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Pairing Jeans with Shoes Stylishly

WHEN IT COMES TO top-quality fabrics, there’s no doubting the versatility and durability of denim. In the form of jeans, it has earned its spot as a global wardrobe staple for myriad reasons. One of which is its ability to pair effortlessly with a wide range of footwear.

Below, you’ll find eight of the most stylish pairings, listed from casual to formal, so you can begin to explore new denim and footwear pairing possibilities.


1. Chunky sneakers

This is a classic combo, but be wary of the very real and very dangerous sartorial monster looming just below the surface. That monster is #normcore (or #dadwear). In order to avoid falling victim to the trend, stay away from looks that pair sneakers with baggy, light-washed jeans. Keep your denim dark and your shoes, well, non-trainer-ish. These picks are a great start:


2. Canvas or slip-on sneakers

Canvas sneakers and slip-ons are trimmer than their aforementioned chunky cousins. Just make sure that the sole on your kicks is kept as white as a dentist’s veneers.


3. Boat shoes or loafers

Boat shoes shouldn’t be overly clunky or feature an ostentatious color. Keep things simple and classic, and wear ’em with a pair of dark, slim-fitting (not tight) jeans for a *onehundred emoji* outfit every time.

Loafers are undeniably sleek, and break the barrier between kinda formal and now-we’re-gettin’-fancy workwear. If you keep things subtle (and sueded), a loafer will give off a consciously relaxed vibe. Colorwise, stick to shades of brown and tan. Anything that creeps into the darker end of the spectrum will look hella tacky. (Kinda like using the word hella…)


4. Chukkas

These typically come in leather and suede, but brands like Native have begun to design chukkas in high-tech fabrics (like the single piece of microfiber pictured above).

Regardless of the material you opt for, recognize that chukkas are critical to any decent footwear collection. And if you’re worried about giving off Deadwood vibes, go with a darker boot to offset Wild West associations (and even make your footwear a bit more formal).


5. Dress boots

Think of these as the chunkier, more rugged version of traditional wingtips. And stick to the four styles listed below when wearing with denim:

2. Cap-toe (pictured)
3. Wingtip


6. Monkstraps

Monks are probably the most underrated member of the dress shoe family. They’re a classic, very masculine option which, despite their clean design, will add a lot of personality to your look. It comes down to the simple fact that not many dudes wear ’em. Monkstraps make your look distinct, but not in a weird, yellow-latex-body-suit-from-a-fashion-week-runway kind of way.


7. Wingtips

This is the classic dress shoe-and-denim pairing. Add a crisp button-down and blazer for an easy, no-fuss ensemble suitable for a first date (as well as the business meeting before it).

When wearing wings with jeans, your best bet is to stick to brown. Black wingtips (and black shoes in general) are tough to pull off with denim. Lighter colors make details like burnished leather, perforations, and texture more visible, and keep you from looking like a 55-year-old Eastern European man who enjoys creeping on 20-year-old women at an all-inclusive resort in the Dominican Republic (no offense to our friends overseas, of course).

Plus, given that brown wings are bound to work with just about everything you already own, you’ll get more wear out of ’em than any other shoe on this list.

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