As my time as a stylist was coming to an end, I was able to put glasses on a woman, and when she saw herself with her new glasses, her reaction was priceless. That’s when I started to understand how much impact glasses can create. What a lot of people dont know is that a great haircut is meant to enhance the glasses, and not simply sit around them. I have learned a lot. Especially the positioning of the frames in relation to the person’s face, how the glass temple pieces sit under the hair, the differences in a person’s looks when they are looking down at their phone compared to when they are looking up at a mirror, and so on. Bad haircuts steal attention from your glasses and compete with them, and no one wins; except for the good haircuts. Those are the ones that look like they are designed to be paired with the glasses.
During my time as a stylist, I have had the chance to interact with a lot of women above the age of 50. One thing that I have noticed, and that did surprise me, is that there is a level of self-awareness that is attributed to the face that is quite apparent and a little bit unusual. I suppose that having decades of experience studying their own reflections can foster that sort of self-awareness. This kind of experience involves choosing frame designs for glasses and using little mirrors that are found in optical shops to see how different frames look.
You can take my word for it that I enjoy all 25 of these haircuts I’ve chosen for you. Each transformation has had every client I’ve seen, at least, gasp. Every cut seemed to elevate their glassed look to the level of some high-end designer pair. I have found in my styling experience that a few of these cuts work best towards the longer end of the bob to create a nice cool in-between length. And I will definitely be straightforward and honest about which of these I like best.
#1: Modern Rounded Bob with Subtle Layers
I always go back to this design because it does one very particular thing I enjoy, it mirrors the outline of most glasses frames, then goes a little further, so you have a nice continuity from the frames to your hair. The layers here are not super bold, they are doing subtle work to create movement through the mid-lengths and prevent the ends from looking boxy. That chocolate color does a lot of the work, it reflects light and elevates the whole look. If your hair has any natural swing to it, this almost styles itself with a round brush and four minutes.
#2 Chic Textured Bob with Soft Waves
This is what I like to refer to as the “just came back from somewhere interesting“ style. There are many styles that are relaxed, laid back or undone, but this one is different in the amount of actual effort that goes into the initial cut and the layering techniques. The waves fall away from the face so they won’t cover your frames, of which, that chin grazing length is appealing to almost everybody. The highlights are working for you because they create the illusion of more density where it’s needed most. I’d reach for some texturizing spray for the days when your hair behaves too well and goes flat, to refresh the style.
#3 Textured Wavy Lob with Soft Layers
I have a soft spot for this length, right above the shoulders, because it is the sweet spot where you still feel like you have enough hair to play with, but you also aren’t dealing with the annoyance of longer lengths getting caught under bag straps or coat collars. The wave, of course, does all the work, and these particular layers are arranged to let that happen without turning into a triangle, which is always the risk with this length if the layering is not done well. If your hair has even the faintest hint of a wave that you’ve been resisting, this is the cut that will make you stop resisting.
#4 Textured Short Bob with Bangs
I like the warm red color a lot! I also want to mention how those bangs and glasses sit right at the frame line, which gives a purposeful touch, as if everything was designed to go together. The length of the jaw is working overtime to showcase the cheekbones, and the texture stops it from looking too strong. I’ll be real; bangs and glasses is a huge commitment because there’s a lot going on in that small area on your face. If you are someone who gets impatient with trims every three to four weeks, it’s probably a good idea to put this one on the “aspirational” list for now.
#5 Textured Short Crop with Soft Volume
This haircut is the equivalent of an unbranded t shirt. Because it doesn’t have any loud branding, it can be appreciated for being simple. The added height on top is great for balancing out heavy glasses. The softer layers mean that there are not harsh lines created around your face. This is a wash and go cut, however if you want to do any styling, use a small amount of cream on damp hair, and you are good to go.
#6 Modern Textured Pixie with Soft Volume
While I’m not usually one to admire my work from behind the chair, I think you’re going to love this silver pixie haircut. The longer layers on top give you versatility, so you can push them forward, do a side sweep, or have a bit of a mess going on. Each way, it’ll look like a whole different cut! She shorter sides do a great job to frame the face so it’s not overwhelming around the glasses too. I’ll be honest, fine silver hair usually falls extremely flat by 2pm. Unless of course you have a game plan that includes a root volumizing powder and a tousled look.
