Versatile Shoes You Can Dress Up Or Down

I get told a lot that I am the “master” of pairing tailored jackets with jeans. I’m not sure if that’s true (people who say that probably haven’t seen @NOBD’s masterful mixing of tailoring with denim, chronicled over many years), but what I do know is that a major element of getting it right is having versatile shoes that work with both tailored and casual clothing equally well.

My footwear choices have settled into a pretty small rotation of shoes and boots that get tons of wear through regular rotation. As always, the major motivational forces behind my choices are versatility and maximizing the dollars I spend. I have settled on the shoes I own because they can be dressed up or down. So I thought I’d share with you the guiding principles I use when deciding what shoes to buy or wear. Before moving on, let me say I am not a sneaker guy, so I have no related guidance to share in this post.

First, here are some basic characteristics I look for in a shoe, with a brief explanation:

  • The less shiny, the better.
    • See this painful WAYWT post from 2011 to understand how I arrived at this point. With denim, a shiny dress shoe just looks like you changed out of your suit but forgot to bring a change of shoes.
versatile shoes styleforum

Kids, don’t do this.

  • The only exception to this rule is shell cordovan. I can’t explain why it works, but it does. #8 Alden tassel loafers were practically invented for selvedge denim, in my opinion.
  • Texture is good!
  • You can’t go wrong with suede, generally.

    • These two go hand-in-hand, but obviously there are textures aside from suede that can work well with denim that aren’t too rugged for tailoring. Pebble grain stands out in my mind as an excellent variation of calf leather that holds just enough surface texture for jeans. Boots in Chromexcel or other matte finishes can work with tailoring, too, but that will often depend on the overall design (e.g. Doc Martens are a no-go with tailoring, but a more classic wingtip boot might).
  • Brown, basically all the time
    • Not that this point needs to be made on Styleforum, but black is usually best reserved for more formal fits. One exception is black suede, which can look great with black jeans as well as gray trousers. The only black shoes I own are black cap-toes, which I reserve for dress wear. However, I think black suede can look awesome with charcoal or mid-gray trousers, as well as dark denim.
  • Not too pointy, not too roundy
    • Super pointy shoes look weird with denim. I think it’s because more pointed shoe lasts tend to feel refined and elegant, which clashes with the ruggedness of denim. The line between too pointy and reasonably pointy is fuzzy, though. Christian Kimber’s last shape from his collaboration with Eidos a couple winters ago had an aggressively tapered toe, but on a chukka boot with a commando sole in dark brown suede. It looked good with slim denim, but I’m not sure it would look good with a wider cut, including a 501-style silhouette. And of course, many Texans swear by pointy cowboy boots with denim (which I can fully get behind).
    • On the flip side, you can’t go too rounded in toe shape if you hope to dress them up. In my mind, a Clarks desert boot looks right at ease with chinos or jeans, but is too round for use with dressier fits, so it fails my versatility test. Somewhere in between these extremes is the range I tend to stay in.

Here are some general, holistic rules to consider:

  • Pointier, daintier, shinier shoes look good with trousers and suits, but not as good with denim or chinos. The blucher style can be dressed up or down more easily than the balmoral style, as can loafers. Thin soles with a narrow welt feel more dainty to me—though some ballsy folks have rocked Belgian loafers with denim to great effect.
  • Rounder, more rugged, more textured or suede shoes look good with denim, but weird with trousers or suits. Ankle boots like chukkas, jodhpurs or chelseas can work with dress trousers as well as denim, but that look does best when the hem is on the shorter side so they don’t have too much of a break. The same goes for higher boots. For both types of boots, just make sure the last shape “toes” the line (heh, get it?) between too pointy or too rounded.

Finally, here are some personal notes that build on the above points:

  • Did I mention that suede looks good with nearly everything?
    • Dark brown or snuff suede is universally attractive and will never look bad. At this point, I pretty much only wear suede dress shoes. Penny and tassel loafers see wear most of the year round, with chukkas and jodhpurs added in the colder months. I only wear my calf double monks and black cap-toes every couple weeks or so.
  • Pebble grain calf leather is the next best thing to suede for dressing up or down.
    • I’ve been eyeing some pebble grain tassel loafers, and am perennially attracted to Scotch grain long wings. 
  • It’s good to have a pair of ankle boots or pebble grain shoes with rubber soles.
    • Boots with a Dainite, commando, or other rubber sole are a must for rain and wintry slush.
  • There is one other pair of shoes I own that gets more wear than all the rest of them combined, but which I don’t generally wear with tailoring: the canoe moccasin. It’s a far more casual shoe, and something I wear with shirt jackets, sweaters, or just with my shirt sleeves rolled up. Mine are beat-to-death Sperry’s that I suspect may be some of the Chinese knock-offs that are sold through Amazon. My favorite well-made ones are the Oak Street version, and I intend to get some of those at some point. On the other hand, it’s kind of refreshing that a two-year old, $20 purchase is still going strong and providing me with so much use.

What are your criteria for footwear that is versatile enough to dress up and down? Sound off in the comments!