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.



