How to Style a Denim Shirt – Men’s Outfit Ideas for Jean Shirts

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The denim shirt finds its origins in workwear and seems far removed from the world of tailoring, yet it has been labeled the most versatile shirt for the modern man and “the new white shirt” by The Rake magazine. Is that really the case? And should you add a denim shirt to your closet?

It’s also one of our ten shirts every man should own. In this article, we’ll examine the value of the denim shirt and how it can be worn in the world of classic style.

What is Denim?

Examining denim close up shows the twill weave of the fabric
Examining denim close-up shows the twill weave of the fabric

Nowadays, “denim” usually refers to a cotton twill fabric, meaning it has a diagonal weave made up of two threads in one direction (the weft) passing under two or more warp threads, though the diagonal appearance of the twill is quite subtle.

Denim exists in various weights, and shirts, especially fine shirting that can be worn with tailoring, would be lighter weight than the denim used for jeans. The name of the fabric originates from the French “de Nimes,” for the place where the weave originated, though it was first used extensively in Britain before it saw explosive popularity in the United States via jeans manufacturer Levi Strauss.

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Denim is usually thought of as being dyed blue with indigo, but it can appear in many colors. For example, Empress Mills in Lancashire has more than 40 shades of plain denim. The strength of denim is its durability, which made it the cloth of choice for laborers, farmers, and cowboys. This is owed to the properties of the weave.

By the same token, the affiliation of denim with workwear has traditionally kept it out of tailoring on the principle of dressing appropriately for the occasion. A man who was dressed up would not think of wearing work clothes, and at a time when one’s dress was a strong indication of his social class, a self-respecting gent who was not of the working class would debase his status by appearing to be one.

Denim shirts are the reason we hear the term Blue Collar Workers

Blue Collar Workers

Because denim shirts were a traditional part of laborers’ garb, it was responsible for the term “blue-collar worker,” which arose in the United States during the early 20th century. No single article of clothing has such a direct connection to workwear, which has presented a considerable obstacle to accepting the denim shirt as part of a tailored style.

Denim, in the form of jeans, also featured strongly as the uniform of the rock n’ roll counterculture that began in the 1950s. This was the start of the casual culture in which we are still mired today and stood in direct opposition to traditional men’s style, which, again, seems to draw a distinct line between denim and formal menswear.

There may be some resistance to wearing a denim shirt as selling out to the trend of casualization. On the other hand, we can see it as a way of appropriating the fabric in the name of classic style. Furthermore, these days, the mixing of high and low style, formal and casual, has become commonplace in dressing, as the democratization of clothing has mirrored the supposed equalization of society.

Why Wear a Denim Shirt?

Denim shirts are great for a “smart casual” look

No matter what else you might hear, denim is always a way to dress down an outfit, so it is most suitable for those who want to wear tailoring but who don’t want to come across as overdressed.

Picking a denim shirt can be a great way to add a casual feel to your outfit
Picking a denim shirt can be a great way to add a casual feel to your outfit

If you want to uphold classic men’s style, you usually wouldn’t wear it with a worsted wool business suit, much less a tuxedo, though the luxury shirtmakers Eton and Marol have each produced a denim shirt with a pleated front intended for this purpose. On occasions where formal evening wear or a suit is the dress code, dressing down immediately makes you stand out as the guy who flouts propriety and rebels against the norms to get attention. This would be more of a fashion statement than a way to maintain the traditional style.

Thus, the denim shirt is best for less formal tailoring like a cotton suit or a sport coat and odd trousers.

It’s an unfortunate fact that these days, wearing a dress shirt, tie, and jacket makes you better dressed than most or all the people around you, so there are times when you may be looking for a way to blend in more while still maintaining your style principles. Denim can help with this. If you embrace the smart casual aesthetic, the denim shirt is a valuable option, perfect for a run to the supermarket or a weekend day out.

Denim shirts can be great all-season wear

Nathan enjoys wearing his denim shirt during warmer weather
Nathan enjoys wearing his denim shirt during warmer weather

The versatility attributed to the denim shirt is most accurately owed to the fact that you can wear it in any season. The texture of a denim shirt and its relative thickness lends itself to winter wear; however, its casual, relaxed style makes it appropriate for not-too-hot summer days if you have a version that is lightweight or perhaps made from chambray. Of course, it can be worn anytime in between as well.

