Glasses, Of The Sun & Eye Variety


If eyes are the windows to the soul, then eyewear is like the architecture that provides context to those windows.

That sounded better in my head.

I used to hate wearing glasses. Before the rise of twee and hipsterdom, glasses weren’t cool. They played hard into stereotypes, whether it was for nerds or Asians (both in my case), making it hard to escape from those connotations. I actually have been wearing since 4th grade but there isn’t much evidence of it because of how embarrassed I was of them.

Perhaps it was because my glasses were never “cool” (if my prescription didn’t change my parents refused to buy new ones) and so I never felt right wearing them; combine that with wearing uniforms five days a week and being forced to wear a suit on Saturdays (for church) and you have a recipe for someone who feels like they’re being forced to default. I had to wear glasses and they weren’t fun or empowering. Sunglasses on the other hand were both of those things.

As a kid, I thought that they were such a cool thing to wear since anyone could wear them. You didn’t need a prescription! So whether it was an expensive pair or something from a mall kiosk, a random person could grab a pair of sunglasses and put them on. There was also much more aesthetic variety on these than regular pairs of glasses, which leads into how fun they can be, at least compared to the practical nature of glasses. Wearing sunglasses was like an outfit for your face, it provides proof that you’ve got somewhere to be and that you don’t want to be bothered by the sun. Hell, that’s not even exactly necessary to wear them—you might come across as a douche if your wear them inside, but hey, at least you’ll feel cool (executional success may vary).

This is probably why I was so dedicated to getting contacts. I wanted freedom, freedom to have have my eyes (and by extension my face) be free from any defaulting while still being able to have good vision. This was especially important after I got into menswear and became much more aware of aesthetics. I knew for a fact that my rectangular IT associate frames were not conducive to any outfit, whether it was any of my older styles, whether it was #menswear or period vintage. I needed to have a free face to do the looks that I wanted. To feel empowered to be “myself”, as the self I wanted to be did not have glasses. I even spent an hour in the bathroom trying to get used to the process of removing/inserting contacts before a date.

During college, I wore these cheap club masters from a mall kiosk. Like my brow line glasses, these were retro but still largely versatile (though I felt like these didn’t excite me).

So for a while, the only frames I really wore were sunglasses. It made sense, as they were acceptable and had the freedom to be worn at anytime you wished— without impairing your vision (thanks to contacts). As I was still being frugal and had other priorities in terms of hobby purchases, I didn’t buy a lot of sunnies or even invest in them; the fact that I had lost eyeglasses and broken one in college (much to my parents chagrin) made me hold off on doing it until when investing felt right and above all, a natural extension of what I wanted to do. This makes them similar to watches but a bit more useful in my life.

Of course my style and wardrobe eventually stabilized and I was able to start thinking of other ways to be the “guy” I always wanted to look like. So perhaps it was finally time to invest in sunglasses that weren’t from a mall kiosk. And most importantly of all, the advent of cooler-designed-yet-accessible/affordable eyeglasses (like Warby Parker or EyeBuyDirect) meant that I could give my constant contacts a break and return to the glasses-wearing guy I was a decade ago, just with cooler clothes. Armed with new knowledge and self awareness/Abed brain, I was able to get into eyeglasses and sunglasses, making intentional choices that played into my style. In short, I was finally given the freedom I wanted.

That’s why the subject of the next podcast is about eyeglasses and sunglasses, which you can listen to below! Spencer never had to wear eyeglasses (the bastard has 20/20 vision), but I’m glad that MJ has been able to hop on more as he is like me: he has bad eyes and requires eyeglasses (and even got contacts in order to be more “face accessory agnostic”).

Podcast Outline

  • 03:48 – Topic Start
  • 10:54 – Our Glasses Experience
  • 33:25 – Glasses on Other People
  • 42:17 – Sunglasses Talk
  • 1:17:38 – Wrap-Up
Adding aviators help lean further into the 70s vibes.

The biggest take away from recording the podcast episode was realizing just how aesthetically important eyewear can be.

