13 Old Money Summer Style Essentials (2026)

So, what does Johnny Agnelli, JFK, Alain Delon, and James Bond have in common? The answer, all four of these timelessly stylish men loved wearing the Johnny collar. Now, what's a Johnny collar you may ask? It's a no-button open collar found on polo shirts, in particular knitted polo shirts. And that, gentlemen, is the first old money item on today's list, the knitted polo shirt. Now, if you know your style history, you know the polo shirt has been around for over a hundred years. Made popular to the masses in 1920s by Rene Lacoste, it was refined by the Italians in the 1930s when they came out with the first knitted polos. Now, a good knitted polo is going to be relatively lightweight, anywhere from 12 to 16 gauge. Gauge, of course, being the number of needles per square inch. Another characteristic of a great knit polo is going to be a fully fashioned construction. This is where it's knitted to shape, so seams lie flat. And overall, it gives the garment a more elegant drape. Now, as mentioned, a lot of times you'll see the stylish Johnny collar, but on occasions with more casual versions, you'll see one, two, and three buttons as well. Now, you'll find these shirts are often ribbed at the hems and the cuff, which overall creates a subtle waist suppression and a more tailored silhouette around the arms. As for the fabrics, you can see anything from a plain weave to vertical ribs or even tone-on-tone vertical stripe. But as a rule, most knit polos aren't going to really have much, if any, branding. As to why this is a classic old money garment I think should be in every man's wardrobe, well, first up, texture hierarchy. A fine gauge knit sits above any cotton t-shirt and just below the tight weave we'd see on a poplin dress shirt. It has an elegant collar that frames the face. The fabric almost always has a bit of a drape and sometimes even a bit of a sheen. And, of course, the heritage association with tennis clubs, yacht decks, spy movies, and titans of industry. Now, speaking of t-shirts, there's undershirts, there's graphic tees, there are plain tees, there are quality tees, and then there are luxury tees. And similar to the knit polo, there is the knit t-shirt. Now, for a lot of guys, the idea of a luxury t-shirt, well, that comes off as an oxymoron. But, for those in the know who want a casual option sans collar and who have the build to pull it off, guys, a luxury tee with that beautiful drape can totally elevate your casual look. Next up on this list, we've got the classic white down. Now, depending on your situation and needs, there are tons of fabric options out there. For cooler summer weather, maybe you want to go with a thicker cotton weave like oxford. If it's hot in your area, a lightweight cotton poplin or jumping over to linen. And an option that I personally love, performance fabrics. And a guy that's been in the clothing industry for coming in on 20 years, I can say it's amazing to see the strides that they've made creating garments that look good and perform when it comes to breathability, stretch, and not having to iron. Because let's face it, that's one of the things a lot of guys hate about linen is that it wrinkles like no other, although that is part of its character. But, seriously, a lot of guys just don't want to have to deal with that. Well, gents, if you're looking for the perfect long sleeve casual button-down or dress shirt, you need to get over to Collars & Co. and check out their new Apex Performance Dress Shirt. Now, gents, I'm wearing their shirt right here and I can tell you it looks and feels amazing. They've got this new cool fiber technology fabric which to the touch is cool. It's incredibly breathable and it has a four-way stretch. The fabric has a beautiful drape, it looks good. And, of course, it's a Collars & Co. shirt, so the collar stands up, the collar looks good. And, in fact, these shirt collars come with removable collar stays. And on a side note, another interesting fact about these shirts is that they're the official performance dress shirts of the Aero McLaren IndyCar team. And, of course, since it's Collars & Co., they got more options than just white. They have tons of different patterns, different colors, different looks to choose from. And those shirts I talked about earlier, the knit polo, the knit luxury tee. Guys, you can grab all of these over at Collars & Co. If you want that Johnny collar, you want to look like James Bond, check out their new Marleno Vintage Stripe Polo with a tailored fit. I mean, seriously, look at this thing. It is going to fit and look great on you. And if you spend time in the gym, you got an excellent build, check out those luxe tees. All that being said, if you are new to Collars & Co., I would encourage you to check out the original dress collar polo. It was this one garment that put them on the map for creating a new hybrid garment that had the structure and collar of a dress shirt, so you could layer it under a jacket, under a sweater, yet made from a comfortable breathable performance material with short sleeves. Guys, personally, when I'm traveling, when I'm giving a presentation, when I simply want something that's comfortable, yet is going to look good, this is the shirt I reach for along with my Maverick Performance Blazer, which I'm wearing right here. Awesome company. And, yeah, check out their new arrivals, their new CEO pull-on pants. They're just like wearing sweats, but they look so much better. So, gents, get over to their website, use that link I'm putting in the description of today's video. I've got a code down there that ensures you get the best deal on the web. Next up, let's talk about footwear. So, you got a few options here. If you want ultra casual, let's look to some maybe braided sandals, which I know aren't going to be for everybody, but they do have a long storied history. They do a decent job of protecting the toes and I think if kept simple in a shade of brown, they can look good. Another often less expensive option is going to be espadrilles. So, these originate out of Spain. And one of the