20+ Old Money Outfits Hairstyles So Chic You’ll Feel Like a Billionaire!

The “old money” look is all about understated sophistication, effortless polish, and a touch of inherited glamour. Think: tailored cashmere, silk scarves, pearl earrings, and timelessly elegant hair. The right hairstyle isn’t loud or trendy; it’s expertly cut, meticulously styled, and always impeccably maintained—whispering confidence and legacy. Whether you’re preparing for a garden party, a gallery opening, or a dinner at the club, these hairstyles will elevate your ensemble with the grace of true aristocracy.

What’s best for you:
Focus on clean lines, gentle volume, and minimal embellishment. Choose a style that flatters your face shape, works with your natural hair texture, and pairs with your most beloved wardrobe classics. For truly personalized polish, consult a professional stylist for custom color and precision cutting.

1. The Glossy Blunt Bob

The glossy blunt bob is pure sophistication—a chin-grazing cut with sharp edges and high shine. Its clean silhouette suggests heritage and wealth, framing the face beautifully and pairing effortlessly with old-money essentials like tweed jackets and silk blouses.

How to Cut/Style:
Cut hair to chin or just below, with zero layering for density. Blow-dry straight using a round brush, finish with a flat iron for glassy shine, and tuck behind one ear for subtle allure.

Time to Attain:
45–60 minutes for cutting, styling, and finishing.

Tools Required:
Precision shears, round brush, flat iron, shine serum.

Maintenance Tips:
Trim every 4–6 weeks to keep edges crisp. Use a silk pillowcase to maintain sleekness overnight.

Suitable Age/Event/Face:
Ages 22–55; best for oval, heart, and square faces. Ideal for business lunches, art gallery openings, or charity events.

Best Outfits:
Tweed blazers, silk camisoles, diamond studs.

Popular Color Shades:
Rich brunette, classic black, cool blonde.

Pro Tips:
For even more gloss, use a lightweight finishing oil after styling.

2. Soft Center-Parted Waves

Soft, center-parted waves exude understated romance and ease. The look is neither fussy nor overdone, with gentle movement that frames the face and drapes naturally over shoulders—capturing that “old money on holiday” aura.

How to Cut/Style:
Medium to long hair, cut with subtle long layers for flow. Create a clean center part, curl with a 1.25″ wand, and brush out for soft, seamless waves.

Time to Attain:
45–60 minutes for prepping, curling, and brushing.

Tools Required:
Large-barrel curling iron, wide-tooth comb, boar bristle brush, smoothing cream.

Maintenance Tips:
Sleep in a silk scarf to reduce frizz and preserve the shape.

Suitable Age/Event/Face:
Ages 18–50; flattering for oval, heart, and long faces. Perfect for garden parties, brunch, or weekend getaways.

Best Outfits:
Cashmere cardigans, linen wide-leg trousers, ballet flats.

Popular Color Shades:
Champagne blonde, honey brunette, sandy brown.

Pro Tips:
Mist with a lightweight shine spray for a healthy, natural glow.

3. Sleek Low Ponytail with Side Part

A sleek low ponytail with a deep side part is the epitome of quiet luxury. The style is simple yet regal, keeping hair controlled and glossy—perfect for showcasing elegant necklines and classic jewelry.

How to Cut/Style:
Medium to long hair, one-length for fullness. Part deeply to one side, smooth hair with serum, and secure at the nape. Wrap a strand around the elastic for a polished finish.

Time to Attain:
20–30 minutes for parting, smoothing, and tying.

Tools Required:
Flat iron, tail comb, smoothing serum, elastic, bobby pins.

Maintenance Tips:
Keep a mini brush handy to tame flyaways. Apply serum to ends daily.

Suitable Age/Event/Face:
Ages 22–60; best for heart, oval, and long faces. Ideal for luncheons, business meetings, or gala dinners.

Best Outfits:
Satin slip dresses, silk scarves, tennis bracelets.

Popular Color Shades:
Deep espresso, dark blonde, natural grey.

Pro Tips:
For extra hold, mist with a lightweight hairspray before leaving the house.

4. Polished French Twist

The French twist is an enduring emblem of refined wealth. Its sculptural elegance lifts the neck and face, providing an air of composure that pairs perfectly with tailored evening attire or formal daytime events.

How to Cut/Style:
Medium to long hair, smooth and one-length. Twist hair upward from the nape, tuck ends inside, and pin securely along the vertical seam. Smooth edges for a seamless finish.

Time to Attain:
30–45 minutes for twisting and pinning.

Tools Required:
Bobby pins, tail comb, strong-hold hairspray, smoothing brush.

