As an Amazon Associate we earn from qualifying purchases.
Many people consider dressing in the old money style easy, but it can become overwhelming once you realize how many options you have in your closet. Picking the right old money style outfit can be tedious as you have to be as neutral as possible while looking uninterested in the outfit you are wearing.
If you have ever purchased what you thought would be the perfect classic blazer and found yourself looking like the one who needed to apologize to a whole boardroom, then you know it can be a struggle. It all comes down to the perfect mix of fit and fabric, and most importantly their combination of restraint, not branding.
These outfits are designed for casual wear like school, work, and meetings, as well as travel, dinners, weekend coffee dates, and those surprise errands where you may bump into an acquaintance!
Grasping the subtleties of old money style can greatly improve your closet. It is important to use materials that look high end, but are also soft and comfortable on the body. Cashmere, silk, and wool are all examples of old money fabric staples. Such materials build sophistication without being flashy.
In terms of color selection, earthy tones and muted colors are dominant. These also are not as easy to stain, making them multiple use day to evening pieces. This way of thinking is sophisticated, as it allows for lots of versatility with the items to be worn in more than one setting.
1. Cream Cable Knit Sweater with Ivory Trousers
The sweater texture gives dimension to the color palette. You can wear it to brunch, casual Fridays at work, or when you’re out running errands. It’s a great outfit solution to the feeling of comfort you get from wearing pajamas. Best styled with loafers and a slim belt with a minimalist watch.
A navy blazer is perfect for dressing up casual outfits for things like lunch or a casual work meeting. If you want more structure while traveling, this works. It helps with the problem of the outfit being too casual, especially with ballet flats, pearl studs, and a leather crossbody.
When it comes to old money outfits, accessories can really make or break the look. The best accessories complement the outfit, but don’t take away from it. Pieces like pearl earrings, leather bags, and classic watches are great additions to your wardrobe as they can improve an outfit, and show a bit of your personal style.
For example, an outfit with a classic gold chain will look better and also feel like a more intentional outfit. Remember, it is always better to have an accessories collection focused more on quality rather than quantity. A few good pieces will be better than a collection full of trendy pieces.
3. Camel Coat with Black Turtleneck and Black Trousers
This is as simple as pairings get, because it takes the guesswork out and lets your outerwear do the job! Worn with black loafers and a tailored bag with a few simple gold pieces, you are good to go! Perfect for dinner, meetings, and winter days in the office, it will keep you looking polished.
4. White Button-Down with Beige Pleated Trousers
White shirts and pleated trousers look great because they are clean and sharp without being too formal. You can wear this combo to the office, parent-teacher meetings, or any daytime event where you need to look put together.
You may be wondering, “What do I wear that’s professional that’s not a suit?” Well, this is the look. It also goes well with loafers and a simple belt, and you can throw your hair up in a low bun to complete the look and keep it out of your face.
5. Striped Breton Top with Cream Chinos
The Breton top is a great way to incorporate some pattern into your wardrobe, while still keeping it classy. Weekend lunches, coastal getaways, school run disguising tired looks. This top is the answer to your “I’m so tired of boring blouses” dilemma. It looks great with cream chinos, navy flats, and a woven tote.
In the old money style fashion world, the fit of clothing is as important as the fabric. In fact, simple clothing can be made into something remarkable by tailoring. For instance, a well-fitted blazer will improve all of your body shapes, and professional tailored trousers will exude class and sophistication. It is best to go to a tailor to get clothing adjustments.
Alterations will achieve the best fit and help showcase all of your best features. The expense of tailor services is often the biggest concern, but the improvement in your clothing will make the investment worthwhile. You will be able to instantaneously look like you possess confident style and class with little luxury effort.
6. Cashmere Polo with High-Waisted Trousers
The knit polo works for a lot of situations since it sits between a sweater and a collared shirt. Perfect for most real mornings. Feels good for the office or travel, and even works for dinner. Great for when you need something soft but don’t want to look messy. Solves the coat collar problem and works great with tailored trousers, suede loafers, and a slim leather bag.
