Jeans and Shoes – Really?

Jeans and Shoes

By TrunkClub

“There was a pretty heated intra-office debate that raged on today about when it’s acceptable for a guy to wear dressier shoes with jeans. I submit that it is never acceptable. Care to weigh in?”

How to Wear Dress Shoes with Denim Trunk Club

Before getting into the Trunk Club–specific take on this issue, we passed Tyler’s question onto Bill White, founder of one of our favorite shoemakers, Scarpe DiBianco.

Here’s what Bill had to say:

“There are some rules that our fathers lived by such as you should always wear a black shoe with a black suit; loafers should never be worn with suits; etc. I do not adhere to many of these rules.

Our generation has evolved our lifestyle to where jeans are a staple in our wardrobes. I wear (jeans) every few days and absolutely wear a dress shoe with them, especially monk straps because the straps make the shoes very versatile, in that they can be worn both casually and dressy.

Dress lace-ups are a bit trickier if the toe is very plain or the color is very conservative. I generally opt for lace-ups that have a pebble grain, interesting medallion on the toe, or a more fashionable color.”

We previously said that for a blazer to work with jeans, both garments need to match in terms of texture. That’s exactly what Bill is saying here regarding dress shoes. In order to look good with jeans, dress shoes need texture.

Just as we discourage guys from wearing smooth suit jackets with jeans, we also advise against wearing jeans with smooth, high-gloss footgear. The next image shows a denim / shoe pairing that we would avoid.

Why would you steer guys away from wearing these black monk straps with jeans?

Dress Shoes with Jeans

Michael Barkin (Trunk Club Director of Sales): There’s only one plane of color, no burnishing or anything like that. More casual shoes will have texture to them or burnished leather, or a matte finish. These shoes have none of those things. There’s just a high-gloss finish. There’s no texture here, unlike what you’d see with something like pebble-grain leather, which can absolutely be worn with jeans.

For a good example of pebble-grain leather, see the shoes in the first image in this post.

Trunk Club has said that, despite its preference for brown shoes, there’s a time and a place for black shoes. If these monkstraps don’t work with denim, could they work with something else?

Jason Smith (Trunk Club VP of Product): They would be fine with a black or gray suit. But even with a gray suit, brown shoes could still be an option.

On the other hand, these brown monkstraps seem to hit on all the points that Bill from DiBianco talked about.

DiBianco Monkstrap Shoes Trunk Club

Jason: Absolutely. They’re exactly what Bill was describing. In fact, the first time I met Bill, he wore these shoes. They have everything. There are highs and lows in the finish; they’re burnished; and there’s broguing. All those elements create the texture that makes them work well with denim.

There’s broguing with these shoes too. Anything else that provides texture?

How to Wear Dress Shoes with Denim

Michael: The leather is really well worn. The toe is kind of a reddish brown but as you get closer to the ankle it’s almost a chestnut color.

We mentioned in our last post that Michael isn’t shy about dipping into his legendary velvet-slipper collection. Why do these work with jeans?

Velvet Slippers Jeans Trunk Club Blog

Michael: Velvet is textured, just like denim. The profile of these slippers is no different than any other low-vamp loafer, like a driving loafer. The profile is exactly the same. This is a way to dress up any casual outfit, more than you could with a driver or suede moc.

Note: The monograms on this particular pair of velvet slippers are tributes to Michael’s wife and newborn son.

Monogrammed Velvet Slippers Jeans Trunk Club Blog

To answer Tyler’s question: As is the case with almost anything style-related, wearing dress shoes with jeans can be done, if done correctly. Texture is the key.

 Like any of the looks you saw in this post? Trunk Club has no shortage of jeans and dress shoes that play nice together. Just let your stylist know what you’re looking for. Who is your stylist????

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