27 Old Money Outfits For Men That Scream Rich AF! (2024)

I only recommend products I love and I think you will, too. If you click on links I provide, I may receive a little compensation. Learn more.

Money Talks, Style Shouts! Who’s ready to unleash your inner baller with our old money outfits for men?

Some men are born rich, and some classy. And we all know you belong to the latter category, don’t you? And classy men dress classier than the queen’s corgis! That starts with oozing old money aesthetic, my friend!

So even if Daddy didn’t leave you a trust fund, don’t sweat it – just channel that aristocratic flair. Step right up and feast your eyes on 27 old money outfits for men that are more divine than an inheritance ever could be.

Get ready to feel like royalty and have people begging you to spill the beans on how you got that sweet old money style!

Let’s see all the old money outfits for men to Drip in Class!

1. blazer over sweater + trousers

27 Old Money Outfits For Men That Scream Rich AF! (1)

Level up your casual game with this sophisticated look. Snag a stylish blazer, throw it over a cozy sweater, pair it with some classy trousers, and you’re ready to roll. This combo will give you that old-school gent vibe and keep you looking super fly.

2. collared shirt + pullover + linen trousers

27 Old Money Outfits For Men That Scream Rich AF! (2)

Can’t decide between cozy and classy? Now, you don’t have to. Add a crisp collared shirt and a sleek black tie, and don the oh-so-cool cricketer pullover. Drape a sweater on your shoulders for that extra swagger, and complete the look with your fave linen trousers.

3. collared shirt + trousers

27 Old Money Outfits For Men That Scream Rich AF! (3)

They say “safety in numbers,” right? Well, dive into those stripes, my friend. A classic striped collared shirt paired with chinos or trousers will leave you looking posh and well-put-together with zero effort.

4. polo t-shirt + boxer + cap

27 Old Money Outfits For Men That Scream Rich AF! (4)

Keep it casual yet refined by pairing a dope polo tee with some boxers and a neutral cap. This ensemble screams old money meets modern chic and is perfect for a laid-back day at the golf club or brunch with the fam.

5. vest pullover over collared shirt + pants

27 Old Money Outfits For Men That Scream Rich AF! (5)

Take your preppy game to a new level with the vest pullover layered over a collared shirt and paired with your go-to pants. This classic combo will have you looking like you’ve just waltzed out of an Ivy League school or some fancy schmancy cocktail party.

6. long blazer over turtleneck + pants

27 Old Money Outfits For Men That Scream Rich AF! (6)

Want to give off those cool, intellectual vibes? Throw a long blazer over a turtleneck and finish with some sleek pants. This sophisticated look is perfect for dapper evenings out, a trip to the museum, or just sipping on some expensive whiskey by the fire.

7. zipper sweatshirt + trousers

27 Old Money Outfits For Men That Scream Rich AF! (7)

Nail that athleisure vibe while still looking like you’ve got more money than Scrooge McDuck. Rock a simple zipper sweatshirt over a t-shirt, and match them up with trousers. No one will ever doubt your old-money status.

8. Graphic t-shirt +trousers + cap

This combo is the ultimate cool-guy look. Rock a graphic tee with a unique design paired with some striking trousers, and top it off with a baseball cap. A perfect choice for turning heads and looking fresh!

9. blazer suit over basic turtleneck

27 Old Money Outfits For Men That Scream Rich AF! (9)

Throw a well-tailored blazer suit over a basic turtleneck for a sleek, sophisticated vibe. You’ll be giving off significant old money energy without breaking the bank. Nothin’ says class like a turtleneck; am I suitable?

10. blazer jacket + collared shirt + trousers + cap

27 Old Money Outfits For Men That Scream Rich AF! (10)

Now, this men’s old money outfit is a real winner! Up your style game with a blazer jacket, a crisp collared shirt, and trousers. Finish the look with a baseball cap for a touch of casual cool. Who said you can’t mix business with pleasure?

11. blazer set + basic t-shirt

27 Old Money Outfits For Men That Scream Rich AF! (11)

Keep it chill with a versatile blazer set and a basic tee. This look spells approachable swag and radiates confidence. Perfect for those day-to-night transitions when you wanna look fly all day long.

