I know that as we reach our 50s and beyond many women begin to feel like they have aged out of blue jean shorts. But I still enjoy wearing these classic, casual shorts during the summer. They can be comfortable but still stylish and appropriate if we take the time to put them together with the right pieces from our closets. So today I’m sharing 5 ways to wear denim shorts this spring and summer.
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For all of these outfits I’m wearing these girlfriend denim shorts from Talbots. They feature a 6″ inseam, a high rise and a rolled cuff. Unfortunately these particular denim shorts are almost sold out. But I’ve collected a variety of other denim shorts from some of your favorite brands in the shopping widget below.
When shopping for denim shorts or any other shorts, the main things to consider include inseam (I prefer a 5-6″ inseam, but that really depends more on your height and proportions than anything), fabric, rise, pocket placement and distressing. The choices are boundless really.
Wear Denim Shorts with a Sweater
I love the juxtaposition of wearing denim shorts with a long sleeve cotton sweater in the summer. This combination may not be appropriate for every hot summer day. But it works great for a cool morning at the beach or a chilly evening in the mountains. My cotton sweater is marked down and available for an extra 50% off with code SUNNY. However, it is final sale. I can tell you that it is very lightweight and breathable, perfect for the beach or mountains. And it runs true to size; I’m wearing a medium. It also comes in other colors.
You can give that sweater a little front tuck…or not. Take into account the length of the sweater and your proportions. You don’t want the sweater to hang over the shorts so long that it makes the shorts look disproportionate. Finish the outfit with either sandals or sneakers, your choice!
Wear Denim Shorts with a Popover
An easy breezy popover shirt is another great option for pairing with denim shorts. You’ll still find these pullover tops in cotton and linen, but this year we’re seeing a lot of them in soft gauzy fabric.
Again, you can tuck the popover a little in the front (or all the way around) or not. My popover is slightly cropped so it works really well untucked over my denim shorts. But just take into consideration your proportions and the rise and inseam of your shorts.
I completed this simple shorts outfit with my Naturalizer Sandals and a straw bag (more economical option). I’d wear this denim shorts combination to run errands or for a family picnic.
Wear Denim Shorts with a Simple Tee
Of course, you can always just pair a simple tee with your denim shorts. Whether you opt for blue, black or white denim shorts, a colored tee tops them perfectly and simply.
My Caslon short sleeve v-neck t-shirt is in a pretty pink flamingo. But this raw edged double v-neck comes in about a dozen different colors and prints. It runs true to size for a loose fit. I’m wearing a medium.
I think the key to elevating this one-two outfit a bit is adding some interesting jewelry and shoes. I’m wearing my gold sandals and a Victoria Emerson wrap bracelet. These Victoria Emerson bracelets or their boho cuffs are such a fun way to add a little style and I find they look especially nice with summer outfits.
Wear Denim Shorts with a Summer Sweater
I’ve always loved summer sweaters. You can find them with 3/4 length and short sleeves, but I think the sleeveless ones are definitely the most casual and cool. I think this rainbow prism sweater tank looks so youthful and fun over my denim shorts. It fits true to size; I’m wearing a medium. I also have the soft periwinkle blue and it comes in a great natural shade, too.
I wore the same jewelry with this simple outfits, but I traded in my neutral birchwood colored Naturalizer sandals. I liked the way these flesh toned sandals keep this more colorful outfit casual and effortless.
By the way, those Naturalizer sandals are soooo comfortable. I wear them frequently already. They run true to size and come in black and a couple of trending summer colors.
Wear Denim Shorts with a Linen Shirt
Finally, I’m wearing my denim shorts with a button up linen shirt (wearing a small). I’ve chosen to wear my chambray blue linen shirt, but you could create a similar look with whatever linen shirt you have in your closet or choose to purchase. But I do love the way the chambray blue (they call it blue ridge/white) works with the blue denim. My linen shirt runs large (as do most of J.Jill’s tops for me), so I’m wearing a small.
Under the linen shirt I’m wearing a linen tank I purchased last year. It’s not available again this year, but any tank could work. I tried to find something similar, but struck out. I completed this outfit with my nude colored Born sandals (and here) from last year (they are still available) and a boho cuff from Victoria Emerson.
I think this is probably my favorite look of the five, so I apologize for creating it with a tank that is no longer available. Maybe you have something loose fitting like that in your closet that would work nicely.
Of course, I also showed these denim shorts in last week’s post about 5 Ways to Wear the Clothed in Strength Tee. The sleeveless tee is indeed out of stock right now, but Pam assures me she is getting more in. So if you’re interested in the Clothed In Strength Tee just select your size and leave your email for notification of restock.
Thanks so much for dropping in today. Now that I have a studio, I’m planning to create lots of these 5 Ways to Wear posts. Do you have a garment or even an accessory that you’d like to see me style five ways? Let me know in the comments below and we’ll see what I can do. Have a great day!
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Blessed for My Day
Over the years I’ve discovered that those who at first seem wise and knowledgeable sometimes later prove to be less reliable than I had first thought. We humans are often enamored with all the wrong things: charisma, impressive vocabularies, piety, exotic accents and picturesque wording. Such things can make a person and their advice sound or look wise when in fact they are not. So how can I know what true wisdom looks like?
