How To Dress Old Money Style

So what exactly does it mean to  dress like old money? In addition,   why would you even want to dress like old  money? It sounds boring. And the reality is,   most people aren’t rich. Let’s start things  off by answering that first question.

So, when you dress old money, typically  this means adopting a style that exudes a   sense of timeless elegance, sophistication,  and wealth. So, based off that definition,   we answered the second question, because it  just makes sense that people would want give  

A signal of, hey, I’m timelessly, elegant,  I’m sophisticated, and who knows? Maybe I   could be wealthy someday. But seriously,  Jens, building an old money wardrobe,   in my opinion, is smart, because you’re building  a wardrobe that isn’t going to go out of style. An old money wardrobe sends the  message that you’re polished,  

That you’re refined, that  you are professional, you.   So the first part of this video, I’m going to  lay out a handful of rules that will ensure you   get the old money look. And then the second half  of this video, I’m going to talk about particular  

Items that you’re going to want to pick up to add  to your wardrobe to give it that old money feel. So, rule number one quality over quantity. Now,  if you’ve watched at least a few of my videos,  

You’ve heard me say this before, but it bears  repeating, especially if you’re going to build an   old money wardrobe, the quality of the items that  you’re going to add to your wardrobe matters. Now,  

Does this mean you’ve got to be rich? That you  have to spend a lot of money on those items? No. You need to be able to spot quality, because  then you can spot items that are on sale,  

Items that normally would cost $1,000, on  sale for 300. And you know to be able to   grab that pair of shoes when you see it,  and it’s a deal. And to be straight up,   Gent, you don’t even have to  spend hundreds of dollars.

You can go into a thrift store, you  can raid your father, your grandfather,   your uncle’s closet and say, hey, he’s not  wearing this anymore. This is a classic item,   and it’s still in style  because it’s timeless. Boom. All of a sudden, you’re able  to add this classic tie,  

This classic blazer to your wardrobe. And  I know so many of you guys are going to   be tempted to buy cheap, but don’t do it.  Instead, stick with the boring classics. Because guess what? They’re going  to be interchangeable. They’re going  

To be versatile. You can work and wear  these with other items in your wardrobe. You’re going to get more mileage out of them.  It’s better to have less than to own a bunch   of just cheap crap that is never going to  look good and definitely won’t fit into  

An old money wardrobe. Rule number  two timeless elegance over trends. I get it. Gents. The whimsical  wins of fashion draws in. We see our favorite athlete  wearing a particular brand,   a particular item. And yes, it’s  trending. We want to jump on it.

We want to look cool. But here’s the thing. If you  go with what that musician is wearing right now,   it’s going to be out of style within a few months. Again, Gents, we want to go with timeless  items that have been around for a decade,  

Have been around for 50 years, because guess  what? If it’s been around for 50 years,   it’s going to be around for another 50. Now,  I get it. Some of you guys are saying, well,   this is boring, but think about how it’s  going to affect your wallet, because you  

Go out there and you spend a lot of money on  a trendy piece, and then it’s out of style. You don’t want to be wearing it. You  only got a handful of wears out of that   item versus something that’s timeless.  You could wear this hundreds of times.

You’re going to get a lot of mileage out of it.   And because you’re going to get more  mileage out of this particular item,   you can justify spending a bit more.  Remember, Gents, the style theory of value. The value is equal to the number of  wears times how it makes you feel,  

Divided by the price. Old Money rule  number three focus in on fit. Gentlemen,   you can spend $1,000 on a suit, but if it  doesn’t fit you, it’s not going to look good. Compare that with a suit you had  handed down to you from an uncle.  

You have it adjusted to fit you. It looks great. In fact, every time you put it on, it feels and  makes you look like a million bucks. Remember,   gentlemen, fit is king. Rule number four  stick with a conservative color palette.

