A Gringo’s Guide to Dressing Better, Style, and Fashion in Latin America

I never expected to write an article about style and fashion in Latin America for the average gringo. It just wasn’t on my radar.

I dress pretty well while traveling, but I’m no fashion blogger. My style isn’t bad, but I’m certainly not stepping up to the Cuban drug dealer look anytime soon.

So, why the article? Well, because someone asked for it.

So, you want a little style advice from Papi Rubio?

After creating a piece about not looking like a gringo bum while traveling around Latin America, I got a request for specific style advice for men traveling down south.

And I figured why not. I’ve been in the region for years, I know what works down here, and there’s no doubt I know what doesn’t.

Below, you’ll find everything you need to know about dressing better as a gringo traveling around Latin American countries like Colombia, Peru, and Mexico.

From timeless fashion tips to specific pieces of clothing that chicks dig, I’ll break things down for the typical traveling gringo who wants to avoid stigmas and stereotypes of the goofy gringo.

P.S: Jump to specific clothing recommendations by clicking here.

How to Dress in Latin America

Luckily, it’s pretty damn easy to dress well in Latin America. You really don’t need much. This isn’t New York City or Los Angeles. A little effort goes a long way here.

The custom suit might even be too much. For most gringos, your goal should simply be to NOT look like this:

I’ve rocked the goofy gringo look before, too.

This is the quintessential gringo look while traveling around Latin America. You’ve got the cargo shots, the flip-flops, and a soccer jersey or tank top.

If you’ve spent enough time in the region, you’ll come to recognize this look from a mile away. You know it when you’ve seen it. The goofy gringo travels all over Latin America – often in herds.

Now, rocking this attire while enjoying some time at the beach or even doing a little tourism in a warm city is perfectly fine.

The problem is gringos have taken this relaxed attire a little too far. Nowadays, you’ll see dudes rolling around major cities like Bogota, Colombia or Lima, Peru looking like scrubs.

Whereas locals are in pants and a button-down, some even in a suit, the gringo is strolling around like he’s at the beach in cities of 10+ million people. Cities that are the capital of said counties filled with business people and hard workers.

It’s not a good look. Unsurprisingly, many Latinos think gringos are complete and utter slobs.

Think about it. If people from different countries came to your city by the thousands and every single time you see one of them on the streets they look like they’re hungover and headed to the beach, you wouldn’t hold a high opinion of them, either.

Instead of rolling around looking like a slob, follow a few of these rules and you’ll soon be seen as the best-dressed gringo many a Latino has ever seen:

  • Wear Pants: Seriously, if you wear pants in public, locals in Latin America will give you more respect. They’ve seen enough of the cargo shorts and swimming trunks from foreigners. A decent pair of jeans during the day is all you need to impress.
  • No Flip-Flops: First off, flip-flops are horrible for your feet and ankles. Second, they look sloppy unless you’re going to the beach. I’ll never understand why gringos walk around in flip-flops so damn much. Just don’t do it unless you’re at the beach or pool.
  • Normal T-Shirts: Tank tops, soccer jerseys, and those weird “hippy clothing shirt” things are typical for the traveling gringo to roll around in while traveling in Latin America. Instead, just wear a normal v-neck or henley t-shirt in a basic color during the day.

    Common sighting in Peru.

Basically, you want to look like you would back home. Think about how you would dress if you went to the library while at university or the coffee shop with a friend. Think how you would dress for a first date back home.

Just dress normally. Don’t come down to Latin America and become a scrub just because you’re a few miles away from home. That type of effort and attitudes gives gringos a bad name all over the region.

A Gringo’s Guide to Dressing Better, Style, and Fashion in Latin America

Now, we’re getting to the good stuff. If you want specific style advice while traveling Latin America, here it is.

Below you’ll find what you need to know about dressing well in Latin America and standing out from the gringo crowd in a good way.