#7 Classic Textured Bob with Side-Swept Bangs
Side-swept bangs make wearing glasses feel more intentional like they’re an accessory rather than something you need to wear. Not that it even matters, but this style resembles a news anchor in an admirable way. The cut is professional and the wave is just enough to keep the style from being stiff or boring. If your hair is fine, you’ll end up with the same lovely effect and if your hair is thick this will be easy to achieve as well. Your stylist will just have to take out more of the weight from around the edges so it won’t end up looking poofy. The lightness toward the ends of your hair will be a plus.
#8 Chic Textured Bob with Wispy Bangs
I really like how these dainty bangs go so well with glasses so that the bangs pop through the lenses without looking too busy. They are also good with jawline length as they draw attention to the narrower part of the face. The highlights are in the sweetspot of not looking ‘too done’ while also looking very natural. A bit of mousse on damp hair and a little thumb scrunch should carry those waves right through.
#9 Textured Shoulder-Length Cut with Soft Curls
Your clients love the soft curls look. This style works for almost every face shape The curls will frame your face and not close in the face. The curls will create space and add movement around the face. Curls are great at hugging and framing your face. This hairstyle is perfect for updos and downdos. It looks great styled and unstyled. You will be impressed with the versatility. It is great straightened, and when the curls are loose, it is great.
#10 Chic Textured Short Pixie with Subtle Layers
I would love to give all the women who tell me “I don’t think I can pull off a pixie” this exact cut because this is the pixie that changes minds. The wispy bangs are doing something really clever near the forehead, they soften the transition from your hairline to your frames so nothing feels abrupt. No one wants a pixie cut where the hair looks flat or helmety, and the layers soften that so it looks good. Seriously, once you get the cut, this is low effort hair.
#11 Softly Layered Curly Bob with Subtle Volume
I’m always really looking forward to curly bobs because styling them is so much simpler for me. With all the work being done by the hair itself, it is all about finding the right shape and everything else falls into place. The way I layered this will ensure that the curls spring up and apart to create that big hair look without having to use 5 cans of hairspray and tons of backcombing. For most people, curls will end up around the jawline which will help to create an amazing glasses frame and almost look like parentheses around your face. If your hair is curly by nature, the routine will be pretty simple — just some curl defining cream on wet hair, and using a diffuser.
#12 Chic Layered Bob with Subtle Volume
I would refer to this type of cut as a “trust me” haircut. While the haircut does look simple, the magic is in the precision layering. The chocolate tone is warm enough to brighten your complexion without going into the territory that would compete with your frames. The layers here are creating movement primarily through the ends, which makes for a tighter look on top that transitions into a more playful look towards the bottom. With fine hair in particular, this shape really helps to keep things feeling full without having to use a lot of product.
#13 Chic Short Textured Pixie with Subtle Highlights
These highlights really accomplish what highlights are intended to do on a short cut, emphasizing that texture illusion even when your hair is just sitting there. I notice the dimension around the crown, which directs the focus up and away from any glass shadow areas. It’s a honestly quick style to keep up day to day, but I won’t lie that you will be in my chair every five to six weeks. Pixie cuts have a lot of opinions when they grow out.
#14 Chic Curly Bob with Soft Bangs
In terms of glasses and curly bangs, it can be beautiful or an eyebrow chaos situation. This one lands on the more beautiful side. The chin length is ideal to balance out the hair so that the curls aren’t overwhelming against the glasses. The tousled look is wonderful, and she looks like she ran her fingers through and just walked out and that is kind of the look that everyone wants, but very few cuts actually achieve. If your curls lose definition by the afternoon, a little curl refresher spray will revive your curls without weighing anything down.
#15 Textured Copper Shag with Soft Fringe
I am slightly biased but I believe copper is one of the most under appreciated colors for women over 50. It’s always a pleasure when I am able to convince a client to try this color. This shag haircut is perfectly imperfect; the choppy layers look effortless while still maintaining enough structure to be a good haircut. The bangs are soft and slightly parted, which is good with glasses because you don’t want a heavy curtain that competes with your frames for forehead real estate. Just a heads up, copper tends to fade faster than most colors so be prepared to use a color depositing conditioner to keep things fresh between appointments.
#16 Textured Short Curly Bob with Soft Volume
I enjoy seeing my customers’ smiles as they look at themselves in the mirror after a haircut. The volume is ready, and with the haircut, the weight of your hair won’t pull your curls down to be straight by lunchtime. The hair is long enough for the curls to bounce, which is nice because otherwise, it could look too ‘sophisticated’ if they were too shiny. If you have some natural wave in your hair, you’re already halfway to this look.
