Thanks for the Q, Thomas. I love a super tactical question, and this one happens to speak to a look I love.
Loafers, for sure.
And lace-ups… absolutely.
Not every pair of dress shoes is gonna look right with every pair of 5-pockets, and we'll get into that in a sec. But generally the answer is Y-E-S. Nothing steps up your jeans (or your overall appearance) like a great pair of dress shoes, either well-polished & cared for or perfectly beat up. (Well… other than a sport jacket.) But you get what I'm saying. It can really elevate you.
Indigo denim and double monks are always a safe bet.
There are a few reasons you might be entertaining this question:
1. You're on a work trip and you forgot casual shoes and you're going out at night and don't wanna wear your dress trousers or your suit.
2. Or it's a conscious decision to get some more combinations out of your kit. If you're investing in a pair of dress shoes, it's great to be able to get some wear out of them beyond formal or work situations.
First off, let's go through the options when it comes to jeans. Our internal inventory hierarchy refers to those (and their non-denim brothers, like canvas, corduroy, etc.) as part of a category called 5-pockets. (Think of the 5 pockets you see on a pair of classic jeans: two in the back, two in the front, plus the little coin pocket at the right hip.) Technically speaking, only denim 5-pockets are jeans. But I think the spirit of your question is about the whole family of 5-pockets. So the options we stock are classic denim, garment-dyed denim, corduroy, cotton canvas, canapa canvas, and super seasonal fabrics like moleskin and wool.
I think the easiest lace-up shoes to pair with jeans are bluchers. The ultimate crossover shoe. I wear these in a very dressy way with suits (you may have seen them with dress trousers and socks in last month's Hey Sid) but they also look awesome with a pair of jeans. Those are the only ones in the group that feel simpatico with short sleeves. Generally speaking, I would keep your sleeves long with the dressier dress shoes like double monks, cap-toes, and two-eyelet Gibsons. Rolled up is fine — I looooove to roll up my sleeves — but short-sleeved shirts suggest a level of casualness that doesn't hook up well with a pair of hard-soled, lace-up dress shoes. But yeah, the cap-toes and the Gibsons are a bit more limited in terms of potential jeans looks. (The hardware and heft of the dubs give them slightly more range.) I can't put my finger on it, but there's something weird about a polo shirt with a pair of cap-toes. Even if you add a blazer, it's a little weird. It really looks like you forgot your casual shoes or you’re a bit... unaware.
Speaking of third pieces like blazers — it can also be helpful to think about your outfits in terms of balance. A third piece like a blazer will help build some connectivity to a pair of formal shoes at the bottom. So if you're working your way up: a pair of cap-toes + a pair of blue jeans + a not-too-casual-not-too-dressy shirt like an oxford… adding a blazer at the top can help balance out the formality from the shoes. Almost like a sandwich. Even a sweater or a piece of outerwear can achieve the same thing. It makes you look more finished. (By the way, this principle works in reverse, too — a casual third piece, like a military or chore jacket, can help you tie in a pair of super casual shoes on the bottom, like camp mocs.)
I had a hard time putting the rest of my thoughts into words here, so here's a chart that outlines (or circles, rather) the combinations that feel right to me. As you can see from the annotations and asterisks, these rules aren't laws… just how I personally think about putting outfits together. it's not super cut and dried. And the level of wear on your shoes can introduce some further nuance… super beat-up, patinated double monks can lean more casual. The level of wear on those will make it feel better with, say, a polo shirt than a pair straight out of the box.
Your question made it sound like you're pretty comfortable with loafers and jeans, but while I was at it with my charts, I did the same exercise for those as well. Those are a lot more "anything goes" with 5-pockets and don't present the same incongruities as the shoes we talked about above. Short sleeves and jeans and loafers? All day long. Think James Dean or Michael Jackson. Handsewn pennies and a polo shirt with jeans are a triple match made in heaven. And I wear tassel loafers/jeans/sport jacket multiple days per week.
Hope this was helpful, Thomas, and that I didn't overcomplicate things with the chart. Unfortunately, I can go down a bit of a rabbit hole with stuff like this… quickly. Taxonomy is kinda my thing. But long story short, dress shoes with jeans can be very cool as long as you keep some sense of balance in mind. I guess that goes for most things. Wear in good health.
