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How to Select & Wear Shorts with Confidence

June 8, 2020

At our ages, many of us gals are opting for alternatives to shorts these days. But then again, during the summer heat, I am still prone to wear shorts a good bit. And if you, like me, still like to wear shorts, you should be able to wear them with assurance and style. So I’ve gathered a few tips to help us select and wear shorts with confidence.

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How to Select and Wear Shorts with Confidence
7″ Chino Shorts in Cafe // v-neck Supima cotton t-shirt in black // similar leopard print belt // Kendra Scott Elisa Necklace (customized) // Kendra Scott Veronica hoop earrings in gold // bracelet no longer available // Tory Burch sunglasses (more economical alternative) // sneakers in white and navy (more economical option) // Bombas Cushioned no-show socks // Reversible faux leather tote

How to Select the Best Shorts for You

Tip #1 – Most women look good in shorts with a mid-length inseam (5-7″). That’s generally anywhere from about finger-tip length to a few inches above the knee. This is a good default inseam to look for. And this is definitely the inseam I prefer for most of my shorts.

Tip #2 – That said, choose the inseam that makes you feel comfortable and confident. You may prefer a shorter inseam (3.5-4″) or a longer inseam (8-11″ – Bermuda).

How to Select and Wear Shorts with Confidence

Tip #3 – Consider your leg length when selecting the best inseam for you. If you have longer legs, you’ll be able to wear Bermuda or 8-11″ shorts well. If you have shorter legs, you may prefer shorts with a shorter inseam, such as 3.5-5″. If you have shorter legs, but want to wear Bermudas, look for petite sizes. I know that Talbots has petite size Bermudas, for instance.

Tip #4 – Just as important as inseam, look for shorts with the best leg opening size for your body. For the most part, you want your shorts to be a little roomy in the leg opening so that your legs don’t appear to be sausages bulging out of a casing. Know what I mean? But you also don’t want them to be so roomy that you get that droopy diaper look. Don’t you love my visuals???

How to Select Shorts

Tip #5 – In most styles, the leg opening should “follow the line of your leg.” However, you may also choose to wear shorts with more of a fit and flare silhouette if you want to accentuate your waist or you’re trying to broaden your hips to balance wide shoulders.

Tip #6 – There’s no need to wear your shorts too tight. Some recommend sizing up in shorts so that they are not too tight. But I haven’t found the need to do that in the brands that I wear, such as Ann Taylor, Loft or Talbots. I do wish I had sized up in the shorts I got from Christopher & Banks, but only to my true size.

How to Select Shorts

Tip #7 – Check out the rear view. Generally, I follow the same guidelines for the rear of my shorts as I do for other pants. I don’t want pockets that are placed too wide or large, which will cause my backside to look large. But I also don’t want my cheeks showing. That’s not going to happen, of course, with the length of shorts I generally choose.

Tip #8 – Bend over and sit down. Just like when you’re trying on pants, jeans or swimwear, it’s extremely important to try sitting and bending over in shorts. I want my shorts to move with me and still look “decent” when I move about. Specifically, I look at how my shorts look across the front of my legs when I sit down. Do they stay at a nice, modest length? Do they lay nicely across my legs without “squeezing” them?

Tip # 9 – Buy good quality shorts. They don’t have to be expensive or designer brands, of course. But as we get older, quality clothing is all the more important. Look for shorts in classic styles, made from good quality fabrics and sewn with precision.

How to Wear Shorts with Confidence

If we’re going to wear shorts at our age, it’s all the more important that we do so with confidence and style. So make sure you’ve chosen shorts that check all the boxes mentioned above, but also that make you feel pretty and smart.

How to Wear Shorts with Confidence

Tip #1 – Keep your look simple and pared down. A basic tee in a solid color or neutral is always a wise choice to top your shorts.