Sunglasses are the best way to see this in action as they are more than just something practical to shade your eyes from the sun. There are plenty of design details to keep in mind, from the shape of the frames to the color of the lenses. Like suits and their treatment of lapels or even overall silhouette, these details are in an aesthetic lean which can be played with or subverted! I automatically think of how brow-line shades/clubmasters feel incredibly 50s/60s whereas wayfarers come across as 80s/90s. There can even be nuance as well: clubmasters feel like classic 60s American corporate where as cat eye shades with colored lenses lean more European or artsy from the same era.

I consider sunglasses to be a functional additive to your wardrobe, as they are the last thing I put on when you walk out the door. That means unlike a sportcoat, shirt, or even a tie, sunglasses aren’t the basis of the outfit; they are added on later. Despite that, the little addition to your face can make an outfit interesting depending on the boldness of the sunglasses. I think of cat eye frames with yellow lenses add that artistic spin to a yuppie outfit, aviators contrasting against ivy, or the crazy choice of wearing Oakleys with bespoke tailoring. There’s also nothing wrong with the classics, like clubmasters or those wire frame, round Ray-Bans with traditional tailoring.

Like a hat, sunglasses can anchor in a look or subvert it, providing personality to something functional. If you dress after a particular period, it’s can be fun to have sunglasses that match it. Sunglasses can also act as the bold focal point of the outfit, such as when guys wear chunky designer frames with plain tee shirts and jeans. Having multiple pairs provides you with options that you can dip into as needed; I guess in that sense they’re like ties, though I personally don’t need more than 3-4 sunnies. In any case, having an intentional attitude toward sunglasses makes the sun less of an annoyance and more like a friend that provides an opportunity to accessorize when you’re out and about. I guess in that sense its like a tie, and I have a lot of ties.

As you’ll see in the photo dump, I tend to prefer quirker sunglasses, no doubt inspired in sorts by the rise of clout goggles. Memes are hard to tie authentically to clothing, but I do think the use of “ironic” sunglasses within streetwear paved the way for designer sunglasses to have a bit of a resurgence in menswear. Just like how wider leg pants became more popular, menswear has started to move away from the middle ground of classics and let in bolder things, which helped show that tailoring doesn’t have to be stuffy. On top of that, fun didn’t have to come in the form of wacky ties or bold suits; it could just be done with the simple addition of sunglasses. Menswear is moving away from being supremely timeless and versatile, allowing room for personal taste, subversion (not irony, which I’ll explore in the future), and the ability to be gaudy on purpose. Eyewear is a big part of that!

While I’ve certainly always had a less “serious” approach to menswear (meaning non-professional or formal), I still had my struggles with where/how to add some character; after all, there is a thin line between owning boldness and narm. Sunglasses, being an additive accessory to style, were always rather standard until seeing clout googles and menswear’s response to them helped me to finally try out something different. In the grand scheme of things, it took a while for me to invest in a few sunglasses that only said “fuck you” to the sun but did so in a fun way that doesn’t have to be congruous with my relatively “traditional” style. As you’ll see later on, my sunglasses aren’t as “out there” as some others, but they still involve a bit of attitude. Attitude that can’t come from being bare faced but instead come with the an eye accessory.

These glasses just feel right. I also wanted to give my contacts a break!

[Prescription] Eyeglasses on the other hand are not an additive because they should technically already be on your face before an outfit is put on. You’ve gotta see, don’t you?

I bring up JTR’s following point in the pod, but eyeglasses serve as context for the body that is wearing the clothes, making it similar to your hairstyle or if you have a facial hair. Eyeglasses provide a mood for the wearer and tells you something about them; it tells you where the person has decided to plant their foot in terms of personal aesthetics with something that they typically have with them at all times.

Now that prescription eyeglasses are much more accessible than they were before (or maybe that’s because I am a working adult), it’s easy to have multiple pairs for the sake of variety (though prescription lenses can still be pricey). You can have the fun that sunglasses provides but without having to be outside and in a way that is more “permanent”; the personality that glasses provide stick with you even when you take off your outfit. That’s why glasses represent a bit of a commitment and why I admire those who opt for quirky ones as daily drivers.