Seriously, over 90% of an old money wardrobe  is going to be in the colors of charcoal black,   navy gray, white, light blue, and camel. What do  all these colors have in common? They’re timeless,   they’re versatile, and they’re sophisticated.  Next up on our list of old money style rules,  

You take care of the items in  your wardrobe shoes in particular. You own a shoe shine box, and you condition and  shine your shoes after every wear. All right,   so maybe you don’t have to condition them  after everywhere, but you’re taking care  

Of them. When you get a scuff, when  you get a nick, you are making sure   to change out the laces after, you know,  100 or 200 wears, when they start to fray. The buttons on your shirts, on your jackets,  whenever they become loose, you actually have  

Them repaired. Your automatic watch that you’ve  had for over a decade, if it needs to be serviced,   you send it in to get taken care of. Now, I  know taking care of your clothing seems obvious   to most, but many men coming from the world of  disposable fashion, of T shirts and sweatpants,  

They’re used to something wearing out  pretty quickly and just throwing it away. With old money wardrobe, these  items can last you decades if   you take care of them. And speaking of  accessories, let’s talk about the next   rule accessorize wisely. So you don’t  want to bring in a whole bunch of bling.

You’re not going to bring  in something that’s trendy,   something that’s oversized. You want to keep it  simple, whether it’s going to be your briefcase,   whether it’s going to be that classic looking  backpack. When it comes to your watch,  

You don’t want anything over the top when it  comes to the jewelry you wear on your hands,   around your neck, you want to keep  this all simple, timeless and elegant. Now, does this mean you need to be boring? No,  

You can definitely bring in a signature piece.  But what I’m saying here is that old money   style is not flashy money style. Remember,  gents, it’s not about signaling wealth. It’s about sending the message that  I don’t have to signal wealth because  

I’m self assured as to who I am. And  that takes us to the next rule about   confidence. So when it comes to confidence in  clothing, that comes from practicing wearing   it and knowing when you put this stuff on  that it feels good, that it looks good.

You’ve received compliments. You know  how to piece items together. In fact,   the outfit that you go to, you’ve actually  worn before you know that it looks good on,   you know there are going to be no issues  with anything having loose threads.

This is your go to, you feel  like a million bucks outfit. Now,   a lot of guys think that somehow wearing a  sports jacket, wearing a blazer, wearing nice   chinos or something is going to be uncomfortable.  Guys, nothing could be further from the truth. Maybe it’s unfamiliar because  you’re not used to wearing it,  

And that’s why you’ve got to put in  the reps. It’s like going to the gym.   Whenever you first show up at the gym,  you don’t know what those machines do. You’re trying to say, hey, what exercises  should I do? In what order? By the 50th time  

You’re going to the gym, you actually have a  routine down. You know where things are at,   and you’re really getting into your groove. In  fact, if you start to miss going to the gym, all   of a sudden, you actually feel like you’re missing  something out of your routine, out of your life.

The same thing is true with an old money  wardrobe. Whenever you don’t dress well   and you’re around others, you actually  start to feel like you’re underdressed,   you’re not representing who you  are. I talk about the clothing   we wear sends the message to others  with you not having to say a word.

And that’s what old money style for me  is all about. You being able to signal,   hey, I’m somebody that’s trustworthy. I’m  somebody that is worth doing business with. I’m somebody that you can invest  your time and money into. All right,  

Guys. So now let’s get into the particular items  that you’re going to want to add to your wardrobe. I’m not going to cover everything,  but I’m going to start off with hey,   these are the basics that you have to have.  First up, the suit. But not just any suit.

You don’t want to walk into a box store and buy  something that is cheap made from. A couple of   issue being is these type of suits, your cheap  ones are going to be glued right here in the   chest piece. They’re also going to have maybe  they’re going to have overstructured shoulders.

They are just going to look  they just don’t look great,   especially when you’re sitting back when you’re  relaxed. And that’s why I highly recommend you   look at suits in maybe the $500 plus range.  Go to the best menswear store in your area.

Go into a store. I’ve talked about a number  of them. Suit supply is a great option. Mostly the suits I wear. What I like about  them is that they’ve got a piece right   in here. Basically, they’re structured  with horse hair and it moves with you.

And this is key that they’re structured  in a way that there’s a bit of movement   because you want something when you put  it on, it’s incredibly comfortable. You   don’t want anything that is just over the top  structured that is going to get in the way.  

