
How to style denim-on-denim, a question that I’m sure still haunts certain celeb Stylists almost 20 years later. If you don’t know of the denim debacle I speak of, I’ve linked it here. It was bad, right? Cringeworthy, but like most women, it didn’t stop me from crushing on Justin Timberlake. When done correctly, denim-on-denim or chambray and denim, or white jeans and a jean jacket/a chambray top are all great looks, virtually seasonless in this day and time, and always give a cool polish to any outfit.
Chambray Shirts and Jean Skirts
With jean skirts making a comeback this season, you have one more option to rock the denim-on-denim trend. I love the look of jean skirts, but I really love a denim pencil skirt above all others, paired with a chambray top. Above, I have on two slightly different shades, and to make this work, bring in a belt to break up the look, a bold accessory, and keep the shoes neutral, leopard is in included in my definition of neutral though I am wearing nude booties above.
You can certainly pair the same washes together. That is perfectly acceptable, as is pairing a darker and lighter shade together as shown next. Just make sure that there are some key accessories that are not denim paired with your outfit. I would recommend bringing in more conservative elements to create a polished look.




Denim on Denim: Jeans
One of my favorite looks; especially, heading into fall are distressed jeans with a chambray top. The key to this look is either wearing similar shades and breaking it up with accessories, or wearing varying shades with a blazer, a vest of some kind or a longer cardigan. Adding one additional element gives the idea that you are not wearing too much denim.
With the above look, I love the grey, but would wear this with navy or a black blazer, a fur or faux fur vest, longer cashmere cardigan (ideally) or something that has a luxe look to it. I did not wear a belt with this, but if I did not have on the jacket, again, I would add one to break it up. You certainly do not have to wear distressed denim, but I think it gives the look a cool edge and helps to make it feel less forced. I did add heels to this to give it a more city-feel, though flats work just as well. I would lean towards a slip on mule, like the ones show below, if I were wearing flats.
Testing the Waters
If you are just testing the waters with this trend, an easy go-to is a chambray shirt in any color, with white jeans or white jeans shorts, or the reverse. That looks perfectly put-together and requires no effort. Add in some fun earrings, a few bracelets and you are ready to go.
Another easy option, pair a jean jacket in the same wash as your jeans, with a graphic t-shirt, white t-shirt, or camisole. Or, a white jean jacket and dark jeans, or the reverse.
For fall bootie inspiration to finish off your denim-on-denim look, take a look here.