5 Bob Haircuts That Are So Flattering On Older Women

We're living in a time where getting older isn't what it used to be. (Cue the onslaught of Demi Moore photos.) Not only are people living longer, but remaining stylish and chic into your 60s and beyond has become the norm. While our grandparents and the generation before them were forced to grow up and age too fast, that's not necessarily the case now. In fact, even what was once considered middle age has increased by decades.

"There's no point trying to impose chronological age on what is or is not middle age," Professor Les Mayhew, head of global research at the International Longevity Centre U.K., tells The Guardian. "With people living longer, your 30s are no longer middle age; that has switched to the 40s and 50s." He adds, "In some cases, in your 50s, you might be thinking about a second or even third career."

What does this ultimately mean? For starters, you're not as old as you may think. Secondly, if you are an older woman looking to spruce up your look, you absolutely can't go wrong with a bob haircut. Bobs transcend time, age, gender, culture, and everything in between. Because there are a lot of bob cuts and styles to choose from, you just need a bit of guidance, and of course, inspiration too, to help you pick the right one for you.

You can never go wrong with a curly lob (or long bob). Not only is it the perfect gateway for trying out short hair, but it's easy to maintain, and as we can see, Viola Davis is nailing this look. "A lob gives you the look of a shorter haircut, but with the feeling of longer hair," hairstylist Ryan Trygstad tells Glamour. "It has the option to look both long and short, and has so many styling options. They can be waved for a beachy look, air-dried for a lived-in cool-girl look, or flat-ironed for a sleek, polished look."

When you add a middle part to the equation, the curly lob becomes next-level. This is because middle parts basically summon all attention to your facial features, amplifying your eyes and lips especially. So, bring on the mastering of the red lip and conquer.

First of all, let's take a moment to admire how amazing this French bob with a side part looks on Michelle Yeoh. When she showed up to the LA premiere of "Wicked" in 2024 rocking this bob, jaws dropped — and some might still be on the floor. You can tell just by looking at Yeoh's hair that it has life to it and pizazz that isn't often found in other cuts and styles.

"Any haircut above the shoulders will lighten the hair and bring luster and bounce back into it, and removing extra weight will help to enhance texture and the wave pattern," celebrity hairstylist Rena Calhoun tells InStyle. The French bob, thanks to its gorgeous subtle waves, is the precise definition of the term "effortlessly chic."

When it comes to hair inspiration, whether you're 25 or 65, Tilda Swinton should always be on your list. Swinton is someone who is fearless in her haircuts and styles, never missing the mark no matter what look she goes with.

If you want a bob that you plan to slick back on a regular basis, then make sure you say that to your stylist when you hit up the salon. Although any kind of haircut can be slicked back, with a bob, you want it to be less layered so all the hair strands can be brushed back with product, and they'll stay put. "[The slicked-back look] is also super easy to achieve," celebrity hairstylist Andrew Fitzsimons tells Real Simple. "This look is also great to do in between wash days."

As we already mentioned, lobs are fantastic if you want a beginner short hair look. But if you're going with a straight lob, then it's fairly low-maintenance too. While some lobs require blowouts, curling irons, and a bunch of heavy hair product to keep everything in place, when you're rolling with a straight lob, you basically have a get-up-and-go cut that doesn't require a lot of muss and fuss. Gayle King is basically the queen of lobs — no matter if it's straight, curly, or wavy — so clearly, she recognizes a good thing when she sees it and hangs on to it.

When it comes to older women and bob haircuts, it would be a major faux pas not to include Anna Wintour. Aged 75 in 2025, Wintour has had her iconic bob with blunt bangs since she was about 14. In October 2019, Rihanna appeared on Vogue's series, "Go Ask Anna," and inquired about Wintour's haircut. "I can't remember how long I've had this haircut for," Wintour told Rihanna. "The one time I tried to change it was a disaster. I had to wear a hat for several months. So I'm way too anxious and too lazy to try it again."

While certainly flattering on older women, bob haircuts work on everyone. "It's a haircut that can work for every face shape and hair texture," celebrity hairstylist Mark Townsend tells Allure. "No two bobs are ever the same, so it always looks new. The bob is about freedom and taking charge." And that's exactly the mentality that all women should be embracing.