How to Look Good in Dress Shoes and Jeans

by Jamie
Sometimes the clothes do not make the man

As the lines of smart and casual become exponentially blurred, the features that constitute a traditionally ‘formal outfit’ simultaneously seem increasingly vague by the season. Wearing formal shoes with jeans is commonplace now, but if you’re not feeling overly confident, here’s an idea of what works.

Outfit Inspiration: Jeans and Dress Shoes

While mixing casual denim and smarter dress shoes doesn’t seem like one of the most natural of pairings, when done correctly it can make for an exceptionally versatile smart-casual outfit. If you’re looking for something to wear to work, a restaurant, a family event or all three – pairing jeans and dress shoes can become one of the most practical foundations for said outfit.

However, before you grab your brogues and start to try and pair them with your best straight leg jeans, remember the importance of shape, material and colour. We’re not saying you have to carefully analyse each piece of clothing before you match them together, but throwing things together could end in disaster. Check out some outfit ideas below so you know exactly how to get it right every time, along with a selection of some of the best men’s casual dress shoes.

Brogues with Jeans

Okay, we’ll start off with the obvious choice. Chances are you’ve worn your best brogues with a nice pair of straight cut jeans before. When pairing brogues with jeans it’s quite important to consider the cut and how extreme you make the contrast between the jeans and your shoes. Jeans that are too loose or overlapping around the ankle will undermine your shoes’ detailing.

Best Jeans to Wear with Brogues:

  • Slim Fit Jeans: If you want to create a clean, sophisticated look keep your jeans slim line and pair them with some classic lace-up brogues.
  • Cuffed Straight Leg Jeans: For a simple outfit that’s easy to throw on, and flatter a range of shapes, get yourself a classic pair of brogues in tan and team them with some straight leg indigo jeans. Roll the denim up a little at the cuff or hem for a nice colour transition.
  • Skinny Fit Jeans: For a bolder look that’s a little more streetwear focused, try pairing some skinny jeans with your brogues. You can keep the look more subdued by ensuring your brogues are slim fit and match with the fit of your jeans.

Loafers with Jeans

Although you can wear your loafers whenever you want, they’re generally better suited to the warmer months, so try planning out how they’ll work into your summer denim lineup before purchasing a pair.

The best jeans to wear with loafers are ones that show the shoes off. Anything that falls too low down will only drown out your loafers and create a sloppy look. Loafers need to be seen in order to compliment your outfit, so keep your jeans at least a centimetre away from the top of your shoes.

Best Jeans to Wear with Loafers:

  • Tapered Jeans: As you’ll want to showcase your loafers, a pair of tapered jeans will draw the eye to your shoes – perfect.
  • Skinny Fit Jeans: Skinny jeans are ideal for creating a clean, streamlined outfit, and, if you’ve got the legs for it, you can easily cuff your skinnies to help emphasise your loafers even more. Try a simple look with a pair of indigo or black jeans and brown shoes, like leather penny loafers, for an understated vibe.
  • Slim Fit Jeans: Much like the skinny jeans, slim fit jeans will keep the overall look tidy and push the attention to your feet – which is exactly what you want. Depending on the cut, as always, you can opt for a pin roll to highlight your shoes further.

Monk Straps with Jeans

The monk strap has truly found its footing, mainly in higher end fashion, and it has become a seasonal staple in the last couple of years or so. With a wide array of takes on the style, you’ll probably want one of the less fussy takes on the shoe in order to compliment, rather than compete with, your jeans.

For something as unique as monk shoes it’s important to get the appropriate legwear to match. They’re detailed, but also slim lined and have an elegant finish, so any jeans that are too loose or chunky are just going to clash with the look and ruin the overall finish. A good option for these shoes are;

Best Jeans to Wear with Monk Straps:

  • Skinny Fit Jeans: The slim fit, alternative style of skinny jeans will match well with the less conventional colouring of the shoes, and is great for making a subtle, yet modern statement with your clothing.
  • Tapered Jeans: A dark pair of tapered jeans with some cuffed detailing at the bottom would go great with a pair of leather dress shoes, with the sleek shape of both of them easily complimenting one another.
  • Slim Fit Jeans: As with the styles above, cuffed slim-fit jeans will sit nicely with any sort of smart footwear.

How to Look Good in Dress Shoes and Jeans

  • The most important thing to consider is the fit of the jeans. Different styles work well with different shoes.
  • Slim fit is the preference, and if possible a cuffed bottom will always look the best and not swamp your footwear.
  • The colour of the shoes important, it needs to compliment your outfit not completely contrast it.
  • Keep the shoes clean and you’ll have a smart dress shoe and jeans look.

On That Note

Why exactly is this such a tricky look to get right? Well, it’s a look that has to carefully combine both smart and casual elements. The dress shoe, designed and crafted to perfection as a finishing touch to a suit, has to match up with a pair of jeans, the original symbol of casual style. It’s a balancing act. Get it wrong, and you’re crawling back to the comfort of the walk-in wardrobe (we wish) with your tail between your legs. But get it right, and it could be your new favourite look.

Feature image from Pinterest

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