Can I Wear These Shoes With Jeans?

What are thooose? They’re tackies

What are thooose? They’re tackies

While we might think of jeans as just a comfortable go-to wardrobe staple for casual, comfortable weekend looks, we shouldn't forget that they're a surprisingly versatile pair of pants. Chinos and joggers have both made a play for pride of place in our rotations, but jeans are still the number one choice for all but the most formal of affairs. You can't really go wrong with a good old pair of denims. Or can you?


Well yes, you really can. And the most common way for guys to get it wrong is selecting shoes that are entirely wrong for the jeans in question. Wear shoes that are too smart and you'll look like an Inbetweener trying to get into a posh nightclub. Wear them with sandals and you'll look like a tourist. And those are just two examples of many.


Finding the right footwear to go with your favourite jeans can be a challenging task. From choosing the right style for your desired look to choosing the colour that will best compliment your outfit, getting it spot on isn't always easy. Luckily this isn't an unnavigable minefield, you just need to read the map. What map? The one I'm about to give you that will guide you to what pairs work with what pairs.


Derbies & Oxfords


While jeans are still technically considered "workwear" the list of occupations that will allow you to wear them to work is not a long one. The closest many will come to manual labour is hammering a keyboard. So even though you might wear leather shoes to work, there's a very clear incongruity between a pair of polished Oxfords and selvedge denim. You could pull off Oxfords with a very smart pair of black jeans worn with no turn-ups (it has a casualising effect), but Derbies, which are a little chunkier than Oxfords, are far better for counterbalancing denim. When choosing a pair of Oxfords or Derbies to wear with smart jeans don't be afraid to get creative. While black and brown styles are classic, navy and burgundy options can create a unique and seriously stylish aesthetic.




Brogues are a relatively casual smart shoe, even if that is a bit of a contradiction in terms. As a general rule, minimally detailed brogues will lend themselves more towards formal looks and chunky, hole-punched brogues are more suited to casual outfits. Colour is an important consideration that affects which brogues work with which jeans, going from black on the formal end and gradually skewing lighter as you reach casual. Relatively casual tan brogues will pair pleasingly with a pair of smart indigo denim. Bonus points for coloured laces.


Monk Straps


While not popular as they were a few years ago, monk straps are still a very solid option, combining some of the formality of Oxfords with a little swashbuckling casual. Again, silhouette and shade are important to consider. There's something inherently Italian about a pair of mid-brown monks with a light blue pair of jeans. Don't forget to take your outfit pic for Instagram and tag it ‘PittiUomo'.


Penny Loafers


A shoe that looks stylish with almost anything, including denim: penny loafers are a versatile Ivy League staple that has found a newfound love among the Insta generation. Tread carefully, though. The low vamp of a loafer (the bit that's missing on top of the foot) combined with a wide-legged jean can make your feet look small and stubby so go for a pair of tapered jeans and roll them up.


Minimalist Trainers



It's very hard to get it wrong with minimalist trainers; they work with almost everything (don't try it with a tux). Sleek, low profile white trainers will match up well with almost all styles of jeans – except bootcut. With white minimalist trainers, the main thing to remember is to make sure to protect them and keep them clean. So invest in stain protector and pin roll those pant legs so that the dye from the denim doesn't stain your shoes.


Dad Trainers


The recent resurgence of dad trainers has come in conjunction with a similar shift in peoples attitude to denim – chunky is once again funky. To get the look right, opt for a straighter, wider style of denim with a higher rise and preferably in stone wash. You'll be daddy cool in no time at all.


Chelsea Boots



Black leather Chelsea boots can skew almost as formal as Oxfords, and therefore risk jarring with straight-legged indigo denim. Wear them with skinny black jeans and suddenly you're in an indie band. The big thing to consider with Chelsea boots is the heel – if it's stacked then you really do need to go for the tighter variation of denim that comes with musical connotations. On the other hand (or foot), a crepe sole takes some of the daintiness away, making them more tonally appropriate with other styles of jean.


Desert Boots


Suede desert boots feature softer uppers and soles than other styles of footwear, but they're still pretty rugged. Able to take a beating and look the better for it, desert boots can be worn with anything in the right set of circumstances, but almost always work well with jeans, smart or casual. There are no real rules here but a good tip is to roll the jeans a little to flash a little more boot-flesh.


Work Boots



Chunky work boots match up well with wider-legged denim; overly slim or skinny jeans, on the other hand, will contrast too harshly, which may well be your desired effect but you're not going to fool anyone into thinking you've done a days work in your life. Also unless you're going for that skinny–stacked look, your jeans will need to be cut a little shorter or rolled up. If you really want to get that vintage lumberjack look then go for a single oversized cuff.

Patrick McLoughney