Even with this new accessibility, I personally prefer safer eyeglasses, since I do want a bit of versatility when I choose to wear them. My current glasses are all ivy-friendly and I think they look best with the true ivy-trad look, though I’m not opposed to wearing round frames with yuppie attire (which makes them even more yuppie) or with Esquire Man; in addition to all the archetypes of glasses wearers, they also just provide a bit of hipster-ness in the modern context that I actually don’t mind. Eyeglasses are simply more conducive in making me feel like I look mature, like an artist or an intellectual (lol) which is something I never felt with my old glasses. They somehow make the outfits feel even more natural, which is funny because prescription glasses are necessary for me and a great way to have some fun with aesthetics. Again, outfits don’t need glasses, but they certainly can help add immensely to a look on the days I decide to forgo my contacts.

Oh and screw the “rules” about face shape and eyewear. They are largely irrelevant, much like those old menswear maxims that tell you short guys shouldn’t have cuffs on their trousers or large men shouldn’t wear DBs. I’ve found that as long as they are “wide enough” (as in they fit your face without physically stretching the piece), you can definitely have fun with different shapes. You’ll see how guys (myself included) wear round, square, and funky frame with ease. In fact, playing with the shape of eyewear is a good way to add some POV and intention, much like how shoulder treatment, silhouette, and button spacing leads to different expressions and styles of tailoring. Details obviously matter!

Overall, it’s fun to recognize how eye and sunglasses play into your desired aesthetic. Think of it as literally playing into the windows to the soul! It’s just funny how after years of being embarrassed for bad eye sight, I finally feel empowered and comfortable with wearing my glasses out. To own up to my bad eyes and utilize them in my continual pursuit of “what I want to look like”. Sunglasses also play a big part in that, being more of the bold, going out brother to practical (and somber) eyeglasses. Overall, both types of eyewear help create a character of sorts that adds a dimension to the outfit (and the person) rather than being “plain-faced” and style-agnostic.

This isn’t anything new, but this only adds to the fact that every piece you wear plays a some part in executing your POV. With frames, it answering the question of “if this ‘guy’ wore glasses, which glasses would they be?” Keep all of that in mind as you look through the following images, noting how they play into or subvert the outfits they’re attached to.

I’m sorry to those of you who have 20/20 vision (like Spencer), but at least you guys have sunnies to get your frame-jollies (unless you’re extremely comfortable wearing non-prescription glasses). Maybe next time I’ll think about how hair can factor into personal style.

Sorry, Spencer.

Recommended Reading

We also did a Twitch stream where we went over what we discussed in the pod! You can always tune in so you can recap with us in real time.