7. Tweed Jacket with Dark Denim
A tweed jacket makes denim look less like you’d just thrown on an outfit and more like an intentional outfit choice. It’s great to solve what to wear with denim issues and is versatile for more formal occasions like lunches, smart casual work events, and dinners at restaurants that have real napkins. Pair with dark jeans, sling backs and a plain shell top for a great look.
8. Monochrome Oatmeal Knit Set
A matching knit set will keep you warm and is much better than wearing mismatched sweats. You can use it for travel, working from home, or even casual weekends when you might see other people. The set helps resolve the problem of feeling confident versus being comfortable. It pairs really well with a nice pair of sneakers, a long coat, and a tote. The tote can hold snacks for real life.
9. Black Midi Dress with a Camel Cardigan
A black midi dress can never go wrong! By adding camel knitwear over it, you can make it look more casual and break up the color block as well. Pair it with a cute bag and some flats, maybe throw on some gold hoop earrings and it really does the trick!
You could wear this to dinner, church, museum dates, or literally any occasion! It’s one of those outfits where you think “I have no idea what the dress code is” and you really don’t have to worry because it’s so versatile, and sooo easy to style!
10. Linen Blazer with White Jeans
The linen blazer gives structure to the outfit, as it keeps the white jeans from feeling too unstructured and keeping it from feeling too much like a vacation outfit.
This is a great outfit for spring lunches, relaxed work environments and any warm occasion where denim is suitable, but you want to look a little more polished. It solves the problem of light denim being too casual and it works with tan sandals, a silk tank and tortoise shell sunglasses.
A navy shirtdress makes getting dressed easy! You simply have to make one decision, and some mornings, that’s totally justified. An easy option that doesn’t feel flimsy, you can wear it to the office, school events, or travel sightseeing. It solves the “dress but not delicate” dilemma. Pair it with brown loafers, a leather belt, and a satchel for a polished look.
12. Silk Blouse with Wide-Leg Wool Trousers
Silk and wool have an elegance that cannot be compared to the low quality and artificial feel of polyester. This is perfect for speaking engagements and meals or whenever your outfit is required to do some emotional labor. It helps with the work-need-to-dress-smart dilemma and goes super well with some pointy flats, a dainty chain, and a fitted blazer if it’s cold in the room.
13. Quilted Jacket with Corduroy Trousers
This outfit looks great for the outdoors, but it doesn’t look like you’re heading into a survival documentary. This can be worn during fall at the weekend markets, school sport events, and errands. It also helps when you don’t know what to wear when it’s cool outside, and it can be worn with leather boots and a cream knit as well as a canvas tote.
14. Black Crewneck Sweater with Camel Skirt
The black sweater goes nicely with the camel skirt, and the skirt keeps it from being boring office attire. One can wear this to the museum, out to lunch, or for a smart-casual day event. It goes well with knee boots, a leather shoulder bag, and a pair of small earrings.
15. Trench Coat with White Shirt and Ankle Trousers
Trench coats are highly valued because they help keep your essentials organized. Trench coats help elevate the same old boring work clothes. In spring and fall when the weather can be a bit iffy, they are perfect for work, meetings, and even travel. They go well with your ankle pants, a pair of loafers and a cute little umbrella, solving the outerwear problem.
16. Cardigan Jacket with Tailored Shorts
Pairing tailored shorts with a cardigan jacket instead of a flimsy top will create a more sophisticated look. This will be great for resort dinners, warmer weather lunches, and sightseeing. This outfit will keep you polished and help you avoid heatstroke. It resolves the issue of shorts feeling too young and will match perfectly with leather sandals, a woven bag, and simple sunglasses.
17. Gray Turtleneck with White Wide-Leg Jeans
The gray and white coloring is perfect for winter as they create a nice contrast to the typically dark outfits people wear. This can be worn for casual Fridays, coffee dates and errands on the weekends when the weather is a little colder. It also solves the problem of boring denim as it goes beautifully with wool coats and taupe boots, as well as silver jewelry.
18. Plaid Blazer with Cream Knit and Brown Trousers
The blazer’s pattern looks great because it adds a good amount of personality to your outfit while also keeping a level of class. They can be perfectly used for work and lunch meetings as well as other occasions that call for a suit jacket. This look can be combined with a cream knit sweater and brown knit pants and shoes that are made of the same leather.
