923805 - Grey Smoke - Warm Grey
Oakley Fives Squared 9238 Sunglasses
$127.00

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Oakley Fives Squared 9238 Sunglasses

923810 - Black - Warm Grey

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Lenses from $29.99 · Ready in 2–7 business days

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Lenses from $29.99 · Ready in 2–7 business days

$127.00

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Color

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DESCRIPTION RATINGS & REVIEWS PRESCRIPTION GUIDE

These Oakley FIVES SQUARED frames feature a Full Rim design and a flex hinge for added comfort. Oakley's Plutonite Lenses offer top UV Protection filtering 100% of all UVA, UVB, UVC and harmful blue light up to 400mm. Patented High Definition Optics (HDO) provides superior optical clarity and razor-sharp vision at every angle. Options featuring PRIZM Lens Technology are designed to enhance color, contrast and detail so athletes can make the most of any activityThese frames are designed with light-weight O-Matter material for superior comfort and durability. These Oakley Sun frames feature a Rectangle shape perfect for square or heart shaped faces.

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J
Jon Whitifield
Great Price.. Great Service.. GREAT Communication throughout order process!

I had never purchased from DesignerOptics before and was pleasantly surprised and delighted by their phenomenal communication throughout all points of the purchase process.. From order to delivery they were awesome. Great job you guys, and you have new customer here! Highly recommend them. - Jon

Frequently Asked Questions

Are Oakley Fives Squared sunglasses good for small faces?

Yes, the Fives Squared 9238 is specifically designed for small to medium faces. Oakley uses Condensed Cranial Geometry—a tapered frame architecture with a 128mm hinge-to-hinge measurement—so the frame hugs your head without sticking out at the sides like conventional wrap sunglasses. This makes them ideal for narrower faces that find standard Oakley wraps too wide.

Can I get prescription lenses in Oakley Fives Squared frames?

Absolutely. The Fives Squared 9238 is prescription-ready and accepts both single vision and progressive lenses. You can customize your prescription with Prizm technology for enhanced contrast, polarized lenses to reduce glare, or Transitions for adaptive tinting. The Three-Point Fit architecture holds lenses in precise optical alignment for optimal vision correction.

What is Prizm lens technology in Oakley Fives Squared?

Prizm is Oakley's proprietary lens technology that fine-tunes specific wavelengths of light to enhance color and contrast. Instead of just darkening your view, Prizm lenses selectively filter light to make details sharper and colors more vivid—helping you read terrain, spot obstacles, and react faster. Prizm Grey, Prizm Maritime, and other variants are available for the Fives Squared, each optimized for different environments.

How does the Oakley Fives Squared compare to the Gascan?

Both are rectangular wrap frames, but the Fives Squared is designed for smaller faces with a more compact, tapered fit (128mm hinge-to-hinge), while the Gascan offers a larger, more aggressive wraparound design. The Fives Squared uses Condensed Cranial Geometry for a snug fit that doesn't protrude at the sides, making it better for narrow to average faces. The Gascan suits those who want maximum coverage and a bolder look.

Do Oakley Fives Squared sunglasses have UV protection?

Yes, all Fives Squared lenses are made from Plutonite, which filters 100% of UVA, UVB, UVC, and harmful blue light up to 400nm. The lenses also meet ANSI Z87.1 standards for impact resistance, providing uncompromising protection during sports and daily wear. Polarized and Prizm options maintain full UV protection while adding glare reduction or contrast enhancement.

What face shapes work best with Oakley Fives Squared?

The Fives Squared's rectangular shape works best for square or heart-shaped faces, and the compact design is ideal for small to medium face sizes. The 8.75 base lens curvature and tapered temples create a wrapped fit that sits close to the face, so if you typically find wrap sunglasses too wide or loose, the Fives Squared's Condensed Cranial Geometry will feel more secure and comfortable.

Compare With Similar Frames

How the Oakley Fives Squared 9238 Sunglasses stacks up against the closest alternatives we carry.

Read the full comparison

Oakley Fives Squared vs. Gascan vs. Holbrook: Which Frame Fits You?

Choosing between the Oakley Fives Squared 9238, Gascan 9014, and Holbrook 9102 comes down to face size, fit preference, and how you'll use them.

Fives Squared 9238: The Compact Performance Wrap

The Fives Squared is purpose-built for small to medium faces. Its Condensed Cranial Geometry creates a tapered, 128mm hinge-to-hinge fit that hugs your head without protruding at the sides—a common complaint with larger wraps. The 8.75 base curve delivers excellent peripheral vision, and the Unobtainium nose pads keep the frame secure even when you're sweating. If you've struggled to find performance wraps that don't feel oversized, this is your frame. It's ideal for cycling, running, and driving, with a sleek profile that transitions to everyday wear.

Gascan 9014: The Bold, Full-Coverage Wrap

The Oakley Gascan 9014 offers a larger, more aggressive wraparound design. It's built for medium to large faces and delivers maximum side coverage, making it a favorite for fishing, water sports, and outdoor work. The Gascan's wider frame and bolder aesthetic make a statement, but that size can feel bulky on smaller faces. If you want the most coverage and don't mind a more prominent look, the Gascan delivers. However, if you have a narrower face or prefer a more refined fit, the Fives Squared's tapered design will feel more comfortable and less obtrusive.

Holbrook 9102: The Lifestyle Classic

The Oakley Holbrook 9102 takes a different approach. It's a retro-inspired rectangular frame with a flatter front profile and less wrap than the Fives Squared or Gascan. The Holbrook excels in casual, urban settings and offers the same Plutonite lens protection and Prizm options, but it's not as secure during high-intensity sports. If your priority is everyday style over athletic performance, the Holbrook's broader appeal and timeless design make it a strong choice. But for cycling, running, or any activity where you need a locked-in fit and peripheral coverage, the Fives Squared's sport-focused architecture is superior.

Our Recommendation

Choose the Fives Squared 9238 if you have a small to medium face and want a performance wrap that doesn't stick out or slip. It's the best balance of sport function and everyday wearability in a compact package. Go with the Gascan 9014 if you need maximum coverage and have a larger face. Pick the Holbrook 9102 if you prioritize casual style over athletic performance and prefer a less aggressive wrap.

At a Glance

Oakley Gascan 9014 Sunglasses

Pros:

  • Larger frame size suits medium to large faces
  • More aggressive, bold wraparound design for maximum coverage
  • Wider range of lens options and colorways
  • Iconic Oakley sport aesthetic with strong brand recognition

Cons:

  • Can stick out at the sides on smaller faces
  • Less tapered fit may feel bulky for narrow face shapes
  • Higher starting price ($99.15 vs $107.06 for Fives Squared)
  • Not as refined for everyday urban wear

Oakley Holbrook 9102 Sunglasses

Pros:

  • Retro-inspired design works for casual and urban settings
  • Flatter front profile (less wrap) for a more traditional look
  • Similar price range ($124.50–$258) with Prizm options
  • Broader appeal for everyday fashion wear

Cons:

  • Less peripheral coverage than the Fives Squared's 8.75 base curve
  • Not as secure during high-intensity sports or cycling
  • Larger frame may not suit very small faces as well
  • Less specialized for athletic performance

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