24 Men’s Old Money Outfits That Look Expensive Without Trying Too Hard

Old money chic in menswear should look intentional without overdoing it. Giving off an old money vibe takes a little bit of effort in the right direction. This means not pulling your clothes out of the hamper or off the corner chair where everything is wrinkled.

It also means investing a little bit more in fewer, higher quality pieces, while not spending more money overall.

1. Navy Blazer, Pale Blue Shirt, and Charcoal Trousers

Navy is a classic old money color, and the pale blue shirt is a good combination color-wise with the charcoal trousers. One old money chic tip for menswear is that you’re going to see a lot of button up shirts and not a lot of t-shirts. A t-shirt should be worn perhaps as an undershirt underneath a button up shirt.

The button up shirt is definitely one of the biggest staples for old money. It can be worn like this, in a more formal or workwear way, as well as dressed down.

2. Forest Green Corduroy Jacket with Gray Flannels

Again, we have a button down. This one is actually a little bit less formal than the one above, maybe a little bit of a thicker material for cooler weather, and something easy to throw on. It does need to be ironed, though. It shouldn’t be wrinkly. This is one of the most basic pieces, and if you take care that just the button down underneath isn’t wrinkled, everything else comes together more easily.

Here he has a corduroy jacket that he just took off the hanger and threw on. The gray flannel pants are warm and comfortable. They’re not too fitted, and they look good on him without trying too hard or looking too dressed up. I like the suede shoes. They also look very comfortable and walkable. Overall, this has a pop of color without being too bright or standing out in any patterned way.

3. Charcoal Turtleneck and Dark Wash Jeans

Here’s another variation of old money chic. We have a turtleneck in this situation rather than a button down. A turtleneck is the second best alternative to the button down. Having the collar, or the turtleneck in this situation, adds an intentionality that you don’t get with a t-shirt. It looks a little bit chicer and a little bit more put together, and it serves a purpose, keeping you warm.

It doesn’t have to be hard. He just pulled this out of his closet where it was folded. Wool turtlenecks like this should be folded so they don’t get warped on the hanger. It probably won’t wrinkle in any way, so if you fold it correctly, you can just throw it on. Here he has a dark wash jean that gives a very dark overall aesthetic with the shoes that he has. It looks very chic with very little effort.

4. Tobacco Suede Jacket with Navy Knit Polo

Here we have another collared shirt, but rather than a button down, it’s a polo. Again, the collar adds a little bit of interest where a t-shirt wouldn’t. If you wanted to, you could put an undershirt underneath this polo. It’s nice to have an undershirt, either a tank or a t-shirt, under any shirt that you’re wearing. I think that’s classic to the old money aesthetic. Be intentional in ways that aren’t as common nowadays. That’s old money chic.

Here we have a suede jacket rather than a hoodie or a denim jacket. Suede is a little bit more elegant.

5. Burgundy Rugby Shirt and Stone Chinos

The rugby shirt is a little bit more of an athletic variation of a polo or a button down. We still have the collar, and it still has a little bit of a preppy feel, but this is the most athletic you can go while still reading old money. You can’t wear athletic wear if you’re trying to reach the old money aesthetic.

Stone chinos look good. They definitely feel a little bit private school uniform, but not in an overt way. I like that he matched the socks to his shoes, showing a little bit of intentionality, and it looks more fashion forward. The brown belt and the brown watch aren’t popping out too much. This is a great color palette. Navy and burgundy together read very old money, as does brown leather.

6. Slate Blue Linen Shirt with Olive Trousers

Here we have a linen button up shirt. This is a great option for the summertime. Linen is a great high quality, high luxury material that’s often forgotten about, especially if you’re trying to put a little bit more effort into your outfits and look a little bit more put together. A long sleeve looks a little bit more put together than a short sleeve. But if the weather is warmer, you may need to go for a fabric like linen, which definitely doesn’t trap heat as much. You still feel cool enough in a linen shirt despite warmer temperatures.

Here he has a suede loafer. It definitely feels casual, but because of the material, suede does need to be taken care of a little bit. It gets scuffs and it gets dirty. It’s very easy to remove dirt and scuffs from suede, you just need to brush it a little bit. But having that long lasting, high quality material is a good way to add old money aspects to your outfit.

7. Olive Field Jacket over a Denim Shirt

A field jacket like this, maybe a Barbour jacket, feels old money in a hunting way, definitely combined with the denim shirt. Lighter denim like this isn’t what we immediately think of when we think old money. However, it’s a sturdy, hardworking, long lasting fabric that can definitely fit into the old money aesthetic. This has an outdoorsy kind of feel, but because of the field jacket, it feels old money.

So do the corduroy pants he has on combined with the leather boots. I actually know a couple of older European men who have almost exactly these leather boots. They’ve lasted them, I want to say, 25 years. You can get the soles redone. It’s a great example of things that should be well taken care of so they last you half of your lifetime.

