If I’ve been invited to an event or a workplace, there are two words in the dress code that can make my heart soar: smart casual.
I’ve never been able to enjoy the constricting feeling of a tie, and I’m always concerned about staining or damaging my clothes when I’m dressed up, and above all: I feel more like myself when I’m not too formal.
Smart casual is the ideal dress code because dressing well is a way to show respect to those around you, but if the level is as low as “smart casual” then you’ve still got plenty of room for self expression and comfort in the way you dress.
You’re also wearing long pants, which means you get to wear the greatest footwear of all: boots.
Can You Really Wear Boots in Smart Casual Outfits?
Some guys hear “boots” and think of work boots like Red Wing and Chippewa, but remember that the word “boot” basically just means leather footwear that covers your ankles, and in a world of endless menswear choices, there are countless models that pair perfectly with the collared
The key to picking a smart casual boot is to go in the opposite direction of chunky, protective workwear: you want boots that are sleek, low profile, and made with a high quality leather.
Fortunately, I’ve spent years flying all over the world investigating every type of boot there is — I even made some myself in Guatemala, but that’s another story.
My point is that you’re in good hands, here. When it comes to casual-but-not-too-casual, there are five kinds of boots that are ideal choices.
The Best Smart Casual Boots
There are no meaty moc toes here! In this list we’ve assembled a few kinds of lace ups and two laceless models that all have their own pros and cons. The bonus: every one of them is available in several leathers, so you can find a smooth black or a more casual tan to suit your needs.
1. The Chelsea: Thursday Boots’ Cavalier Chelsea Boot
Is there any better boot than the Chelsea? Once you’ve spent a week wearing these, you’ll wonder why you ever bothered futzing with laces.
The Chelsea’s only real downside is that it can be hard to find a very casual one that’s easy to wear with torn jeans and a t-shirt — but that’s why it’s just right for smart casual.
Thursday Boot Company has a huge range of boots and that includes three kinds of
With an almond shaped toe and flat sole with recessed lugs, this model actually rose to become the brand’s bestselling Chelsea — even though it was meant to be “the dressy one.”
Why? Because it looks like
The suede called “Sandstone” is the bestseller because suede dresses a boot down, so when it’s combined with a slimmer boot you’ve got one of the most versatile options around.
I’d certainly recommend it for smart casual affairs, but there are also two smooth brown leathers that you might find easier to take all the way to business casual as well.
Whichever leather you choose, you’ve got a resoleable boot for under $200 — extraordinarily rare.
2. The Service Boot: Grant Stone’s Diesel Boot
The term “service boot” refers to lace up boots that are lower profile than your chunky work boots, and while there are plenty of service boots with round, informal toes, Grant Stone has mastered the genre of “smart casual.”
Chief among their models is the Diesel, a plain toe model with a flat sole and impeccable finishing.
They’re pricer than Thursday, but this brand has risen to the top of the food chain among the internet’s most discerning boot aficionados for their excellent quality control, sturdy feel, and world class leathers.
The Diesel comes in just about every color and leather you could want, including ostrich and kudu (a kind of antelope) but for smart casual you’re better off with one of the suedes (sourced from the world leader in the stuff, England’s C.F. Stead).
Or you can choose from their array of Chromexcels, sourced from Chicago’s Horween Leather Company and arguably the most popular and beloved boot leather on Earth.
3. The Chukka: Clarks Desert Boot
If you ever spent much time on r/malefashionadvice, you’ve probably come across the smart casual mantra of “OCBD + CDB” — an oxford cloth button down
The reason they’ve become the default option is their comfort and their great price, which is usually about $150.
They can’t really be resoled, but these unstructured chukka boots are enormously comfortable and, surprisingly, they achieve a low price despite also being made with C.F. Stead suede.
Expect great shock absorption from the crepe sole but if that’s too casual for you, you can try the Evo model and its sturdier rubber sole for just ten bucks extra. You’ll soon realize why this is the boot that made the Clarks brand.
4. The Wingtip: Allen Edmonds’ Hamilton Wingtip Dress Boot
While the term technically refers to the extra long toe piece that extends down to the midfoot, wingtips are typified by broguing: the little holes dotted around the boot (or shoe) that were originally intended to help water run off the surface.
That’s because wingtip boots started as outdoor wear for traipsing around the English countryside, and it was once unthinkable to wear them anywhere that called for attire deemed “smart.”
Today, though, wingtips have swung all the way around to the other end of formality, and it’s not uncommon to see guys wear them with a suit and tie.
My opinion? That’s too formal for wingtips, but they’re dynamite in smart casual and business casual environs.
Allen Edmonds’ bestselling Hamilton boot is made in the USA, resoleable, bottomed with the world famous Dainite rubber sole, and comes in an astonishing ten different widths.
Paired with chinos and a button down or polo
5. The Jodhpur: Beckett Simonon’s Douglas Jodhpur
Jodhpurs are a fantastic way to stand out from the crowd without being ostentatious — and that’s the kind of balance that most guys like.
With your trousers falling to your ankle, jodhpurs will look more or less like you’re wearing Chelsea boots, but Jodhpurs are so much more.
With origins in the Indian city of Rajasthan, Jodhpurs have a strap of leather encircling the ankle that allows them a far superior fit to Chelsea boots, and Beckett Simonon’s Douglas is one of the brand’s bestsellers.
You’re able to pick them up in one of five leathers, and they stand out on this list by being made with a construction called the Blake stitch. Unlike the Goodyear welt, which is common on boots, a Blake stitch makes a boot lighter and more flexible.
You sacrifice a bit of the water resistance, but we think it’s worth it — especially because it’s also cheaper to make, causing these boots to come in at $259.
Just note that Beckett Simonon also keeps their prices down with a made to order model, meaning you’ll wait a few months for your boots to arrive.
Their reputation is rock solid, but if that’s too long to wait then you can always try similarly priced models from Meermin or Thursday.
Why “Smart Casual” Outfits Literally Make You Happier
In fact, research suggests that smart casual may be the “best” mode of dress for self perception. What do I mean? Well, researchers at Virginia’s Old Dominion University surveyed 50 people with a series of questions intended to reveal how different levels of dressiness influenced their confidence, self perception, and behavior.
Predictably, they found that you feel better about yourself in casual clothes than loungewear, and “dressy casual” (their term for smart casual, laying between casual and business casual) makes you feel better still.
But what’s interesting is that smart casual ranked higher than business casual or business professional. Respondents felt better in smart casual outfits than in any other level of dressiness — except for formalwear. Fair enough, every guy feels himself when he’s dressed way up.
My theory is that if you’re business casual or business professional, you’re likely following a dress code that’s been imposed on you and/or you’re at work. In either case, you’re not doing what you want to do that day.
Whatever the cause, smart casual means you’re still able to express your individual style while hitting a balance between comfortable and put together.
Wrapping Up
Whether you’re heading into a casual office or a dressier backyard barbecue, these options will get you there with style and comfort. After all, being able to combine the two is the best part of smart casual — that and the approving looks of your peers.
