This week, I want your help answering a Very Pressing Question: is it really possible to dress up your shorts?

I have all sorts of issues with shorts. Most women (and men!) are wearing the wrong shorts — wrong size, wrong style, wrong fabric (no more denim shorts, I’m begging you all). But even a really great pair of shorts is still … a pair of shorts. They’re meant for casual wear, and the insistence on dressing them up drives me batty. It’s ok to have clothes that are just for the weekend! Really! You don’t need to wear your shorts to work!

In fact, I say steer clear of shorts for the office. Always.

At the same time, though, shorts are so … easy. It’s hot where I live, and my day often includes doing kid things outdoors in the heat, and while I’m not above wearing a dress to little league, sometimes a pair of shorts just seem more appropriate.

In other words, I’ll wear them, but I’m not happy about it. At all.

I feel like there should be a way to rehabilitate shorts, to make them both a functional and a stylish part of my wardrobe. LOFT’s quick video on wearing shorts everyday is full of great ideas — but I’m still not buying it. I’ve tried to dress my shorts up, but it never works; instead of looking chic, I look like I’m trying to dress my shorts up.

Not the look I’m going for.

So does that mean you can’t dress up your shorts? No, it just means that you can’t dress up your casual weekend shorts. In order to make your shorts work as a trousers alternative — for work (because i know you’re going to) or date night or wherever you’re going, here’s the secret: you need to upgrade your shorts.

Instead of pairing a silk blouse with your basic chinos, opt for a pair of dressier shorts, in a wool gabardine, or a linen or silk blend. A rayon blend will also work — just something a little more substantial and serious than your cotton khakis.

Dressed up shorts also need to be crisp and pressed, just like dressed up pants. Hate ironing? Steam them, either with an actual steamer or by dampening them with a towel and hanging them in the bathroom while you shower.

Finally, think carefully about what you pair your dressy shorts with. You can wear dressy shorts with a plain tee or tank (add a statement necklace or a scarf for visual interest) but I would suggest that you go all out and wear them with a beautiful blouse — you know, something dressy. After all, this isn’t an outfit you’re wearing to little league.

I won’t be dressing my shorts up this summer; I’ve tried, but I can’t make it work. My shorts are all of the soft cotton variety, and when I need to look a little spiffier, I swap them out for a silk or linen skirt. But if you’re looking to balance staying cool with looking hott, dressy shorts might be just what you need.

What say you — can shorts really be dressed up? Or is this one of those Urban Fashion Myths?

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