reasons they're so inexpensive is they're usually made from an inexpensive cotton rope-like material. And in general, unless you buy some higher-end ones, they're made usually just the last one season. That being said, their elegance is in their simplicity and their heritage with the elite that travel. Now, of course, if that's not your thing, you could always go with a pair of simple white sneakers, although I really like the option of suede sneakers. And if you really want to step it up, let's bring in some classic loafers. So, the fancier styles we're going to see out there are going to be Belgian, Italian, and tassel loafers. Besides the tassel, these are going to be relatively simple, although occasionally you will see them in a little bit more extravagant colors. My favorite option though here is the classic penny loafer style. When I'm looking for summer loafers like this, I always look for a low vamp. That's where it's going to expose more of the sock, more of the foot versus a pair of classic loafers made for more four-season wear. That low vamp is going to make the shoe a little bit more casual, but cooler to wear in the summer. Next up, let's cover a couple of accessories. First up, sunglasses. There are three classic styles that every man should know, aviators, wayfarers, and clubmasters. Now, I'm assuming that most of you guys have a pair of classic aviators. That's a great start and I'm going to skip those for this video. Now, the styles I want to bring your attention to are the other two that are often overlooked, the wayfarer and clubmaster stuff. Now, for a lot of guys, when they put on a pair of wayfarers, they feel that it's too much. It's too in-your-face, the frame is too strong, too high contrast with their looks grabbing too much attention. I get it. Not for everybody, but if you do go with this option, just go with the classic black. It works in pretty much any situation and is a fun classic style. However, if you really want to level up, look to the clubmasters. In particular, look for a tortoise design. Now, I'm not recommending you grab anything made from animal product. In fact, finding a pair of glasses that are made from actual tortoise shell I think is next to impossible. Note, nowadays, that refers to the actual pattern. And we're going to see it in a variety of strong plastics. And for me, when it comes to old money, when it comes to a sophisticated timeless style that will set you apart from the crowd, I love this look. The next classic accessory, the weekender bag. Now, most of us have backpacks, carry-on luggage, even duffel bags. But, a proper weekender in most men's wardrobes gets overlooked. And really, that's too bad because this soft piece of luggage is incredibly versatile. And as the name implies, it's large enough to hold everything you need for anywhere from two to five days. Most weekenders have defined rectangle-like shape. Longer handles make it easy to carry and to throw into the back of the car. Now, I personally recommend if you're going to invest in one, pick one up in leather, so as it ages, it looks better. Now, weekenders come in a wide variety of different materials from waxed canvas to ballistic nylons to simple cotton to leather. And, of course, many use combinations of those materials. Next up, we've got the classic straw hat. Now, the Panama is the most famous, but it's also one of the most pronounced. If you're going to wear this hat, you need to practice, you need to have the confidence to be able to pull it off. Summer straw hats can also come in the shapes of fedoras, trilbies, and occasionally you'll even see some boaters out there. Which one is going to suit you? A lot of this depends on your face shape, your head size. So, my best advice here, if you really want to wear a hat, go into a hat store, try on a variety of different styles and choose the one you feel comfortable wearing. And remember, choose function over style because then you're more likely to wear it and the more you wear it, the more confident you'll feel. Now, when it comes to belts, there's not really any hard and fast rules here, but I would maybe try a braided belt. It's a bit more casual and I think can look really good with the next item we're about to talk about, a classic pair of light-colored trousers. Now, when it comes to your pants, if you want to go for an old money look, let's drop the jeans, at least for the summer. Because, seriously, gents, you got so many better cooler options. They got the classic chinos made of cotton. These were brought back from soldiers serving over in the Philippines over a hundred years ago. And these soldiers brought them back because they loved them. They wore them in their off time, they were light-colored, they were great weekend wear. And to this day, chinos are a casual staple in any well-dressed man's wardrobe. But, if chinos and cotton aren't your thing, then look to all the other options you've got when it comes to light-colored trousers. So, my favorite colors are cream, stone, and off-white. And great materials to consider besides cotton are going to be linen, linen cotton blends, and of course, performance fabrics. Like I said, these things have come a long way and you got tons of options out there that are going to be breathable, lightweight, not require ironing, and they look good. And, of course, when we're talking old money, we can't forget the classic blazer in navy. Or, if you're really eclectic, maybe go with a regatta stripe. But, seriously, a dark-colored blazer like this, a white shirt with those light-colored trousers I was just talking about, an easy simple classic combination. Throw in a simple white pocket square, which by the way with this maverick blazer it comes with, I can hide it and put in my own pocket square if I want. Guys, that's it. Let me know if I missed anything in the comments below. And, yeah, here's your next video. I got you covered right here. Go check it out. Yeah. You know I appreciate you guys. Having you dress great this summer, I got you covered. And if you want to talk a little bit more about accessories, I got you covered right here.