Brogues and a suit. Boots and jeans. Some pairings are so obvious, we instinctively choose them as we get dressed.

But what if we could throw all rules out the window, choose a completely unexpected pair of shoes for every outfit, and come up with a refreshing look that just works?

Today, I’m going to give you three different pairings; these are shoes and outfits you never thought could work together.

Think outside the box before saying, “But, but… the rules say that you can’t…” Keep an open mind and realize that inspiring, unique personal style is often found by breaking the rules.

First, what is High / Low style?

High / Low style is the idea of mixing formal pieces and casual pieces together in one outfit. I explain it in more detail in this article.

An alternative definition of High / Low style would be mixing higher-end, luxury items with more affordable things, e.g. Levi’s denim with a Tom Ford blazer.

I tend to use it more when referring to casual and formal garments mixed together according to the Spectrum of Style Formality. That’s what I’ll be doing in this article going forward.

All the shoe examples I show you here are from M.Gemi.

I first discovered this brand when my wife, Kate, showed me a pair of shoes she really wanted. I checked out the website and loved how well-designed everything was (and honestly, at the time, I wondered why they weren’t doing men’s shoes).

A few months later, they released a men’s line. I was an instant fan.

They have a well-curated selection of sharp looking footwear that covers the spectrum from casual to formal. You’ll see a few of my favorites below.

M.Gemi partners with the best family-owned Florentine factories to carefully handcraft their shoes before bringing them straight to you. This means luxury-level, top-tier construction without the usual middleman or store markup.

True, this direct-to-client method is becoming more common.

But what I like about M.Gemi is they combine that feeling of being a hip, of-the-moment brand with the care and quality of Italian craftsmanship, while sticking to the classic silhouettes that will be relevant for years to come.

Thanks to M.Gemi for being a part of this article and for being generous enough to hook you guys up with a sweet offer. Just click here to shop M.Gemi and receive $40 off your purchase.

Ready to see some of these shoe and outfit combos?!

Let’s get into it.

1. Sneakers with a suit

M Gemi sneakers

BUY THE NETTO LEATHER SNEAKER »

Here’s how to make a suit work with sneakers.

Sneaker style: You have to wear the right kind of sneaker. No, your old Asics cross trainers that used to be white but are now some disgusting color of tan/grey won’t work.

A sport-specific silhouette or style doesn’t work as well as a pair of understated, minimal, non-sporty, leather sneakers.

Leather or suede is best: Remember the Spectrum of Style Formality I always refer to? In general, sneakers are on the casual end of the formality spectrum.

But you can increase their perceived formality. Choose a more luxe, upscale version made with better materials, like leather and / or suede. Also, keep its styling minimal and free of in-your-face logos.

Your suit has to be tailored perfectly: If you have a frumpy, old-fashioned suit that doesn’t fit well, wearing sneakers with it won’t make you look stylish. It’ll only make the whole outfit even worse. So focus on having a perfectly-tailored suit first.

The more casual your suit, the better this pairing works.

Jackets with casual details (patch pockets, for example) and fabrics (hopsack, twill, corduroy, nappier wools) also work better with sneakers. Though that’s not to say your standard all-season worsted wool suit can’t pull it off.

Chino suit with sneakers? Easy.

Double-breasted, pinstripe power suit? Not so easy.

What you wear with your suit also determines how much the sneaker and suit pairing works. Suit + polo? Sneakers fit right in. Suit and shirt sans tie? Sneakers fit in with that look, also.

Lastly, a suit with a trendy, slim, modern silhouette tends to work better with sneakers compared to a traditional, full-cut suit.

2. Military-inspired boots with trousers

M. Gemi boots

BUY THE GROTTA BOOT »

Military-inspired combat boots are more rugged and casual than a brogue dress boot or sleek chelsea.

But that makes it perfect for your high/low outfit. It’s a shoe choice people would least expect!

Go with leather: A tough leather boot provides great contrast to a well-tailored trouser. If your trousers are a bit cropped and show off more of the boot, even better.

No polish? No problem: The point of wearing boots is to reinforce that high / low vibe. So if your boots are a little beat up, don’t worry about it.

Speaking of trousers: Thicker, more casual trouser fabrics work best, e.g. wool flannels, tweed, moleskins, and corduroy.

I prefer a tapered leg, or even a straight leg so long as there is no break.

