7 Items I'd Buy FIRST If I Started Over

So, the first item on this list is the penny loafer. Now, really quick, let's define what a penny loafer is and what it isn't. Now, as you can see from the infographic here, the penny loafer aka the Venetian style loafer is easily recognizable by its lack of ornamentation. Specifically, it's a mid-heel slipper with an upper part that is slightly open to the kick of the foot and the ankle ball. Venetian loafers are slip-on shoes with no laces with a moccasin style toe construction. Another key characteristic and where traditionally some men would put a penny is the slotted strap stitched across the vamp. In its simplest form, it's a slip-on loafer with a tongue and strap only. Now, when you compare Venetian style loafers to other styles of loafers such as horsebit loafers, tassel loafers, Belgian loafers, monk straps which I know are technically not loafers, but they are slip-ons, and even boat shoes which have the moccasin design, but are using laces, you can see that Venetian style aka penny loafers are so much cleaner, simpler, and in my opinion, versatile. And that's why, gents, I put them right here at the top of this list because you can dress them up, you can dress them down. If you invest in a good pair of versatile penny loafers, you're going to be able to get your money's worth out of them. So, as many of you guys know, the polo shirt design has been around since the 1860s. First made popular by polo players, it was later adopted on the tennis courts. But, all those early versions of the polo, well, they were made from peat cotton and were made for performance, not style. No, it was the Italians in the 1950s who embraced fine gauge knitwear as an expression of la bella figura, which literally translates to the beautiful figure, specifically meaning to dress well and make a good impression. I mean, those Italians, you got to hand it to them, they love to look elegant, but they also want to look relaxed. In the style world, we call this transitional dressing, which is basically blending formality with comfort. And that's why the Italians loved and perfected this garment. Knitwear artisans in Milan, Florence, and Naples all began to reinterpret the sporty polo in wool, silk, and cashmere. The result, the long-sleeve knit polo was a garment that became an emblem of Italian spazzatura, understated sophistication without trying too hard. And it didn't hurt that this garment was adopted by some of the most stylish men out there. Men like Alain Delon, Marcello Mastroianni, Gianni Anginelli. Now, the key features of this knit garment, it's going to be made from either wool, silk, cashmere, or cotton silk blends. It's going to be a fine gauge usually from 12 to 18, so that's going to give it a nice smooth luxurious feel that's relatively lightweight and makes it easy for layering. Now, we're going to see a wide variety of plackets out there from three buttons to no buttons. The collar because it's knitwear is soft. And at the end of the sleeves and the hem, we're often going to see a ribbed form that gives it a bit of structure. Now, if you're looking to grab one of these garments, stick with a neutral color. You want something that's going to be versatile, easy to match that you're going to be able to wear again and again. Whenever I'm wearing a mine underneath, I'm usually wearing an undershirt. And over the top, I would wear either a suede jacket, leather jacket, field jacket, or an overshirt. You see, when you're layering, one of the best things you can do is bring a contrast in the texture. And, again, assuming that you went with a neutral, this is going to work with a wide variety of trousers and shoes. Now, let's jump over to the quarter zip. Now, the quarter zip, as many of you guys know, is trending right now, incredibly fashionable. TikTok has been pushing it to the younger crowd like it's a new thing. But, for you guys, you know that the quarter zip has been around for over half a century. Now, although it has its origin in sportswear, it has become a classic in menswear because, again, it hits the three Cs. First up, the cut. The quarter zip is designed to hug the body a bit. So, if you've got a well-built profile, it's going to show it off with a nice silhouette. And even if you've got a dad bod, what's really nice about the quarter zip is the way it builds up the shoulders, the way it can enhance the thickness of the neck. And overall, build up give a little bit more depth to the torso. And that V opening right at the neck, again, helps to reinforce the masculine V right below the face right there on the chest. Now, when it comes to the quarter zip, you're usually going to find the construction is pretty good especially if they're using a merino wool or even if they're using a natural blend. Oftentimes, you'll see cotton, cashmere combined especially in sweater types that they're trying to get a little bit of a napped weave or maybe a ribbed type of look. And by the way, ribbed textures are really nice because they not only provide a little bit of elastic around the torso, but they also because of the texture also add a little bit of thickness. They're still soft and, again, they're usually going to fit. So, if you've got a good build, you spend time in the gym, ribbed sweaters can look really, really good on your natural silhouette. Now, patterns like this are going to be more casual, but they're great to be able to wear with jeans or just a pair of nice chinos. But, yeah, a quarter zip and a ribbed texture, this is great to be able to wear on its own. Now, if you wanted to layer a quarter zip, you definitely want to go for one that's going to be of a lighter construction. And that's why I like the merino wool. It's just a finer wool with a lighter hand. It's going to be very soft to the touch, so don't think about the wool that's itchy. No, merino wool is usually very, very soft. When you're looking to style a quarter zip like this, yes, you can wear it just with a pair of nice dress pants, even a pair of dark denim. This type of sweater could also be layered under a jacket. It can be dressed up, it can be dressed down, incredibly versatile. Pay attention to the small details, aka the hardware, the zipper, everything around it. You want to make sure the trim, those details don't make this sweater too casual especially if you want something that you can dress up. Next up, we've got chinos. So, chino cloth by definition is a twill fabric made from 100% cotton. Now, as we seem to be talking about, weaves, a basket weave, simple. Twill weave, a little bit more complex and more dense and