Wear a denim shirt for elegant nonchalance

Raphael adds a denim shirt to this look for a touch of sprezzatura
Raphael adds a denim shirt to this look for a touch of sprezzatura

It’s often said of a linen suit that the more you wear it, the softer and more comfortable it gets. This is even more true of a denim shirt because it’s washed often and worn right on your skin. Just like some people talk about their favorite pair of jeans, you’re likely to treat your denim shirt as a comfortable favorite. It will also fade some from its original color until it reaches a certain point, lending your garment a sprezzatura quality. It’ll age into a particular sort of beauty.

What Kind of Denim Shirt Should You Wear?

Not all denim shirts are created equal, however. For wear with tailoring, you don’t want thick, distressed denim or one that hints in any way that it can be worn to a country music concert or rodeo. This means no pockets, especially not the double, button-flapped chest pockets of a Western shirt – which is typically thought of as the classic denim shirt. Such shirts also have shoulder patches and a defined center placket where the buttons are.

All of these render the shirt very casual. Similarly, avoid any sort of unusual washes. Nor should there be obvious contrast stitching, as these suggest jeans and are therefore too casual.

Snaps on a denim shirt instantly make things more casual

Make it Snappy

Whether or not you want to incorporate more casual elements, such as snaps, into your denim shirt will largely depend on how casual you want the shirt to be. Closure styles such as snaps can be a great way to relax the look of a denim shirt, while buttons will always be more formal.

To avoid trends and add a denim shirt to your tailored closet, go with lighter-weight denim, something with a higher thread count and a tight weave that creates a smooth finish. Shirts made of high-quality denim can be recognized by their slight sheen, which makes them look more refined.

These are found most readily at a smaller menswear brand like Proper Cloth rather than department stores or can be obtained from European makers like SuitSupply, Boggi Milano, and Pini Parma. Japanese mills are renowned for their denim, so if you can find a shirt made of fabric from Japan, it will usually fill the bill.

By choosing a denim shirt with long sleeves you can retain a classic look

Getting the Sleeves Right

Typically, denim shirts are made with long sleeves, but it is possible to find them with short sleeves. This may be useful if you’ll be using your denim shirt as a working garment, but long sleeves are without a doubt going to be more formal, therefore, easier to incorporate into a refined closet.

Though not denim, chambray is a close cousin of the fabric in appearance and also shares its origins as workwear. So, if you really want a finer material with a similar look, you can cheat and wear chambray instead, which is usually sold in mid-blue as well.

The difference is that chambray is usually thinner and lighter than denim, being made of a simple weave instead of the double-threaded twill of denim. Thus, it looks more elegant as a shirt, which accounts for its popularity in menswear. Chambray isn’t as durable as denim, but since you’re not wearing it for manual labor, this doesn’t matter.

What to Wear with a Denim Shirt

Because of its casual nature, a denim shirt is perfect when going tieless with a jacket and odd trousers. Indeed, most pictures you’ll find of denim shirts will be styled without a tie. In this case, you’ll be better off incorporating a button-down collar on your denim shirt so the points of your collar don’t collapse under your outer layer. Simply put, your face will be framed excellently with a denim shirt cut in this style.

Kyle chooses a denim shirt with button cuffs

Off The Cuff

When it comes to the end of your sleeves, it’s typically best to ensure your denim shirt ends with a button or barrel cuffs instead of the formal double or French cuffs associated with dress shirts. Whether you choose to go for pleats in the sleeves will largely depend on your personal style, but a nice button cuff closure makes for a great denim shirt.

If you want to wear a necktie or bow tie, it’s best to choose casual fabrics to match the relaxed nature of the shirt. Ties in knitted silk, linen, cotton, and shantung or blends (silk-linen, wool-cotton, etc.) pair best with the texture and informality of a denim shirt.

If you truly want to wear a more formal silk tie, try a large-weave (Garza Grossa) grenadine because its visible weave will stand up to the texture of the shirt. Whatever you do, avoid wearing a tie lighter than your shirt, as this enters the realm of trends that is not the look you want to achieve. When choosing a tie, select a shirt that is no darker than mid-blue and wear a dark tie.