Tip #2 – Add a front tuck to balance your proportions. Just like when you’re wearing jeans or pants or a skirt, you want to do what is necessary to create that aesthetically beautiful proportion of thirds. If you wear a long shirt hanging over your shorts, your proportions will look “off.” So create a pleasing shorter drape with a gentle front tuck instead. Or wear a slightly shorter top than usual.

Tip #3 – Draw attention up toward your face with a pretty neckline and appropriate jewelry, such as dazzling earrings or a nice necklace.

Tip #4 – Maybe wear a little self-tanner if you choose. I’ve been wearing the St. Tropez Self Tanning Mousse this spring and liking it pretty well.

How to Wear Shorts confidently

Tip #5 – Choose footwear that will help you create the longest leg line possible. Especially if you’re wearing shorts that shorten your leg, choose sandals in a tone close to that of your skin. Or you could opt for a metallic sandal (see my recent post on styling metallic sandals). Of course, sneakers are always a suitable option, too.

7″ Chino Shorts in Cafe // v-neck Supima cotton t-shirt in black // similar leopard print belt // Kendra Scott Elisa Necklace (customized) // Kendra Scott Veronica hoop earrings in gold // bracelet no longer available // Tory Burch sunglasses (more economical alternative) // sneakers in white and navy (more economical option) // Bombas Cushioned no-show socks // Reversible faux leather tote

Besides the elements in my outfit shown here, I’ve included a selection of shorts in today’s shopping widget. Most of the shorts I’m showing are on sale, so you’ll need to click through for accurate pricing. Thanks so much for stopping in today for a little style inspiration. I hope you have a wonderful day as you begin a new week.

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Blessed for My Day

You are who God says you are. Period. You are loved and valued. He has paid the ultimate price for your redemption and freedom. He has called you for a unique purpose and gifted you to fulfill that purpose. He has great plans for you.

Do not let a wave of emotion to push around your confidence. Do not listen to one voice or a choir of voices that try to define you or set your course. You can stay true to who you are and who you have been created to be by clinging to the anchor of your soul, Jesus Christ. Listen to His voice today. Cling to His Word, His character and His activity in your life. Let Him establish your path and then walk it obediently and joyfully.

This hope we have as an anchor of the soul, a hope both sure and steadfast and one which enters within the veil, where Jesus has entered as a forerunner for us. ~ Hebrews 6:19-20a

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xoxo, Kay
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8 thoughts on “How to Select & Wear Shorts with Confidence

  1. Morning,
    For those of us with bellies would you please make suggestions for those of us who do not want to highlight them with a front tuck. The front tuck is so popular in today’s fashions and helps with the portions of thirds. But for myself, and I’m assuming others also, the front tuck just does not create a good look for those of us with bellies.

    Thanks Kay, I love your blog and look forward to it every day!

    1. Hi Cathy. You bet. I’ve got two looks coming this week that fit the bill. But tomorrow specifically I’m sharing a shorts outfit for hiding the tummy. Basically I suggest fitted shorts (preferably pull-on so they don’t have a front closure that protrudes) with a smock type top, such as a tunic or other loose fitted shirt. I’ll share more tomorrow. Thanks for asking.

  2. You look so nice in that pretty shorts outfit Kay! For the ladies like myself that prefer to wear pull on shorts, I highly recommend the Kim Rogers brand from Belk. The fabric is really nice and the shorts are extremely comfortable with a nice leg opening. I can’t wait to see what else you have to share with us this week!

  3. Hi Kay…..I’m hoping that favorite Ice Cream place is…..Graeter’s Ice Cream!!
    I know that’s our favorite?

    Love the shorts…


  4. Good Morning, Kay
    Loved your blog on buying shorts since I always have a problem finding the right fit. I also have some Talbots shorts and they fit very nice especially in the legs since my legs are not my finest part!! I like your idea of sitting down when trying on shorts to make sure they are comforable in the leg area! Never thought of doing that!!

  5. Your comment about sitting down to try on shorts is not a bad idea for pants. I don’t wear shorts but I love the colors in this outfit. I always say I’m getting rid of black but sometimes it just works so well. Black and white just always work.