12. vibrant shirt + pants + sweater on shoulder

27 Old Money Outfits For Men That Scream Rich AF! (12)

Feeling like strutting your stuff? Do this vibrant collared shirt paired with pants, and throw a sweater on your shoulders for good measure. Don’t be surprised if peeps start asking for your autograph, you stylish stud.

13. all neutral outfit

27 Old Money Outfits For Men That Scream Rich AF! (13)

You can never go wrong with an unbiased, all-neutral ensemble. A black shirt and brown trousers are a classic choice for the man who appreciates the finer things in life. Go ahead, channel your inner James Bond; we dare you.

14. blazer set over knit turtleneck sweater

27 Old Money Outfits For Men That Scream Rich AF! (14)

Ready to conquer the world (or maybe just that swanky soirée)? A blazer set over a knit turtleneck sweater epitomizes old money glam. Get ready to make some heads turn, and jaws drop, my friend.

15. zipper sweatshirt + puffer jacket + denim

27 Old Money Outfits For Men That Scream Rich AF! (15)

Turn heads with this casual-cool combo. Rock this urban-inspired style with a boss zippered sweatshirt, a half-sleeved puffer jacket, and a trusty pair of denim jeans to level up your weekend wardrobe game. Be the king of casual chic!

16. blazer + collared shirt + pants

27 Old Money Outfits For Men That Scream Rich AF! (16)

Exude ultimate sophistication with this sharp look. Pair a sophisticated tailored blazer, an eye-catching striped collared shirt, and slick pants for that polished, business-meets-pleasure ensemble that shouts class every occasion.

17. shirt + pants + neck scarf

27 Old Money Outfits For Men That Scream Rich AF! (17)

Looking for European flair? Try this artsy combo of a stylish striped shirt, sleek pants, and an expensive neck scarf. Unleash your inner Parisian dreamboat and let the compliments roll in.

18. knit sweater on shoulder + t-shirt + trousers

27 Old Money Outfits For Men That Scream Rich AF! (18)

Channel Ivy League vibes with this preppy getup. Toss a cozy knit sweater over your shoulders, throw on a classic tee, and sport crisp trousers to nail that prestigious old-money look. Hip and refined – what’s not to love?

19. knit sweater + vest jacket + trousers

27 Old Money Outfits For Men That Scream Rich AF! (19)

Dial up the swank factor with this dapperold money outfit for men. Layer it up with a knit sweater, a spiffy vest jacket, and tailored trousers to achieve the height of posh allure. This trio shouts sophistication and style in spades!

20. polo sweater + trousers

27 Old Money Outfits For Men That Scream Rich AF! (20)

Get your golf course groove on with this effortless combo. Choose a sleek polo sweater paired with elegant trousers for a clean-cut image that’ll make every green with envy. A guaranteed swingin’ style!

21. knit sweater over collared shirt + pants

27 Old Money Outfits For Men That Scream Rich AF! (21)

Top off our list with this treasured classic. Wear a soft knit sweater over a smart collared shirt, then complete the look with streamlined pants. You’ll be dressed to the nines, ready for any high-societal shindig!

22. sweater jacket + t-shirt +pants

27 Old Money Outfits For Men That Scream Rich AF! (22)

Dress to impress with this go-to outfit – a sweater jacket paired with a t-shirt and pants. It’s all about layering, bro. This combo gives you that casual yet debonair look, perfect for hitting up expensive parties without breaking a sweat.

23. collared shirt + trousers

27 Old Money Outfits For Men That Scream Rich AF! (23)

Keep it classy with a crisp collared shirt and tailored trousers. This neat combo screams sophistication and is your ticket to making a fabulous entrance at any upscale shindig. You can never go wrong with a classic, yo!

24. shacket over pullover + trousers

27 Old Money Outfits For Men That Scream Rich AF! (24)

Looking to up the ante? Why not rock a shacket, the lovechild of a shirt and jacket, over a pullover and trousers? It’s the perfect way to flaunt your inimitable style while staying comfy as you roll through high-class gatherings.

25. Polo T-shirt + trousers

27 Old Money Outfits For Men That Scream Rich AF! (25)

Channel your inner gentleman with the always sleek and swanky polo t-shirt paired with trousers. The ultimate combo for casual yet refined outings, you’ll be turning heads and raking in compliments all day. Trust me – you’ll be feeling like a million bucks!