Maintenance Tips:
Carry spare pins and a small spray for touch-ups.

Suitable Age/Event/Face:
Ages 28–65; universally flattering, especially for oval and long faces. Best for galas, society weddings, and boardroom presentations.

Best Outfits:
Tailored sheath dresses, pearl necklaces, silk shawls.

Popular Color Shades:
Silver blonde, chestnut, raven black.

Pro Tips:
Tease the crown slightly before twisting for extra lift.

5. Smooth Long Hair with Velvet Headband

Smooth, straight long hair adorned with a velvet headband is both preppy and patrician. This style channels equestrian club heritage and is ideal for pairing with blazers, riding boots, or classic cocktail attire.

How to Cut/Style:
Long, blunt cut or micro-layers for movement. Blow dry hair straight, flat iron for perfection, and place a wide velvet headband just behind the hairline.

Time to Attain:
30–40 minutes for blow-drying and accessorizing.

Tools Required:
Flat iron, smoothing brush, velvet headband, shine serum.

Maintenance Tips:
Brush daily with a boar bristle brush; replace the headband to avoid flattening roots.

Suitable Age/Event/Face:
Ages 18–45; ideal for oval, heart, and round faces. Great for daytime events, luncheons, or museum visits.

Best Outfits:
Structured blazers, silk blouses, riding boots.

Popular Color Shades:
Glossy brunette, chestnut, cool blonde.

Pro Tips:
Tuck hair behind one ear for subtle sophistication.

6. Soft Chignon with Face-Framing Layers

The soft chignon with gentle face-framing layers radiates quiet refinement and vintage grace. Its low, loose knot at the nape gives a romantic, effortless appearance—always in style at charity teas or art gallery openings.

How to Cut/Style:
Medium to long hair with long face-framing layers. Smooth hair back, leaving layers out in front. Secure a low ponytail, twist into a soft chignon, and pin at the nape. Lightly curl the layers for natural softness.

Time to Attain:
30–45 minutes for smoothing, twisting, and curling.

Tools Required:
Bobby pins, elastic, curling iron, smoothing brush, light-hold hairspray.

Maintenance Tips:
Keep pins on hand for touch-ups and lightly mist the chignon with hairspray for flexible hold.

Suitable Age/Event/Face:
Ages 25–60; especially flattering on oval, heart, and round faces. Perfect for brunches, teas, or formal daytime gatherings.

Best Outfits:
Cashmere wrap dresses, brooches, silk scarves.

Popular Color Shades:
Ash brown, champagne blonde, chestnut.

Pro Tips:
Curl the face-framing layers away from the face for a soft, luminous effect.

7. Classic Half-Up Bouffant

The classic half-up bouffant blends old Hollywood glamour with subtle aristocratic flair. Lifted at the crown and pinned back, it’s perfect for showing off statement earrings and bare shoulders while exuding control and confidence.

How to Cut/Style:
Medium to long hair, lightly layered. Tease the crown for volume, smooth over the top section, and pin at the back of the head. Curl the lower half for gentle, cascading waves.

Time to Attain:
40–50 minutes for teasing, curling, and pinning.

Tools Required:
Teasing comb, bobby pins, curling wand, smoothing brush.

Maintenance Tips:
Retouch volume at the crown as needed. Mist with flexible hold spray.

Suitable Age/Event/Face:
Ages 22–55; flattering on heart, oval, and long faces. Best for cocktail parties, formal dinners, or weddings.

Best Outfits:
Off-shoulder strapless dresses, pearl drop earrings, silk evening gloves.

Popular Color Shades:
Golden blonde, dark brown, rich mahogany.

Pro Tips:
Secure the bouffant with hidden bobby pins in a criss-cross for extra staying power.

8. Loose Side-Swept Curls

Loose side-swept curls whisper effortless luxury. Gathered over one shoulder, these polished waves evoke yacht-club weekends and villa holidays, pairing perfectly with strapless gowns and heirloom jewelry.

How to Cut/Style:
Medium to long hair, cut with long layers. Curl all hair with a 1-inch iron, part deeply to one side, and drape over the opposite shoulder. Pin discreetly if needed.

Time to Attain:
40–50 minutes for curling and arranging.

Tools Required:
Curling iron, boar bristle brush, light-hold spray, pins.

Maintenance Tips:
Brush gently to retain shape and touch up ends with serum.

Suitable Age/Event/Face:
Ages 18–50; best for oval, heart, and square faces. Ideal for galas, weddings, or high-society receptions.

Best Outfits:
Strapless evening gowns, diamond necklaces, satin wraps.

