As we age and our bodies change, it may feel like a constant struggle to find flattering hairstyles for women with glasses. Embracing a whole head of gray takes a lot of guts and courage, so we’re emotionally worn out by the time we have to worry about what cut, color, and style will work well with our frames. And of course, no matter how many pictures of short hairstyles with glasses we save to show our stylist, the end result never feels right. (Honestly, having nice hair can be exhausting, especially if you’re suffering from hair loss.) Fortunately, there are dozens of hairstyles that look good with glasses to choose from.
The key to finding the best hairstyles for glasses wearers is to look at the whole picture before going in for your haircut. Not only should your hairstyle match your glasses, it should also mesh well with your face shape, makeup preferences, and lifestyle habits. You can save all the photos in the world of cute hairstyles with glasses, but if the cut won’t complement your face shape or involves blunt bangs that will be in the way of your oversized glasses frames, you should opt for another style entirely.
Short Hairstyles for Women Over 50 With Glasses
Hair length is another factor that should be considered when deciding on haircuts that look good with glasses. When it comes to short hairstyles for women over 50 with glasses, remember that your face — and your frames — will be on full display. If you have a feisty fashion sense and want to show off your spunky specs, opting for a short ‘do is the way to go. This way, the focus will be on your chic eyewear. Jamie Lee Curtis is the standard when it comes to flattering short hairstyles for women over 50, and her cropped cut allows for her brilliant bifocals to take centerstage.
Medium-Length Hairstyles for Women Over 50 With Glasses
Medium-length hair is ideal for ladies with a wide face shape who want to instantly slim their features. Adding face-framing layers can create a stylish and sexy look for women over 50 without the added effort of caring for very long hair. You can’t go wrong opting for a shoulder-skimming cut — no matter your age, face shape, or hair texture. It’s no wonder so many celebrities who wear glasses also opt for medium-length hair. Actresses Allison Janney, Barbra Streisand, and Sally Field are all fans of this style of hair.
Because it’s popular to have bangs with longer hairstyles, you need to take them into account when choosing your style. If you have blunt bangs that fall just a few centimeters above your glasses, be prepared to visit your salon every two weeks or so for a bang trim. If you’d rather skip the expense of bi-weekly hair cuts but still want bangs, opt for piece-y bangs that can be swept to the side and behind your ears when they get a little too long between trims. Side-swept bangs with glasses can look simply stunning too, even if they aren’t what you first imagined yourself with.
Long Hairstyles for Women Over 50 With Glasses
Women over 50 can absolutely rock long hair — even with glasses. (Just ask Demi Moore!) But some thought will need to go into the decision-making process. There’s nothing wrong with preferring hairstyles with glasses and bangs (some of us were blessed with face shapes that flatter bangs), but it can make choosing the right cut a bit difficult. All the same rules apply for long hair with bangs and glasses as they did for medium-length and short haircuts with glasses. Be aware of your beauty budget and know how often you’d feel comfortable sitting in a salon chair so you can factor those costs into the price of your new look.
Of course, the best way to discover haircuts that look good with glasses is to look around you. Chances are you have some spectacled friends, and if you love their hairstyle, ask them who cut it. Hairstylists are most familiar with their own work, so if you can show them one of their own clients whose hair you adore, they’ll be able to give you exactly the same cut or at least tweak it so it works for your hair texture, face shape, and glasses.
Whether you’re seaching for the best red hair and glasses combo or are seeking hairstyles for round faces with glasses, we’ve got all the inspiration you need. Keep scrolling to see your favorite glasses-wearing celebs and their stylish hairdos.
Best Hairstyles For Women Over 50 With Glasses Michelle Yeoh
Best Hairstyles for Colorful Glasses — Michelle Yeoh
Pulling off colorful glasses can be tricky, but Crazy Rich Asians actress Michelle Yeoh does it with ease. Her two-toned blue and black frames add an element of fun to her muted ensemble and are a bright contrast to her dark locks.
Best Hairstyles For Women Over 50 With Glasses Vanessa Marcil
Best Long Hairstyles for Glasses — Vanessa Marcil
Soap actress Vanessa Marcil's sleek straight hair is a deep, rich brown that makes her tan, rectangular frames pop.
Best Hairstyles For Women Over 50 With Glasses Julia Louis Dreyfus
Best Hairstyles for Big Glasses — Julia Louis-Dreyfus
Julia Louis-Dreyfus' chunky black frames are a classic silhouette that suit any face shape.
Best Hairstyles For Women Over 50 With Glasses Megan Mullally
Best Hairstyles for Round Glasses — Megan Mullally
Megan Mullally's round tortoiseshell glasses perfectly suit her deep reddish-brown hair.
Best Hairstyles For Women Over 50 With Glasses Courteney Cox
Best Hairstyles for Black Glasses
Most glasses frames look beautiful in black, which is why this hue is a classic color. When it comes to picking the best hairstyles for pairing with black glasses, there are no rules. Actress Courteney Cox pairs her black rectangular frames with an angular long bob.
Best Hairstyles For Women Over 50 With Glasses Annette Bening
Best Short Hairstyles for Glasses — Annette Bening
Actress Annette Bening's tousled pixie cut is a beautiful short hairstyle for women with glasses, as it adds a bit of interest to her look without stealing the show.
Best Hairstyles For Women Over 50 With Glasses Anjelica Huston
Best Hairstyles for Square Faces With Glasses — Anjelica Huston
Longer bangs that hit right below the brow are ideal for women with square faces. This style softens the face's angular jaw.
Best Hairstyles For Women Over 50 With Glasses Allison Janney
Medium-Length Hairstyles for Women Over 50 With Glasses — Allison Janney
The I, Tonya actress has rocked dozens of different hairstyles, but we're huge fans of her medium-length mane. Her soft-brown, face-framing waves flow seamlessly with her black rectangular frames.
Best Hairstyles For Women Over 50 With Glasses Jamie Lee Curtis
Short Hairstyles for Gray Hair and Glasses — Jamie Lee Curtis
With her bright silver hair and boyish haircut, Jamie Lee Curtis is the epitome of cool. Curtis' chunky black frames are front and center, popping against her short pixie cut.
Best Hairstyles For Women Over 50 With Glasses Demi Moore
Long Hairstyles for Women Over 50 With Glasses — Demi Moore
Actress Demi Moore makes a strong case for growing out your hair — even after 50! Her silky smooth tresses are almost identical in color to her rounded frames, helping her specs blend in. Overall, Moore's glasses and hair combo keep her looking fun, fashionable, and youthful.
Best Hairstyles For Women Over 50 With Glasses Oprah Winfrey
Ponytail With Glasses — Oprah Winfrey
Oprah Winfrey is known for her voluminous curls, but she prefers to wear her hair in a high, slicked-back ponytail when she wears her glasses. As a result, her patterned frames are the stars of the show and add some character to her monochrome outfits.
Best Hairstyles For Women Over 50 With Glasses Barbra Streisand
Straight Hair With Glasses — Barbra Streisand
Even though Barbra Streisand's natural hair is big, curly, and beautiful, she prefers to wear her locks pin-straight nowadays. Paired with her small, tinted oval glasses, Streisand's look is totally fuss-free.
Best Hairstyles For Women Over 50 With Glasses Sally Field
Short Hairstyles for Women Over 50 With Glasses — Sally Field
Sally Field's big brown glasses blend in seamlessly with her chocolate-colored curls. The oversized frames make her eyes appear bigger, giving her a friendlier look overall.