#17 Charming Textured Short Cut with Wispy Layers
I see this as a haircut for the woman who wants to go short, but isn’t quite ready to make the full pixie commitment (and there’s nothing wrong with that; I was that woman for years with my hair!). The wispy layers create a nice soft texture to the hair which makes for nice photos. And that’s even more important than it used to be given that everything ends up on someone’s phone. The highlights are subtle enough to read as natural dimension rather than “I just got highlights” which, for me, is always the goal.
#18 Playful Textured Short Cut with Subtle Layers
The tousled effect is perfect for the whole cut giving it a relaxed vibe that works for running errands to going out for dinner. That is the criteria I recommend for all my short hair cuts. The layers are working quietly to give movement so the hair isn’t just sitting there in one flat piece. If you wear glasses, this length is great as it keeps everything above the frames line looking neat and intentional. A texturizing paste will do the trick. Just rub it through and you’re good to go!
#19 Elegant Textured Pixie with Soft Bangs
I like the gray shades in your hair, and I wish more of my clients would let their grays show like this. When hair is cut properly, it looks like an intentional choice and, in this case, it definitely is. The soft bangs work well with the glasses as they fell just at the top of the frame, creating a nice line across the face. The highlights interlaced with the gray add warmth and avoid that “flat silver” look that can wash people out. I find this modern in an extremely feminine and pleasant way.
#20 Chic Textured Pixie with Subtle Highlights
I keep seeing this cut and it showcases the models cheekbones, which is one of those things that sounds like a stylists cliche, until you see it happening on a real person and you go “oh, right”. The wavy textures are styled to have the most volume at the crown which balances out a pair of glasses with bottom heavy lenses. Fine hair really gets a bad rap for being limiting, but a pixie like this is where fine hair really gets to shine, both literally and figuratively. I would say a root boosting volumizing spray will do the trick!
#21 Modern Silvery Pixie Cut with Soft Layers
Bright silver hair has a certain quality that makes it stand out, and this cut captures it perfectly. The layers feel soft and give movement without bulk, which is fine hair’s most sought after attribute at this length. I think what aids this look so much with glasses is the nice, clear definition around the ears and temples. There is no competition for space, the cut is very well done, and there is a lot of room for everything to breathe. Shorter cuts like this are a commitment and require lots of upkeep at regular intervals to maintain the nice, clean, and sharp look, so if you’re the type to neglect rebooking until it’s really shaggy, setting a reminder may be a good idea.
#22 Chic Layered Copper Bob with Soft Bangs
This is my second copper look and as you can see, I have a type. The bangs look softer and less blunt than other options. This is nice because the framing doesn’t create two separate horizontal lines across the face. The layering is more focused at the ends so the top stays smooth while the bottom is interesting which creates a great balanced look. The warmth in this copper is gorgeous and complements most skin tones. This color combination gives the complexion a glow which is often hard to achieve with hair color and this one really nails it.
#23 Stylish Textured Pixie with Soft Volume
I enjoy the tousled look because it seems less polished which means I don’t have to worry about every little hair being in the right spot. You can tell the difference in a haircut when a style is full of volume, and that isn’t because of any products or teasing. This sits nicely with glasses because of how proportionate it is. Nothing feels too long or too short in relation to the glasses. For day to day styling, I would just use my fingers, some warm air from a blow dryer, and then be done.
#24 Textured Short Shag with Wispy Bangs
Shags are making their return and they are coming back strong. In particular this shorter version, which I believe suits more people compared to the longer seventy’s inspired shag that’s everywhere on social media. The jawline length offers structure while the layers throughout provide that signature shaggy movement. Wispy bangs are key here, they create softness around the glasses without being obtrusive, which sounds simple enough but is surprisingly hard to achieve. Those subtle highlights are adding dimension where it is needed and keeping the look modern rather than retro.
#25 Soft Textured Bob with Curtain Bangs
Curtain bangs are a great hairstyle choice since they seem to go with all face shapes. They naturally break and part around the bridge of the nose, and works to perfectly frame your glasses. I love this bob because the layering is more towards the ends; it gives the bottom a lot of movement and playfulness while the top stays sleek around your frames. You can push the ends behind your ears to make it look more everyday or leave some down for a more polished vibe. It also goes without saying that keeping hair styled through the week can be a hassle. I definitely recommend a silk pillowcase if your hair goes flat quickly after styling. I finally took that advice and it has helped me a lot.
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