And just a timeless old money type of style is  going to be a suit that you can actually wear. You’ve heard of lounge suits. I’m not going  down that range, but I am saying that this  

Is a suit you could actually relax and you  could take a nap in if you so choose. Point   being is you’re going to feel comfortable  enough in this that you can be relaxed. And that’s key to actually getting the right  type of suit we’re looking for. Now, do you  

Want to go fully unstructured in the shoulders?  You don’t need to. But I do like it personally. Again, try on a variety of different styles.  Again, go to the best menswear store in your   area and feel the jackets, feel the  shoulders. A lot of them actually,  

They overstuff the shoulders and  they don’t pack the cotton correctly. This one right here, it pretty much doesn’t  have anything. Just a little bit of structure   here. And I know that that for me is what’s  a signal of a better quality made suit.

When I’m saying suits, I’m talking a  jacket and trousers made from the same   material. A lot of guys always think suits are  something that you wear when you’re going to   go going to an interview, maybe a formal  occasion. But there is such a thing as a  

Suit that you can lounge around and you  want to become comfortable in the suit. That’s the key is to actually have  a few of these that you can start   wearing and you can actually dress  them down. You don’t always have to  

Wear them with a tie. But another  thing with the suits is the color. So in general, charcoal, navy, and  medium gray. Those are going to be   the first three that you want to start  with. But if you’ve already got those or,   you know, hey, Antonio, I feel pretty comfortable.

Want to bring in maybe just a  little bit of pattern. You can   bring in a subtle pattern.  I always like herringbone. You can also bring in bird’s eye  right here. I’ve got a little bit   of a check pattern. You can’t even really see it.

It looks solid from a distance, and if  it looks solid from about two to 3ft out,   you’re pretty much safe with the pattern.  I do think that patterns can add a bit of   they can make it a little bit less versatile,  but we’re splitting hairs here. Point being is  

That you find something that is  incredibly comfortable for you. That, to me, is the most important part. And  again, you’re following the rules that we   talked about the very beginning. You’re making  sure you get something that fits your body.

You want to make sure the suit fits you really  well. If you’re a little bit heavier set,   maybe go with higher waisted trousers, and  you’ll be wearing suspenders with this. If   you’re really trim or if you’ve  got a bigger built upper body,  

You’re going to want to make  sure it fits you right up here. And you may have to get it adjusted again by  the tailor to make sure it contours to the   curves of your body. Now, remember, one  of the rules we talked about was neutral  

Color palettes. You’re going to make sure  to stick with that with the suits because   they’re going to be one of the more expensive  items that you add to your old money wardrobe. But again, if you get the right suit, you  go with a classic notch lapel. You’ve got  

The shoulders right on this. You’re  not doing anything crazy on this. Everything here is classic in design. This is  a suit that could last you 20 years if you take   care of it. And if you’re looking at materials,  you’re wondering, okay, what is the super 120  

Versus a 110 versus a 150 versus a 180? Know that  pretty much anything over 100 is going to be fine. You’ll see some super 80s out  there, maybe in vintage shops,   and that may be a little bit too  rough. Usually the higher the number,  

The tighter the weave and the softer  the material is going to be, which isn’t   always a great thing. You don’t want something  with too much sheen or too much shine to it. A super 120. A super 140 in worsted wool,  which is basically just a tightly woven wool,  

Is in general, what I look for. Now,  depending on the number of suits you have,   let’s say it’s three, you want to have at  least two to three times as many dress shirts. It really depends on how often you’re wearing  these items, but if it’s pretty much every day,  

Let’s say you’re working a white collar job,  or you’re just simply, hey, I wear suits quite   a bit. I think you should have three shirts for  every suit, and you want to make sure that these  

Are three shirts that work. And the easiest way  to do this is to stick with a classic white. It’s pretty much going to work with  any suit color, even a white suit,   which I’m not going to recommend is one of  your first ten. But light blue is another  

Great color combination, and you can change up  the styles of the collar. You can go right here. I’ve got a classic button down, which is going  to be very casual, and we’ll talk about that in a  

Second. You could also bring in stripe patterns  on the shirts. I think that a very thin blue   stripe on a white background is a very classic  look and is a great actually pretty versatile. You can wear this with a wide variety of  different suit combinations. That being said,  

