Fashion & Beauty

The Lazy Man’s Guide To Wearing Shirts With Jeans

Pair a shirt with jeans. It’s a classic combo that sounds simple enough but gets trickier when it comes to execution, because there are so many possibilities. Here, we work out the combinations so you can skip the trial and error and go straight to rocking the look.

First, the Jeans

Generally speaking, darker shades fall at the more formal end of the spectrum while lighter denim has more casual vibes about them. When it comes to fit, if you want a no-brainer, slim cut jeans that skim the legs tend to be the most flattering and versatile. You get some polish without sacrificing comfort, and can easily go from Friday at the office to a smart-casual cocktail bar do without too much effort. Skinny jeans can look polished and urbane but they remain more suitable for informal occasions. As for baggier, relaxed fits, when in doubt, just save them for the weekends. Rips, patches and faded denim are, needless to say, for days when you answer to no one but yourself.

The White Shirt

Throwing on a white shirt over denim is your safest bet on days when you simply do not want to think about what to wear and yet still have to look pulled together. Heading to work? Tuck a slim fit shirt into dark indigo jeans. Prepping for a date? Leave the shirt ends out over raw denim and cuff your jeans for a bit of interesting detail. A white shirt worn with sleek, black denim can feel quite fresh and a little bit edgier when accessorised right — keep the hair smartly slicked back and don’t forget the sunglasses.

The Black Shirt

Black shirts look great with lighter blue or grey jeans. Alternatively, pair with black denim for a monochromatic look that can be quite stylish. Keep the top and bottom streamlined, and throw on a light jacket like this season’s technical parka (traditional hiking gear turns fashion must-have) so you don’t get mistaken for the wait staff.

The Checked Shirt

Checked shirt over indigo is as lumberjack as you can get, which is not necessarily a bad thing if you can pull it off. Keep it classy and not sloppy with a streamlined fit, and avoid chunky shoes that scream “hiking” or “woodshed”. White sneakers are a good bet.

The Striped Shirt

While complicated prints require a bit more fashion finesse and premeditated thought to put together, stripes are a good way to wear pattern without having to put too much effort into making the outfit work. To spice things up, try this season’s vertical stripes, which come in irregular widths and more striking colour palettes. Whether it’s pinstripes or supersized stripes that you like, wear them with sleeves rolled up and half-tucked into lighter jeans. Complete with sports sneakers for an offbeat laidback look.

The Denim Shirt

Denim on denim remains an interesting fashion proposition because as much as it has caught on in recent years, a divisiveness remains about whether it’s a fashion no-no. Still, there are no rules when it comes to style these days. Quite simply, if you like the look, just wear it. A casual blue shirt paired with black or grey jeans is an easy way to go about it. Also try a boxy, lightweight denim shirt buttoned to the neck and worn with cuffed, darker blue jeans.

The Dress Shirt

The formality of dress shirts are taken down a notch when teamed with jeans. Dress shirts look best with a slim fit that sits close to the body but without any strain at the buttons. Tuck it in if you’re wearing it with slim fit jeans, and pair with sneakers or loafers for the right mix of smart and casual. Keep the shirt ends out if you’re wearing it with relaxed or baggy jeans. Note that your shirt should not hang longer than your hip bone because it’s going to mess with your proportions and make your legs look stunted. Similarly, it should not be too short. No one wants to catch glimpses of your belly button, really.


For the true lazy man, head on to and shop these looks from the convenience of your home!


Click to comment

Leave a Reply

Your email address will not be published. Required fields are marked *

Latest Reads

To Top