03 - How to Style-Down Dress Shoes
Making classic footwear fun ðª
I have a bit of a love-hate relationship with classic dress shoes. On one hand, they are beautiful works of art, the artifacts of superior craftsmanship. On the other, they are completely useless as far as footwear goes.
Dress shoes simply have no function in my wardrobe: I dress casually at all times, mostly leaning toward denim and street wear. I also tend to wear a lot of color and have some fun statement pieces in my collection.
Itâs a bit of a situation. So, through a lot of trial and error I figured out a way to make formal (and formal-ish) dress shoes work for me. This guide summarizes my approach.
It wonât work for everyone, but I hope reading it could inspire you to experiment.
The basics: colorful shoelaces and socks
Ditch the black. I mean it. The absolute easiest way to make formal dress shoes more fun is to play with color, and swapping black shoelaces and socks for something more exciting is a straightforward way to do so.
Shoelaces:
Shoelaces could tie your entire look, not just your shoes.
Try going for something bold and high-contrast. Think white, red, cobalt blue, or mustard yellow. The key is to match the color tone of the laces to the color of the leather, and find the appropriate level of contrast.
Pro tip: Experiment with matching the laces with other elements of your outfit, such as: socks, gloves, scarf, pocket square if you wear one, bracelets, watch strap, hat or cap. Thereâs A LOT of creative opportunity here.
Socks:
Fun socks are underrated, and we have four variables to work with here: color, texture, print, and cut. Start experimenting by going for something simple, like single color socks. My go-to options are white, red, orange, and neon yellow; all other colors are a fair game, too.
There are no rules for finding what feels right.
You can then try different textures and prints to see what works best with the outfit. The key is balanced contrast: you donât want the outfit to look too busy, and you also donât want it to look like you worked too hard putting it together.
If your overall outfit leans minimalist, go wild with the socks and make them the statement piece.
If youâre already wearing a lot of patterns up top, choose socks that complement them instead of competing for attention.
Last but not least: Footsies arenât just for loafers. You can show some skin with any other type of classic shoe, even the Churchâs oxford.
The interplay between shoes and textured clothing
Matching dress shoes with textured clothes creates a cozy casual feel.
Denim: Raw denim, especially aged and beautifully faded, contrasts well with the slick dress shoes. You can also cuff the denim and add a relaxed shirt or a tee for a modern look.
Knitwear: Chunky knit sweaters and cardigans bring warmth and softness that offsets the rigid vibe of dress shoes. Opt for neutral tones and tonal dressing for a sophisticated yet relaxed outfit.
Chinos: Lightweight chinos (especially in pastel or earthy tones) are a natural match for dress shoes. You can level up the look if you pair them with a rolled cuff and no-show footsie socks for a summer look.
Pro tip: You may find yourself looking a bit too preppy by following the last advice. If thatâs not your jam, opt out of pastel colors by going for something bolder, and make sure to avoid polo shirts.
Tonal Dressing: stealing from K-fashion
Monochromatic, or tonal dressing is a trick inspired by Korean fashion, and it works super well for styling down dress shoes.
The idea here is creating a sleek, cohesive look by matching pieces from a single color palette. The common options are grey, beige, navy blue, but other tones could also work well.
This approach works because tonal simplicity shifts the focus toward the textures and details of your outfit, including your shoes.
A simple example is pairing suede Oxfords with chinos and a matching linen blazer in varying shades of khaki creates a relaxed yet refined vibe. Add a tonal knit sweater for depth, and youâre good to go. Tonal dressing allows the material of your dress shoesâwhether itâs smooth leather, rough-out, crosshatch finishesâto shine without distraction.
Experiment with textured leathers and patterns
Not all dress are made from smooth leather. Consider adding a bit of funk to your footwear collection and get a pair or two (or as many as youâd like, really) of shoes and boots with interesting textures.
Some ideas to get you started:
Crosshatch leather: The most subtle option on this list, it has a rather understated finish which still manages to add a layer of sophistication.
Suede and Rough-out: Matte textures bring a casual vibe to dress shoes. The most accessible option here is suede. Most brands sell suede shoes, and this type of leather goes well with casual stapes like cuffed denim and chinos.
You can also opt for a more rugged rough-out or waxed suede leather (e.g. Waxy Commander from C.F. Stead tannery). Hereâs an example:
Bonus point: With time, waxed suede and roughout leathers develop unique patinas that add lived-in, cozy flair to any look.
Exotic Leathers: Materials like bison, shark, or ostrich can add a ton of character. To make things even more interesting, shoes made with exotics often develop an incredible patina over time, further enhancing their look. Thereâs a seemingly infinite variety of options here, so I wonât go in further detail. My only advice is to get familiar with the types of exotics out there and find the leather and textures that youâd really love to include in your footwear rotation.
Spectator Shoes: With their contrasting panels, spectators offer a playful yet classic twist. Pair them with cropped pants for a street-ready vibe.
Proportions and Exaggerated Features
Playing with proportions can completely transform the feel of dress shoes. Certain styles, like Paraboot Michael derby, have accentuated features that lean more casual.
The chunky soles and relaxed stitching on these shoes match with oversized or cropped pants, creating a bold and streetwear-friendly yet surprisingly balanced silhouette.
(This combo, by the way, is a staple on many menâs fashion Instagram accounts from Japan and Korea.)
You can easily pair these with a loose-fitting blazer for a Korean-inspired look. If youâre going for street style, though, a relaxed bomber jacket or an oversized hoodie could add an edgy urban twist.
Adapting dress shoes to fit street style
To me, the most exciting thing about street style is that you can mix high fashion, business, and hyper-casual DIY and vintage clothing to create an eclectic flavor thatâs unapologetically your own.
Thereâs no right or wrong here, and the best approach is to experiment. That said, I feel obligated to give you a few starting points:
Combine blazers and graphic tees: Go liberal with a bold graphic tee and combine it with a tailored blazer and slim trousers. Your dress shoes could then ground the outfit and provide structured elegance. Donât forget to add interesting laces, though.
Look for vintage clothing: Raid the next vintage faire you can find and try finding unusual pieces that could work with your shoes.
Accessorize: Add a crossbody bag, a miki hat or a bucket hat, or bold jewelry to inject an edge into your look.
Custom Patina: Make It Personal
Nothing styles down dress shoes quite like a well-worn, custom patina. Hereâs how:
DIY Patina Projects: Strip your leather shoes of their factory finish and apply your own layers of dye. You can go classic with rich browns or go bold with a tri-color gradient. Think deep burgundy fading into navy, for instance.
Wear Your Story: A natural patina developed over time is just as striking. Scuffs, wrinkles, and color variations tell a story of miles walked and moments lived. Embrace it.
Professional Services: Not into DIY? Look into artisans who specialize in custom patinas. They can transform your shoes into a personalized work of art.
About KÅbÅ Mono
KÅbÅ Mono is a blog about quality boots and shoes.
Itâs currently run by one person: me. (Talking about myself in a third person has never felt more odd.)
Itâs a place to connect with the fellow footwear enthusiasts, share what I work on, and build a community.
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And since weâre at it, I want you to know that my long-term dream is to start a shoe company. Weâll see how that goes.
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