more durable. Not great for shirts necessarily, but amazing for jackets and especially trousers that you want to be able to stand up to a beating. And knowing that, then it makes a lot of sense that chinos were originally a military uniform. They came from British, from the French, and then it was during the Spanish-American War that the United States had a whole bunch of them issued and they brought them back from the Philippines. So, you got all these veterans coming back and they're taking these chinos, reusing them in their wardrobes and they absolutely loved them. Now, chinos come in a wide variety of colors. And I do think that in a classic wardrobe, you can bring them all in. But, the one that you're going to want to start with is the classic khaki. And khaki actually is a shade of brown and that's why, you know, this chino and sometimes you'll hear the name synonymous chinos, khakis. But, understand, chino, it's more about the twill weave and the pant style versus khaki is actually going to be a specific color. Now, when choosing a pair of chinos and if you go with the khaki color, make sure that the fit is right. You want these things to not necessarily fit as tight as jeans for a lot of guys, they can be a little bit looser, but they should drape well and you don't have to go with the twill fabric. If you want something that's a little bit lighter, maybe you want to go with a tropical weight wool, you can go with this color. And what I like about these is you can wear them with a wide variety of items in your wardrobe. They definitely have a bit of a summer feel to them, hence the original design. But, you can wear these into the fall, you can definitely wear these in the spring. Well, gents, if you're looking for a group of growth-minded individuals, check out our community over on Skool. And in this community, you're going to find that guys are stepping up their style, improving their presence. And in this group, we challenge each other to become our best self. So, if this sounds interesting, get over to Skool.com. I'm putting that link in the description and the comments. Now, if you get yourself a pair of chinos, what to pair with them? How about the classic navy blazer? If you really don't want to own a blazer, maybe look at the sports jacket. But today, I'm going to make the case for the blazer. Now, I know most of you guys are familiar with suits. Suits are jackets and trousers made from the same fabric. But, odd jackets and blazers and sports jackets both fall under these. These are jackets made separately. They don't have a matching pair of trousers and you can wear them with a wide range of odd trousers from jeans to khakis as mentioned earlier. And, of course, as I mentioned, tons of colors of chinos. What I love about a blazer is that you can have fun with it bringing a pair of red chinos with that navy blazer. Actually, that combination looks great and it's classic. But, if you wanted to dress it up, maybe look at a pair of gray flannel trousers. And you can wear this during the winter with that navy blazer right there. And navy blazers in general are going to be navy dark blue in color. They technically do come in a wide variety of different fabrics from hopsack to serge, but the majority of them are going to be made from 100% worsted wool. And navy blazers in general are going to have a little bit more fun with the buttons. We're going to sometimes see a nautical theme, we're going to have gold buttons, you're going to have silver buttons, sometimes mother of pearl buttons. And, yes, I do think you can take a navy suit jacket maybe that has lost its trousers, it fits and looks well, just simply get the buttons changed out, all of a sudden you got yourself a blazer. And in case you're wondering formality-wise, blazers do fall below suits in formality, but it's that time that you simply want to dress up look especially if you want to go for a tie, if you're going to be on the east coast, if you're going to be down in Florida, if you're going to be down, you know, Marina del Rey for a presentation in California, I think that a blazer looks really good. And, again, it's got the whole nautical theme. And, I don't know, you go into a lake in Wisconsin, you could probably still find a way to pull it off. Now, this next one seems obvious, but I got to state it and that is having a nice classic watch that is mechanical preferably. Now, you can go with quartz and there's some amazing quartz movements out there, but I think in general what you want to have is something that is mechanical because that is really why a lot of people nowadays wear a watch. If you want to accurately tell time, simply look at your phone or get something that's electronic. But, if you want something that is going to be about your relationship with time, something that you can pass on, something that's an heirloom, something that is going to maintain a high level of value, then you want to invest in a watch. And, yes, the higher end watches are going to be expensive. You could be spending thousands if not tens of thousands of dollars. But, don't sleep on others, you know, Seiko, I think it's Orient, a number of these brands that, you know, for a couple of hundred dollars, you can get a watch that looks really good is going to get the job done. And maybe it's your placeholder until you can afford a more expensive watch or maybe you realize, hey, everything I need is here and it's going to be the sentimental value you attach to the watch when you travel the world when you're out doing things and achieving results and you wear that watch as you're doing it. Next up, we've got the overshirt. So, did you know that this garment first originated in 1952 as the Army's OG107? This was a thick cotton utility shirt designed as part of the Army's basic work and combat uniform. Now, an overshirt by its design is very similar to the shirt especially in the sleeves and the overall fit of the garment. Now, where it separates itself from the shirt is the thickness of the material and the placement of functional pockets. Usually, we see two flat patch pockets on the chest. And because of the thickness and durability of the cotton, this garment right here is perfect for everyday wear, easy maintenance, and this is an excellent item to layer with. Now, gents, if you enjoyed this video, but you felt I missed something, you felt like, hey, there should have been some more with this, guys, I got you covered with another detailed video, summer warm dressing. Come on, you guys know I got you covered. How to dress in hot weather, how to look good, boom, right here. Oh, yeah.