If you want to bring in other shirt colors,  look to pastels. You’re going to see pinks,   you’re going to see lavenders,  you’re going to see mint greens. I think that these are not as versatile as  the aforementioned colors. That being said,  

I know a lot of guys like it. And  if it works with your color tone,   let’s say you’ve got really  dark skin or really light skin. And again, you hold those colors up to your  skin, and you really just like the way they work,  

Then go for it. Now, what about dark colored dress  shirts? Well, technically, they don’t exist. It’s   only going to be in the lighter colors that we  see dress shirts, but I know that they do exist. But they are more casual button downs than  they are dress shirts. If you really like the  

Combination, you’re going for a monochromatic  look, that’s great. It could be your style. But understand it’s not going to  be an old money look. Old money.   They stick with a lot of these rules  that have been around for decades. Does it make sense? Not really. But these rules,  

And they’ve been used by class to be able  to kind of identify who understands the   rules. One of them is going with a lighter  colored shirt with a darker colored jacket. Pretty much the white with a darker  color, the light blue with a darker  

Color. This right here just sends  the signal that you understand how   to pair these two together. Now, I talked  about I’m wearing a button down collar. There’s a wide variety of shirt collars  out there. The two most common are going  

To be the spread collar, and by far the  most common is the point collar. Point   collars are actually made to be worn with a  necktie that’s when they look most complete. So if you’re going to be not  really wearing a necktie,  

I would recommend going with a spread  collar or a button down collar. Now,   the button down collar, this came out of the  polo field. It’s been around for over 100 years. The company, Brooks Brothers are  the ones that made this popular.   I think it looks great on a classic Oxford shirt,  

Which is another option. It’s technically not  a dress shirt, but it looks like a dress shirt. And it’s made from an Oxford fabric,  which is going to be a looser,   heavier weave. It’s great for spring, great  for the fall. It’s a very hard wearing fabric,   and it’s classic, and I think looks good.

And yeah, nothing wrong with adding  an oxford shirt to your wardrobe. Now,   we talked about suits, but what about the blazer?  What about the sports jacket? So both of those,   I think, should be in an old money  wardrobe. And the question is,  

Are you going to find reasons and times to  wear it? I think the answer should be yes. For me, sports jackets are where it’s  at. Actually, this is part of a suit,   but I am wearing it separate, almost like a  sports jacket. If you watch any of my videos,  

The majority of the time  I’m wearing sports jackets. Now, why go with the blazer? They’ve really  fallen out of fashion for a lot of people,   but they are still in an old money wardrobe  because there are so many options, especially  

When it comes to the materials. So you’re going to  see surge out there. You’re going to see jersey. You’re going to see a lot of lightweight materials  that are very breathable in these blazers. The  

Majority of them are going to be of a navy color  or a dark blue. You’re going to occasionally see   a regatta blazer out there that’s not part  of an old money wardrobe, so skip on that. But what I like about navy, again, this palette  right here and not using just a suit jacket,  

Is that you’ve got a separate jacket that’s made  to be worn with a variety of other trousers,   other colors right there.  Combination with the navy,   I think is a really nice combination. And you  can pull off a suit jacket with odd trousers.

But the problem there is when you separate  your suit, you risk damaging it or maybe   sending it off to cleaners or bleaching.  It a little bit lighter than your trousers   if you wear it enough. And then all of a  sudden, you’re out a suit versus actually  

Just your blazer is made, I think, and  it looks better because of the styles. And you’re going to see the buttons also change up   on the blazers. Often they have a nautical  theme. They’re going to be gold, silver.

You could even go with a white, ivory or a  mother of pearl. Next up, let’s talk about   your shoes. And can you notice what we’re doing  here? We’re putting a full outfit together. So for every suit you have in your wardrobe,  

I like to think a man should have a pair  of shoes for them. Not saying you need   to go overboard. I know tons of guys that got 20  suits, and they’ve only got five pairs of shoes. So first up, let’s talk about oxfords, in  particular, balmoral oxfords. Some people  

Just call them balmorals, other people call  them oxfords. I’m going to use both of them. Right here we’ve got a capto, so it makes it a  little bit more casual. But right here we’ve got   what’s known as a closed lacing system. A closed  lacing system is when the back part of the shoe,  

