How To Wear A Dress Shirt With Jeans: 17 Outfits That Get The Combination Right

Dress shirts and jeans. We all own a bunch, but how often do we wear them together in this menswear world dominated by sweats and relaxed casual looks? The answer is not as much as we should, because although these garments sit at seemingly opposite ends of the formality spectrum, this is a versatile pairing that can adapt to the occasion.

For example, a classic pinstripe shirt looks very different when worn with a pair of raw denim jeans, than when it is teamed with cropped, stonewashed wide-legged jeans.

The dress shirts and jeans combination has infinite variability – one moment classic and smart, another edgy and contemporary – and below we’ll show you how to get the most from your collection in 2024.

When should you wear a dress shirt with jeans?

On the spectrum of smart-casual, the dress shirt and jeans combination lies at the more casual end, but it can veer into smart depending largely on the cut of the shirt and the jeans.

Slim, tapered jeans worn with a well-fitting shirt will most definitely look smart – especially if you bookend the duo with loafers, throw on a relaxed, unstructured blazer and tuck the shirt in. Could you get away with that in the boardroom? Probably not, but in most workplaces these days, that business-casual aesthetic would be perfectly acceptable.

On the other hand, slouchy distressed jeans and a boxy shirt will have much more of an off-duty appeal and would be much better suited to your casual weekend fits with sneakers.

So, there’s definitely something for everyone here, but generally speaking, the slimmer the cut, the smarter it looks, so bear that in mind.

17 dress shirts with jeans outfits for men

White dress shirt with light blue jeans

First up, props for the layering prowess here. The tonal blazer/knit/shirt trio is right on the money, while the addition of the pale blue tapered jeans balances out the top half.

It’s casual with a soft tailored edge, and the peep of the white shirt provides a clean accent that allows the other colors to pop. Top marks.

White dress shirt with tapered cropped jeans

Once again, a white shirt and jeans. But look how different this outfit is from the last, demonstrating the versatility of the dress shirt and jeans combo.

In this case, the jeans are equally tapered, but darker and cropped for a smart finish that works perfectly with sockless loafers. Meanwhile, the blazer brings a degree of structure to the outfit and the white shirt provides a clean canvas.

Pale blue shirt with dark tapered jeans

A smart preppy vibe is achieved here with the svelte silhouette, neat tonal crew neck knit and the essential addition of the pale blue dress shirt peeking out of the top, hiding a cheeky polka dot neckerchief.

Sophistication is reinforced by opting for a dark wash in the jeans and rounded off by the leather penny loafers.

Striped shirt with straight-leg distressed jeans

Stripes can offer both a smart and a casual attitude depending on their width, with the wider the stripe typically being more casual.

This boxy shirt is perfectly complemented by the straight-leg jeans, while the subtle distressed details give the outfit a relaxed appeal. The rolled sleeves and nonchalantly hung jumper add to the effect.

White shirt with classic tapered jeans

This outfit is all about those clean lines. Utilizing another classic menswear combination – the shirt under a sweater – the open neck of the white shirt is mirrored by the shallow V-neck finish of the cashmere knit.

With the upper half being quite fitted, the lower half follows suit, with the tapered pale denim jeans creating a sleek silhouette.

Super easy to pull together.

Chambray shirt with white jeans

The classic blue/white combination never fails, as this look proves. Simple yet effective, the white jeans have a neat tapered cut, while the shirt adds subtle texture and tone.

Tucked in, the button-down shirt has quite a slim silhouette, which gives the combination a smart, slightly nerdy appeal.

You could easily add a cardigan or suede jacket to this and completely change the vibe.

White shirt with black jeans

Monochrome looks take a lot of the thinking out of getting dressed and always have a smart edge to them. Simple contrasting tones such as black and white create great separation between top and bottom.

The brushed cotton fabric of the shirt gives it a textural finish and a nice weight for a natural drape. The great thing about this outfit is the number of outerwear options it affords you, from long coats to bomber, leather and field jackets.

Off-white shirt and dark selvage denim jeans

The quality of the denim and the richness of the dye shine through in these jeans, which are finished with a slim tapered cut for a polished aesthetic.

They’re nicely complemented by the off-white dress shirt, worn tucked for additional sartorial points and to retain a degree of professionalism. The cutaway collar gives the shirt a business-like edge which could call for a sleek navy blazer for a great office look.

