Let’s Talk About Shorts

Jun 27, 2024

I love dresses. For 15 years, I wrote an entire blog about how much I love dresses. And while I’ve found several dresses that can be worn while chasing a toddler, sometimes that’s just too much to ask of a favorite frock. So in the summer, that means wearing shorts.

But how do you find the right shorts for you? The ones that are comfortable and flattering? And then how do you style them?

Great Lengths. There is no law or rule or dicta that says that a woman over-35 needs to wear longer shorts. If you want to rock a 3″ or a 4″ short, feel free. On my body, those shorts bunch up uncomfortably at the inseam, and by noon, I look like I’m wearing swim bottoms. Instead, I love a 5″ short. They’re still short, but not too short.

Obviously, the J.Crew Chino short is the favorite in the 5″ category, also in plus and petite. The Factory shorts come in at under $20 and are roughly the same quality. The High Waist Sculpt shorts from WHBM are also worth a look. If you’re looking for denim, these Old Navy shorts come in several washes and plus-sizes.

Style. Recently, I discovered the glory of a-line shorts. As a pear-shaped person, I can’t get enough of them. The style pulls slightly away from the body, de-emphasizing my hips and defining my waist. They also never feel tight or uncomfortable. They’re a joy.

For an a-line short, these ones from Spanx are the best. They’re 50% off right now and worth every cent, even at full price. If you know your measurements, the size guide on these is exactly right. Also in plus.

I just bought these linen shorts from BlankNYC. These Remi shorts from J.Crew (also in plus) are also a great option for that retro 90s look.

To Belt or Not to Belt. Wearing a belt with shorts can be weird at first, but when you’re moving around throughout the day, things stretch, and no one wants to pull up your shorts over and over again. With shorts a thinner belt with a subtle buckle is best.

This black Mango belt is a great, affordable option. I also love this Ralph slide buckle belt, because you never have to worry about notches lining up perfectly; the belt is fully adjustable.

Do you have a favorite pair of shorts? Leave them in the comments.

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How To Wear It, Posts, Style

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  1. Jennifer says:

    I’m pear shaped as well, and a-line shorts and the longer lengths in style right now are great. I’ve never enjoyed wearing shorts as much as this summer! I’ve had a lot of luck with any Madewell short they offer in “curvy” and any Abercrombie (yes, Abercrombie) short that’s in their curve-love line.

  2. LO in TX says:

    This is the first summer I’ve bought new shorts in perhaps five years (thanks to a healthy purge of the wardrobe when I moved in January). I really like both of the new ones I’ve purchased:

    Athleta Brooklyn Mid-Rise Short: I bought these in tall (I’m 5’10”) and really appreciate the extra length. I went one size up because the waistband essentially has a mistake–a seam is running right through it so it doesn’t stretch, I had to break the seam. Now, they are a little looser than I’d like, but are so comfortable, can be dressed up or down, and are long enough that I feel like I can wear them on a plane and minimize skin contact with the airplane seat.

    JCrew Factory “Classic Denim Short” in DARK PACIFIC BLUE WASH: I bought my usual size and they fit like a glove as soon as i put them on. Good length, nice color wash, and are so comfortable. They HAVE now stretched out to the point that I can take them off without unbuttoning, but don’t look like Mom shorts of yore. I think a wash and dry will fix this though!

  3. jules says:

    for whatever reason ONLY shorts with short inseams work on me. 3 or less. My favorite are the Aerie Daydream denim shorts with the elastic in the back. I have two pairs and wear them 99% of the time.

    • Kara says:

      Second this Aerie short recommendation! I wish they came in a less deconstructed version, but they are stupid comfortable AND affordable.

  4. noco says:

    If you’re willing to spend a bit more $, AGOLDE’s “Parker” denim shorts can’t be beat. They come in a 2.5″ and a 4″ inseam, and speaking as a 40-year-old, short, bottom-heavy lady, the 4″ shorts are perfect — not too long or too short, loose around the thighs in an effortless way, and rear pocket placement is excellent (very flattering). A+ recommend!

  5. Lindy says:

    As a BTDT parent to 3 kiddos, I highly recommend skorts. I’m pear shaped and while I’m loving the longer/wider shorts currently, there is nothing better than a skirt. The trick is to style it so it doesn’t look like you just went golfing…..which would be a great follow up post if you needed ideas.

  6. Elizabeth says:

    Abercrombie makes some great loose shorts in cotton / linen blends. I love the print on these: https://www.abercrombie.com/shop/uk/p/linen-embroidered-pull-on-short-55097323?

    And for a more tailored look I have and love these: https://www.abercrombie.com/shop/uk/p/a-and-f-sloane-tailored-linen-blend-short-55097328

    Both look great styled with a linen button up, tied around the waist.

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