While I’m no fashion blogger, here’s a little bit of specific advice about fashion in Latin America and how the average gringo can dress better:

Shoes For Travelers

They say shoes make a man and I cannot disagree. Just by not wearing flip-flops, you separate yourself from the gringo herd.

But there’s more to it than that.

If you want to look damn good while you’re living and traveling in Latin America, here’s what shoes and footwear I recommend:

  • Sperry Sneakers: I’ve worn this pair of Sperry’s for years. I think I’ve had three different pairs. Latin girls love them for some reason and I regularly get compliments on them, which is odd to me – as they’re a basic pair of shoes. These are my daytime shoes. I wear them to coffee shops, co-working spaces, and more. They look good with jeans.
  • Thursday Boot Company: I’ve worn this pair of boots by Thursday Boot Company for the past few years. They look impressive with a pair of dark jeans or nice travel pants. Plus, they’re durable as hell. One pair will last a couple years when properly shined every couple weeks while living in Latin America. Oh, and you’ll get compliments on them. Trust me.


 Jeans and Travel Pants

You should get used to wearing pants while traveling in Latin America. Even when it’s hot as Hades outside, Latinos will wear pants. Hell, even when you start sweating the minute you step outside, people in Latin America will still wear pants.

It’s the culture. Unless you want to stick out like a sore thumb, and not in a good way, you’ll want to wear jeans or pants most of the time while living in the region.

Here are a few of my favorite jeans and travel pants:

  • Outlier Slim Dungarees: These are the best pair of travel pants I’ve ever seen, worn, or even heard of. They’re seriously awesome. Pricey, but awesome. I found them ideal for walking around during the day in Latin America, as they’re somewhat lightweight and you don’t get overheated.
  • Hudson Jeans: I’m a huge fan of Hudson Men’s Jeans, especially the darker washes. They look great while on a date or partying at night and match well with t-shirts and button-down. You can even dress them up with a blazer and look pretty damn stylish.


T-Shirts, V-Neck, Henleys

It’s super easy to dress better than the average gringo in Latin America during the daytime. Just wear a normal looking t-shirt, v-neck, or short-sleeve henley. Most travelers wear tank tops or scraggly soccer jerseys all day.

So, let’s dive in. A few of my favorite travel t-shirts include:

  • prAna Men’s V-Neck: For those who don’t like merino wool, the prAna men’s v-neck is the best travel t-shirt I’ve found. This shirt looks damn good. After wearing my heather grey prAna v-neck for years, I can attest to the style and durability of their products. Highly recommended.
  • Woolly Clothing Merino Wool Short Sleeve Henley: I have three of these merino wool travel shirts. Currently, I don’t travel with any other “t-shirts” while on the road. The Woolly Clothing Merino Wool Short Sleeve Henley looks fantastic and offers numerous benefits for travelers. I can’t recommend this product enough.

P.S: Read my full post of the best travel shirts here. 

Rocking that short sleeve henley in Cali, Colombia. 

Long-Sleeve Shirts

Generally, Latin America is a fairly warm region. You really don’t need too many long sleeve shirts unless you plan to go hiking in cooler regions often.

As such, I typically only bring one long sleeve shirt with me while traveling Latin America. I recommend you do the same. No reason to overpack. Packing light is always packing tight.

Here’s my favorite:

  • Woolly Clothing Merino Wool Long Sleeve Henley: I’ve been wearing this long-sleeve henley all winter and it’s been fantastic. The Woolly Clothing Merino Wool Long Sleeve Henley is warm and it looks damn good. If you’re looking for one long sleeve shirt to pack, this should be the one.


 Dress Shirts

I’ve met more than a few gringos who didn’t have a single button down in their backpack while traveling around Latin America. Only t-shirts and tank-tops. That’s fine and dandy, but not exactly ideal when trying to look stylish.

Plus, in many cities throughout the region, you’re not getting into a decent nightclub without at least a button down shirt on. T-shirts and sneakers aren’t flying at Lima Bar in Miraflores or Hotel V in Zona T.

