28 Best Old Money Outfits For Your Inner Rich Society Debut!
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It’s time to swap out the flashy, over-the-top designs for more subtle and refined choices to recreate the perfect old money outfits!
When I think of old money—I think Kennedy family summers in the Hamptons or poolside soirees with the likes of Jay Gatsby. Ha, totally the gyst of it!
And let’s be honest, who wouldn’t want to look like they come from old money? That sophisticated, elegant, and effortless style is to die for. There’s something about it that seduces literally everyone.
So babe, if your goal is to look like you’ve just stepped off a yacht with a glass of champagne in hand, you’re in the right place.
Because not only we know a thing or two about how to dress like old money, but we also have some outfit inspo for to you to replicate! Let’s swoosh in!
Let’s look rich with these old money outfits now!
1. Oversized striped shirt + trouser pants
Get ready to strut your stuff in this ultra-luxe combo that screams old money extravaganza. Simply pair an oversized striped shirt with tailored trouser pants for an effortlessly chic look.
To complete this ensemble, add a statement bag and kitten heels for that perfect touch of opulence.
2. Neutral pullover thrown over shirt & pants combo
Stay warm and look fabulous in this timeless combo. Layer a neutral pullover over a crisp white shirt and tailored pants, giving you a sophisticated edge. Pair with loafers and a classic leather bag to elevate this look to old money status.
3. Monochrme high-neck jumper + pants
Nothing says old money like a monochrome outfit. Rock a high-neck jumper in a neutral tone, paired with matching pants to exude understated elegance. Throw on some pearls for good measure, and you’ll be mistaken for a classy heiress in no time!
4. Crewneck sweater + mini skirt
This outfit is the epitome of old money style with a modern twist. Pair a chic crewneck sweater with a mini skirt and knee-high boots for that luxurious yet fun vibe. Finish off the look with statement earrings and a chic sling bag to elevate the whole ensemble.
5. Slip dress with a tweed blazer
Channel your inner Blair Waldorf with this timeless outfit. Pair a sleek slip dress with a classic tweed blazer to give off old money energy. Add a string of pearls, black pumps, and a structured purse to polish off this sophisticated look.
6. Vest over an oversized shirt + pants
Who knew being posh could look so cozy? Layer a sweater vest over an oversized shirt and tailored pants to show off your old money aesthetic. Complete the look with loafers or oxfords, a leather clutch, and some delicate jewelry for that perfect touch of class.
7. Classy pant suit
Nothing speaks power and elegance like a well-tailored pant suit. Own any room you walk into with this old money staple.
Emulate the ultimate sophistication with a bespoke blazer and matching pants, a sleek blouse, and pointed-toe pumps. Don’t forget the designer bag to really flaunt your refined taste!
8. Button down t-shirt with midi skirt
Nothing screams sophistication quite like a crisp button-down shirt paired with an elegant midi skirt. To nail this look, opt for a neutral or pastel-colored shirt and tuck it into a pleated or A-line skirt. Finish off your old money outfit with a pair of classic kitten heels or pumps and a simple gold necklace.
9. Tweed crop blazer + skirt
What’s a better way to channel your inner royalty with a tweed crop blazer and matching skirt ensemble. This fabulous outfit is perfect for those chilly days when you want to feel extra cozy and stylish.
10. T-shirt + shorts + scarf
Elevate your casual summertime wardrobe with a simple yet chic combination of a classic T-shirt, tailored shorts, and a luxurious scarf. Choose a neutral-colored shirt and shorts, and let your scarf steal the show with a vibrant print or delicate silk material.
Accessorize like a pro: Add oversized sunglasses, gold hoop earrings, and flat sandals to complete the ensemble.
11. All white, styled with scarf
An all-white outfit is the epitome of elegance, especially when accented with a colorful scarf. Opt for white linen or cotton pieces to keep the look breezy and sophisticated. Drape your scarf around your head or neck or use it as a belt to cinch the waist.
Old money tip: Choose a scarf with a vintage print or design to complement the timelessness of the outfit.
12. Ribbed dress, layered with a sweater
For an effortlessly chic look perfect for transitional weather, try a figure-hugging ribbed dress layered with a cozy knit sweater. Aim for neutral colors or autumnal hues for a classic touch. Pair with knee-high boots or ballet flats, depending on the occasion.
You can drape the sweater over your shoulders or tie it around your waist for a nonchalant, old money outfit.
13. Shirt with trouser pants
Step into the world of classic sophistication with an oversized shirt paired with well-fitting trouser pants. Tuck in or half-tuck your shirt to achieve a polished yet relaxed aesthetic. Pair with elegant loafers or pointy-toe flats and timeless accessories.
