When it comes to dressing old money, it’s all about timeless elegance, understated luxury, and a wardrobe that speaks volumes without shouting. Whether you’re attending a casual brunch, a formal dinner, or a weekend getaway at the country club, knowing how to adapt the “old money” aesthetic to different occasions can help you create a look that exudes sophistication and class—without looking like you tried too hard.
In this article, we’ll break down how to dress old money for various occasions and give you some stylish tips on achieving that polished yet effortless look.
What Exactly Is Old Money Style?
Before diving into the specifics of how to dress old money for different occasions, it’s helpful to understand the essence of this trend. The old money style revolves around:
- Timeless, Classic Pieces: Think tailored blazers, pleated trousers, cashmere sweaters, and sleek leather bags.
- Neutral and Muted Colors: Navy, beige, grey, and soft earth tones are staples. The focus is on quality and fit, not loud patterns or bold colors.
- Understated Accessories: Fine leather shoes, simple jewelry, and elegant watches add a touch of luxury without being ostentatious.
Now, let’s take a closer look at how to pull off this style for different occasions!
1. How to Dress Old Money for a Casual Day Out
Casual doesn’t mean sloppy, and that’s the core of the old money style. A well-thought-out casual outfit still exudes sophistication, and it’s all about mixing comfort with elegance.
For Men:
- A Crisp Button-Down Shirt: Opt for a high-quality cotton or linen shirt in a light, neutral color like white or pale blue. A well-fitted shirt adds a touch of refinement to your outfit.
- Tailored Chinos or Well-Fitted Jeans: Avoid anything too baggy or too tight. Go for chinos in a neutral color (beige, navy) or dark, straight-leg jeans.
- Leather Loafers or Brogues: Slip into a pair of polished loafers or brogues for an effortlessly stylish finish.
- Subtle Accessories: A leather belt, a simple watch, and perhaps a silk pocket square can elevate the look without drawing too much attention.
For Women:
- Soft Cashmere Sweater or Blouse: Pair a cashmere sweater or silk blouse with tailored pants or a midi skirt. Choose soft, muted tones to keep the look chic.
- High-Waisted Trousers or a Knee-Length Skirt: When in doubt, high-waisted trousers in a neutral tone or a simple A-line skirt can add a polished touch to your ensemble.
- Ballet Flats or Leather Loafers: For footwear, choose leather loafers or ballet flats—simple, but elegant.
- Minimal Jewelry: Keep jewelry understated with a pair of classic pearl earrings or a delicate gold bracelet.
2. How to Dress Old Money for a Formal Event
Attending a formal event like a gala, black-tie dinner, or charity fundraiser? Old money style shines here, too, but the key is opting for classic, tailored pieces that ooze sophistication without any need for extravagant embellishments.
For Men:
- Classic Tuxedo or Suit: A well-tailored tuxedo or a dark, single-breasted suit (think navy or charcoal) is always a winner. Ensure the fit is impeccable and go for timeless fabrics like wool.
- White Dress Shirt: A crisp white dress shirt with a stiff collar never goes out of style.
- Silk Tie or Bow Tie: Opt for a silk tie or a classic black bow tie for a refined look.
- Leather Oxford Shoes: Polished black leather Oxfords or brogues complete the ensemble. Ensure your shoes are sleek and shine.
- Minimalist Cufflinks: Avoid anything too flashy; stick to simple, elegant cufflinks that complement your shirt.
For Women:
- Chic Evening Gown or Classic Little Black Dress: If it’s an evening event, you can never go wrong with a classic black dress, ideally in a high-quality fabric like silk or satin. Alternatively, a floor-length evening gown with subtle details (think a high neckline or a slight A-line cut) exudes old money elegance.
- Delicate Pearl Jewelry: Simple pearl earrings, a matching necklace, or a diamond bracelet can provide that refined touch without looking over-the-top.
- Timeless Pumps: A pair of simple, pointed-toe pumps in black, nude, or navy will elevate your look without drawing attention away from your overall outfit.
- Sleek Clutch Bag: Opt for a simple clutch bag in leather or velvet that complements your dress. Avoid anything too sparkly or flashy.
