18 Haircuts Women in Their 60s Regret Not Trying Earlier When They Had More Options

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As women reach their 60s, the reflection in the mirror often evokes nostalgia for the days when hairstyle choices were as vast as their dreams.

Hair, after all, is a canvas of identity, a palette of expression. While many haircuts have graced the heads of women over the years, there are some that hindsight reveals as missed opportunities.

This list compiles 18 haircuts that women in their 60s often wish they had tried when they had more options. These styles embody the spirit of adventure, elegance, and timeless beauty that transcend the years.

The Classic Bob

The Classic Bob
© lizoalex

Embrace the elegance of a classic bob, a style that never fades from fashion. This timeless cut frames the face with precision, highlighting features with its clean lines.

It’s versatile, allowing for both sleek sophistication and playful texture.
Whether worn straight or with a gentle wave, the bob adapts to any occasion.

Women in their 60s often look back and wish they had embraced this chic style earlier, as it offers a youthful yet refined look.
With its low maintenance yet high impact, the classic bob is a perennial favorite.

Pixie Perfection

Pixie Perfection
© Goldsupplier’s Blog

A pixie cut radiates confidence and a spirit of adventure. This daring style is all about embracing one’s features, drawing attention to the eyes and cheekbones.


With its short length, the pixie is easy to maintain, yet it offers a world of styling possibilities. Women who hesitated to try this bold cut often find themselves regretting the missed opportunity to showcase their bold side.


Perfect for those looking to make a statement, the pixie cut exudes an air of modernity and strength.

Layered Shag

Layered Shag
© tamra70

The layered shag is synonymous with effortless cool. This haircut adds volume and movement, making it perfect for women seeking a youthful vibe.


Its layers provide texture and body, creating a look that’s both laid-back and stylish. Many women in their 60s regret not trying the layered shag earlier, as it flatters any face shape and hair type.


With its carefree allure, the shag is a playful nod to the rebellious spirit of the past.

Chic Chignon

Chic Chignon
© jchwartzmann

The chignon is a symbol of elegance and sophistication. This updo is perfect for formal occasions, exuding grace and poise.


Women often overlook the chignon, only to realize its potential for elevating their look. It’s a versatile style that can be worn sleek or with soft, romantic tendrils.


Perfect for weddings or galas, the chic chignon is a timeless choice that enhances any ensemble with its understated beauty.

Curly Afro

Curly Afro
© sheworeitlikethis

The curly afro is a celebration of natural beauty and individuality. Embracing one’s curls can be liberating, offering a bold statement of self-love.


Women who have embraced their natural curls later in life often wish they had done so sooner. The afro exudes confidence and a joyful spirit.


This style is all about volume and texture, allowing for endless creativity. It’s a testament to the beauty of natural hair, inspiring others to embrace their unique tresses.

Long Layers

Long Layers
© CreativeBooster

Long layers offer a sense of timeless beauty and grace. This haircut adds dimension and movement, making hair appear fuller and more vibrant.


Women who opt for long layers can enjoy the versatility of styling, from loose waves to elegant updos. Many reflect on not having embraced this style earlier, appreciating its ability to flatter any age.


With its endless possibilities, long layers are a tribute to elegance and femininity.

Feathered Flip

Feathered Flip
© julieholland64

The feathered flip brings retro charm to the modern age. This hairstyle is known for its soft, feathered layers that gracefully frame the face.


It’s a nod to the past, evoking memories of iconic hairstyles from decades ago. Women in their 60s often wish they had explored this fun and energetic style earlier.


The feathered flip is all about movement and volume, creating a look that’s both playful and sophisticated.

Sleek Bob with Bangs

Sleek Bob with Bangs
© Fabmood

The sleek bob with bangs offers a touch of chic sophistication. This hairstyle pairs the classic bob with the playful addition of bangs, creating a modern and elegant look.


Women who try this style often find it transforms their appearance, adding a youthful flair. It’s perfect for framing the face and highlighting the eyes.


Many look back and wish they had experienced this stylish combination earlier, as it brings both refinement and a sense of fun.

Tousled Lob

Tousled Lob
© addworin

The tousled lob is the epitome of casual elegance. This longer bob, or “lob,” offers a relaxed yet stylish vibe, perfect for any occasion.