19. Silk Scarf with Sweater and Straight-Leg Pants
If tied loosely (think flight attendant, but relaxed), a silk scarf can really elevate some separates and make them look intentional. It can be worn to weekend markets, lunch, or when you want to add some color on the travel days. It takes simple outfit fatigue away, and goes really well with a navy sweater, ivory pants, and loafers.
20. Chocolate Brown Suit with Cream Tank
While black is more serious, chocolate brown feels softer but can still be used in adult spaces. For work, meetings, or dinners where you want to look smart but not too formal, it works really well. It removes some of the stiffness of a suit and pairs well with a cream tank and brown loafers, as well as either a slim portfolio or a structured tote.
21. White Poplin Shirt with Khaki Midi Skirt
The shirt matches well with the khaki skirt. It keeps the look relaxed but not too messy. It’s great for summer lunches or daytime events when jeans aren’t an option, and even relaxed workplaces. It achieves the smart casual look for warm weather while also pairing perfectly with a tan belt, leather sandals, and a raffia bag.
Navy knit dresses are definitely more well-behaved than some of the skirts I had in my twenties. It’s perfect for autumn dinners, workdays, and relaxed weekends that might involve a stroll. It solves the ‘needs too much styling’ dress dilemma and pairs nicely with riding boots and a camel coat, plus a leather tote.
23. Cream Blazer with Black Cigarette Pants
The cream blazer paired with black trousers breaks the uniformity of the outfit. It can also be worn to business breakfasts or presentations. It lightens the problem of all black outfits looking heavy. It also goes with ballet flats and ivory blouses and black top handle bags.
24. Striped Button-Down with Ecru Denim
Combining ecru denim with a striped button-up shirt can work for running errands, casual lunch meetings, and road trips where you want to look nice without thinking about it too much. It can help solve the outfit problem posed by light jeans. It also goes great with a brown belt and loafers and you can even add a canvas jacket!
25. Sleeveless Turtleneck with Full Midi Skirt
The sleeveless knit balances out the fullness of the skirt. This makes sure the outfit doesn’t look costume-y. You can wear this to gallery openings, dinners, and events in air-conditioned rooms. Helps solve the cute skirt but what top issue, and can be worn with black flats, pearls, and a small clutch.
This outfit is a relaxed option that is also versatile and a bit more feminine. You can wear it to lunch, church, a baby shower, or a daytime party. It also solves your occasion dressing dilemma and can be styled easily with some slingback flats, a structured handbag, and a cardigan over your shoulders if you like a little insurance.
27. Beige Sweater Vest with White Shirt and Trousers
A sweater vest adds shape to a white shirt and prevents things from getting too bulky under a jacket. In the fall when a whole sweater is too warm, you can wear it to work, the library, or on weekends. It solves the problem of being layered and lumpy and looks good over taupe trousers, loafers, and a leather watch.
28. Black Blazer with Cream Satin Skirt
The black blazer prevents the satin skirt from feeling overly delicate or too specific to wedding guest attire. Slip it on for dinner, cocktails or any other evening occasion where denim won’t suffice. It addresses the dressy-separates conundrum and looks great with chic flats, a black cami and a compact bag.
29. Camel Sweater with White Button-Down and Dark Trousers
Finding out what works for your wardrobe is a long journey for anyone, so having versatile outfit options in your closet is a go to for work, travel, family events, or last minute get together. This outfit helps you decide what to wear so you can get ready fast. You can match it with brown loafers and a tote bag. If you roll your sleeves up, people will think you actually mean business.
About the Author
Rachel Meyers
Contributing Fashion Creator · Amazon Influencer
Rachel Meyers is a contributing fashion creator for The Better Fit, filming try-ons from Orem, Utah. She has spent three years in the Amazon Influencer Program and is an All-Star contributor in the Viral Vue creator community, and her storefront, Rachel's Reviews and Fun Finds, leans into women's fashion and shoes. Rachel is also a certified life and health coach, and that double life shapes how she reviews: she cares less about how a piece photographs and more about how it feels on a school run, at work, or on the third wear. Her latest try-ons land on YouTube at @rachelsfunfinds.