3. How to Dress Old Money for a Weekend Getaway
A weekend trip to the country or a leisurely weekend in the city doesn’t mean you can throw out the elegance. Old money style translates perfectly to weekend wear, blending comfort and luxury effortlessly.
For Men:
- Cashmere Sweater or Polo Shirt: A soft cashmere sweater paired with tailored trousers or well-fitted chinos is an easy yet sophisticated option for a weekend getaway.
- Tailored Shorts: If the weather calls for it, opt for tailored shorts in a neutral tone, paired with loafers or boat shoes.
- Leather Weekend Bag: A classic, high-quality leather weekend bag will not only look stylish but is also practical for your getaway.
- Sunglasses & a Classic Watch: A pair of understated, classic sunglasses (nothing too oversized) and a minimalist watch are all you need for accessories.
For Women:
- Breton Stripes or Silk Blouse: For a chic but laid-back look, pair a striped Breton shirt with high-waisted jeans or tailored trousers. Alternatively, a silk blouse tucked into an A-line skirt offers a great balance of comfort and style.
- Tailored Shorts or Linen Pants: Opt for linen or cotton trousers for a casual yet polished look. If it’s warm enough, tailored shorts with loafers are an option too.
- Classic Leather Tote: A simple leather tote bag can carry all your essentials while completing the look.
- Sleek Flats or Espadrilles: Comfortable but elegant flats or espadrilles work perfectly for weekend trips, whether you’re strolling around town or lounging outdoors.
4. How to Dress Old Money for a Business Event or Networking
When attending a business event or a networking function, you’ll want to strike a balance between professional and stylish—without appearing too corporate or too laid-back.
For Men:
- Well-Fitted Blazer and Dress Trousers: A tailored blazer paired with matching dress trousers in neutral tones is a go-to for business events. Add a button-down shirt in a light color for an effortlessly polished look.
- Oxford Shoes: Classic black or brown Oxfords are the best choice here. You can never go wrong with them.
- Simple Accessories: A leather belt and a sleek, minimalist watch will keep your accessories subtle but effective.
For Women:
- Tailored Pantsuit or Pencil Skirt: A well-tailored pantsuit or a pencil skirt with a silk blouse is ideal for business events. Stick to neutral colors like navy, black, or grey for a sophisticated look.
- Pointed-Toe Pumps: A classic, neutral-colored pair of pumps will elevate your business look while remaining professional.
- Structured Handbag: Opt for a leather handbag with a structured shape. Avoid anything too large or slouchy.
5. How to Dress Old Money for a Family Gathering or Casual Dinner
Family gatherings and casual dinners are all about being comfortable while still looking refined. The key here is dressing with simplicity, choosing clothes that don’t require a second glance but still make you look put-together.
For Men:
- Polo Shirt and Chinos: A perfectly fitted polo shirt paired with chinos can give you a smart casual look that’s appropriate for a casual dinner or family gathering.
- Dressy Sneakers or Loafers: Leather loafers or dressy sneakers in neutral tones are an easy way to complete the look without being overly formal.
- Classic Watch: Keep accessories minimal with a classic leather-strapped watch.
For Women:
- Simple Knit Dress or Tailored Pants: A simple, knee-length knit dress in a neutral color or a pair of tailored pants with a relaxed blouse is perfect for a casual family event.
- Flat Shoes or Loafers: Go for something comfortable but polished, like ballet flats or leather loafers.
- Subtle Jewelry: A delicate bracelet or a pair of stud earrings add just enough sophistication to your outfit.
Wrapping Up
Sporting the old money look comes down to a few simple ideas—quality over quantity, keeping it simple instead of flashy, and looking elegant without trying too hard. Whether you’re headed out for a casual day, attending a formal event, or enjoying a laid-back weekend, the trick is to stick with timeless pieces, choose fabrics that last, and go for accessories that feel luxe but aren’t in-your-face.
Old money style isn’t just about the clothes—it’s also about how you carry yourself and how you make others feel when they see you. Follow these easy tips, and you’ll dress with confidence for any occasion, all while keeping that polished, effortlessly chic vibe. Enjoy!