Grenadine neckties to wear with your denim shirt

This silk grenadine tie from Fort Belvedere features a mixed weave of both garza fina and garza grossa.
This silk grenadine tie from Fort Belvedere features a mixed weave of both Garza fina and Garza Grossa.
Grenadine Silk Tie in Navy Blue

Fort Belvedere

Grenadine Silk Tie in Navy – Fort Belvedere

Grenadine Silk Tie in Brown - Fort Belvedere

Fort Belvedere

Grenadine Silk Tie in Brown – Fort Belvedere

Denim Shirt FAQs

Can you wear a denim shirt with jeans?

It is possible to wear a denim shirt with your jeans without fear of the “double denim” or “Canadian Tuxedo” looks. The key is to ensure that both your jeans and your shirt are of two contrasting tones to acheive the best look.

What is a denim shirt?

Simply put, a denim shirt is any style of shirt that has been crafted from denim fabric. Typically speaking, they will follow the same sort of construction you would find in a dress shirt, but denim shirts can also feature more casual elements such as multiple patch pockets and snap closures.

What is so special about denim shirts?

Unlike a regular dress shirt, denim shirts can be added to an outfit to relax the overall formality. Although we wouldn’t suggest wearing a denim shirt with a formal worsted business suit, denim shirts can be added to many types of odd combination outfits for a touch of sprezzatura.

What can you wear with a denim shirt?

Denim shirts can be worn with a wide range of different clothes, but they are best suited to more casual elements of your wardrobe. If you prefer a relaxed look, try chinos and knitwear, and if you prefer a dressier ensemble then go for sport coats and odd pants.

Is a chambray shirt the same as a denim shirt?

Technically speaking, chambray is a plain weave, and denim is a twill weave. While this does make them different on a level of construction, they are often viewed as being interchangeable. Thus, you can wear a chambray shirt in much the same way that you’d wear a denim shirt.

How do you dress up a denim shirt?

By using an odd sports jacket, you can really amp up your denim shirt to the next level. If you enjoy wearing neckties, the majority of denim shirts can be paired with one, but it’s typically best to stick with casual options such as a grenadine or knit tie. Otherwise, add a colorful pocket square to your jacket pocket to dress up your denim shirt outfits.

Colors for Denim Shirts

Denim shirts in darker shades can be a little trickier to pull off well
Denim shirts in darker shades can be a little trickier to pull off well

You’ll probably start and stick with mid-blue as your denim color since the vast majority of shirts sold come in this tone. You may be able to find some darker indigo ones, but they are only as versatile as a regular navy cotton shirt would be, whereas mid-blue can always be combined with more colors and more easily with neckties.

Keep in mind when you select a color that most denim will fade to a certain point when it is washed. A popular approach when wearing a mid-blue denim shirt is to pair it with other shades of blue, like a navy blue jacket and tie, with gray, white, or off-white pants to complete the look, depending on the season. That being said, it’s often best to avoid extreme fades on your denim shirts, such as you might find in stonewashed denim. These finishes can come across as a little too fashion-forward, which is not conducive to a classic wardrobe.

Make sure you take into account the multitude of color options available to you when wearing a denim shirt
Make sure you take into account the multitude of color options available to you when wearing a denim shirt

Treat a denim shirt like a more relaxed version of your standard blue dress shirt and pair it with the traditional menswear colors that you’d use with blue, like brown or gray. Ties and pocket squares in the red or orange family work beautifully against a denim shirt. Green sport coats tend to be underappreciated because men find them rather difficult to coordinate, but blue denim creates an effortless pairing that opens a gateway into a new color family.

A swatch of gray carded flannel with a white windowpane

Check the Box

For more sophisticated outfits, a jacket in a coordinating color with a blue windowpane check is your best friend; these give you an added layer of sophistication by carrying the blue of the shirt into the jacket in a subtle way.

When you wear a denim shirt, it does tend to stand out as the center of attention, so it should be treated that way, which means keeping the rest of your look simple.

