The term old-money aesthetics is getting quite common this year. It’s not just because those luxurious timeless looks are all over social media, but the trend is also getting bigger in real life, including Taylor Swift who wore ultra-casual attire, looking sleek and chic in her all-black fit outfit.
Since old-money outfits manage to captivate and inspire generations, the look is characterized by elegance, sophistication, and a seamless blend of past and present, giving you an undeniably pleasant look.
To achieve an elegant and expensive look, you don’t just have to focus on clothes, but it’s about how you carry yourself. Well, the key is that you should prioritize quality over quantity. My tip for you is to strike a balance between classic pieces and personal style. Doing that will make you look timeless “old money chic” without getting outdated.
If you are looking to invest in old-money styled clothing then in my recommendations would say that go for big luxury labels such as Gucci, Prada, Versace, & so on when choosing accessories such as bag, sunglasses, shoes, & etc. For dresses, top, & bottom choose the brands with classic and sophisticated styles but no need to go with expensive brands here because the accessory alone doing all the work to create overall old-money outfit. Also. only go with linen, satin, cotton, cashmere, wool, and fine silk fabric to give a sense of luxury.
In short, for old-money summer outfits, the most important aspect of acquiring that look is the way you carry it and that’s exactly how YDYW’s favorite 50+ old-money summer outfit are that you can blend to make a perfect attire for yourself.
Old-Money Chic Outfit Ideas For Summer
Black & White Slim Fit Dress + Black Fur Scarf + Black clutch + Diamond earrings
If there’s one other staple you shouldn’t be caught without this summer, it’s the black & white slim fit dress. No matter what things you choose to pair this timeless basic with, it will always make you look like you have a trust fund. If you really want to lean into the old money feel, keep your outfit minimal by pairing it with a black fur scarf, diamond earrings, and a sleek black clutch.
Black satin slip dress + Pink Mary Jane shoes
What’s another easy way to look elegant this summer? A black satin slip dress. Pair it with pink Mary Jane shoes for a super-simple outfit formula that always looks sophisticated.
Black cropped cardigan + White satin midi skirt + Black handbag + Gold ballet flats + Gold earrings
Beyond trends, there’s classic combo that will give you that old money look this summer: sticking to timeless black and white. Whatever the occasion, you can rely on this elegant pairing with gold accents to keep you looking effortlessly chic.
White cropped button-up shirt + White satin maxi skirt + White handbag
If your summer plans involve giving off old-money vibes, this outfit is your go-to. You can create a timeless, elegant look by pairing the white cropped button-up with the matching satin maxi skirt. Add the white handbag for that final touch of sophistication. Perfect for garden parties or seaside brunches, this ensemble captures effortless class.
Black cropped cardigan + Black flared pants + Black handbag + Black belt
Think all-black outfits can’t channel that old-money vibe? Think again. Elevate your summer style with a black cropped cardigan, paired with black flared pants. Complete the look with a black handbag and a black belt. This ensemble brings sophistication and elegance effortlessly. Perfect for making a statement at any summer event.
White short-sleeve knitted blouse + Cream high-waist trousers + Cream handbag + Gold ballet flats + Sunglasses
Another secret to pulling off that old money look in the summer comes down to having one staple on hand: a white short-sleeve knitted blouse. When in doubt, you can’t go wrong with pairing it with cream high-waist trousers and gold ballet flats—it’s a failproof formula for easy and elegant summer dressing.
White halter top + White high-waist shorts + Brown belt + Beige woven shoulder bag + Brown sandals + Sunglasses
While it’s definitely better to opt for more covered-up styles for a classic look, that doesn’t mean you must. In fact, you can make the more casual white halter top and high-waist shorts work for a sophisticated summer look by adding a brown belt and beige woven shoulder bag. Finish with brown sandals and sunglasses for that effortless old money vibe.
White button-up shirt + Black high-waist shorts + Black belt + Black sunglasses
Just because it’s hot outside doesn’t mean you can’t look cool. (Excuse the pun.) When it comes to dressing for summer, don’t be afraid to embrace the old money look with a white button-up shirt, black high-waist shorts, a black belt, and black sunglasses. It’s a look that will work for whatever summer plans are on your agenda.
Black sleeveless top + Black high-waist trousers + Black belt with gold buckle + Gold necklace
Currently on my outfit inspo moodboard? Audrey Hepburn, Grace Kelly, and classic Ralph Lauren runway looks. The timeless appeal of an all-black ensemble with a touch of gold is unbeatable. This look exudes the elegance of old money without ever feeling outdated, making it perfect for summer sophistication.