Now, the style of button down you wear is a little more varied than other clothing items. The type of dress shirts you wear will be determined by your age, physique, hair color, skin color, and more.

So, it’s a bit difficult to give specific examples of dress shirts. But I’ll do my best.

Generally, one-color shirts or pattern shirts fair well in Latin America. Think sharp business attire or full-on Cuban drug dealer swag.

I often just rock a slim-fit white dress shirt when partying in Latin America. Just something basic like this:

It’s essential to unbutton as many buttons as possible.

Upper-class Latinos often like to rock one-color dress shirts that have a business or professional vibe. Mimicking that style tends to work damn well and looks great, especially in nightclubs.

The Cuban drug dealer look is also popular in Latin America. What do I mean by the Cuban drug dealer look? Well, it’s generally chino pants and a printed button-down shirt. Occasionally, they’ll rock a blazer.

Think about what Pitbull would wear during a Miami winter. In my mind, it’s something like this:

Cuban Drug Dealer 101.

Printer dress shirts like the one above fair well in Latin America, especially when mixed with a clashing color of paints. For example, you wouldn’t wear that shirt with jeans. You’d rock chino pants with it.

Here are a few other buttons downs that would look good in Latin America:

Jackets and Blazers

In many Latin American locales, you won’t have any need for jackets, blazers, or suits. In other places like Bogota, Colombia, some nicer clothing really comes in handy from time to time.

While I won’t give any specific blazer recommendations, as that’s too specific to the individual, I will say that military-style jackets seem to get a great reception here. I rarely bring a jacket, but when I do it usually looks like this:

Hard to see it.

I don’t see a ton of leather jackets in Latin America. Honestly, they just don’t seem to popular here. I can’t say I’d recommend leather down here.

Instead, bring something like this if you’re going to spend some time in a cooler, big city in the region.

Jewelry and Accessories

The accessories a man wears is pretty personal and it’s a bit difficult to give specific advice. But there’s one thing I’ll say about wearing accessories, watches, and jewelry in Latin America:

Don’t wear anything you’re not willing to lose.

Or don’t flash your status and wealth with jewelry. That’ll only lead to more problems than it’s worth. Trust me.

Don’t rock your Rolex in Colombia. You don’t need to bring your gold chain to the Dominican Republic. It’s just unnecessary.

With regards to specific style advice, most gringos in Latin America rock some bracelets they bought while traveling. This can actually look pretty decent when paired properly with a decent watch.

Speaking of watches, I recommend wearing something like this while traveling through Latin America:

Watches like these look great and sophisticated but aren’t something you worry about too much if you get robbed. This is a major key in Latin America, the most dangerous region in the world.

You can definitely rock necklaces and earrings down here, too. Although, I’d say the watch and bracelet combo is by far the best way to go.

Oh, and sunglasses are a must. I usually just buy a knock-off pair of aviators from a street vendor for $5-6 USD when I arrive. No reason to spend big bucks on them, as they’ll probably get lost while you travel.

Gym Attire

I’ve gotten more hate for wearing basketball shorts to the gym than any other fashion faux pas in Latin America. Seriously, I’ve found Latinos absolutely hate baggy basketball shorts with a passion.

I even had a girl offer to take me shopping for proper gym clothing, as she was so turned off by my Jordan shorts and high-top Nike shoes.

Many people in gyms throughout Latin America dress pretty well. Stylish track pants are common and name brands are always found. This is especially true in nice gyms, like Smart Fit or Body Tech.

Personally, I can’t be bothered to overpack on fancy gym clothes, but I did ditch the baggy basketball shorts and cutoff t-shirts.

In Cali, Colombia. Boardshorts still a little too baggy, but I’ll live.

These days I travel light, so a pair of trainers, one merino wool tank top, and a few pairs of board shorts is all I rock these days.