Double Denim

The Levi's denim tuxedo as worn by Bing Crosby in 1951
The Levi’s denim tuxedo as worn by Bing Crosby in 1951

Lastly, something must be said about the possibility of wearing a denim shirt with another denim item, most commonly a pair of jeans. A lot of mockeries have been directed at the so-called “Canadian Tuxedo” or “double denim,” which was a popular – and polarizing! – casual look in the 1990s. The good news is that it’s actually easier to wear two articles of denim following traditional style than to do it casually, although it is still considered an advanced style move. A sport coat in another material helps tone down the use of denim.

There are several other keys to success with double denim. The first is, again, to choose a finer denim: smooth shirts and selvedge jeans. Secondly, make sure you create contrast through two distinct colors of denim: your mid-blue shirt with a dark indigo pair of jeans.

Lastly, it’s probably best to stick with gradations of blue, again to beat back the denim. A pair of jeans are not a popular choice among many Gentleman’s Gazette readers, but those who venture in this direction now have another option.

Outfit Rundown

In today’s outfit:

Kyle is wearing a denim shirt that has a medium spread collar and some really unique contrasting buttons. A burgundy sport coat with some gray flecks woven in as well from Hugo Boss is paired on top of the denim shirt. This really unique pocket square from Fort Belvedere adds a splash of color. The color shown on Kyle actually happens to actually be a prototype. The actual one that’s being sold right now on the Fort Belvedere website is more of an ivory tone.

Kyle wearing a denim shirt for a smart casual ensemble (Pictured: Ivory Silk-Wool Pocket Square with Hunting Motifs from Fort Belvedere)
Kyle wearing a denim shirt for a smart casual ensemble (Pictured: Ivory Silk-Wool Pocket Square with Hunting Motifs from Fort Belvedere)

The outfit is finished with a nice dark brown pair of dress shoes and a cream pair of chinos. The medium to light color denim shirt because it pairs wonderfully against both the trousers and the darkness of the sport coat.

Ivory Silk-Wool Pocket Square with Hunting Motifs - Fort Belvedere

Fort Belvedere

Ivory Silk-Wool Pocket Square with Hunting Motifs – Fort Belvedere

Mid Brown Shoelaces Round - Waxed Cotton Dress Shoe Laces Luxury by Fort Belvedere

Fort Belvedere

Mid Brown Shoelaces Round – Luxury Waxed Cotton Dress Shoe Laces by Fort Belvedere

Reader Comments

  1. Beckham does it right in the last shot. He looks like the just finished pounding in some spikes in the Canadian Spike Driving competition.

  2. The new most versatile shirt? Not for me – I think the oxford blue or white still fits that category. However, once I decided to wear one of my chambray riding shirts to my office with a tie, and received many compliments on it.

  3. There can be a very fine line between making an effort to look good, and looking like you tried too hard. Some of these looks fall into the tried too hard category. If you look like you’re wearing a costume, and you’re not at a costume party, you’ve fussed too much with your clothes.

  4. I go with an earth tone sports jacket, Square bottom silk tie, jeans in a darker hue and a tan brogue boot. Denim has earned it’s place in a gentlemans closet.

  5. I love denim shirts because you can literally wear them with slacks, jeans, a casual sport coat, and even combine with dress shoes. Topping it off with good smelling cologne such as Givenchy, Moschino, Tom Ford, Amouage or Creed will keep her nearby admiring your cologne in secret.

  6. My wife wears a lot of Native American jewelry with denim or black outfits. Under the assumption that the first rule of men’s fashion is to dress to complement your partner, I had a couple of denim French-cuff shirts made to wear with the cufflinks she has bought me. Worn with a brown leather or green tweed sport coat, they fit in well in the West (where we live). I wouldn’t wear that look in New York or Paris though.

