Strictly speaking, it is physically possible to wear jeans with a dress shirt and a tie. However, just because you can do something doesn't necessarily mean that it's always advisable. But like everything, there's a time and a place.
Men's jeans with a dress shirt, a tie, and a blue blazer is a kind of uniform—and it works well for serious creative types, actors, writers, fashion editors, and designers. You may not upend the conventional wisdom surrounding art and pop culture, but you can learn a thing or two about wearing jeans with a men's dress shirt and a tie based on how famed artists pull it off. Here are our tips on how to wear a dress shirt with jeans.
The first thing to acknowledge is that pairing jeans with a dress shirt and a men's tie inherently takes the outfit in a much more casual direction. Obviously, this look is a more casual approach to dressing than wearing a dress shirt and a tie with a suit. But it is also more dressed down than pairing your dress shirt and tie with a pair of men's khakis pants. In effect, you're pushing the tie outside of the context in which it is typically worn and has meaning. This begs the question: why are you wearing jeans with your dress shirt and tie?
Artists have it easy. As a successful artist, you're entirely in charge of your own lifestyle and have the ability to dress in any way you please. You're not wearing jeans with a dress shirt and a tie to the office, and we wouldn't suggest that you do either. Wear jeans with a dress shirt and a tie because you want to.
If you feel so inclined to wear jeans with a dress shirt and a tie, you'll have to consider how each of its elements can best work with one another. You'll want to keep the jeans blue and on the darker side, and free of any distressing, embellishments, or other bells and whistles. A pair of dark-blue, men's straight-leg jeans is the closest that denim comes to looking dressy, and that's precisely the sort of denim you want to be wearing as part of this look.
For the dress shirt, consider something on the more casual side. We favor white oxford cloth shirts with classic button-down collars. A men's oxford shirt with a button-down, spread, or point collar can work for this look, but also look out for patterns and colors that make the dress shirt more casual and thus more adaptable to jeans. Patterns like plaids or stripes can do the trick, as can colors like powder blue and pink.
Also, pay attention to the "sheen" of the shirt. A shirt in a more finely woven fabric like broadcloth tends to have a tighter weave that appears more formal and even a little shiny. When wearing your dress shirts with jeans, avoid those finer fabrics, and look for fabrics with more open weaves such as oxford cloth.
Now for the tie itself. Like the dress shirt, some ties are more casual than others, and you'll want to seek them out. At the very bottom of the tie, formality ladder are knit ties, which can pair excellently with oxford cloth shirts and denim. Slightly higher on the peg are repp ties, which have a preppy connotation that naturally lends them to a more carefree, slightly crumpled aesthetic.
As with the dress shirt, keep away from anything that seems too tightly woven or "shiny," as these qualities place ties on the more formal end of the spectrum. And if you're looking for a patterned tie, select something in a larger-scale pattern rather than a smaller scale.
One way that you can really dress up the dress shirt, tie, and jeans look is with dress shoes. Shoes can completely change the feel of an outfit. Sneakers will dress it way down, sandals would be really out of place, but a pair of dress shoes would elevate your outfit. Black or brown dress shoes would be best–and try to match them to your belt if you can. This will make your more casual look be a bit more office-appropriate.
With these tips in mind, you'll be a master of the elusive jeans, dress shirt, and tie combo in no time at all.