Here are a few gym attire recommendations for Latin America:

  • Chuck Taylors: These are ideal gym shoes while traveling because they don’t take up a lot of space in your luggage. Plus, Chuck Taylor shoes are stylish in the gym. Couldn’t recommend these enough.
  • Boardshorts: While boardshorts are not as stylish as track pants in the gym and look a little gringo beach bum, the benefits far outweigh the downsides. Boardshorts from brands like O’Neill look great and can be worn in the gym, to swim, and more.
  • Merino Wool Tank Top: I’m wearing a merino wool tank top in the photo above. It looks great in the gym and holds up during a good sweat. I love the Woolly Clothing tank-top and highly recommend it.
P.S: Read my full travel tank-top review here.

Beach Wear

As a gringo, you instinctively know what to wear to the beach. You shouldn’t need my advice on this one. Plus, no one is really going to judge you for what you wear to the beach down here.

I typically just wear a travel tank-top I’ve bought locally, some boardshorts, and a pair of Reef sandals.

Pretty much like this. Santa Marta, Colombia.

Socks, Underwear, Etc.

No need to get too detailed here, as locals won’t really see your socks or underwear if you’re wearing pants while living and traveling in Latin America.

Well, some will 😉 But that’s a whole different ballgame. Literally.

With packing light and looking tight in mind, I’m a huge fan of merino wool products, especially socks and underwear. Thus, I suggest grabbing items like:

Going the Extra Mile: Getting Custom Clothes Made in Latin America

Last, but not least – I want to talk about one simple way to truly take your style to the next level in Latin America and back home.

What’s that? Getting custom clothing made while traveling.

Now, this may be above your pay grade or interest level, but it’s still worth talking about. In Latin America, you can get custom dress shirts, blazers, and suits made for rock bottom prices.

You just have to know where to look and how to find the high-quality craftsmanship.

I’m certainly no expert in this regard, but many of my buddies have gotten custom suits, blazers, and shirts made for pennies on the dollar compared to back home.

The quality is impeccable and the fit unbeatable. You can get fully customized suits created for $200-400 USD in places like Bogota, Colombia.

A custom cut dress shirt, made from a material you selected out of hundreds, only costs anywhere from $40-80 USD.

Stunning blazers handcrafted to your specific size often only cost $120-150.

If you’re into style and fashion, consider getting custom clothing made in Latin America. You’ll find prices 50-80% cheaper than back home and the quality is comparable.

Just make sure you search for custom clothing in big cities known as financial capitals of their country. Things Bogota, Colombia or Mexico City.

Also, remember that a good tailor isn’t going to turn around your suit or shirts in one weeks time. You’ll usually need to give them 2-3 weeks to finish your clothing, although a little bribery goes a long way here.

A Gringo’s Guide to Fashion in Latin America

Whew, that was a long one. But I wanted this post to be thorough. I wanted to give you an idea of exactly how to dress while traveling around Latin America.

I want my fellow gringos to look damn good.

Just remember – I’m no fashion blogger. I’m just a dude traveling around who puts an effort into not looking like a slob.

It’s pretty easy.

Drop the cargo shorts, flip-flops, and tank-tops. Just wear clothing like you do when you’re trying to look presentable back home and then add in a little Cuban drug dealer swag.

Y ya. Ahora, te ves bien, marica!


P.S: Don’t forget to check out the best travel shirts before you go. Just click here!
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Jake D

Travel junkie turned blogger. Location independent. From the Midwest, but often based in Latin America. Big on beaches, rumba, and rum. Addicted to the gym. Committed to showing a different style of travel - one that involves actually interacting with locals and exploring different cultures.

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Kris Cantu - October 6, 2018

Great article Bro! I’ve been slowly changing my dress code here in SE Asia from cargo shorts/cut-off beer tee’s/joggers to more stylish dress.

This article helps solidify the idea that I need to stay away from the typical “farang” dress code and instead bear the heat here to wear jeans and proper shirts.

I bought a custom suit here for around $320 USD and got 4 custom shirts made. They fit great! Pennies on the dollar.

Look forward to more guides like this. I think next winter I’ll be hitting up South America and will reference this blog often.

Thanks Jake!

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