I have to confess that I am ambivalent about shorts. I understand their utility, but I always wind up feeling like throwing on a pair of shorts is the equivalent of giving up, like I could wear something cuter if I would just try a little harder. But there are times — baseball season, say, or August — where shorts are the most appropriate option for my life.

Cheer up! A button-down give your shorts some edge.

The trick to making even the most casual shorts look stylish is really in what you wear with them. My shorts wardrobe (all two pairs) are basic chinos — durable, versatile, machine washable. I have no illusions about dressing them up (in fact, I’m not a fan of “dressy” shorts, or of shorts for the office — shorts are for casual wear, period). But I do want my shorts to be flattering, and I do not want to look like I just came from cleaning out the garage when I leave the house in shorts.

I assume you feel the same way about your shorts. So what do you wear them with?

Tops
Style your shorts the same way you would your favorite pair of jeans; look for tops that flatter your figure and draw attention to your face. A basic crew-neck tee is fine but not very exciting; opt instead for a tee with some visual interest at the neckline (a V-neck, for example, or some pretty detailing). Embellished tees are also nice with even the most basic shorts; you can find great embellished tees at places like Old Navy and Target for not a lot of money — perfect for busy moms. (Bonus: an embellished tee also works well with a skirt, for slightly dressier moments.)

Want to get out of the t-shirt rut? Look for structured or tailored tops in washable fabrics. I like a sleeveless blouse for summer, something both lightweight and crisp. We have long stretches of spring where I live when shorts and a long-sleeved top are appropriate; I’ll opt for a button-down or Oxford with my shorts, for a menswear-inspired look that’s still kid-friendly.

Try layering a tee over a button-down for a more visually interesting look.

Shoes
The right shoe can change the entire look of your shorts. Pair a basic chino with a comfortable flat (loafers are a great Preppy look) or with an athletic-inspired shoe. As the weather heats up, wear your shorts with strappy sandals, but look for a style that doesn’t cut your leg off at the ankle. If you have very slim legs, a sandal with an ankle strap is fine; otherwise, look for shapes that elongate your foot and leg. Embellished sandals — like embellished tees — are also an easy way to dress up your shorts. I love the look of a basic leather sandal with some beaded detailing. And of course you can pair the same sandals with a dress for date night.

Need a little more on your feet than just a simple sandal? Choose a sneaker with some style. I have a basic pair of white leather Keds that have lasted for years; the leather makes them easy to clean, and they have enough cushion inside to keep my feet comfortable during long treks around the zoo. Wear the lowest-cut socks you can stand, or skip socks all together, if possible; I’ll wear toe socks with my Keds most of the time. Again, the idea is to lengthen your legs as much as possible.

Accessories
Sometimes the simplest detail makes the biggest difference. Add a beautiful necklace or elaborate pair of earrings to your shorts outfit, or pile on some fun bracelets — don’t be afraid to wear jewelery with your shorts. A big, bright watch is also a good option for summer, and is both functional and chic. For days at the park invest in a cute hat and some big sunglasses; again, function meets fashion!

Images via J. Crew.

Subscribe to blog via RSS