Can’t have a post on glasses without this guy.
Jamie wears glasses!
These frames certainly add some character. Their mid century lean makes sense when you know about what inspires Jason.
Glasses aren’t always elegant. I love their practical use against more rugged pieces.
That being said, there is some sophistication involved, even when they’re fun! Its nice to have glasses with character.
Round frames are always retro.
Hector has multiple frames and definitely likes to play into his aesthetics. His round tortoise shell eyeglasses are a good match for the flannel suit and ivy-inspired accoutrements.
Blue tinted shades are perfect for a summer look.
Here they provide attitude to another ivy-inspired look, calling to mind the style of jazz musicians in the 1960s.
He has a theme!
Andre also prefers a round frame, though his use feels less dandy thanks to his own personal style.
Love the fun frames with a somber party look.
Sunglasses are additive, turning this normal #menswear look into something bolder.
Sunglasses provide instant cool in a small way.
Buzz has a variety of glasses but seems to prefer the round 20s-ish frames. They add to his look!
The yellow acetate plays into the warm tones of his summer outfit.
These 1950s style glasses on John provide a bit of an “intellectual” spin to an otherwise rugged combo.
Ethan Newton gives us a good case study with how frames interact with the outfits. The wire frames give an “aged” look to a ivy-inspired separates.
The glasses soften up the “severity” of the “rugged” tailoring.
Brow line frames always call corporate Mad Men attire to mind, which is fun to see it used here with decidedly non-business attire.
Again, delicate wire frames with a beanie, heavy tweed, denim shirt, and flannels.
And then chunky yellow acetate with a corporate attire. Contrast!
Kenji prefers round, thinner frames. I think they look elegant on him!
Sunglasses are where the fun begins. Chunky provides a jazz or rock and roll spin to a summer look.
Browline shades are pretty agnostic.
But here, chunkier browline shades with a tint play into the dark vibes.
These look to be the same glasses, but Kenji wears it a bit more buttoned up, with a 3PC suit, duffle, and beret.
Tony likes his sunglasses.
Black Ivy by Jason Jules has a big section on jazz musicians and glassses.
I wonder if these photos helped cement glasses as an “artistic” accessory. As in, many creatives wear glasses!
Herbie Hancock.
Jason loves his big glasses. They work for his personality and style.
JTR does too!
Add Josh to the list. I love the frames with a tailored look.
You can also play into the fun!
There’s just something about eyeglasses that gives off sophistication.
Even when the outfit is casual, the vibes are still there.
Yung Chomksy typically wears one pair of glasses (round frames). It seems to work across his style and makes sense for him.
Sunglasses and an open shirt are a classic combination.
Sora likes his round, wire frames. It suits him well and adds to the 90s-ish take on menswear that he has.
Jay also has the round wire frames, but it definitely feels a bit more “hipster” in aesthetic. It plays into his style but is also a fun contrast to his more traditional job in finance.
He keeps the same theme with his sunglasses.
Glenn of Junior’s wears glasses!
The glasses lean into the ivy look.
Michael has tortoiseshell round frames and they work with his minimal take on ivy.
A smart looking guy!
They definitely add to the 80s/90s RL look.
Scott Fraser likes thin, round frames.
I love thin, round frames with tailoring.
Chris has cool glasses.
I love the consistency. It’s forced versatility at work!
Aviators seem to be one of the best matches for workwear as they turn the vibe more 70s (even if the garments are older).
I’ve always found aviators intimidating and love seeing guys just rock them across different aesthetics.
Not exactly aviators, but these have that same round-ish shape.
Big square glasses are a move too!
Peter certainly likes glasses of all kinds.
Elias opts for personality in the best way possible.
The clear/yellow frames with green lenses are a great classic, providing a slightly retro charm that feels modern. A good match for Henry and his Dead Head Dressed Up look.
Thin round frames always look “creative” which works for Silvia’s style.
Glasses Gang!
Doug also likes those wire frames.
Fred has fun glasses.
I like the consistency of his frames.
A classic shape! Who doesn’t love tortoise shell?
You can see the difference in vibe here, with Chase’s more subtle frames compared to the more intense wayfarers worn by Matt.
Acetate looks great for summer.
Mark Cho has beautiful glasses that are varied in their shape. They certainly exude personality, even if its subtle.

