How To Match Dress Pants With Shoes

The Biggest Mistake Men Make When Dressing Up, Revealed

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Wearing a suit can be stressful. If you’re not the type of guy who wears a full suit to work every day, then chances are you only wear one a couple times a year for special occasions. Personally, I’m lucky to have a chance to wear a suit once a year. Since the Dom Perignon Incident of ‘07, I don’t get invited to many weddings anymore.

That means, at least for me, every time I put on a suit it feels kinda like the first time. I have to re-remember what the hell I’m doing every time I dress up. What tie goes with what shirt? What belt goes with what watch? Am I supposed to wear socks? And the most difficult choice of all is what shoes to wear, and how to match ‘em to dress pants. But does shoe choice really matter that much? Can’t you just pick something general that goes with everything?

No. A resounding no, you cannot.

If we know that shoes make the outfit, and that the color choice is as important as the style of shoe, then we’ve got some serious planning to do here. But not all pants are created equal. Each type of trousers, be they khakis or pinstripe dress pants or jeans, need individual treatment. They’re unique and they deserve to be treated as such. There’s no silver-bullet solution for shoes that go with everything. You need to adapt.

Sounds complicated, right?

Don’t worry, my guys. I’m putting this issue to bed once and for all. I did some research. I looked into it. And now I know how to match dress pants with dress shoes. And guess what — I’m about to show you how, too.

We’ll start with styles of pants, and what to wear with ‘em.

Khakis

Khakis are the most forgiving and casual of dress pants. There are a few major no-no’s to avoid, and a few sure-things to shoot for. As with anything in style, feel free to break the rules and make things your own. But if you’re not sure where to start, take a peek here.

Wear With: Loafers

The most chill option for a semi-formal setting; loafers slip on, can be worn with or without socks, and give off a certain calculated laziness. The perfect vibe for an outdoor party or non-black-tie wedding. Match sand colored khakis with rich cognac loafers.

Match Mens Khakis, $39.99 at Amazon.com

Rockport Loafer, Starting at $47.76 at Amazon.com

Wear With: Oxfords

A classic, easy option, Oxfords always look good — you could pair ‘em with jeans as easily as with dress pants. By the way, oxfords should always have an almond-shaped toe. Wear olive khakis with oxblood oxfords.

Enimay Mens Pant, $44.99 at Amazon.com

Wholecut Oxford Plain Toe Diablo Antique, $265.00 at AceMarks.com

Dress Pants

The step in between khakis and a full suit, 4-pocket dress pants can be tricky. You don’t wanna go too casual, nor do you wanna overdo it. I’ll give you two options here, whether you wanna dress ‘em up, or dress ‘em down.

Wear With: Monk Straps

Monk straps look fancy but are surprisingly easy to wear. Monk straps, especially double-monks, give a snug and comfortable fit and look super sharp, plus they are actually quite versatile. Match black trousers with black monk straps.

Frank + Oak Trouser, $60.00 at FrankAndOak.com

Calibrate Double Monk, $99.90 at Nordstrom.com

Wear With: Penny Loafers

For a more casual look than monkstraps, opt for penny loafers. Again, you can wear this with or without socks, but if you’re gonna go sockless make sure to crop those trousers high. That’s an adventurous look, to be sure, but very distinctive and fashion-forward. Wear navy trousers with tan penny loafers.

Frank + Oak Trouser, $65.00 at FrankAndOak.com

1901 Penny Loafer, $89.95 at Nordstrom.com

Full Suits

There’s a ton of options to run through in terms of suits, but we’ll just touch on a few for the sake of brevity. Matching shoes to full suits could be its own article, maybe its own book — but we’ll just get to the meat of the issue here.

For A Classic Navy Suit

Try a navy wingtip with a navy suit. I know that probably seems a bit crazy, but here’s the secret to making it work: contrast-color socks. That’s it. You just need to break up the lines of your outfit a little with your “color story.” That means blocking things off and making the lines of your suit apparent with little pops of color.

Frank + Oak Pant, $90.00 at FrankAndOak.com

Ted Baker London Wingtip, $129.90 at Nordstrom.com

For A Slick Pinstripe Suit

Pinstripes, if not worn carefully, can vibe mobster, ancient Italian man at a funeral, or snake oil salesman. If you go too flashy on your footwear, you run the risk of vibing like Don Corleone. Which is a look all in itself, but chances are you don’t wanna scare people at your cousin’s wedding. Even if his name is Vinny.

Lots of dudes would go for a high-gloss oxford or monk strap here. I’m gonna advise you go with a more muted derby shoe here - that’s how pinstripes become “distinguished” instead of “delinquent.”

Historical Emporium Trouser, $75.95 at Amazon.com

Cole Haan Derby, $139.90 at Nordstrom.com

For Formal Occasions

Unfortunately, for truly formal black-tie occasions, you don’t really have any choice. You gotta wear formal shoes. If you’ve got a tux on, these are expected.

I know, I know, you were expecting a hot take from me on how to break the rules of black-tie dress. It can’t really be done, guys. If you’re expected to wear a tux, there’s expectations about your footwear too. Don’t play games with this one.

Neil Allyn Tuxedo Pants, $35.00 at Amazon.com

Calibrate Loafer, $89.95 at Nordstrom.com

For A Fashion-Forward Look

As long as the event you’re attending isn’t a super-formal black tie type of thing, you can play around with these rules a bit. If you’re feeling adventurous, try a these options with a full suit for a head-turning and somewhat eccentric look.

Guess Chelsea Boot, $58.50 at Amazon.com

Clarks Moc Toe Derby, $125.00 at Nordstrom.com

Blazers & Jeans

Wearing a blazer with jeans is the most forgiving look to match footwear with. You can almost do whatever you want here — I’d be inclined to wear sneakers with a blazer and jeans.

Wear With Sneakers

If you’re at an event or situation that allows for so casual a look as a blazer with jeans, you can definitely get away with sneakers on-foot.

Frank + Oak Pant, $65.00 at FrankAndOak.com

PUMA Sneakers, $70.00 at FrankAndOak.com

Now, like I said — these rules aren’t unbreakable. But they’re a great frame of reference if you need a starting point.

Formalwear is super complicated. But it doesn’t have to be difficult — and if you recall just one thing from reading this, remember that rules are there for a reason - but they’re meant to be broken.

Do your thing, wear what you’re comfortable in, play with trends, and give a nod to the classics, and you’ll be all set.

Related Reading

How To Swap Out Your Sneakers For A Pair Of Equally Chill Dress Shoes

The 5 Types Of Dress Shoes Sure To Snag You The Corner Office

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