12 Old Money Summer Outfit Ideas For Men

Outfit 1: Preppy Chic

First of all, I do want to say sorry for not tying my shoelaces. I noticed they were untied after I finished taking the pictures.

Even though I’m using four colors here(if you count the sweater) it doesn’t look like a mess thanks to all the colors being neutrals and muted. When you build a wardrobe around these tones, you can create endless combinations that look good without even having to think about them.

The polo shirt is from Hugo Boss, and I simply love the color. It’s breathable and the fit is probably the best part. The pants are from H&M and they look good with sneakers(not so much with loafers). The reason for this is that they are cropped. The shoes are an everyday essential from Cole Haan.

Outfit 2: Weekend Getaway With A Navy Polo Shirt

If you’re wondering about the background, the picture was taken at Fuerte San Cristobal in Gracias, Lempira, which is an old fort in my home country, Honduras.

It was a sunny day, and I decided to wear a a navy polo shirt from H&M with a pair of beige pants. I added the white sneakers to be as comfortable as possible, while remaining stylish.

Outfit 3: Preppy Casual Outfit

I thought I wasn’t able to pull off a “preppy” look, but then I reminded myself that I have a telenovela name (Roger Esteban). That made it much easier for me.

Again, here I’m wearing the light blue polo shirt from Hugo Boss with the same pair of H&M beige pants from the last outfit with my beloved white sneakers from Cole Haan.

Outfit 4: Night Out Outfit

I wear loafers when I’m trying to be more stylish and I know I won’t be walking a lot. This photo was taken at a Sushi restaurant with amazing food: Nacion Sushi.

Now, let’s get back to the outfit. The polo shirt is one I can’t recommend enough. It’s from U.S. Polo and even though it’s quite affordable, I’ve had it for a long time now and it hasn’t just retained it’s color, it also keeps it’s shape. The trousers are from Perry Ellis, and the loafers are from a brand called Robert Wayne.

Outfit 5: Summer Days In A White Polo Shirt

A white polo shirt is a summer essential. It’s more elevated than a t-shirt and more comfortable than a dress shirt. When you add the fact that white reflects light and doesn’t absorb it, you end up with a summer shirt capable of withstanding the hottest days. To top it off, I also included a light-colored pair of beige pants from H&M and a pair of tan loafers.

This white polo shirt is right now one of my favorite items in my wardrobe, it’s made of 100% cotton and I simply love the fit. I’m wearing a size a slim fit size S. Tommy Hilfiger receives a lot of backlash, I haven’t tried many of their products, but this polo shirt and a baseball cardigan I bought a couple of months ago have been great purchases.

Outfit 6: Red Polo Birthday Outfit

This one is a bit of a stretch when it comes to the old money style. The polo is in a color called “Nautica Red”. As a quick bit of background, I decided to wear it for my birthday dinner with friends. However; I’m including it in here, because I muted the rest of the outfit by pairing it with black pants from Perry Ellis and loafers from Cole Haan.

Outfit 7: Old Money Smart Casual

To be honest, I don’t know if Old Money smart casual is even a thing. If it is, this outfit perfectly resembles it. It uses neutral  light colors and pieces that can help you withstand extreme temperatures and high humidity, like what you’d find in my beloved hometown, San Pedro Sula.

The difference between this look and outfit 5 is the white sneakers and the sunglasses, which make it more comfortable and convenient.

Outfit 8: Ivy League?

This will be another one of my go-to summer outfits if it’s over 100 degrees Fahrenheit (38 degrees Celsius) and I have to go outside. Keep in mind that there are very few places with air conditioning in my hometown, so I usually skip any type of sweater. This one was to achieve a preppy vibe.

The navy pants are from a brand called Manhattan, I bought them at a retail store in my home country years ago and haven’t been able to find them online since. They’re the most breathable pair of pants in my closet, so if you find the brand anywhere, please let me know.

Outfit 9: Coastal Old Money Outfit

We’re bringing the light blue polo shirt back and mixing it with the navy pants for an old money look that’s comfortable yet stylish, with just a bit of color. One thing I haven’t mentioned about this polo shirt is that it’s made of 100% Pima cotton.

Outfit 10: Green Shirt Look

This is actually one of the most saved “Old Money Outfits” on Pinterest. Obviously, not my image, but another guy wearing the outfit while taking a mirror selfie. You’ve probably  seen it by now if you’ve searched for “old money outfits”.

For this one specifically, I’m bringing back the gray pair of trousers. They are an essential item in every wardrobe. However, be careful with this pair during the summer.

What’s new with this specific outfit is the Olive Green Polo shirt from Nautica, a neutral color that you can mix with almost anything in your closet. I do have polos made from higher-quality cotton, but olive green is a color that  I don’t often. I usually spend more on items that I’ll wear multiple times.

Outfit 11: Making The Light Blue Polo Preppy(again)

If we are talking about summer, this is an outfit I recommend for an event during the day like a brunch. where you’ll be in the sun a lot but don’t need to walk much.

The loafers are a comfortable pair of dress shoes, though not as comfortable as white sneakers. I added the crewneck sweater to give the outfit a preppy touch, but to be honest (again), I wouldn’t go near a sweater with a ten-foot pole in my city during the summer.

Outfit 12: Business Casual Old Money Look

Fun fact: I took this picture at Sunglass Hut while trying on this pair of sunglasses.

We’re bringing back the white Tommy Hilfiger polo and styling it with a black pair of trousers from Perry Ellis and an almost perfect pair of black loafers from Cole Haan.

The colors are neutrals. The fit of the whole outfit is amazing, and I simply love the style. This outfit is a timeless classic you can wear now or ten years from now, and it’ll still look good.

Outfit 13(Bonus): Knit Polo Old Money Look

Fun Fact: This is the first church outfit I ever took a picture of. I did a GRWM that you can find on both the Tropa Uno Pinterest and Tik Tok accounts.

For my final act(outfit), I’m adding texture to elevate the look. This knit polo is comfortable and breathable. I’m wearing it on a sunny day with a lightweight pair of navy pants and white sneakers.

I even wrote a blog post featuring six different outfits styled with this same knit polo shirt.

The knit polo is from H&M and I couldn’t recommend it enough.

Disclaimer: If you want to support my work, you can buy any of the items I’m wearing using the affiliate links and I might receive a small commission.

Old Money Style Basics

The old money style is all about muted colors and timeless pieces. Even though the term “old money” has been trending for a couple of years now, the style has always been around.

Here at Tropa Uno, I try to keep most of the outfits timeless. That’s why, up to now, it’s the only trend I’m willing to style. The items are versatile and work for a wide variety of looks. A navy polo, for example, is an essential you can wear in many different ways.

Investing In Quality Pieces

The old money style is also about buying less, but getting high-quality pieces that will last a long time. Some of the clothing you’ll see me wear in this post is quite affordable like the Nautica polos, but they are 100% cotton. Quality doesn’t mean each item needs to be expensive. Two of the four pairs of pants and two of the polos are actually from H&M.

Don’t Forget About Fit

Some of the items you’ll see me wear are off the rack, while others are tailored. It all depends on how they fit my body when I buy them. For the old money style, fit is key. You have to wear clothes that fit you well without being baggy or skinny.