Checked blazers have been wardrobe staples for men for decades. Yet recently, these timeless jackets have enjoyed a surge in popularity thanks to updated styling. Oversized, relaxed silhouettes have given classic check patterns a modern, casual twist.

Gone are the days when checked blazers were strictly reserved for stuffy suiting or banker uniforms. Today, these jackets can be worn in both tailored business looks or dressed-down weekend outfits.

From versatile glen plaids to bold buffalo check, the range of patterns available is endless. With the right styling, it’s easy to incorporate checks into your personal aesthetic.

This blog post will cover everything you need to know about styling checked pattern relaxed blazers. We’ll discuss:

By the end, you’ll feel confident rocking checks for any occasion. Let’s dive in!

The Top Checked Pattern Relaxed Blazer Styles

Before styling your checked blazer, you first have to choose the pattern itself. Here are five of the most popular checked blazers giving classic looks a relaxed twist:

1. Classic Prince of Wales Check Blazer

The Prince of Wales check is arguably the most iconic pattern for blazers. It features a black and white houndstooth base with tan and gray windowpanes overlaying the check. This instantly recognizable pattern has been used in men’s suiting since the early 1900s.

Relaxed versions of the Prince of Wales blazer have a roomy silhouette meant to be worn open. The oversized shape makes it perfect for layering over shirts, sweaters, or even hoodies. For business casual offices, it’s just as dashing when buttoned up.

2. Oversized Buffalo Check Blazer

Buffalo check offers a bolder look with its large blocks of black and red or blue plaid. This eye-catching lumberjack pattern gets a modern upgrade when tailored in a slouchy, oversized blazer.

Shoulders are left wide and dropped. The length hits longer than a traditional blazer for an exaggerated shape. Paired with skinny jeans or leather pants, this roomy buffalo check blazer makes a stylish statement.

3. Green Windowpane Check Blazer

For a fresh color update on checks, look for windowpane blazers in shades like olive green, mustard yellow, or burnt orange. The neutral base contrasts beautifully with the colored overlay.

As with traditional windowpanes, the fine grid pattern stands out against the neutral background. Relaxed styling keeps the preppy pattern feeling casual instead of stuffy.

4. Relaxed Gray Glen Plaid Blazer

A gray glen plaid blazer has an easy, menswear-inspired vibe. The glen plaid features small scale black and white checks with thin lines of tan and gray throughout. This versatile pattern works year-round.

When cut in a roomy silhouette, the gray glen plaid blazer layers effortlessly over Oxford shirts, knits, tees, and more. Shoulder padding provides structure to balance the slouchy shape.

5. Oversized Madras Check Blazer

Madras check offers a handwoven, artisanal look. Irregular lines and bright, saturated colors like pink, yellow, and green give madras a joyful preppy feel.

When oversized, the madras check blazer takes on a relaxed, indie vibe. The vibrant pattern truly pops against the casual cut. Just be wary of matching madras with other busy patterns.

How to Choose the Right Checked Blazer for You

With endless checked blazers to choose from, narrowing your selection can feel overwhelming. Here are tips for picking the right pattern, fit, and color:

Choosing the right blazer depends on your personal style and wardrobe needs. Use the tips above to find a pattern, color, and fit that makes you feel stylish and confident.

Expert Tips for Styling Your Checked Blazer

You found the perfect checked blazer – now it’s time to style it! Follow these expert tips for wearing your jacket seamlessly:

Follow these tips to expand your styling possibilities. Soon you’ll see how easy it is to incorporate checks into any outfit!

FAQs About Checked Pattern Relaxed Blazers

Still have questions about styling checked blazers? Here are answers to some frequently asked questions:

Q: How should a checked blazer fit?

A: Traditionally, checked blazers have a tailored, structured fit. But oversized and relaxed silhouettes have become popular. Go at least one size up for a roomy, casual shape. The shoulder seams should extend past your shoulders.

Q: What do you wear with a buffalo check blazer?

A: Tone down the bold buffalo plaid with neutral basics like white, gray, or black. Try a white tee, black jeans, and white sneakers. Or pair with an all-black outfit of skinny pants, turtleneck, and booties. Lean into the lumberjack vibe with a navy cable knit sweater and dark denim.

Q: How do you style a Prince of Wales check blazer?

A: The Prince of Wales check works well with business and business casual looks. For the office, wear it with a button-down shirt, trousers, and oxfords. For a weekend look, pair with a v-neck sweater, dark jeans, and leather loafers. You can also dress it down over an OCBD shirt and chinos. Stick to solid colors that complement the black, white, and gray pattern.

Q: What is the difference between glen plaid and Prince of Wales?

A: Glen plaid features small scale black and white checks with thin lines of color like tan or red. The Prince of Wales check has large black and white houndstooth combined with thick tan and gray windowpanes overlaid on top.

Q: Is a checked blazer in style?

A: Checked blazers are a timeless wardrobe staple that have evolved to feel modern and stylish. Oversized, relaxed silhouettes have given classic patterns like buffalo check or Prince of Wales an updated, casual vibe while still retaining their sophistication.

Q: Can you wear a checked blazer casually?

A: Yes, checked blazers can definitely be worn casually. Styling tricks like choosing a roomy, slouchy fit, rolling up the sleeves, leaving it open over a tee, and pairing with jeans will make a checked blazer feel relaxed. Stick to casual fabrics like cotton, linen, or corduroy rather than formal wool suiting.


Checked blazers have come a long way from their origins as stiff suiting. With endless pattern and color options plus relaxed new silhouettes, it’s easy to find a checked blazer to fit your personal aesthetic.

Whether you opt for a bold buffalo plaid, classic Prince of Wales, or understated glen plaid, checks offer visual interest to any outfit. Oversized fits have given these timeless jackets a stylish, modern update.

Use the tips outlined in this guide to select the ideal checked blazer for you. With the right pattern, fit, and styling, you can seamlessly incorporate checks into smart business looks or casual weekend outfits alike.

So embrace one of fashion’s greatest comebacks. The versatile checked blazer is back and better than ever!

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