As the leaves change and the autumn air grows crisp in September 2025, I’ve been reflecting on my recent beauty journey. At 66, I decided to tackle an age-old challenge for women with round faces like mine – finding a short haircut that actually creates a slimming effect. After consulting with three different stylists, I tried eight distinct short cuts over the past year. The results were surprising, some disappointing, and others genuinely transformative.
The round face challenge in our mature years
Having a round face at 66 presents unique challenges. As we age, our faces naturally lose definition, and a round shape can make us appear heavier than we are. The right haircut, however, can create the illusion of a slimmer face while highlighting our best features. My stylist explained that what works in our 40s often needs adjustment in our 60s due to changing hair texture and facial contours.
Why I decided to experiment with short cuts
After years of maintaining shoulder-length hair, I was tired of the maintenance. Thinning hair had also become a concern, making my usual style appear flat and lifeless. I was inspired by a friend who underwent a dramatic transformation with a haircut that took years off her appearance. Could the right short cut do the same for me?
The cuts that didn’t work for my round face
Not all experiments were successful. Three styles actually made my face appear rounder:
- The classic bowl cut – created a horizontal line that emphasized width
- The blunt chin-length bob – formed a perfect circle with my face shape
- The super-short pixie with flat top – removed height where I needed it most
The game-changer: textured pixie with volume on top
The most transformative cut was a textured pixie with added height at the crown. “Volume at the top creates vertical lines that elongate your face,” explained Dr. Lisa Chen, a dermatologist specializing in aging. The choppy layers broke up the roundness of my face while the tousled top drew attention upward, creating a slimming vertical effect.
This style was similar to the hairstyle that makes women look 7 years younger that I’d read about, and I found the results equally impressive.
The angled bob that contoured my face
The second most successful cut was an asymmetrical bob with the front pieces falling just below my chin. The angular lines created definition where my round face lacked it. The shorter back added volume where my hair tends to fall flat, similar to the benefits of an ultra-short bob that adds volume where thinning occurs.
The surprising power of strategic bangs
Side-swept bangs proved to be a secret weapon for slimming my round face. By creating a diagonal line across my forehead, they broke up the circular shape and drew attention to my eyes. When paired with a round bob with an even perimeter, the effect was surprisingly youthful.
The maintenance factor
One crucial consideration for women our age is maintenance. The most flattering cuts required regular trims every 4-6 weeks to maintain their shape. My blunt bob added impressive volume, but demanded consistent upkeep.
Fall 2025’s best short cuts for round faces
As we head into fall, these styles are particularly flattering:
- Layered pixies with textured crowns
- Asymmetrical bobs with face-framing angles
- Soft shags with curtain bangs
- Bixie cuts (pixie-bob hybrids) with height on top
What I’ve learned about confidence at 66
The most profound lesson from my experiment wasn’t just about finding a slimming haircut – it was about embracing change at 66. My pixie cut didn’t just make my face look slimmer; it made me feel lighter, more modern, and unexpectedly confident. Sometimes the most transformative beauty decision isn’t about looking younger, but about looking like your best self at exactly the age you are.