The quarter, actually goes under the  front part of the shoe, known as the vamp. Now, this shoe right here in black is going to be  a classic dress shoe. If I were to wear this with   a dark colored suit, a white shirt, and dark  colored necktie right there, that’s going to  

Be a classic business suit combination.  Next up, let’s talk about the blue tur. The big difference here is these  are going to be more casual because   of their open lacing system. So the back  quarter of the shoe actually goes on top  

Of the vamp. This style has always  been considered to be more casual. You can also tell this is a more casual  shoe because of the color. You’re going   to see bluechers in a variety of lighter colors,  although you will still see oxfords in lighter  

Colors. But I think that lighter colored dress  shoes in general are going to be more casual. And the design also signals that  this is more casual. So I could   wear this with a light colored suit,  maybe if I’m just wearing a polo with  

It or a dress shirt. Deciding  to opt not to wear the necktie. Now, another classic shoe for old money is going  to be the brogue. Now, the brogue, as you can tell   right here, is because of all the design, and  you’re going to see brogues both in open and  

Closed lacing systems. This one actually has a  closed lacing system, so a little bit dressier. And there are all types of brogues out  there. You’re going to see quarter bros,   you’re going to see semi brogues, full  brogues, and even long wing brogues. Now,   full brogues are also known as wing tip brogues.

And that’s actually the style that I’ve got right   here. The holes used to go all the  way through. Nowadays they do not. They’re for straight up decoration. But  right here, as you can see on the toe,   we’ve also got a medallion.  Again, it’s just a design.

It does make them a little bit harder to  polish, but I really like the look of it,   and it gives a bit of a more casual  feel. And let’s not forget loafers.   What I love about loafers is that  they come in a wide variety of styles.

You can find them with rubber  bottoms. So incredibly comfortable.   Even if you’re going to be walking  through Chicago during the summer,   you’re going to be covering 10  miles on your going miracle mile. Having a great time there on Michigan street.  Yeah, you can wear these in a variety of  

Situations. This pair right here has a leather  sole, and this is going to be the dress. Can you still wear this with a suit? Yes,   you can wear this with a casual suit. I  wouldn’t necessarily recommend it wearing   with a business suit. With the necktie,  it’s going to be out of its element.

You could even wear this with shorts.  That being said, it’s something I think   every man should have a pair of loafers  in his wardrobe. They can be dressed up,   dressed down, and again come in a variety  of colors, materials, and different styles.

Next up, let’s talk about the polo  shirt. I’m not talking about those   cheap ones that you can find for 1015  $20. I’m talking about higher end polos. The beautiful thing about the polo,  especially for an old money wardrobe,  

Is how it can work with a number of the trousers.  You can dress down a suit by wearing it with a   polo. You can actually dress up just regular pair  of trousers or shorts by pairing them with a polo.

You’re also going to see the polos are  going to start to bend. And I talked   about going with a lot of neutral colors. And  yes, you’re going to see tons of white polos,   dark navy polos in the colors  very similar to the suits.

But you’re also going to see polos in a variety  of brighter colors, of colors that just simply   pop a bit more. And this is where I think in  an old money wardrobe, you can really have fun  

With color and still find ways to mix and match  it with the other items in your wardrobe. Now,   you will see some polos out there in a variety of  patterns and really bright, over the top colors. I would stay away from those. They’re not going to  work with your interchangeable wardrobe. And they  

Just give yeah, they’re just not something that’s  going to work in an old money type of style. Now, really quick, I want to talk  about the necktie. You’ve probably   heard the reports. The necktie is dead, guys. Nothing could be further from the  truth. Things in fashion and style,  

They trend one way and the other. For the majority  of men right now, wearing a necktie is not in. But if you look at history, the use of neck wear,   this goes back thousands of years. And as long  as the elements, what happens when it gets cold,  

We still pull out the scarf. But scarves, why  are they a variety of colors? Because color,   especially around the neck,  is a way to draw attention. Now, with an old money necktie, you’re  going to want to go with a classic color.  

Looking at a variety of regimental stripes.  Now, understand there are certain rules,   especially over in the UK and that side of the  pond, with wearing certain regimental stripes,   but they’re less followed over  here in the United States.

