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Our Recommended Dress Shirts
Wear it with dress pants and you’ll look like you’re going to work. Wear something too casual, and the look may appear unbalanced. Fear not – this article will teach you how to look sharp in that dress shirt while staying comfortable in jeans!
The type of jeans you wear is important. While you can choose between a dark, light, or classic colored jeans in a variety of cuts, here are some things you must never do.
Use caution when wearing ripped jeans. If they’re stylized rips on fitted jeans, and your dress shirt is a bright color that is unbuttoned, you might be able to get away with this look, but usually ripped jeans and dress shirts are a no fly zone. Save them for your casual outfits.
Important: Rips are ONLY acceptable when they are stylized. Any time this article mentions ripped jeans, it refers to stylized rips. If you’ve worn through your favorite pair of jeans so hard that you gained genuine rips in unfavorable areas and have flyaway strings hanging all over, then it is time to let them go.
Baggy jeans are definitely not an option with dress shirts. Sorry men, but it’s pretty true that you won’t look sharp if you’re wearing saggy, baggy, ill-fitting jeans with that dress shirt. It’s just not the right pairing, even if you can get away with baggy jeans in a more casual outfit.
There are always exceptions to the rule, but usually you will want to wear dark wash jeans rather than light denim. If you decide to go a little extra and try a colored jean, then stick to white or black for the best versatility.
Fitted jeans are usually the right option. You want the jeans to look tailored to your body, so slim and fitted will pair better with a dress shirt than loose fitting jeans. In general, they also cuff better at the ankle for a more tailored look.
Women have known about this fashion technique for ages, but layering is everything when it comes to the best ways to wear jeans with dress shirts.
Have you ever seen anyone wearing a great pair of dressy shoes with some dark wash skinny jeans, a neutrally colored dress shirt, and a bright colored blazer with some chunky accessories? Or reversed – where the shirt is bright and the tailored jacket is black? This look was inspired by men!
Believe it or not, blazers are making a big splash in the dressy casual look of sophisticated urban fashion. Ditch the tie, leave the top button and collar undone, and wear raw denim instead of dress pants. It's a perfect polished look that is one step above casual and great for going to church or a date if you're not trying to dress up too much.
If this isn’t appealing to you, there are several ways you can take advantage of this fashion option to make yourself look sharp, besides the 2 ways described above. Try pairing fitted dark wash jeans with an untucked white dress shirt and a khaki colored blazer in a fun fabric, woven texture, or pattern.
The key to making this look work is the fit of the jacket or blazer. You want it to still be fitted to your body so it can show off your torso, but you also need to add a little slouch and softness so it is nice and casual.
Cardigans and Sweaters
Another really sharp look is to wear the dress shirt under something else. Swap out the blazer for a chunky crew knit sweater. For this, you want complimentary colors or a bright contrast. Wearing a dark grey, black, or blue sweater would go well with a steel grey, white, or lighter blue dress shirt.
Teacher cardigans are also great looks with dress shirts and jeans. Seriously – one of those really loose, light (but not too baggy, keep it fit) cardigans with the large, chunky buttons and 2 rounded pockets looks fantastic thrown over a darker shirt and some dark wash jeans. Pair it with shoes in a similar light colored pattern for a great look.
Another, still more casual, way to layer shirts is to use the dress shirt on top of your look instead of under something else. This can really dress down a look, and these are the places you can typically get away with lighter wash denim or ripped (but still fitted because that is very important) jeans.
A great way to wear this look is by taking a really rugged Henley shirt and wearing it underneath a dress shirt. This look will let you play with jean colors, too. For example, try a dark blue short-sleeved Henley shirt underneath a light blue dress shirt or flannel shirt. Roll up both sets of sleeves to the elbows then pair the look with olive colored jeans and some beige or khaki colored ankle boots. A good rule of thumb to follow with this look is to work in color tones for bold pairings.
You can also pull off a great street look by wearing a basic undershirt with a basic dress shirt, some fitted dark jeans, and black sneakers. Keep the colors in blocks, but play around. For example, you could wear a grey dress shirt with a white crew neck undershirt with jeans and black sneakers.
See Our Rankings of the Best Dress Shirts
You could also do a casual t-shirt (grey, white, colored, however you want to rock it) with your standard white dress shirt and shove the sleeves up to your elbows. (Don’t roll them if you want to be very casual; just bunch them.)
Tee shirts can be a really fun look to choose, too. If you want to be very casual while still rocking that dress shirt for an almost effortless look, then wear lighter jeans with some rips in them, cool sneakers with some personality, and your favorite funky t-shirt with a neutral, untucked and solid colored dress shirt.
You can tone down the tee with darker colors in complementary shades or play it up by going for the same bright colors of your tee! If you have a bright design on a dark t-shirt then definitely go for a brighter dress shirt in the same color as the design to bring out those colors and make them pop.
You have to be careful about when to tuck and when not to tuck when it comes to wearing jeans and dress shirts. In general, a very good rule of thumb is to leave your dress shirt untucked. This means you will have to make sure the length is right; if your shirt is too long it’ll look like you’re wearing a dress, which isn’t the look most of you are going for if I had to place my bets.
When to Tuck
The exception to the untucked rule is a dark blazer or jacket. If you’re wearing one of these, then it is okay to go ahead and tuck in your shirt. You can still pull off a sharp look by letting the jeans and open collar do the talking.
Again, this isn’t a hard and fast rule. In fact, with lighter and more informal jackets in those beige tones and fun patterns, leaving a light dress shirt untucked helps seal the casual and effortless look. This is especially true of white underneath khaki and brown, longer jackets that are straight down instead of fitted.
If you want to go for a belted look, then tuck. Put the focus on a classy belt with the jeans and tuck in your shirt. Again, for this look you will want to leave your collar unbuttoned and skip the tie. You can make this look more casual by cuffing your jeans at the ankle and wearing more casual footwear or make it dressy-casual by wearing more formal loafers with the look. In any case, the key to casual here is to leave off the tie.
The other instance where you will want to tuck your shirt is when you’re wearing it under a bulkier sweater. Let he baggy sweater do the casual talking for you. Having a dress shirt peeking out under the sweater is great at the cuffs and collar but it just looks sloppy at the waistline. Tuck that shirt!!
When to Leave Untucked
The answer to this question is pretty much: always. The advantage of jeans is that you’re not required to follow the same rules of dress shirts.
Make sure that your shirt is the right length. If you’re standing straight, your untucked shirt should just barely hit the bottom of your pelvis area at the longest length and should always come down mid-pelvis at shortest length. Any longer and it looks sloppy, any shorter and it looks awkward.
If you’re going to skip layering and just wear the shirt, this untucked rule is especially true. A great look can be something as simple as long, fitted jeans in a dark wash paired with khaki or beige loafers or ankle boots, and a plain white dress shirt with your sleeves cuffed at the elbow.
What about a half tuck?
Half tucks can be great ways to dress down your shirts. If you’re going for this look, a good way to pull it off is with looser, lighter jeans, a striped shirt in neutral colors (like white with blue or grey stripes), a half tuck, and a belt.
Complete the outfit by wearing high tops or tennis shoes in a fun color and tucking the front half of your shirt. It also helps to get an aggressive V by leaving 2 buttons plus the collar undone instead of one and wearing either a bright undershirt or nothing underneath and letting a little chest show through.
This half tuck look is also a great way to earn some leeway on length if some of your shirts fall a bit longer than they should. With this look, the back of your shirt can come down to the bottom of your butt without it looking too sloppy.
Rule: If you’re wearing a half tucked look you must also wear a belt. Otherwise, this will look sloppy instead of intentionally cool and casual.