How to Wear Dress Shoes with Jeans and Rules You Should Follow

Wearing dress shoes with denim is a great, smart casual look that can work in tons of different situations. However, there are some definite do’s & don’ts when it comes to pulling off this look with class. First off, let’s talk about the denim for a second. So, the jeans you choose should be a fairly dark wash with zero to minimal distressing.  This look does not work very well with light wash jeans with heavy distressing. Next, your jeans should fit you well and be the appropriate taper and length. Wide foot openings or excessive material puddling at your foot can really hurt the overall look you’re probably going for.

Now let’s get into the shoes.  I would absolutely stay away from formal dress shoes with a high shine, because it just doesn’t look right. Black shoes can work, but I’d go with brown because it’s so much more versatile and more casual. An Oxford from Allen Edmonds is perfect and you guys know how much I love these shoes. The color goes with just about anything and the broguing (the little hole punch outs) by nature make the shoe more casual.  You can also go with a pair of double monks like the ones in the video from Magnanni, but something like the whole-cuts from Beckett Siminon are a little too formal to pair up with jeans. Another slightly more casual option instead of an Oxford, is going with a Derby. Unfortunately, I don’t own any Dreby’s at the moment, but consider a Derby to be the little brother to the Oxford.

Here’s how you tell the difference.  On an Oxford, the leather that the laces pass through is essentially sewn closed.  On a derby, (see video for the example) these flaps are sewn on top of the vamp and they’re open at the base. That’s the basic difference between an Oxford and a Derby, with the Derby being the more casual of the two.

Loafers are another great option, but keep the shoe design in mind.  The more stuff or broguing on a shoe, the more casual it is. For example, a tassel loafer is more casual than a penny loafer.  Both are still acceptable though. Also, a brogue wingtip Derby is more casual that a cap-toe Oxford.

Lastly, if you’re going for the smart casual look, you’ll want to be wearing some sort of button down dress shirt.  The shirt can be just about any type of pattern, but the smaller or finer the pattern, the dressier it is. To really polish off the look, throw on a sport jacket. You’ll look like a million bucks.