8. Chocolate Brown Suit with Pale Pink Shirt

The pink and the chocolate brown is such an unexpected combination. I really like it here. I think with his complexion, it really sets it off in a great way. I feel like chocolate brown could be combined with another pastel color if that suits you better, maybe a pale blue.

The pink is definitely an old money move, especially with the little burgundy popping out of his pocket. It feels intentional, and it feels old money with the button down shirt that fits him really well. A suit like this can last for years. You can get it tailored, or even buy it secondhand, paying attention to the width of the shoulders and tailoring the rest. This is a great investment piece that will last for years.

9. Pale Blue Oxford, Navy Sweater, and Khaki Chinos

Here we have the oxford shoes, which are inherently old money. I think these have actually been coming back for men and women in recent years. I’ve seen different brands coming out with more and more oxfords and boat shoes. I like that he’s not wearing a sock here. The mistake I often see with oxfords or boat shoes is wearing a no show sock that’s showing, or an ankle sock. It should either be a long sock or no sock at all with a boat shoe.

The button down shirt popping out of the sweater is a great move. I like this for men and women. It adds warmth without taking away the chicness of either the sweater or the button down.

10. Camel Topcoat with Black Knit and Gray Trousers

Black and camel are such a great color combination. I have a harder time combining charcoal with beige or camel. Charcoal with brown is a little bit harder to get away with. However, black and charcoal definitely work together. Black and camel, and black and brown, go very well. Having the black with the charcoal here makes everything make sense.

He also has leather gloves. They almost look like a brown leather glove. That’s a great accessory to have. They feel a little bit chicer than the cheaper gloves you might get from a sports store or something similar. These leather gloves should last for years and years, whereas athletic gloves definitely don’t. The camel coat should also last for a long time. This is a simple combination of pieces, individually, but it looks very chic together.

11. Deep Teal Blazer with Ecru Knit and Brown Trousers

The brown trousers with the brown shoes look like a classic combination. They’re very well fitting. It almost seems like he doesn’t even need a belt in this situation. Usually I would say always add a belt, there’s no reason not to, but here I guess they fit him well enough that he doesn’t need one.

The teal blazer is slightly off from navy. It’s not so far off, or so bright a teal, that he would have a hard time combining it with other colors. I think navy is one of the easiest blues to combine with other colors, so having a deeper teal like that is a good staple piece to have in your wardrobe. An ecru knit, like a light beige knit, is a good one to have as well because of how versatile it is.

12. Rust Cardigan with Navy Trousers

The rust cardigan, especially with this shawl collar, is so cozy for fall. It reads very academic, very professor, very old money. I love that he’s combined the pinstripe blue button up with the rust colored sweater. That’s an unexpected combination, but with these rich, deep colors, as long as they’re fairly simple, you can make great combinations that are eye-catching without a lot of pattern. Here, it’s just the pinstripe and the rust that are adding attention to this outfit.

The navy pants and the navy socks are great with the chocolate loafers that he’s wearing. That’s another classic color combination. Overall, this is a very interesting outfit without doing too much.

13. Black Cashmere Crewneck with White Jeans

The white jeans are definitely a statement piece. I think we often see white jeans in women’s wardrobes. They’re such a great staple to have. The fit here is very masculine, and the material is very thick. That’s important when looking for white or light colored jeans.

This is a very simple outfit: black shoes, black belt, black sweater. The sweater being cashmere definitely feels more old money. That’s a great fabric to invest in. You can have just one perfect cashmere sweater in your repertoire, and all of your outfits will be elevated.

14. Moss Green Tweed Sport Coat with Tan Corduroys

This is a very versatile outfit that can read as casual or as formal as you’d like it to. He has the tweed sport coat with a checked button up shirt underneath. The check of the shirt combined with the green of the sport coat adds interest. He definitely added a little bit of formality with the pocket square coming out of his pocket.

The pants feel appropriate for wintertime, almost like a wool or tweed themselves. I like the combination with the dark leather. The shoes are well taken care of and shined.

15. Plum V-Neck Sweater with Gray Suit Trousers

The gray suit trousers could be combined with any number of tops. We could have something like a black turtleneck for a simple, darker silhouette on top, or a plain white button down, or a patterned button down. Here he’s chosen the plum v-neck sweater. With a v-neck sweater like this, it looks more old money with the button down popping out from underneath. With just a t-shirt underneath, it would look a little bit more athletic casual.

Plum is a little bit more of a statement color than a brown or a navy, which are more often reached for. But with other subtle pieces like the charcoal pants, the plum doesn’t stand out in any bold way.

16. Tan Suit with Blue Chambray Shirt

Here he has a suit with a suit jacket. I love the tan and the blue together. Chambray shirts aren’t often reached for when putting on a suit, but it definitely helps it read a little bit more casual. This outfit would be great for a time when you would throw on a button down with some nicer pants and call it a day.

