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How To Wear Heels And Shorts Without Feeling Awkward And Uncomfortable

It's not an easy look to pull off but! The Fashion Mailbag is here to help with your shorts-and-heels messaging.

I like the idea of wearing heels and shorts, but whenever I try to do it, I just look WRONG. Like, it always comes off too suggestively. What's the best way to pull off heels and shorts without looking like I'm trying to look like some gyrating scantily clad pop singer on a stage?

This is a fraught issue, I know — a reminder that outfits, like presidential campaign slogans, are all about messaging. You don't want to be too Forward., but you want a nice looking pair of gams that the populace can Believe In. Heels add a little bit of muscle tone which makes legs look extra nice if you're not wearing tights, and the right pair can add some all-important personality to your image. However, it's really easy to send the wrong message, and I think that might be because shorts, thanks to the fact that they contain a crotch, can afford to be shorter than many skirts. Ladies tend to not be so concerned about walking around in underwear-sized shorts but they feel slightly differently about walking around in underwear-sized skirts. So the some shorts + heels combos might not be much different from some bikini bottoms + heels combos. But I've devised a few tips to make this look more comfortable for wearing out of the house without looking like it was styled to to draw the attention of cat-calling sidewalk hecklers.

Tip 1: Wear loose-fitting shorts that don't rid up your ass.

You'll show slightly less leg and won't be giving away the precise curve of your rear end. This may seem novel in the age of Nasty Gal but just think: a little conservatism! Like Mitt Romney's tax records, you don't have to give everything away just because people want to see what you've got going on.

Step 2: Try flatforms.

If you do have a pair of shorts that rides up your ass (and let's face it, we all probably do in our weekend, not-safe-for-work drawer) you don't have to marry them to only flip flops and boring ballet flats. I enjoy a flatform if you want some height without the full-on discomfort of heels. I especially enjoy this pineapple onesie Rihanna smartly paired with flatforms. If she wanted to put her feet through the torture of stilettos she easily could since she's probably got four huge security guards that could pick her up and carry her around when she gets tired of walking with her at all times. But no, she chose flatforms.

Flatforms are not a "sexy" shoe. They're not a stiletto with red soles and studs that say LOOK AT MY SHOES AND ME. They're cute — you could play a game of corn hole in them without looking like a freak if life put you in a position where you had to play corn hole so you don't look like a bitchy spoil sport.

Tip 3: Try low wedges.

A wedge is less extreme than a heel, therefore a wedge + shorts situation will be less extreme than a stiletto + shorts situation (oh MATH, how I've missed you). Here's a basic yet cool style by Rebecca Minkoff that was easy to find, would go with just about anything, transition from day to night, and probably won't lacerate your feet after two hours of wear.

Tip 4: Wear a conservative top.

Leg-exposing outfits are less in-your-face when paired with a nice summer blouse with sleeves. Try something simple and lightweight. Here's a Madewell one, but the style is so basic you can surely find something similar in a store like Zara or even American Apparel easily. If it's sheer, throw a cami underneath and you'll still look and feel covered-up.

And really, if you're going out for a night of fun, shorts and heels might be more practical than skirts and heels. If you drink a lot you're much less likely to replace Britney Spears as the Internet vagina everyone still remembers.

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