Let’s be honest, is there any combination more timeless than a shirt and a pair of jeans? It’s the unofficial uniform for... well, just about everything. From a casual Friday at the office to a weekend brunch or a night out, pairing men's shirts with jeans works.
But getting it right—that perfect balance of sharp and relaxed—can sometimes be tricky. How do you avoid looking sloppy? How do you match different shirts and washes?
If you've ever stood in front of your wardrobe wondering how to wear shirts with jeans for the perfect look, you're in the right place. We're breaking down seven essential, stylish ways to nail this classic combo, featuring our favorite casual shirts for men.
1. The Timeless Classic: Check Shirt + Dark Wash Jeans
This one is a legend for a reason. It’s the ultimate "I look good without even trying" outfit. A good check shirt is a must-have in every man's wardrobe, and pairing it with dark wash or indigo jeans creates a look that’s both rugged and refined.
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How to Wear It: You can't go wrong here. Wear it buttoned up for a sharper look, or wear the first two buttons undone for a more relaxed vibe.
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Best For: Casual Fridays, weekend outings, a casual dinner.
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Pro Tip: Roll up the cuffs just past your wrist. It shows you're paying attention to the details.
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Get the Look: Pair our Chic Burberry Melange Shirt with a pair of dark blue slim-fit jeans.
2. The Statement Maker: Bold Print Shirt + Black Jeans
Want to show off your personality? A prints shirt is your best friend. The key to wearing a bold print—whether it's floral, abstract, or geometric—is to let it be the star of the show. Pairing it with simple, solid black jeans anchors the look and keeps it from becoming too "busy."
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How to Wear It: This is one of the most stylish casual shirts you can own. Wear it confidently, untucked.
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Best For: A night out, a concert, a creative event, or date night.
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Pro Tip: Make sure the fit is spot on. A well-fitted print shirt looks intentional; a baggy one can look like a vacation mishap.
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Get the Look: Our Enchanting White & Mauve Hypnosis Shirt is the perfect conversation starter.
3. The Effortless Cool: Solid Cotton Shirt (Untucked) + Light Wash Jeans
This is your go-to weekend uniform. Think of a high-quality, solid-colored shirt—like a premium cotton in white, sky blue, or even a rich olive—worn untucked over a pair of light wash jeans. It’s relaxed, comfortable, and endlessly cool.
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How to Wear It: Untucked is the key. Choose a shirt that isn't excessively long (it should hit around mid-fly).
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Best For: Weekend brunch, running errands in style, a casual get-together.
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Pro Tip: This look is all about the fabric. A premium solid cotton shirt drapes better and looks far more elevated than a cheap alternative.
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Get the Look: You can't beat a Classic White Twill Shirt for this.
4. The Layering Pro: Open Shirt + T-shirt + Distressed Jeans
One of the most versatile ways to wear men's shirts with jeans is to not wear it as a shirt at all, but as a jacket. Grab your favorite check, solid, or flannel shirt and wear it open over a plain white or black t-shirt. Paired with some distressed or faded jeans, this look screams relaxed confidence.
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How to Wear It: Wear the shirt completely unbuttoned. This works best with slightly heavier fabrics, like twill or flannel-style cotton.
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Best For: A concert, a casual barbecue, or any time you need a light layer.
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Pro Tip: This is a great way to add a pop of color or pattern without overwhelming your outfit.
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Get the Look: A Blue Checkered Twill Shirt is the perfect layering piece.
5. The Smart Casual: Tucked-In Solid Shirt + Dark Jeans
Yes, you can tuck a casual shirt into jeans. This is how you take the combo up a notch for a "smart casual" dress code. Pick a crisp, solid shirt, tuck it into a pair of dark wash jeans, and add a nice leather belt. Suddenly, you're ready for a dinner date or a creative office.
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How to Wear It: A clean tuck is essential. Pair with a brown or black leather belt that matches your shoes (think loafers or Chelsea boots).
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Best For: Smart casual offices, dinner dates, semi-formal events.
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Get the Look: Our Black Satin Charm Slim Fit Shirt creates a sleek, sophisticated silhouette.
6. The Sharp Contrast: White Shirt + Black Jeans
It's a classic for a reason. The sharp contrast between a crisp white shirt and jet-black jeans is modern, minimalist, and incredibly stylish. It's a step up from a T-shirt but just as effortless.
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How to Wear It: This look can be worn tucked or untucked. For a rock-and-roll vibe, go for a slim-fit shirt and skinny black jeans. For a more classic feel, a regular-fit shirt untucked works perfectly.
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Best For: Art gallery openings, a stylish bar, or looking great anywhere.
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Pro Tip: The whiteness of the shirt is key. Keep it bright and crisp.
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Get the Look: A Satin Glow White Slim-fit Classic Shirt is the ideal candidate.
7. The Tonal Look: Blue Shirt + Blue Jeans
A blue-on-blue (or "Canadian tuxedo") look can be incredibly stylish when done right. The trick is to vary the shades. Pair a lighter blue casual shirt with darker blue jeans, or vice versa. This creates a deliberate, put-together look that’s very on-trend.
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How to Wear It: Make sure there's a clear distinction between the shade of your shirt and your jeans.
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Best For: A stylish daytime event, a coffee date, or just looking fashionable.
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Pro Tip: Brown leather accessories (boots and a belt) look fantastic with this all-blue combo.
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Get the Look: Our Sky Blue Dobby Cotton Shirt provides the perfect pop of light blue.
Final Thoughts
The men's shirts with jeans combination is a blank canvas. By simply swapping a check shirt for a prints shirt, or a light wash jean for a dark one, you can create an outfit for virtually any occasion.
The most important part? Start with high-quality shirts. A premium cotton fabric, a great fit, and stylish patterns are the foundation.
Ready to find your perfect pair? Explore the full collection of casual shirts for men at Tailors Cove.