14. Tank top with trouser pants
Dress up your classic tank top with a pair of tailored trouser pants for a chic and fuss-free outfit. Keep the color palette neutral or classic and finish off the look with a sleek statement belt and gold accessories.
15. Linen shirt + pleated shorts + sweater
Stay cool while looking chic with this delicious combination. A linen shirt paired with pleated shorts is the epitome of casual elegance, while a cozy sweater thrown over your shoulders adds the perfect touch of sophistication.
16. Striped oversized shirt + linen shorts
Stripes, darling! There’s really nothing more timeless than a good ol’ stripe. An oversized striped shirt tucked into linen shorts will keep you looking effortless and graceful in the summer heat. And, you know what they say – the wider the stripe, the better the vibes!
17. Tweed blazer + pants
No old money list would be complete without the legendary tweed blazer. Pair it with matching pants for a head-to-toe sophisticated look. Don’t forget to add a silk scarf or pocket square to level-up the outfit and make sure you’re giving off major $$$ vibes.
18. Tweed blazer + t-shirt + jeans
When casual Fridays meet the upper crust. Mix and match your favorite tweed blazer with a simple t-shirt and jeans combo. This modern approach to old money attire will leave you looking cool, collected, and utterly fabulous.
19. Flowy, classy A-line dress
Float through your day like the queen you are in a flowy A-line dress. These elegant numbers are universally flattering and evoke the old-money aesthetic with ease. Pair your dress with kitten heels and delicate jewelry for a look that would make any royal swoon.
20. short Cardigan + wide leg pants
Bridge the gap between classic and trendy with a short cardigan and wide leg pants combo. Choose cozy, textured fabrics like wool or cashmere to elevate your look to old-money status. For bonus points, top off your outfit with a vintage-inspired beret.
21. Striped tank top with a midi skirt
How about we replicate the classy brunch look by pairing a nautical-striped tank top with a midi skirt for a stylish summer ensemble? This effortlessly chic attire will have you feeling like a million bucks (old money, of course) and make your day even brighter.
22. Tank top + linen pants
A trendy tank top combined with a pair of chic, breathable linen pants is the ultimate summer go-to outfit for that old money laid-back elegance. Add some statement accessories, like a bold necklace or a wide-brimmed hat, to make your outfit pop and embrace the old money aesthetic!
23. Shirt + mini skirt + blazer
Rock an uber-classy look by pairing a crisp shirt with a playful mini skirt and a sharp blazer. This combo will have you looking as if you just stepped off a yacht! Complete the outfit with loafers or heels and a simple clutch for a timeless, polished appearance.
24. High neck top + crop blazer + jeans
Embrace that old money glam with a high neck top, a cropped blazer, and a pair of well-fitted jeans. This powerful combination gives a nod to the classic style while maintaining a contemporary flair. Add a statement belt to elevate your look and you’ve nailed that affluent vibe!
25. Ribbed top + tennis skirt + pullover
Channel your inner preppy princess with a ribbed top, a cute tennis skirt, and a cozy pullover tied around your shoulders. This outfit screams old money and is perfect for a day at the country club. Amp up the look with a leather belt and statement sunglasses.
26. Classy black dress
You can never go wrong with a sophisticated, sleek black dress. Whether it’s midi, knee-length, or even floor-length, this timeless piece embodies the epitome of old money style. Accessorize with pearls, pumps, and an understated clutch for a glamourous event or gathering.
27. Tweed skirt-blazer set
What is tweed not perfect for? Except beach, of course, lol. Carry it to the office or a countryside getaway, this old money outfit is the epitome of sophistication. Add a touch of whimsy with a patterned silk scarf and some brooches to make heads turn.
28. Turtle neck sweater + mini skirt + long blazer
Combine a cozy turtleneck sweater with a flirty mini skirt and an eye-catching long blazer for a trendy, yet timeless, old money vibe.
This versatile look works equally well for a daytime adventure or evening soiree. Finish off the outfit with knee-high boots and a statement bag for the perfect fashionable flair.
Final thoughts on Old money outfits
There you have it! The 28 best old money outfits to bring out your inner socialite and conquer the world with your elegance and charm. 💅💎
So whether you’re attending a luxurious soirée or just strutting your stuff down the street, you’ll be sure to look like a million bucks. Remember, it’s all about a classic cut, vintage accessories, and an air of confidence that’s worth more than the Koh-i-Noor diamond.
Your ticket to high society is shining in these old money outfits— now, it’s time to snatch it! Don’t forget to share your fabulous old money looks with me on social, and let us know which outfit had you swooning! Go on and get your glam on, darling!
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