Its tousled texture adds an air of effortless chic, making it a popular choice among women seeking a contemporary look. Many regret not embracing this style sooner, as it’s both easy to maintain and versatile.


With its modern appeal, the tousled lob is a go-to for those looking to refresh their hairstyle with minimal effort.

Asymmetrical Cut

Asymmetrical Cut
© kylenana

An asymmetrical cut is a bold statement of modern style. This unconventional haircut features uneven lengths, creating an edgy and dynamic look.


Women in their 60s often find themselves wishing they had experimented with this daring style earlier, as it offers a fresh perspective on traditional cuts.


With its unique shape, the asymmetrical cut highlights individuality and a willingness to embrace change, making it a standout choice for the adventurous at heart.

Messy Bun

Messy Bun
© cristagabriela

The messy bun is a quintessential blend of relaxed charm and effortless style. This hairstyle is perfect for those who want to achieve a chic look with minimal fuss.


Women often overlook the beauty of a simple messy bun, only to discover its versatility and ease later in life. It’s ideal for casual outings or relaxed gatherings.


With its laid-back appeal, the messy bun is a timeless choice that suits any occasion, offering a touch of elegance without trying too hard.

Fringe Benefits

Fringe Benefits
© Pinterest

Fringe, or bangs, can add a playful and youthful touch to any hairstyle. This simple addition can transform a look, drawing attention to the eyes.


Women who incorporate fringe often find it refreshes their appearance, offering a sense of fun and flirtation. As they age, many regret not having explored the transformative power of bangs earlier.


Whether blunt or wispy, fringe offers endless possibilities for personalization, making it a delightful addition to any haircut.

Beachy Waves

Beachy Waves
© mbdor

Beachy waves capture the essence of a relaxed, carefree lifestyle. This hairstyle is all about texture and movement, reminiscent of a day spent by the sea.


Women who embrace beachy waves often find themselves wishing they had discovered this style sooner, as it offers a youthful and vibrant look.


With its tousled appeal, this hairstyle is perfect for those who desire a low-maintenance yet stylish appearance, bringing a touch of summer to any season.

Voluminous Curls

Voluminous Curls
© Blissy

Voluminous curls offer a glamorous and bold style that stands out. This hairstyle is all about volume and bounce, creating an eye-catching look.


Women who choose voluminous curls often find it enhances their natural beauty, providing a sense of drama and flair. Many wish they had embraced the power of curls earlier in life.


With its striking appearance, voluminous curls are perfect for making a statement and celebrating one’s individuality.

Blunt Cut

Blunt Cut
© owensm7

The blunt cut is a statement of modern elegance. This sleek hairstyle features straight, even ends, creating a polished and sophisticated look.


Women who try the blunt cut often appreciate its simplicity and boldness, as it draws attention to their facial features. It’s a versatile style that can be worn straight or with a slight wave.


Many reflect on not having tried this chic and contemporary cut earlier, wishing they had embraced its minimalist allure.

Soft Curls with Highlights

Soft Curls with Highlights
© sheworeitlikethis

Soft curls with highlights offer a harmonious blend of warmth and dimension. This hairstyle adds depth and texture, creating a vibrant and lively appearance.


Women who opt for this style often find it enhances their natural beauty, providing a youthful glow. Many regret not experimenting with highlights earlier, as they add a touch of elegance to any look.


With its soft, cascading curls, this hairstyle is a perfect choice for those seeking a fresh and radiant appearance.

Edgy Undercut

Edgy Undercut
© johnsonschaefer

The edgy undercut is a daring choice for those looking to make a statement. This hairstyle features shaved sides with longer hair on top, creating a striking contrast.


Women who embrace the undercut often find it empowers them, offering a sense of individuality and boldness. It’s a style that breaks the mold and defies traditional norms.


Many wish they had explored this fearless look earlier, as it symbolizes strength and confidence at any age.

Timeless Updo

Timeless Updo
© Journée Mondiale

The timeless updo is a classic choice for formal occasions. This elegant hairstyle elevates any look, offering grace and sophistication.


Women who opt for an updo often find it enhances their poise, creating a polished and refined appearance. It’s perfect for weddings, galas, or any event that calls for a touch of class.


Many regret not having embraced this sophisticated style earlier, as it embodies the essence of elegance and timeless beauty.