Popular Color Shades:
Honey blonde, espresso, rose gold.

Pro Tips:
Pin the hair at the nape beneath the curls to keep waves in place all night.

9. Polished Slicked-Back Bun

The polished slicked-back bun channels an equestrian club or couture luncheon vibe—sleek, controlled, and unadorned. This style puts facial structure and fine accessories in the spotlight, radiating quiet power and confidence.

How to Cut/Style:
Medium to long hair, blunt or slightly layered. Comb hair straight back with smoothing gel, secure into a low or mid bun at the nape, and use a bristle brush for a flawless finish.

Time to Attain:
20–30 minutes for slicking and bun creation.

Tools Required:
Fine-tooth comb, boar bristle brush, strong-hold gel, bobby pins.

Maintenance Tips:
Smooth flyaways with a dab of gel during the day.

Suitable Age/Event/Face:
Ages 25–55; especially flattering for oval, angular, and heart faces. Perfect for business meetings, luncheons, or charity events.

Best Outfits:
Tailored pantsuits, silk blouses, sapphire studs.

Popular Color Shades:
Jet black, dark brunette, natural grey.

Pro Tips:
Mist the bun with a shine spray for a “glass” finish.

10. Softly Tousled Long Layers

Soft, tousled long layers deliver effortless, inherited glam—evoking English countryside estates and weekends in the Hamptons. The look is healthy, natural, and always in fashion, perfect for pairing with classic cashmere and pearls.

How to Cut/Style:
Long hair, cut with subtle, face-framing layers for bounce. Use a large-barrel iron to create gentle bends, then shake out and mist with texture spray.

Time to Attain:
30–40 minutes for curling and texturizing.

Tools Required:
Large-barrel curling iron, texture spray, paddle brush.

Maintenance Tips:
Brush gently and revive with a mist of dry shampoo for volume.

Suitable Age/Event/Face:
Ages 18–50; flattering on oval, long, and heart faces. Perfect for casual brunches, picnics, or weekend gatherings.

Best Outfits:
Cashmere crewnecks, pleated trousers, loafers.

Popular Color Shades:
Chestnut, buttery blonde, soft auburn.

Pro Tips:
Part slightly off-center for a casual but refined effect.

11. Graceful Braided Headband

A graceful braided headband offers a touch of feminine charm and regal elegance. This soft, woven crown style channels the image of country manor afternoons and garden parties, adding youthful polish to any old money ensemble.

How to Cut/Style:
Medium to long hair, softly layered. Section off a piece from just above one ear, braid it, and sweep across the top of the head, pinning securely on the opposite side. Leave the rest of the hair softly curled or straightened for contrast.

Time to Attain:
30–40 minutes for braiding, pinning, and finishing.

Tools Required:
Tail comb, bobby pins, curling iron (optional), flexible hold spray.

Maintenance Tips:
Refresh the braid as needed. Lightly mist with flexible hold spray for natural movement.

Suitable Age/Event/Face:
Ages 18–40; works well on oval, heart, and round faces. Perfect for bridal showers, afternoon teas, or daytime receptions.

Best Outfits:
Pastel strapless dresses, lace gloves, pearl accessories.

Popular Color Shades:
Strawberry blonde, caramel, honey brunette.

Pro Tips:
Gently tug at the braid to soften and widen for a more relaxed, ethereal look.

12. Sleek Middle-Parted Long Ponytail

A sleek middle-parted ponytail embodies modern old money sophistication—elegant, minimalist, and quietly powerful. This style pairs perfectly with tailored classics, allowing fine fabrics and jewelry to shine.

How to Cut/Style:
Long, one-length hair for uniformity. Part precisely down the center, smooth hair with a flat iron, and secure at the mid to low nape. Wrap a small section around the elastic for a seamless finish.

Time to Attain:
25–30 minutes for parting, straightening, and securing.

Tools Required:
Flat iron, fine-tooth comb, smoothing serum, elastic, bobby pin.

Maintenance Tips:
Keep a serum handy for flyaways and brush daily with a boar bristle brush.

Suitable Age/Event/Face:
Ages 22–55; best for oval, angular, and heart faces. Ideal for luncheons, business events, or club dinners.

Best Outfits:
Tailored wool trousers, silk button-ups, loafers.

Popular Color Shades:
Glossy brunette, platinum blonde, rich chestnut.

Pro Tips:
Tuck hair behind the ears for an ultra-sleek, face-framing effect.

13. Old Money Barrel Curls

Barrel curls evoke timeless glamour, with large, defined curls that bounce with movement. This classic look is reminiscent of vintage society photos, ideal for upscale soirées or romantic evenings at the opera.