3. Double monks with denim

M. Gemi monks

BUY THE MAESTRO DOUBLE MONKS »

I’ve always looked at dub monks as a bit dressier than regular brogue lace-ups, though purists believe it’s very much the opposite (less formal than brogues).

In any case – you like the double monk shoe. You know you can wear it with formal getups. But you want to know how to wear it casually, too.

There’s a good chance you’ve dressed up denim before, but here’s a bit of a refresher, just in case.

Your jeans should be slim and fitted to you – nothing baggy. No break works best. Stacking, i.e. having extra fabric pooling by the ankles, does not.

Dark, raw denim tends to go better with double monk strap shoes (both brown and black leather).

There is room to experiment, because it also depends on what you’re wearing with the rest of the outfit. But the fail-proof choice is always going to be dark, raw denim.

Both brown or black monks can work. My favorites are brown leather with a burnished heel and toe. And while they have a unique silhouette, wear them as you would your other brogues.

Finish off the outfit with your favorite dress shirt and sport coat, or OCBD and sweater… the look possibilities are endless.

Brogues with denim, too

M.Gemi brogues

BUY THE TAPPO CAP TOES »

The same idea extends to your other leather dress shoes as well. You can wear brogues with your favorite pair of denim, if you’re more of a laces guy over buckles (which you have with the dub monks).

I prefer the balance of high / low / high in this case. You balance the overall look by finishing the outfit with dressier details up top. Something as simple as a tucked-in dress shirt and a shawl collar sweater or sport coat would be perfect.

Imagine your outfit from top to bottom: high (shirt and sport coat), low (denim), high (brogues or double monks), similar to the first image in the series below.

You can also go the opposite way, wearing more casual details up top that complement the “low” denim choice (like the middle photo above).

The important thing here is to utilize the Rule of Three. Having another layer in addition to your shirt and pants (shoes don’t count) is an easy way to add visual interest to an outfit.

So a sweater, sport coat, military jacket, shirt jacket… these all count as your third piece. Take a look at the outfits above and see if you can identify the third pieces.

As you can see, there’s no right or wrong way to put together an outfit when starting with denim and brogues or denim and double monks. Try it out and see what you come up with (and share it with us in the comments!)

4. Bonus! Drivers or Loafers with shorts

M. Gemi Drivers

BUY THE VELOCE DRIVER »

M.Gemi penny loafers

BUY THE GIRO GOMMA LOAFER »

What do you normally throw on your feet when you’re wearing shorts? I’m going to assume sneakers or flip flops.

Next time, take your casual outfit up a notch by wearing driving shoes or loafers instead of sneakers. This “high” detail instantly elevates your whole look, even if you’re just wearing (well-fitting) shorts and a T-shirt.

I prefer loafers and drivers in a light-colored suede. Typically, you’ll be wearing this in warm weather. Go with a neutral tone, something like sand or light grey.

Your shorts must fit well. The leg should be slim and fitted (though not tight or restricting), just like your pants.

The ideal length depends on your proportions. But at the longest, they should end right in the middle of your kneecap. To me, above the knee (like the examples in this series) looks best.

To balance the “low” shorts with something “high”, throw on a sport shirt or OCBD instead of a T-shirt.

Which look is your favorite?

Guys, don’t forget to pick up a pair of M.Gemi shoes (and one for your lady, while you’re at it!) to complete the outfits just like you see above.

All new customers will get $40 off their first purchase, just click the button below 🙂

CHECK OUT M.GEMI »

So, tell me: Which ones do you think you can’t pull off? Why or why not? Tell me in the comments.

Learn a few shortcuts to dressing well

Enter your first name and email, and I'll send you a free eGuide with quick and easy tips you can use today.

PUBLISHED December 15, 2016


Barron is a Lean Wardrobe Advocate and Founding Editor of Effortless Gent. He's from San Francisco but currently living in New York. Connect with him on Instagram, Facebook, Pinterest, Twitter, or Tumblr.



  • Joseph Padilla

    Hmmm… How about black leather jacket outfit with brown leather shoes?

    • For leathers, I’d stick to one color, either black or brown.

  • Charlie Brown

    Mixing formal and informal is tricky, because it can go hugely wrong. Useful tips on jackets (casual details and fabrics). And the loafers look great with shorts. Thanks for sharing all the pictures.