After you invest in a nice pair of dress shoes, you want to show them off! Sport them on the streets, in the office, on date night and while running errands. Your favorite leather shoes don’t need to be stored away for special occasions; they can be easily paired with jeans for everyday use. 

Get the most out of your leather dress shoes with these styling tips.  

First, choose your look. 

Are you dressing up for an important occasion? Are you trying to look sharp for a business meeting? Or maybe it’s the weekend and you’re keeping it casual. What you’re dressing for will help guide your next decisions. 

Second, pick the wash and style of your jeans. 

Choose the wash of your jeans. If you’re opting for a more formal look, stick to darker-washed jeans. If you’re running errands or out on the weekend, faded and/or distressed jeans are suitable.

Men’s jeans come in a variety of styles which are classified by the fit and leg. An important rule to remember when pairing dress shoes and jeans is to never pick a baggy or loose style fit. 

Luckily, there’s a variety of different styles to choose from. 

  • Slim fit jeans are a good match for your dressier days. They have a tapered waist and are a low-to-medium rise. 
  • Regular fit jeans are the classic style pants with a straight leg and cut naturally at the waist. 
  • Skinny jeans are typically low rise and are tight throughout the glute, thigh and leg. 
  • Straight cut jeans are exactly as they sound, straight throughout the thigh and leg. 
  • Bootcut jeans are wide at the bottom so they fit comfortably over a boot. 

Next, put your outfit together.

Casual Outfit

Combine any regular fitted, faded or distressed denim with a pair of low-top leather sneakers. Throw on a nice t-shirt for a stylish, yet laid back look. Add a cuff to your jeans to elevate the outfit. 

Leather boots are great for casual wear. The distressed Brewer’s Boot in Copper offers a rugged texture to enhance your outfit from bottom to top. Pair these boots with slimming boot cut jeans in your preferred wash, and you’ve got a trendy look for the weekend. Opt for the Brewer’s Boot in Oxblood if you’re looking for a more polished version of this outfit for a night out.

Business Casual 

For a tasteful business casual look, pair your dark washed, slim fitting jeans with a crisp button up shirt. Loafers and derbys are appropriate shoe options for this type of outfit. The natural leather sole of the Brown Westmorland Derby gives off a refined look with a casual touch. It’s the perfect option for everyday wear. Similarly, the Chocolate Suede Aberdeen Loader offers a contrasting natural leather sole. This shoe is a sophisticated staple for warmer weather.  

Don’t rule boots out of your business casual outfits. The Bedford Boot comes in three colors that are bound to enhance your look, no matter the occasion. Pair the premium pebbled calfskin Country Calf Bedford Boot with your favourite dark wash jeans and a knit sweater for a fashionable look during colder months. 


The York Oxford in either black or brown paired with a dark, slim or skinny fit jean will help you exude a stylish, put together outfit. This wingtip oxford portrays class, while being a touch casual with its intricate broguing detail. Throw on a tailored sports coat with this shoe and denim combination, and your outfit will surely turn heads and get the attention it deserves. 

Finally, how do you wear your nicest pair of black leather shoes with jeans? Slim fit, black denim jeans paired with either the Black Beaverbrook Oxford or Black Director will radiate an elegant and polished look. To elevate this look even further, check out our recent post on how to achieve the ultimate mirror gloss shine on these shoes. With a collared button down and a suit jacket, this outfit makes you look absolutely debonaire.  

Hopefully these styling tips encourage you to take your leather dress shoes out of hiding! Think about the occasion you’re dressing for, decide on the wash and fit of your jeans, and then match your shoes accordingly. Add some personality to any outfit with your favorite pair of patterned socks. 

There’s a denim and dress shoe combination for any occasion! Let’s see yours.

Adriana Spragg