The Bible is my guide in spotting wisdom. First of all, the Bible is wisdom. Wisdom is always from God’s perspective. In fact, the wisdom of men is called foolishness by the Bible. And God’s Word tells me that true wisdom is first of all pure (never straying from the precepts of the Bible). Finally, true wisdom is spoken or written from people who have true godly character. They bear the fruit of the Spirit. Let’s be careful as we read and listen today, carefully discerning between that which is truly wisdom from above and that which simply sounds good.
But the wisdom from above is first pure, then peaceable, gentle, open to reason, full of mercy and good fruits, impartial and sincere. And a harvest of righteousness is sown in peace by those who make peace. ~ James 3:17-18
Hi Kay!
What a blessed and beautiful wedding!! Thank you for sharing the pictures, it is apparent there was a lot of happiness and love all around!
Loving the denim outfits. I, like you, are a little careful with shorts these days, although I still want to wear them from time-to-time. The tops you styled with them are great and give me a go-to!
Thank you!!
All of the looks you created around the denim shorts are so nice, Kay! And I think the backdrop James has set up is perfect! It’s very interesting while not taking away from you. My strength tee from Sadie+Jane should be waiting on me when we get back home from the beach. I have more VE bracelets than I care to admit. They can add so much interest to an outfit. The magnetic wrap bracelets are my favorite from them. I really enjoyed the BFMD.
Hey Kay!! I wear my jeans shorts 90% of the time and I’m almost 73 years of age. I have lost a lot of weight and I’ve got to buy new. The ones I have cannot be altered. That to say, if you see any roll cuff 5-7 inch inseam, will you please post? I’m in a Size 8. Your outfits are just lovely and you look beautiful. I have experienced with linen years ago. But I do love. Going to get back in the band wagon. I love the look. So glad your daughter had a Wonderful wedding and you have recouped. I love your blog. Keep the great outfits coming. Linda🌹
Please post wedding pics on here! Im not on insta or fb! I recently lost over 25 lbs (and hoping for 15 more). Could you please explain how to “front tuck”? Im not sure if its because most of my shirts are a little longer, but it looks very awkward when i attempt it. Also i have bought 2 pair of wide leg linen pants but am not sure how to style them. Im still not ready to tuck (there might be sit ups in my future to attempt to get rid of my baby belly from 32 years ago lol). I am trying to pick up some of the shorter length shirts but it is so unfamiliar to me after being a 16 for so many years!
Thanks! I love your posts!
I am wearing my denim shorts even as I read your blog today!! I also love the look of a long-sleeved cotton top or sweater with shorts! And I have several J.Jill linen button downs that I have collected over the years.
Thank you for your sneak peaks of your MOB dress and the bride and groom on Instagram! So beautiful and your dress was so stunning and flattering!!
Those shorts fit you perfect!! Mine always seem to loose in the legs or not long enough!! Talbots clothes don’t always fit me well but I may have to try those!! Thanks for a great post!!
I liked all of your denim shorts suggestions. However, I think shorts should stop just above the knee. The smallest part of our thighs. I watch other influencers who always say pants no shorter than ankle and shorts no shorter than just above the knee. This is actually a good guide for any age. Capris not good for anyone! Lol !
Hi Bonnie. I’m glad you enjoyed the blog post. However, I disagree with you on the length guidelines. I agree that it’s smart to have our pants end at the smallest part of our calves, usually around the ankle. But when it comes to shorts we are all built a little differently and proportions plays a bigger role. I’m 5’8″ and height plays a big role in what looks good for shorts, too. Taller women can generally wear Bermuda and longer length shorts nicely while more petite women generally do better with shorter inseams. However, the inseam length is not the only measurement to consider. Leg opening width also plays a vital role. If the shorts fit close to the leg the leg tends to look a little fuller, but if the shorts have a little room in them the thigh tends to look a little smaller. So I just don’t think it’s as simple as everyone buying shorts that hit just above the knee. That length can actually make some women’s legs look all the shorter.
So happy that you’re well-rested after the wedding. The milestone events in life are so joyful! ,
I took out my summer clothes and tried on my shorts only to find that they are too big. I know most people are happy about that but my weight loss is because of an RX side effect for breast cancer. I find the longer shorts draw attention to the knees more than the shorter. Your length is perfect for the leg blending in with the line of the leg. The knee is not the first skin seen. I think a few extra pounds is a good thing as we age because of gravity. My saggy knees are proof of this.
Thanks for the post
Good morning Kay. I just tried to order
The Relaxed collared sweater from
J. Crew through your blog and used the code SUNNY but they would not honor
The code. So I cancelled the order
Thought you might want to check this out the lady said I should go directly to
J.Crew I said know you get credit for the sale through you blog. Keep up the good work Kay I love your information and your blessing. Susan
Huh. Isn’t that just crazy? When I bring up the sweater in the search feature on the website it says extra 50% off sale items with the code. But then on the actual page it now says 25% off with the code. That’s just bad on J.Crew. Sorry for the frustration. It did indeed say extra 50% off this morning. But don’t worry about me and my credit for the sale. It all comes out in the wash! Thanks for the alert however.
Hi Kay, I cannot wait to see mother of bride dress and other wedding pics. I do not do instagram ,
Kay, thanks for a great and helpful post. Could you please do one on different pants lengths and styles and what footwear goes with them. I especially have trouble with the wide leg and straight leg pants. Thanks.