White cut-out top + Cream high-waist trousers + Light beige coat + White ballet flats
One of the easiest ways to elevate this chic summer outfit is by adding classic pieces like white ballet flats or a light beige coat. This look captures the essence of old money sophistication while keeping you cool and stylish all summer long.
Black blazer + Burgundy turtleneck top + Black mini skirt + Patterned tights + Black knee-high boots + Black belt with gold buckle + Brown handbag + Gold chain necklace
It might seem straightforward, but styling this mini skirt with other timeless pieces is one of the easiest ways to make it feel more sophisticated. It will always look good with a burgundy turtleneck, bold black belt, and a brown handbag.
White cropped tank top + Black high-waist trousers with white detailing + White sneakers + Black handbag + Sunglasses
If you want to keep the old money vibe casual, pair the outfit with white sneakers and sunglasses. It will give the high-waist trousers a relaxed, yet refined look.
White mini dress with sweetheart neckline + Black handbag with chain strap + Black sunglasses + Pearl necklace
I’ll be wearing this all summer, thank you very much.
Cream button-up jacket + Black skirt + White handbag + Black pointed-toe flats
Not sure what to wear to a summer brunch? Consider pairing your cream button-up jacket with a black skirt and pointed-toe flats. Although it’s a bit more classic, it’s an outfit formula sure to give you that old money look.
Black sleeveless top + White leather mini skirt + Black handbag + Black sunglasses
White leather mini skirts can seem too bold, but pairing them with a sleek black sleeveless top creates a balanced and chic silhouette. For a subtle visual contrast, add black sunglasses and a handbag to complete your look.
White sleeveless wrap dress + Beige and brown headscarf + White heels
Besides the classic charm of a white sleeveless wrap dress and beige-brown headscarf combo, maximize your look by choosing white heels. This outfit is the blueprint.
White T-shirt + Beige mini skirt + Cream jacket + Black sunglasses
Not all summer days are for lounging at the beach. When you’re invited to a classy garden party or a stylish outdoor café, elevate your look with a white tee and a beige mini skirt. Add a cream jacket and black sunglasses to channel that old money aesthetic. This outfit will transition seamlessly from day to evening, making you feel like a true style icon.
White strapless dress with floral details + White parasol + Gold earrings + Black sunglasses
You just may want to live in this dress. I’d pair them with simple sandals.
Black cropped polo shirt + White pleated mini skirt + Black loafers + White socks + Sunglasses + Headband
Okay, so it’s not easy to score an invite to a private tennis match, but it’s quite easy to enjoy a day at a chic summer resort. Whether you’re exploring the Hamptons or relaxing at a country club, you’ll want an outfit that’s both stylish and comfortable. May I suggest this ensemble for inspiration? This simple outfit formula will ensure you’re the most sophisticated person at the resort for the day.
Black tank top + White high-waist shorts + Black and white belt + Black and white handbag + Straw hat + Sunglasses
Although it’s great to dress up for special occasions, sometimes a more relaxed look is just what you need. If the vibe is casual, consider recreating this outfit. Pairing a black tank top with white high-waist shorts keeps you comfy and chic. Add a black and white belt, a matching handbag, a straw hat, and sunglasses, and you’ll have that effortless old money summer style down pat.
Beige short-sleeve knit top + Black high-waist shorts + Beige strappy sandals + Black bucket bag + Black sunglasses
Another simple way to look stylish while spending the day out is to embrace a classic outfit, like the one above. If you’re going to be around town, you might as well wear one or two standout pieces that make you look effortlessly chic (e.g., a beige short-sleeve knit top and black high-waist shorts). This combo will not only keep you comfortable throughout the day but will also make you look cool and collected.
Polka dot dress + Cream blazer + Black handbag + White Mary Jane heels
This is the perfect sundress for any sort of heat wave you may encounter.
Light grey satin dress + White handbag + White heels
This dress is the definition of elegance.
Light grey blazer + Light grey shorts + Light grey top + Cream handbag + Beige ankle boots + Sunglasses
One more alternative to a traditional summer look? A monochrome light grey ensemble. Pairing a light grey blazer, shorts, and top creates a sleek, coordinated outfit. Add a cream handbag and beige ankle boots for a touch of sophistication, and finish with sunglasses. This combo is perfect for achieving that old money vibe while staying effortlessly chic.
Navy blue polka dot top with lace trim + Black capri pants + Black handbag
If you want a bit more coverage for your summer outings, consider opting for a chic matching set (as seen above). Whether you choose a delicate lace-trimmed polka dot top or classic black capri pants, this combo will always make you feel comfortable and ensure you look sophisticated. Add a black handbag to complete the ensemble and capture that timeless old money vibe.
