The Men’s Sunglasses Matrix

At the center of the Sunglasses universe lies the Ray-Ban New Wayfarer.  If you had to buy one pair of sunglasses, and wear them for the rest of your life everywhere, the Ray-Ban New Wayfarer wouldn’t let you down.  They are as well balanced as it gets.  Chart below is broken up into four quadrants.  X axis reflects how modern or retro the overall styling is, while the Y axis shows to what level the sunglasses can be easily dressed up.  As always, there will be exceptions (i.e. Steve McQueen’s 3-piece suit in The Thomas Crown Affair with the Persol Foldables.)
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From top left, moving down, then over:

• Persol Monoblock Wire Aviators – $205.00 Nasty expensive, but the epitome of well balanced, dressed-up modern sunglasses.  Not goofy futuristic in the least.  Lenses don’t droop, and the key detail is the thicker than wire frame ear pieces made of acetate/plastic which complete the look.
• Calibrate Navigator – $45.90 ($69.50) Many of the same characteristics of the Persol Monoblock, for less.
• Ray-Ban Cockpit – $90 – $145 Slimmed and gently curved.  Updated version of a Caravan and Classic Aviator Hybrid.  Not the easiest to find on sale without gold frames and/or gradient lenses.  (Yet somehow Amazon is selling polarzied grey on grey direct for $120.)
• Banana Republic Corbin – $54.60 w/ BRTIME ($78) Oddly well balanced and good looking for what at first glance appears to be a thicker plastic frame.  Can be dressed up a bit.
• Randolph Engineering Raptor – $129 Sunglasses + Matrix + These = Neo?  Made in the USA
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• Ray-Ban Caravan – $125.00 The standard for squared off aviators.  Cleans up the look, as opposed to traditional aviators that’ll droop too far on plenty of faces.  Keep an eye on Fossil for less expensive versions.
• Ray-Ban New Wayfarer – $80 – $125 The center.  $80 direct through Amazon for Tortoise is plenty fair.
• Ray-Ban Classic Aviator – $100ish Plenty of less expensive versions out there.  The bigger lenses make them more casual and won’t look right on everyone.  Careful where/who you buy from.
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• American Optics Original Pilot – $40ish A favorite for many.  Authentic.  The separation of the lenses make them lean more towards the retro side, but still plenty versatile.  Made in the USA
• Banana Republic Johnny – $68.60 w/ BRTIME ($98) One of the less expensive key-hole pairs of sunglasses out there.  Obvious retro shape around the nose.  Looks costumey on some.
• Persol Foldable – $360.00 Wallet killing.  Got real popular thanks to all things McQueen and has started to be replicated by plenty.  Best trusted place to get them at a discount would be Macy’s during site wide codes.
• Ray-Ban Original Wayfarer – $80 – $150 Wayyyy too big, bold, and now hipstery for most.
• Carrera Aviator – $79.20 ($120)  Young, bold, and risk dominating your face (and personality).  70’sish.
• Ray-Ban Clubmaster – $116 w/ ME ($145) Ray-ban’s sunglasses take on the Browline eyeglasses frame.  Iconic, but awfully hard to pull off without looking like you’re trying too hard.

The Bottom Line

In general, the more plastic = more casual.  Also, the bigger the lenses the more casual they’ll look.  Wire frames tend to look more dressed up, as long as they’re proportional to your facial features (think rule of 3rds).  The more exaggerated a retro detail gets, like chunky key-hole or sweat bar details, and the harder they’ll be to wear.

Plenty of expensive shades on that list.  Feel free to add affordable alternatives you’ve had success with in the comments below.  Agreements?  Disagreements?  Additions?  All welcome in the comments…