here’s many different types of shoes and jeans/denim you can wear but depending on the shoes, your jeans need to be certain colors and fit certain ways in order to look their best, so today we’re going to show you the best ways to wear jeans with High and Low top Sneakers/Trainers, Boots, Chukka Boots, Chelsea Boots, Work Boots, Dress Shoes, Brogues, Monk Straps, Loafers, Penny Loafer and more.
Due to the low profile of lowtop sneakers its really hard to mess this up. They’ll work with almost any cut of jeans.
As for denim colors or styles, unless they’re all black sneakers (which we discussed before), you can pretty much wear any color or style you want. The one caveat is that if you’re wearing white sneakers and dark indigo jeans, they can stain the tops of the shoes. So soak the pants in cold water for about 30 minutes to get rid of any excess dye that may rub off on the shoes and then spot clean the shoes, as necessary.
If you want to avoid staining the shoes all together, either get them hemmed or cuff them to not touch the tops of the sneakers. We’ve done a whole article and video about cuffing your jeans here.
If you’re going to buy hi-top shoes and wear them with the hem going past the tops of the shoes, you should just get a lowtop pair of sneakers instead. We’ll assume you are wearing hi tops because you like the look of them and want to show off the whole shoe.
To do this well, either gets your pants hemmed shorter or cut them with scissors for a frayed look to show off the shoes or simply roll them to just below the top of the hi tops. Never more than twice, though, otherwise you’ll have a really thick cuff on the bottom and it will look very heavy and off on your shoes.
There’s two schools of thought here and it depends on how “chunky” the running shoes are. If they’re low-profile and sleek, then stick to a similar cut as low-top sneakers – which means wear any cut of jeans. You can even cuff your pants if you want a sportier look.
If you’re going for the Dad/Ugly sneaker look, then the chunkiness of them dictates you go for a straight leg, more relaxed cut. The more stonewashed, the better!
These will pair really well with dark-wash or black jeans. Just make sure you’re jeans have a slight to no break to match the sleeker and more polished dress boots. Wearing dress boots and stacked hems is like wearing tuxedo shoes with jogger pants – it just doesn’t look good.
These boots tend to have a chunkier sole and more casual appearance, so definitely play up the workwear version and wear them with dark wash denim or denim that has some fading. And cuffed or uncuffed, you can wear them anyway you want. If you’re going for the super slim fit jean and chunky boot look (Justin Theroux), get them hemmed or roll them up to be shorter and leave no break. If you want a super vintage look, then try a single, oversized cuff and a more relaxed fit.
Desert & Chukka Boots
Wear them with any color and cut of jeans you prefer and they tend to look best with a slight or no break, depending on the look you’re going for. You can achieve this by cuffing your jeans or getting them hemmed.
As we talked about in a separate video, Chelsea Boots are not for everyone- if you’re a bigger guy, stick to work boots unless you want to look like Humpty Dumpty with little tiny legs. Chelseas need to be paired with slim jeans to look their best. The color and material of the boots will determine what you should pair them with.
If you’re wearing black leather or suede chelseas, they’ll look best paired with black or gray skinny jeans. Anything outside of this will be much harder to pull off.
For brown or tan suede Chelseas, especially with a gum sole, go with a lighter blue or gray denim, which can also have some distressing.
If you’re going with brown (not tan) leather Chelseas, a dark wash denim will look best since browns and dark denim are a match made in heaven.
Debries & Brogues, Oxfords, Wingtips, Monkstraps (Dress Shoes)
Derbies, like Doc Martins, feature a chunkier profile, so they’re better suited for casual outfits that include denim. Black looks great with black or dark wash denim, while brown looks great with dark washed, stonewashed or even distressed lighter denim. If you want those late 80’s or early 90’s vibes, pinroll your jeans and wear them with white socks (I know we’ve talked about our hate of white socks before, and that still holds true 99.9% of the time. This is literally the .1% of times it will look good due to the specific, era-related look you’re going for.
For Brogues, as a general rule, the sleek, minimally detailed brogues will skew more formal while chunky, hole-punched ones will skew more casual. The color of the shoes affects which jeans your brogues will or won’t work with, going from black at the formal end and getting gradually lighter towards the casual end will work best. Casual tan brogues pair well with indigo or lighter denim while other colors like oxblood and black will look good with black denim. As for cut, they’ll work for any cut of denim you wear, regardless of the length of jeans you wear.
You can pull off Oxfords with black or indigo jeans, as long as they’re slim, and either cuffed or hemmed with no break so they’ll feel a little more casual, but still sleek and polished.
Loafers & Penny Loafers
The penny loafers’ low vamp (that’s the section of upper that covers the front of the foot) combined with a wide leg opening can make your feet look weirdly stubby. So opt for jeans that are tapered and cropped or pin-rolled. As for colors, we love a medium brown pair that goes well with dark wash indigo but can also be paired with any lighter colors up to white denim. Black penny loafers will look great with gray or indigo denim.