The denim chambray shirt tones down the outfit while keeping the collar, which is important. And then adding the suit jacket adds another layer of warmth if the day calls for it. It also adds a little bit of formality and intentionality. With the chambray shirt, it looks more fashion forward than if he were to just wear a plain button down or a checked button down, something that would be more expected.

17. Maroon Velvet Dinner Jacket with Black Trousers

Here we have the maroon, almost like a burgundy color, again. I like that it’s in a formal setting like this. It goes to show that you can have color while dressing formally. What’s important is that everything fits him well and nothing is wrinkled. It looks like he knows how to dress because he chose a color intentionally.

There’s not so much color that he looks like he’s in a show, but it’s a little pop of color. It’s understated because of how dark this maroon is, but it still draws your eye nevertheless. Adding the texture as well, the velvet of the dinner jacket, is another way to add fashion forwardness and trendiness to your outfit choices.

18. Medium Gray Suit with Denim Blue Tie

Gray and blue are a great color combination that always works well. I think we usually see gray with a little bit of a lighter blue, but here, with the white shirt, the dark blue definitely pops more than a light blue would.

I also think the dark blue makes the dark shoes make sense. If he were to wear a lighter blue tie, or a tie in another color, I could see brown leather shoes making sense.

19. Sea Green Knit Polo with Navy Linen Trousers

A knit polo like this, in a little bit more of a luxurious texture than we often see men throwing on, definitely reads old money. The sea green is pretty casual for a color. I like that it’s combined here with trousers. They look like comfortable trousers, and he’s not even wearing a belt. It’s definitely casual, but that added interest of texture makes this read old money.

He looks like he has quality pieces in his wardrobe for casual days as well as formal times. Being able to put on a casual shirt like this knit, instead of a t-shirt or a cotton button up, is very old money coded. I also like that his loafers are textured as well. They’re almost like a woven, or maybe a faux crocodile texture. These are interesting pieces without trying too hard. They’re very subtle in color, but still interesting in texture.

20. Chestnut Quilted Vest with Navy Corduroy Trousers

A vest is another unexpected piece to have. It serves a purpose. It definitely keeps you warm while still allowing for more mobility than a jacket would, and it genuinely makes sense on days that you might be walking around. The quilting also adds durability to the vest, and a little bit of insulation to keep you warm. Rather than a puffer vest, which is more of an athletic leaning piece, we have quilted material here. Quilted reads more horseback riding, old money working in the barn, rather than athletic wear.

Here he’s chosen a dark autumn and winter color palette with the sage green check. This is again showing our old money color palette. We have dark green, navy, and dark blue. We have the chocolate brown, especially with leather. He has a little brown scarf here, and leather brown gloves are a long-lasting piece that’s somewhat less expected than an athletic glove.

21. Indigo Shawl-Collar Cardigan with Cream Trousers

Again, we have the shawl collar cardigan here, this time in a navy. I love the navy. I usually see shawl cardigans in a neutral color like a cream or a beige. The navy is a good piece to have if you need to darken up an outfit a little bit.

Here he’s wearing it to maybe a country club, on a day that’s warm enough to be outside, maybe the beginning of fall or the end of summer. He has the white jean on. This white jean, again, isn’t too fitted. It feels loose but still structured. The navy and the light blue combine well with the dark brown of his shoes.

22. Mustard Crewneck with Charcoal Overcoat

Mustard is a little bit of a deviation from the colors that we often see in the old money aesthetic. However, like plum, it’s not too bright, while definitely adding a little bit of a statement to an otherwise plain outfit. It feels like he knows how to dress because he can use a color like mustard, but he’s not pairing it with any other bright colors.

We have a charcoal overcoat, which is a solid staple piece in a high quality material, and then denim straight jeans. They’re fitted but not too tight and not too baggy. This is definitely an old money cut. And then again, we see the lace-up boots that last forever.

23. Wine Merino Zip Neck with Taupe Trousers

This zip neck is definitely on the more casual side, while still reading old money. In a different material, this zip neck could look more athletic, but because it’s a merino wool, which is definitely a high quality material, it’s not looking too athletic.

He could have any number of shirts underneath, like a t-shirt or a button-up, and he could even throw a jacket over this zip neck. It looks old money because of the color as well as the material. Taupe is a great color to add to the dark, rich color palette that we see in old money. Taupe isn’t necessarily a brown, but it works well with darker gray, black, and brown.

24. Midnight Navy Suit with Silver Grenadine Tie

This navy suit is such a rich color. It’s almost black, but not completely. It really makes his tie and shirt pop. We’re very much drawn to the crisp white accents of the pocket square, the tie, and the sleeves popping out.

I like that he paired this with a black shoe. That draws us even more to the bright white of his shirt. For summertime, or something a little bit more casual, I could see a brown leather shoe. But since this looks like a formal event, the black leather definitely makes sense, especially with navy not being as formal as straight black. I like the black leather instead of the brown leather here.