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What Is Casual Attire to Wear on a Date?

by Jennifer Blair

When you're headed for a date at a posh restaurant, it's easy to come up with the ideal outfit -- slip on your favorite cocktail dress and you're good to go. But if you're going to the movies or you plan on watching a ball game at your local pub, it can sometimes be difficult to look sexy and stylish while not overdressing for the venue. The key is to focus on casual pieces that fit well, so your outfit is flattering but still appropriate for a low-key date.

Versatile Jeans

For casual-date attire, jeans are the versatile centerpiece. If you’re meeting for drinks, team dark-wash skinny jeans with a fitted black blazer, white tank top and simple black pumps to look stylish and put together. When you’re headed to the sports bar to watch the big game, go for a polished, low-key look with a black leather jacket, maroon V-neck sweater, boot-cut jeans and black, heeled ankle booties. Don’t overlook the classic combo of simple jeans and a T-shirt, either -- pair a sunny yellow tee or your favorite graphic tee with straight-leg jeans and black ballet flats if you’re going for a picnic or a walk in the park.

Stylish Shorts

When the weather’s warm, a pair of shorts works well for a casual date. For a brunch date, opt for a pair of magenta Bermuda shorts and wear them with a white tank top, black tailored vest and black gladiator sandals for a classy, relaxed look. If you’re heading for an active date like hiking or golf, simple khaki shorts and a white or pastel-colored T-shirt are ideal -- just make sure you choose tailored styles so they fit well and look as good as they feel. Add colorful athletic shoes and sunglasses, and bring along a snug, white velour hoodie in case it gets cool to finish off the look. You can even wear shorts for a casual dinner -- try a black scalloped pair with a pink silk blouse, and step into a pair of black suede pumps for a flirty, relaxed look. Shorts can still work when the weather's chilly; just add a pair of tights that match to extend the line of your leg and give you some extra warmth.

Flirty Skirt

A skirt can be a stylish, feminine option for a casual date. Opt for a high-waisted, denim pencil skirt topped by a white cap-sleeve tee and finished with bright wedges if you’re headed to lunch or an early dinner. In the fall, switch the denim for a slim corduroy skirt in a rich color like chocolate brown. Slip a slim-fit, camel cardigan over a white button-down blouse, and step into brown tights and knee-high boots -- and you’ll be set for a cosy night at the movies. In the spring, a floral-print swing skirt and a bright pink tank top work well with ballet flats for dinner or drinks.

Relaxed Dress

Just because your date is casual doesn’t mean you can’t wear a dress -- but leave your favorite little black cocktail dress in the closet. A maxi dress in navy and white stripes is an ideal option for lunch or dinner. Layer a navy cardigan over it and add red wedge espadrilles for a little nautical flair. If you’re headed out for drinks, try a camouflage shirt dress with olive ballet flats and a gold necklace. In the summer, a simple, white eyelet sundress and beaded sandals are ideal for a date at the beach. You can also throw a cropped denim jacket on over the sundress if the sun starts to go down.

About the Author

Based in New York City, Jennifer Blair has been covering all things home and garden since 2001. Her writing has appeared on BobVila.com, World Lifestyle, and House Logic. Blair holds a Bachelor of Arts in Writing Seminars from the Johns Hopkins University in Baltimore, Maryland.

Photo Credits

  • Frederick M. Brown/Getty Images Entertainment/Getty Images