5 Style Secrets to Look Casually Chic in Shorts

Shorts are sporty, relaxed, playful, and fun. So how do you style them to look casually chic? Here’s a pair of my new favorite shorts from Not Your Daughter Jeans and the sophisticated way I like to wear them.

Deborah with nydj shorts1. Choose Classic Shorts

If you want to create a chic shorts look, the best way is to start with a pair of classic shorts. These five-pocket NYDJ stretch twill shorts are ideal (also in black and green). They’re streamlined and unfussy, with a 7-inch inseam. The leg is not too tight but not too loose.

Deborah with nydj tan shortsThe beauty of these shorts is you can style them in multiple ways to give you different vibes. Recently, I wore them with a beautiful coral boho peasant blouse, and this week I’m creating a more urban look, and they look equally as fantastic.

Deborah with nydj beige shorts

Other style tips…

2. Wear a Blouse with Your Shorts

For a dressier look, wear a blouse with shorts rather than a tee. You’ve heard me talk about NYDJ’s Perfect Blouse because I own three. This blouse is perfect because of the cut.

It’s just the right length and width (I find many blouses are too long and a bit baggy to wear out), and it’s got a rounded hem, which gives your hips a beautiful shape, plus 3/4 length sleeves are always flattering, and the slit detail on these makes this blouse extra chic.


Deborah wearing nydj brown shorts

3. Opt for Elegant Colors

If you want to have more of a sophisticated look with shorts, you have to wear elegant colors. Flamingo pink and bright turquoise are more resort-like. I decided to go with black with the tan shorts because this is always a very chic color combo.

Do you recognize the blouse? I wore it in a black and white jeans outfit a few posts back, and I’ve just recycled it for this look. The great thing about having a few basic pieces in neutral colors. You can mix and match and get more for your fashion dollar.

Deborah wearing nydj short outfit

Here’s the denim jacket I wore in that post too. Looks cute with the shorts.

Deborah wearing nydj jeans

4. Wear  Classy Jewelry

Another way to make shorts look chic is to add some elegant jewelry. Dainty romantic pieces won’t give you the look you are after. You need sleek, contemporary jewelry for more of an urban edge. Choose simple jewelry with clean lines and more architectural than a frilly feel.

Deborah wearing nydj short look

5. Avoid Heels

One way to look tacky in shorts is to wear high heels.  Chic shorts look understated and a little sporty, which equals youthful too!  Try a pair of cute flat sandals or ones with a shallow heel. Or, go with exclusive statement sneakers like these black knit ones I’m wearing with the touch of metallic at the heel.

black knit sneakers

These Michael Kors sneakers fit well with the classy look of this outfit. They’re knit sneakers, so they are lighter than most sneakers, and the gold trim makes them dressy and a bit glam. Have you ever tried knit sneakers? They’re super comfy too!

nydj tan shorts black top

There’s the look! I would also suggest wearing a pair of oversized sunglasses to get that just stepped-out-of-Vogue look, Lol!  Check out the other ways I wore these fabulous pieces, Boho style, and Monotone. It’s interesting to see how easy it is to mix and match.

The links for this outfit are above. Just click the icons to shop and buy, or check out NYDJ.

Don’t miss my tips for wearing shorts confidently after 40, 50, 60, and beyond!

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11 thoughts on “5 Style Secrets to Look Casually Chic in Shorts

  1. The tips and points that you have mentioned in the above article will be very helpful to look chic. Thank you for listing it together and sharing it with us. Keep sharing more such articles with us in the future.

  2. Love this outfit! Did you size down in the top and the shorts? I know that NYDJ can run a bit big.

  3. I love your posts and have learned so much about how to dress for my age in a chic, fun way and how to accessorize. Question re: shorts for a petite hourglass shape. I’m 5’3″, 130 pounds and find longer-length shorts make my legs look even shorter but shy away from shorter lengths as I don’t want to appear to dress “too young.” Any advice on what to look for? Keep up the awesome work you are doing. You are a bright light shining for the over 40 gals!

    1. Hi Cathy, Thanks so much for dropping by. I don’t think you will look too young with a skirt length an inch or two above the knee. This will be your best length because you are right, a longer skirt will make your legs look short. Play around and see what looks good. I suggest taking photographs in the mirror as this will instantly tell you!! If you are not sure you can always join my private Facebook group- it’s free- and post your photos there. I have some wonderful ladies there who love to help you and I drop by to see what everyone is up to as well. Thanks for your lovely compliment and please let me know what else you would like me to write about. Cheers, Deborah

    1. Thanks, Barbara, so to anyone who says you can’t wear shorts after 40….. I’m 59. I’m sure lots of other women my age and older look just as good in shorts.

      1. Very cute shorts outfit! I must have gotten confused cause I thought you said you’d also be styling what to wear to a wedding, mother of bride hairdos, etc.

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