Pink off-the-shoulder ribbed top + White wide-leg trousers
Hopefully, by now, you have a good grasp on what to wear for a summer outing of any kind. But it’s worth starting with the obvious: The best thing to wear on a sunny day is a stylish yet comfortable outfit. Especially if you’re planning to enjoy outdoor activities, it’s important to have an ensemble that will make you look sophisticated. Luckily, a pink off-the-shoulder ribbed top paired with white wide-leg trousers is up for the task. The best thing about wearing this combo is that it’s the easiest option, yet it will ensure you look elegant throughout your day.
Blue button-up shirt + Black vest + Black shorts + Black knee-high boots + Black sunglasses
When in doubt, a well-coordinated outfit will work for a warm day. If you want to make this ensemble shine, add statement pieces such as a black vest and knee-high boots. Pairing a blue button-up shirt with black shorts keeps it sophisticated and stylish. Complete the look with black sunglasses for that perfect old money vibe.
White midi dress + White socks + White loafers + Black sunglasses
The dress silhouette the fashion set loves.
White off-shoulder top + Black high-waist trousers + Black sandals + Black handbag + Black sunglasses
If the idea of wearing bright colors on a balmy summer day isn’t appealing, swap it for a classic monochrome look. This outfit is great because it can be styled for a corporate environment or in a more casual manner (like above). Pair a white off-shoulder top with black high-waist trousers and finish with black sandals, a handbag, and sunglasses. This combo ensures you capture that old money vibe effortlessly.
Black tank top + White wide-leg trousers + White belt + Black sandals + Beige sun hat
While wide-leg trousers are certainly a great option for a sunny summer day, they also work well for nighttime outings. Whether you’re going on a first date or having dinner with friends, you can’t go wrong with pairing a black tank top with white wide-leg trousers and a white belt. Finish the look with black sandals and a beige sun hat to capture that old money aesthetics.
Black strapless midi dress + Silver heels + Black clutch
It’s hard to think of many occasions this dress wouldn’t be perfect for (aside from someone else’s wedding).
White mini dress + Black Mary Jane shoes + Black handbag + Black sunglasses
If you’re into a sleeker look like the one above, this outfit would be perfect for you.
Yellow knit polo shirt + White wide-leg trousers + Brown belt + Yellow sandals + Beige straw tote bag
Looking for an effortless yet elegant ensemble that can be worn from day to night? Look no further than the above. Wide-leg trousers styled with a knit polo shirt, matching sandals, and a straw tote bag will keep you cool on a warm day but still look sophisticated enough to wear into the evening. This combo captures that old money summer style perfectly.
White off-shoulder top with flower detail + Black midi skirt + Black handbag + Black flats + Black sunglasses
Although skirts don’t always feel practical for every occasion, the key to pulling them off in the summer is to pay attention to details. By opting for a stylish off-shoulder top with flower detail and a classic black midi skirt, you’ll ensure you look polished and make a sophisticated choice for an 80-degree day. This combo, paired with black flats, a handbag, and sunglasses, captures that old money vibe effortlessly.
Black and white striped sleeveless dress + Beige tote bag + Black sunglasses
This outfit is quite literally less than a round of post-work rooftop drinks with your friends.
White long-sleeve textured top with flower detail + Beige high-waist trousers + Beige handbag
Can’t be bothered to put on a dress when it’s super hot outside? We get it. The next best option is a pair of high-waist trousers, which can be worn in a corporate setting. Style them with a white long-sleeve textured top with flower detail and a beige handbag, and you’ll be the chicest person in your office.
Yellow sleeveless button-up top + Yellow shorts + Brown sandals + Beige straw bag
When the forecast says it will be an 80-degree day, but the humidity is high, the last thing you want to wear is lots of layers. Luckily, matching shorts sets exist. For those incredibly warm days, a pair of yellow shorts paired with a sleeveless button-up top and brown sandals will allow the only hot thing to be your outfit.
Black and white striped body suit + Black tiered maxi skirt + Black clutch + Black sunglasses
By now, we’ve hopefully provided you with ample inspiration for what to wear on an 80-degree day. However, if you’re still stumped, opt for the most classic option of all: a black and white ensemble. Whether you pair this striped bodysuit with a tiered maxi skirt and a black clutch, this formula will never fail you.
