Heels & Picks: A tale of two outfits

Sep. 16, 2015 | 0 Comments


BY ERIN SMITH / Special to the Star-Advertiser

Don’t judge a girl until you’ve walked a mile in her Jessica Simpson boots, or so the saying goes. Okay, that’s totally not a saying, but it should be.

Those who know me are well aware that if there’s one thing I can do well, it’s overdo it on the fashion and wear a totally impractical outfit. Feather vest at Wholefoods? Check. Stilettos and sheer pants at the post office? Done that.

So it was surprising to no one when I went on a California beach excursion last week in one of my most epically impractical outfits to date. Though they expect it, my friends still make fun of these ensembles each time, which is half of the fun of it. What’s the point in wearing something fabulously off-kilter if you can’t laugh at yourself?

Since the fall fashion season is upon us, and fashion week festivities are popping up left and right, I thought we’d kick things off properly over at Heels & Picks with a tale of two outfits.


The beaches in California can be a lot cooler than our Hawaii coastlines. But because the days can shift in temperature, it’s important to be prepared for anything.


Boots at the beach. That’s where it’s at.

When it comes to pants, wearing jeans with stylistically placed giant holes and tears allows you both wear pants AND have air conditioning at the same time.

Have you ever encountered a seagull at a coastal beach? Those things can be aggressive. They grow them big on the California coast, and if you happen to have a French fry in your hand, forget about it. You just earned yourself a full-on wrestling match with a giant bird.

There is no predictability to when you might encounter such a seagull, so it’s best to wear a plain, boxing style white tank top so that you are prepared to throw down.

Everybody knows that beach walking is great for your calves, so why not try it in a pair of Jessica Simpson boots? Sure, you may be miles behind your friends on the walk, but man your legs will look good in your evening dress later on.

Finally, black and white never goes out of style. And also, zebra is my spirit animal. Go for that beach chic with an over-the-shoulder striped sweater and you can never go wrong.


If you’re not over-doing it, you’re not fully committed to your outfit. But let’s be real, you have to gauge how far you’re going to have to walk, and compare it to your ability to handle each pair of shoes you are considering.

It’s important to have heels that you can run in.

Though I was tempted to wear a pair of camouflage platforms with gold spikes for a night out in Santa Rosa wine country, I assessed my situation and opted for a pair of black strappy heels. Those camouflage shoes are fierce, and my ability to walk quickly in them is practically nil.

However, those black strappies, I can full on run in. I have no idea why I would be running in a party dress in Santa Rosa, but a girl’s gotta be prepared.

Sure, your friends may be wearing slacks and T-shirts, but it’s important to be prepared for a night out with an evening dress. And a little red dress always does the trick. This one is a bandage-style, Leger copy, and it’s great for hugging curves. Of note – be prepared to not have to do much bending over. You are a lady, after all.

If there’s one place this fashionista falls short, it’s in the handbag department. I envy my friends who can switch purses and always still manage to have all of their stuff. If I were to take things out of my trusty purple Coach bag, I would never know where anything is. It’s like a Mary Poppins bag – it has been speculated that there is a lamp and a guitar in there.

Since I use that bag daily, it’s starting to be a little worse for wear. That’s where the wine comes in – the wine goggles of your companions allow you to sneak a beat-up purse into the ensemble without anyone noticing.
Erin Smith is a singer and guitarist who performs as a solo artist and with Maui-based Na Hoku Hanohano Award-nominated band The Throwdowns. Born in Canada, she moved to Hawaii in 2004 and now resides in Kailua. Contact her via e-mail or follow her on Twitter.

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