Although if you went to an Ivy League  and that’s what a lot of this stuff was,   it signaled what club you were in. And  that’s where the only neck ties men were   actually able to wear going back over 100  years ago. Nowadays, it’s not the case.

And so you can bring in a variety of patterns,  but I wouldn’t go over the top. Go with, again,   muted colors, muted tones. You can go with solids. I think navy is always a really nice you  can bring in woolen neckties. Paisleys,  

I think, are great if they’re really small  and subtle. Be very careful with dots. You don’t want anything overly large. Small dots,  though, are perfectly acceptable, but keep the   patterns small and repeating. Next up, let’s  talk about chinos, also referred to as khakis. And the difference. Yeah,  we’re splitting hairs here,  

Really. Remember, we talked about  those rules at the beginning. The key here is to get the proper fit. A lot  of you guys take care of your body. You want   to have a pair of chinos, you want to have  a pair of khakis that actually fit you well.

Now, chinos come in a wide variety of colors,   but I would stick again with the  neutral palettes. That being said,   if you want something different, maybe look  at cavalry twill. That’s a great option. Moleskin and Corduroy, believe it or  not, is going to be a classic look. Now,  

If you’re going to go with corduroy,  make sure that it’s got eleven whales,   not seven whales, seven whales. And  that’s the number of cords per inch. You want to have eleven. It just  looks dressier, and in my opinion,  

It works better in a man’s wardrobe. So we  sort of covered accessories already when we   talked about, hey, understand the rules,  you definitely don’t want to overdo it,   but you want to make sure you’ve  got the right accessories.

When you wear a pair of trousers, pants, and  they’ve got belt loops, you wear a belt. And   if you’re going to be wearing those, you wear  a shirt that can tuck in. That being said,   are you going to be tucking in a  polo all the time? Not necessarily.

But if you’re wearing a dress shirt, if you’re  wearing a button down that needs to be tucked in,   yes, you are. Now, you don’t want  anything over the top. You want   to make sure that the measurements  are about one and a quarter inches.

Anything over one and a half inches is going to  be a more casual belt that you would wear with   jeans. And remember the simple rule of matching  metals with metals and matching leathers with   leathers. Do they need to exactly match up? No,  but it does look good whenever they’re close in.

Addition, let’s not forget the pocket square. If  this is too much for you, then look at a simple   white linen pocket square. You fold it the  right way, just go with a presidential fold. And for some reason, if you’re  super conscious about this,  

You can actually just let it tuck right in  out of the way. But I do find that, hey,   just go ahead and with all my jackets,  a trick that I do is that they already   have pocket squares in them. I leave them so  when I put the jacket on, it’s already there.

If it works with the combination, I’d  leave it. But a lot of times I’m not   even thinking about it. And that’s where  I want you to get with pocket squares. Go with the classic presidential fold.  It’s going to match anything. Now,  

When it comes to watches, do you need to go  out there and spend gobs of money? Do you   need to buy a Rolex or something even  higher end? No, I don’t think you do. I would say in general, you want to keep it  muted. If you’re going to grab a Rolex, maybe  

Look at the classic Explorer, one of my favorite  watches. Maybe you want to go look at Carte. You want to look at the classic Tank. You want to   look at the Santos. Actually,  I absolutely love the Santos.

Anyone else there out there? Love it. But you  want to go with something that has been around,   something that’s classic. What you’re going to  find is a lot of guys I remember I had a friend,   and this guy did come from money,  and he just loved his tutor.

And this was something, it was an old classic had  been passed down. It was like over 50 years old,   and the guy just wouldn’t part with  it. It was a little bit beat up. But this is the thing. And old money again,  it’s not like faking it till you make it.  

Here what I’m trying to impart on you is  there’s a lot of things that we can take   from an old money wardrobe, which is  buy good quality and take care of it. Now, gents, if you enjoyed this video, I think  you’re going to love this video. Stop wearing  

Pajamas. Why did men stop dressing sharp  to travel? Talk a little bit of history,   get into yeah, why you shouldn’t be wearing  pajamas when you’re on the airplane. And yeah, check it out, guys. It’s a  good video. Really enjoyed making it. And I think that you will  love it. Boom. Click here.

Go check it out.

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