keep it convenient. You’ll be using porta-potties all day. Reconsider leotards or body suits, especially in combination with tights. Tights in summer? That brings me to my next point.

Plan to keep your legs covered. Pants are a smart option no matter what time of year, but if you want to wear a skirt or shorts, throw a pair of tights in your bag, even if it’s the middle of summer. You’ll likely want them all day, but even if we have unusually warm weather, you’ll be pretty miserable without them after 4 p.m. or so.

Bring a little bag. It’s nice to be hands-free, but nicer to have a travel sized sunscreen, a place for cash and ID, sunglasses, and somewhere to store your scarf, sweater and tights when you don’t want to wear them.

See you next year.

7 thoughts on “How to Dress for Outsidelands

  1. Darn. I’m kicking myself for not taking your picture on day 2. You looked so fabulous. Also, we’re doing Hardly Strictly Bluegrass in October too!


  2. I’m seeing a fair amount of acid wash in that link. Can someone please tell the kids these days that’s not ok? I know I’m far from hip, being jumping distance to 40 with two kids, but come on.

    I recently saw a pic of Wise Blood at Grasslands (you should check him out if you haven’t already, because wow. Here —, standing in the crowd next to a guy in a black leather jacket with Tom Hanks circa Big painted on the back and that makes more sense that wearing acid wash.

    Cranky old lady out.


  3. For Bring a Little Bag, I highly recommend a drawstring backpack. Either pre-fab (lots of athletic companies make them), or of your own making. They are so easy to sew so you can make something in a fabric that works for you. (I like using a quilted fabric for more stability and cushion, but canvases also work nicely.) It’s a Little Bag for the necessities and keeps you hands free!


  4. Thank you for this very practical post. This is something I need to remember when I travel… I am in the deep south, and it is hard to remember that some other places don’t have real summer. I found a few years ago that Scotland is such a place – the weather changes so completely from morning to noon and night, that you have to prepare very much this same way. Another thing I learned there was long hair must be tied down! It is so windy!

    Anyway – I will remember these things if I ever come out your way! It just occurred to me that your summer sounds like an Alabama December. 🙂


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