Pale lilac dress shirt with white jeans

A tidy summer outfit, the lilac tone of the button-down shirt blends into the white jeans rather than contrasting them, which probably calls for another layer in a different color to give the look some depth.

A suede jacket or shacket/overshirt in pale grey would be perfect. Alternatively, you could try an unstructured linen blazer in a pastel tone.

Navy dress shirt with tapered jeans

Who says jeans can’t be sophisticated? When they have a high rise and are beautifully tapered like this pair, then a trim navy shirt and a pair of loafers will combine to create a nicely elevated look.

The belt is an important addition, helping to create a sense of separation and smartness.

Navy shirt with light grey tapered jeans

A classic combination, the slim off-white jeans are perfectly deployed with their long-time dance partner, the navy dress shirt.

The tan suede shoes inject a subtle textural detail, too. All that’s missing is a pale blue blazer for an effortless summer Riviera look.

Beige dress shirt with white jeans

Tonal looks can sometimes look flat if you don’t mix up the fabrics, but this fit does that nicely with the brushed cotton shirt.

The jeans are nicely tapered, following a smart natural line right down to the tan suede loafers, which finish the look off with a textural touch of summer sophistication.

Light blue striped shirt with pale blue jeans

Similarly, another great tonal look, only this time complementing the blue of the jeans with a subtle blue striped shirt. The tuck and belt, in combination with the slightly high rise and tapered leg, give the outfit a modern preppy feel, which is only accentuated by the baseball cap.

Slightly nerdy, but in a good way.

Dark green dress shirt with raw denim jeans

Raw denim jeans are a great investment and rarely will you go back to anything else after you’ve properly worn them in. They work well with almost every tone of shirt you can think of, but in this instance it’s a dark green style that does the job.

Understated yet undeniably smart, the suede shoes add an extra element of texture to the outfit.

Pale blue shirt with pale blue jeans

First up, what we instantly love about this look is the silhouette of the jeans – straight leg and with a few turn-ups to create a contemporary cropped fit that helps to accentuate the high-tops.

The tucked-in pale blue dress shirt keeps the balance, while the tan blouson brings it all together by coordinating with the tan soles of the kicks.

Multi-stripe dress shirt with blue jeans

The multi-stripe shirt has an inherently preppy attitude about it, which makes it a good dance partner with relaxed tapered jeans.

This look reinforces the collegiate cool aspect by adding a woven leather belt and suede loafers with white socks to the mix. Old-school cool.

You could add a shawl collar cardigan over the top or a knitted blazer if you wanted an extra layer.

Plain white shirt with stonewashed jeans

If in doubt, keep things simple with a white shirt. It’s best to opt for a brushed cotton style if you’re going for a relaxed look like this as you don’t want people to think you’ve just picked up a work shirt.

The stonewashed jeans keep the fit looking relaxed, while the white minimalist kicks bookend the outfit perfectly.

The right dress shirts to wear with jeans

The question of what type of dress shirt to wear with jeans can be answered by the aesthetic you’re going for. But on the whole, the broad spectrum of dress shirts will work, with the only exceptions being very formal styles that are typically worn with formalwear and eveningwear.

The single most important thing to look out for is the cut of the shirt, especially the ‘skirt’ (i.e. the bit that is often tucked in). More formal business shirts often have a long skirt with a rounded hem so they don’t ride up when tucked in, but this looks terrible when untucked so you need to know how you’re going to style it.

Another consideration is the fabric: cloths such as brushed cotton, commonly used to make Oxford cloth button-downs (or OCBDs), have a slightly furry nap and so are better suited to more casual fits, whereas silky cotton poplin is a good option for smart tapered jean styles. With the former you can afford to go slightly more boxy and loose, while with the latter you’ll want a trimmer cut.

The jeans you should wear with dress shirts

Similarly, virtually all styles of jeans will work with dress shirts, provided both garments have some degree of synchronicity. Let’s say most of your jeans are slim-cut styles – you’ll want to opt for slim, fitted shirts that you can wear both tucked and untucked. More of a straight-leg guy or prefer a wider leg that’s cropped? You’ll want a looser-fitting casual shirt.

Denim quality is a personal preference since super high-quality Japanese selvage denim can still be casual – it all depends on the silhouette of the jeans and the look you’re trying to achieve. The same goes for color and wash – white, black, grey, blue… everything is fair game, so long as you match the vibe and formality to your dress shirt.