Beige blazer and wide-leg pants + Black crop top + White sneakers + Black sunglasses
Just because beige isn’t the “trendy” color of the moment doesn’t mean it can’t be trend-forward; case in point: the look above. The simplest way to make this hue feel fresh is by opting for fashion-forward pieces (like a blazer and wide-leg pants) in this color for the perfect summer outfit. Pair them with a black crop top and white sneakers for a chic and modern take on the old money look.
Beige long coat + White knit top + Blue jeans + White pointed-toe shoes + Black sunglasses
Beige long coats are a staple among the fashion set—and for a good reason! This beloved piece acts as a blank canvas; the styling possibilities are endless, and you can’t go wrong. But should you need somewhere to start, pairing it with a white knit top, blue jeans, and white pointed-toe shoes is a surefire way to look chic this summer.
Light color wrap dress + Brown handbag + Beige ballet flats
Dress this style up or down and you will look awesome.
Blue and white striped button-up shirt + Beige trousers + Brown loafers + Brown and black crossbody bag + Black sunglasses
I’ll admit that most button-up shirts already err on the classic side, but when it looks like the outfit above, it screams sophistication. Of course, you don’t have to dole out all the dollars to look rich, and you don’t even have to book a trip to the Barcelona—you just have to find a great blue and white striped button-up shirt and pair it with beige trousers, brown loafers, and a chic crossbody bag for an outfit that will make you feel old money rich.
Black bikini top + Brown ribbed knit skirt + Beige oversized crochet shirt + Black sunglasses
Not to be dramatic, but I think I need to wear this outfit.
Black halter jumpsuit + Silver high heels
Combo above will ensure you exude that old money elegance with a modern twist.
Cream vest top + Beige shorts + Beige crossbody bag + Beige open-toe sandals
Reminder: You don’t have to wear head-to-toe beige to get the full benefits of this chic color palette. Style a cream vest top with your go-to pair of beige shorts, open-toe sandals, and a crossbody bag. Do this, and you’ll be instant chic!
White long-sleeve maxi dress with cherry prints + White handbag + White pointed-toe shoes + White cat-eye sunglasses
I must admit that anything with prints never falls within my definition of “polished,” but the outfit above scores points with me in a way I never thought possible. Who would have thought a simple white maxi dress with cherry prints, paired with a white handbag, pointed-toe shoes, and cat-eye sunglasses, could look so chic? This combo perfectly captures that old money summer look.
Black and white bikini top + White high-waist shorts + White bucket hat + Black sunglasses + Black small handbag + Black flip-flops
My favorite holiday task is lounging by the pool with snacks, a drink, and a view. That’s why this outfit is a summer must-have for me. For swimwear, the black and white bikini top is a classic choice. When it comes to cover-ups, high-waist shorts are perfect. And for beach or poolside bags, a black small handbag is my go-to for carrying all the essentials (mainly, the snacks). The white bucket hat and black sunglasses complete the look, ensuring you achieve that old money summer style effortlessly.
Black tweed cardigan + Black pants + Black ankle boots + White handbag
Packing a versatile set is a smart way to optimize your wardrobe. Black tweed goes with everything, and a cardigan-and-pants combo can be easily mixed and matched with other pieces.
Cream pleated gown with cape + Pearl jewelry + White open-toe heels
Now I just dream about this outfit often.
Black off-shoulder top + White layered maxi style trouser + Black flip-flops + Straw handbag
Yes, off-shoulder tops are a viable option for summer travel! Opt for a chic black off-shoulder top and pair it with white layered maxi style trousers for great looks!
White halter mini dress + Brown shoulder bag + White strappy heels
This summer’s timeless outfit trend may be everywhere in New York already, but we’re bringing the adorable style across the pond.
Tan blazer + White dress + White handbag + White pointed-toe shoes
If comfort is your primary concern, then you’ll be hard pressed to find a more versatile combo than a white dress with a tan blazer. A blazer adds a polished touch to the airy dress. Try pairing yours with white pointed-toe shoes for a put-together finish.
White deep V-neck mini dress + White handbag + White pointed-toe heels
This dress looks straight out of a fairytale. The deep V-neck silhouette is so pretty.
Black mini dress with large white flower accent + Black strappy heels + Black handbag
A pretty floral-print dress is always a good idea.
White sleeveless maxi dress with black trim + Black sandals + Light grey handbag
A white sleeveless maxi dress with black trim is one of the best sartorial investments you can make. It goes with everything, but it looks especially classic with black sandals and a light grey handbag.
White off-shoulder dress with eyelet details + White handbag + Pearl necklace + Black sunglasses + Wide-brimmed straw hat
The epitome of South of France chic.
White floral dress with blue and green accents + Blue sunglasses + Straw handbag
Summer in a dress for ultimate old money look.