One of the greatest photographs of all time!
Antonio seems to love narrow frames.
Chad has different sunglasses and eyeglasses dependent on mood.
Always love to see how the glasses interact with the outfit.
He really osld me on wire frames a long time ago.
Small wire frames work with this vintage-inspierd look.
A chunkier frame plays into the midcentury vibe, even if the clothes aren’t necessarily styled that way.
JMM and other chunky, square frames are being favored a lot lately as the 60s/70s has their moment.
Sunglasses and cigs. Instant cool.
Wayfarers look great with subdued looks.
Horn rimmed/cat-eye frames have attitude. And it’s good.
Thin sunglasses are a move that my big round face can’t enjoy.
Quite a lot of attitude in these frames. Makes the hoodie outfit feel a bit more interesting.
Also plays with the suit, though granted the suit and shoes also make the outfit atypical.
Square sunglasses!
True vintage sunglasses are always the move to get some real character. Especially when the whole look is vintage, as seen on Christopher.
Dick and Chris both going for that 60s look and the sunglasses certainly help.
Modern sunglasses also help anchor in that 60s/70s aesthetic look too!
More cat eyes!
A variety.
Nolan is a good example of using sunnies. The big, orange tinted shades directly play into the 70s look.
The look isn’t exactly 70s, but designer frames tend to go with designer outfits. It’s a maximalist vibe I guess!
Sunglasses can also act as the bold focal point for a more subdued outfit.
Imagine if i still wore these glasses lol.
They never felt like “me”; I awaited the day I could get contacts.
They just never fit the vibe of my developing style.
I eventually got these Warby Parkers but they still didn’t feel like me!
My wire frames were one of the first “cool” glasses I owned that really felt empowering and appropriate. They worked for modern outfits and could also be paired with my period accurate vintage attire.
I always liked using them to “calm” my edgier fits. It turns this all black fit into a softer, “hipster-y” look rather than straight forward edge.
I also liked using them for cozy pandemic attire, like this one (with sweatpants).
Still great with vintage leaning looks!
More intellectual/collegiate, though I think the corduroy suit and jaunty scarf help that.
I think the glasses (and hair) make this minimal outfit a bit more interesting.
Glasses with suits is a good look!
My clear/yellow P3 style frames. A bit more “classic” compared ot the wire ones.
Still kinda hipstery though.
Normally I like to wear these glasses with a darker outfit in order to play up the contrast.
Makes the neo-ivy look!
I really love wearing glasses with suits.
The thicker tortoise shell P3 style frames that broke.
I had these since grad school!
Again with the suits!
I replaced them with a similar pair that was just a bit thinner.
Glasses and fedoras can be tricky, but when it works it works!
Kinda going for something 90s here.
MJ has a similar pair!
These are my first “square” frames in years. They feel a bit more modern (and style-agnostic), so I rely on the styling to give it more of an aesthetic lean.
Perfect for the midcentury nerd look.
This one also feels like a good pairing.
I ebayed these vintage “Gatsby-esque” glasses and they were fun to wear….with vintage only.
Then I found these wire sunnies also at a mall Kioski. They used to be the only sunglasses I’d wear.
While they were still a bit style-agnostic, they were a better match with my developing style. And as a result they were my only sunnies for a long time.
I tried to go a bit earlier with these tortoise shell frames from Uniqlo. Not bad!
I think they worked, though they were still leaning a bit too classic (agnostic).
They did go with everything!
Specific outfits can bring out the personality within the frames.
Then I got these wayfarers that were just a bit more jazzy with the elongated width.
I love them!
Spencer has a similar pair that are a bit more “cat eye”.
Works with dark outfits.
And light ones!
Spencer loves his 1940s aviators. Despite the era, they provide a quite 70s/80s vibe.
My aviators are a bit wider (rectangular?) and have a reddish tint.
I do struggle to wear them because they are quite bold in their shape, but I like breaking them out every once and a while. Especially for 70s inspired outfits!
Aviators are pretty summery.
Also works with that post pandemic look.
I’m not a big fan of them with tailoring though, at least with the way I do it.
This was better.
I call this Harrison Ford-ing.
I had to get these clear/yellow frames with green lenses. They feel “current #menswear” but with more personality than agnosticness.
They work with everything but in a bold way.
These are much more square than the wayfarers but I like them! It feels very mid century in a way that feels artsy and also 50s Hollywood.
These are my favorites: the chunky 50s style frames with yellow lenses. The Akila Apollos hit all the spots providing a bold retro vibe to any outfit. It’s fun to play into it.
It also works with somber outfits.
See how it just makes everything feel like its Paris in the 60s?
I definitely like that the lenses are more transparent than the others, making this one skirt the line between sunnies and eye glasses (though these are not prescription).
This was the perfect pairing.
I use them when I don’t want to be 70s.

I love them with regular old tailoring. Makes it more interesting, don’t you think?
Man, glasses are cool.

Thanks for listening and reading along! Don’t forget to support us on Patreon to get some extra content and access to our exclusive Discord. We also stream on Twitch and upload the highlights to Youtube.

The Podcast is produced by MJ.

Always a pleasure,

Ethan M. Wong

Big thank you to our top tier Patrons (the SaDCast Fanatics): Philip, Shane, Austin, Jarek, and Henrik.

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