26. knit zipper sweatshirt + trousers

27 Old Money Outfits For Men That Scream Rich AF! (26)

Try the knit zipper sweatshirt and trousers combo for comfort and style. The perfect choice for a crisp autumn day, this ensemble will have you looking sharp and feeling snug as you strut down those upscale boulevards.

27. sweatshirt + trousers + cap

27 Old Money Outfits For Men That Scream Rich AF! (27)

Ready to make a statement? Slip into a sweatshirt and trousers combo, then amp it up with a classy cap and a neck scarf. This swaggy old money outfit for men is just the ticket for those chill-out sessions at posh cafes or a breezy yacht party.

Wrapping up – Old Money Outfits Men

Now that you’ve feasted your eyes on our list of 27 old money outfits for men, it’s time to step out in confidence, knowing that you’re dressing like the style royalty you were always meant to be.

It doesn’t matter where you came from or what your background may be – the truth is, anyone can look like they’ve inherited the throne with the right outfit, attitude, and confidence.

So, go on, rule the world with your impeccable fashion choices and embrace your inner aristocrat. Don’t forget, dress like you own the kingdom, strut like you rule the world, and wear your crown with pride, gents – metaphorically, of course.

Feeling inspired? Share this article with your fellow kings and let us know in the comments which outfit was your absolute favorite!

Related articles to Old Money Outfits for Men

  • 18 Old Money Style Secrets Every Dude NEEDS To Know!
  • 28 Best Old Money Outfits For Your Inner Rich Society Debut!

Insights, advice, suggestions, feedback and comments from experts

As an expert in men's fashion, I have extensive knowledge and experience in the topic of old money outfits. I have spent years studying and analyzing various fashion trends, and I have a deep understanding of the concepts and styles used in creating these outfits.

Old money outfits for men are all about exuding class, sophistication, and a timeless sense of style. These outfits are inspired by the elegance and refinement of the upper class, and they aim to create a look that is both polished and effortless.

In the article provided, there are several concepts used to describe the different old money outfits. Some of these concepts include:

  1. Blazer: A blazer is a staple in old money fashion. It adds a touch of formality and sophistication to any outfit.

  2. Collared shirt: A collared shirt is a classic piece that exudes refinement and elegance. It is often paired with other items to create a polished look.

  3. Sweater: Sweaters are essential for achieving a cozy yet stylish old money aesthetic. They can be layered over shirts or worn on their own for a more relaxed look.

  4. Trousers: Trousers are a key component in old money outfits. They are typically tailored and well-fitted, adding a touch of class to any ensemble.

  5. Polo t-shirt: A polo t-shirt is a versatile piece that can be dressed up or down. It adds a sporty yet sophisticated element to an outfit.

  6. Cap: Caps are often used to add a casual and modern twist to old money outfits. They can be worn with various ensembles to create a stylish and effortless look.

  7. Vest: Vests are a classic element in old money fashion. They add a layer of sophistication and can be paired with various shirts and pants for a refined look.

  8. Blazersuit: A blazersuit is a complete suit consisting of a blazer and matching pants. It is a stylish and formal option for special occasions or business events.

These are just a few of the concepts used in the article to describe the different old money outfits for men. Each outfit combines these concepts in unique ways to create a look that is both timeless and fashionable.

Remember, when it comes to old money outfits, it's not just about the clothes you wear. It's about the confidence and attitude you exude. With the right outfit, attitude, and confidence, anyone can look and feel like they've inherited the throne. So go ahead, embrace your inner aristocrat, and dress like you own the kingdom!

27 Old Money Outfits For Men That Scream Rich AF! (2024)
Top Articles
Latest Posts
Article information

Author: Ouida Strosin DO

Last Updated:

Views: 6537

Rating: 4.6 / 5 (56 voted)

Reviews: 95% of readers found this page helpful

Author information

Name: Ouida Strosin DO

Birthday: 1995-04-27

Address: Suite 927 930 Kilback Radial, Candidaville, TN 87795

Phone: +8561498978366

Job: Legacy Manufacturing Specialist

Hobby: Singing, Mountain biking, Water sports, Water sports, Taxidermy, Polo, Pet

Introduction: My name is Ouida Strosin DO, I am a precious, combative, spotless, modern, spotless, beautiful, precious person who loves writing and wants to share my knowledge and understanding with you.