  7. Recently I picked up for just a lil money a beautiful denim shirt from Gieves & Hawkes. It’s in a very dark colour and I think it’s a great alternative to a plain twill dark blue regular dress shirt. I wouldn’t have expected it but it’s one of the most versatile garments I have, become being casul by definition it allows me to dress down any jacket and look less “abbottonato” (italian word for “buttoned”, often used for too formal looks) and that’s definitely something I need being only 17 yo. I love pairing it with tweed garments and going tieless, even if I might try to wear it with a double breasted grey blazer and a pair of jeans. It might be daring but I guess it would look nice.
    Great article Raphael, my best regards

  8. Great article, right on target! Thanks! I recognize myself and my own dressing problems here; the denim shirt really is perfect to create a stylish but not too dressy look

  9. Hey there. This is my first time leaving a comment here, so just going to cover that I come from a slightly different background then a lot of the readers here and from you. I’m a 21 year old college student from a small rural Washington hometown. For obvious enough reasons, this means I’m probably one of the only people in my friend group who like to dress up, and this actually helps me appreciate denim and chambray shirts a bit more. There are plenty of situations where I do like to wear a button up, since it helps show a bit more effort and care than just a simple t-shirt, but I don’t necessarily want to go all the way to a nice shirt and tie. Light denim shirts tend to have a versatility that helps bridge the gap in situations where you want to dress nice, but not necessarily dress up. I think one example would be first dates, since you want to show you put in some effort to your date, but don’t want to make them feel underdressed (especially apt in my age group). Also in the case of first dates, denim shirts have more personality than other button ups, and give you a more rugged feel.

  10. So first it’s “denim jeans with everything” and now it’s “denim shirts with everything”. Indeed, they may have their place in their original habitat: but I am neither an Iowa farmhand, nor a Texas oil rig worker nor a New York construction worker. Wearing denim shirts with a proper jacket is just as pretentious as wearing cowboy boots with a suit – a desperate cry: “You may find me dull, but I am an enchanted James Dean or Bruce Springsteen”. And if you’re an ageing man wearing denim is never a good style (unless you’re name is John Wayne).

    Dr. Lee actually has given the answer himself: it’s indeed nothing but “selling out to the trend of casualization” and a sign of the “casual culture in which we are still mired today”. Quote: “there are times when you may be looking for a way to blend in more”. Frankly, I can’t recall the last time I felt that that urge. So my answer to “How to wear a denim shirt” is: “Don’t”.

  11. Thanks for pointing out the distinction between chambray and denim. Its a minor irritation to me when an uninformed person continually refers to chambray as denim. I’m not a fan of the denim with dress-wear look, but it is popular. Personally, I think it looks like a fellow is trying far too hard to appear “hip”.

    1. The only thing that looks worse is the dress shirt, tie and sports jacket with jeans. It makes a man look like some liberal school teacher trying to look “hep” for his students so he can get invited to their parties.

  12. I read your article and I don’t think it cool to wear a denim shirt under the coat or suit Its look weird and unusual.

  13. Great read. Well thought out. I appreciate the history, and you’ve included a breadth of examples. A denim dress shirt can be a great way to introduce some casual fell into an outfit. I’m not sold on it with a suit, but definitely with sport coats. Choosing the right tie is key, should you choose to wear one. Texture is the right advice.

    Cheers,

    Colin

  14. Not really crazy about most of these examples, but that green jacket with the brown tie pic – wow, that looks great! I assume the jacket is linen? I’m too old to wear denim shirts anymore, but I liked blue chambray shirts when I was younger, often with khakis, Bass Weejuns and a tweed jacket.

  15. Greetings,

    Back in the 1990’s, radio personality Don Imus promoted a line of U.S.A.-made denim shirts sold through brother Fred’s “Autobody Express” business in Santa Fe, New Mexico.

    Priced at $57.57, reflecting Fred’s affinity with the 1957 Chevrolet automobiles his company admired, these shirts were made of medium-weight 100% cotton fabric, featured a seven-button front and a button-down collar, had a locker-hanger loop, and barrel cuffs.

    Over the decades, I bought several such shirts.

    They wear like iron, and fit beautifully.

    Sincerely,

    Andrew Gregg,
    Palm Springs, CA.

  16. A friend recounted having the following conversation with his father when he was a boy:
    Boy: Dad, how come you never wear jeans?
    Dad: Because I’m not a farmer.
    Applies to denim shirts as well, I believe.

  17. If rich & powerful they only worry about being embarrassed or outdone. My few toys or clothes as good as their many or much more has cost me often and a lot. Denim in MILD doses has at times taken the heat off and left me going.

Comments are closed.