The Diagonal Siding Dilemma

Billy Howe
Jun 15
3 min read

Diagonal siding once made a bold statement—but today, it’s more of a hassle than a charm. Here’s why Hilton Head homeowners are choosing to replace it.

Many Hilton Head homes built in the 1980s feature diagonal wood siding patterns — typically under windows or in small accent areas. It was a popular design choice at the time, especially on homes sided with cypress, a local favorite for its natural beauty and durability.

These days, more and more homeowners are ready to modernize. And when we're already on-site, it’s the perfect opportunity to take a closer look at those dated details and make a lasting improvement.

What is Diagonal Cypress Siding?

Many homes we paint in the Lowcountry use cypress — a local favorite for its resistance to insects, rot, and moisture. One of the most common styles is known as Pattern 139 — a tongue-and-groove profile with clean vertical lines.

In the 1980s, some builders started using this pattern on the diagonal to add visual interest, especially under windows or on gables. It was eye-catching at the time, but today, it often feels dated — and can come with some practical downsides.

Why We Recommend Replacing It

Weathered wooden window with broken panels, surrounded by leafy green bushes. Sunlight casts soft shadows, creating a warm, serene mood. — Typical example of aging diagonal cypress siding under a window — peeling, warped, and no longer protecting the home as it should.

1. It's harder to maintain

Cypress is naturally rot-resistant and well-suited for our coastal climate — but even it has limits. Diagonal boards introduce more seams and angles, especially below windows where rainwater tends to collect. That extra complexity can trap moisture over time.

When water sits, even cypress can start to show signs of wear: swelling, cupping, or softening in spots where the design isn’t shedding water properly. Switching to a simpler, straighter pattern can go a long way in keeping your exterior solid and looking sharp.

2. It's difficult to repair

Matching the exact size, grain, and weathering of older diagonal boards can be tricky. Even if new boards are cut diagonally, they rarely blend cleanly with the original siding — especially after decades of sun, salt air, and paint layers.

That makes small repairs stand out and large ones look pieced together. In most cases, it’s more effective (and better looking) to replace the entire section with a fresh, cohesive pattern that ties in with the rest of the home.

3. It dates the home

Diagonal siding had its day, but it’s rarely seen on homes built today. Replacing those dated sections with a cleaner, more timeless pattern gives your home an instant facelift — and if you’re planning to sell, it could make all the difference in a buyer’s first impression.

Our Go-To Replacements

When it’s time to move on from diagonal siding, we typically recommend two standout options — both proven to perform well in the Lowcountry climate and blend beautifully with Hilton Head architecture:

Wooden shingles on a beige wall with a window above. Sunlight creates a warm glow. Green leaves are visible at the bottom. — We replaced the damaged siding with natural cedar shakes for a fresh, lasting improvement.

Cedar shakes – A coastal favorite that brings warmth, texture, and a touch of character to any home. Shakes work especially well on small accent walls, gables, and dormers, where they add visual interest without overwhelming the overall look. They’re also naturally resistant to moisture and insects, making them as practical as they are charming.

Horizontal or vertical cypress – A clean, classic look that aligns with the rest of your home’s existing siding. Whether you go with a traditional horizontal overlap or a vertical Pattern 139 profile, cypress offers long-term durability with a refined appearance that never goes out of style.

Either choice will give your home a fresh, cohesive look — and better protection from the elements.

Ready To Update Your Siding?

Gray house with beige trim and large windows. Bushes line the front, a palm tree branch hangs above, set against a clear blue sky. — Vertical cypress boards and painted cedar shakes keep the look crisp and coastal.

If your home has diagonal siding and you're considering a change, now’s the perfect time to explore your options. We’re happy to assess your siding, answer your questions, and help you decide what makes the most sense for your home and budget!

Contact Daygig Painting to talk materials, patterns, and what will work best for your exterior. We’ll handle the details — and you’ll end up with a home that’s cleaner, sharper, and built to last.