How to Cut/Style:
Medium to long hair, cut with minimal layers for the body. Set hair with a large-barrel iron, pin each curl to cool, then brush out gently for uniform waves.

Time to Attain:
45–60 minutes for setting, cooling, and brushing.

Tools Required:
Large-barrel curling iron, sectioning clips, boar bristle brush, shine spray.

Maintenance Tips:
Pin curls overnight to maintain shape, and use a silk scarf to prevent frizz.

Suitable Age/Event/Face:
Ages 20–60; flattering on oval, long, and heart faces. Best for black-tie events, theater, or society weddings.

Best Outfits:
Strapless evening gowns, opera gloves, vintage brooches.

Popular Color Shades:
Butter blonde, espresso, classic auburn.

Pro Tips:
Always let curls cool completely before brushing for best longevity and bounce.

14. Elegant Low Side Ponytail

The elegant low side ponytail combines ease and chic, keeping hair tidy while exuding effortlessness. Draped gently over one shoulder, this style draws attention to necklines and pearls, perfect for modern classic wardrobes.

How to Cut/Style:
Medium to long hair with soft, blended layers. Part hair to one side, smooth and secure just below the ear, wrapping a small strand around the elastic.

Time to Attain:
20–30 minutes for parting, smoothing, and tying.

Tools Required:
Elastic, fine-tooth comb, smoothing cream, bobby pin.

Maintenance Tips:
Refresh ends with a shine serum. Tuck stray pieces behind the ear for extra polish.

Suitable Age/Event/Face:
Ages 18–50; suits oval, heart, and square faces. Perfect for cocktail hours, rehearsal dinners, or art openings.

Best Outfits:
Strapless A-line dresses, pearl strands, satin pumps.

Popular Color Shades:
Light caramel, warm brunette, champagne blonde.

Pro Tips:
Curl the ponytail’s ends under for an ultra-sleek finish.

15. Soft Blown-Out Volume

Soft, blown-out volume signals affluence and vitality. This style, with its airy lift and swing, is a favorite for high-society gatherings and country club brunches, complementing classic tailoring with effortless movement.

How to Cut/Style:
Medium to long hair, cut with long layers for natural fullness. Blow dry with a round brush, lifting roots for body, and use a volumizing mousse for light, touchable hold.

Time to Attain:
35–45 minutes for drying and styling.

Tools Required:
Round brush, blow dryer, volumizing mousse, paddle brush.

Maintenance Tips:
Sleep with hair loosely pinned on top to preserve your body. Revive with a spritz of dry shampoo at the crown.

Suitable Age/Event/Face:
Ages 25–60; flattering for oval, long, and heart faces. Ideal for luncheons, charity events, or afternoon teas.

Best Outfits:
Pastel sheath dresses, silk cardigans, diamond studs.

Popular Color Shades:
Beige blonde, golden brown, soft copper.

Pro Tips:
Blow dry hair upside down for extra lift at the roots before finishing.

16. Classic Sleek French Bob

The classic French bob is the epitome of Parisian refinement—chin-length, blunt, and flawlessly sleek. Its polished simplicity signals taste and tradition, drawing focus to bone structure and high-quality fabrics.

How to Cut/Style:
Chin-length blunt cut, ideally just grazing the jawline with no layers. Blow-dry smooth with a round brush, finish with a flat iron for ultra-gloss. Tuck one side behind the ear for subtle allure.

Time to Attain:
30–40 minutes for drying, smoothing, and perfecting.

Tools Required:
Precision shears, round brush, flat iron, shine serum.

Maintenance Tips:
Trim every 4–5 weeks to preserve the crisp line. Sleep on a silk pillowcase to reduce friction.

Suitable Age/Event/Face:
Ages 22–60; best for oval, heart, and square faces. Perfect for art fairs, club meetings, or upscale dinners.

Best Outfits:
Crisp white blouses, cashmere sweaters, gold chain necklaces.

Popular Color Shades:
Classic black, deep brunette, pearl blonde.

Pro Tips:
Finish with a spritz of shine spray for that high-society luster.

17. Regal Low Twisted Chignon

The regal low twisted chignon is a salon classic, elegantly coiled at the nape for understated grandeur. Its clean finish and secure shape ensure it never distracts from couture or vintage jewels.

How to Cut/Style:
Medium to long hair, one-length or softly layered. Gather hair into a low ponytail, twist and coil into a chignon, and pin at the base of the neck. Smooth edges with serum.

Time to Attain:
25–35 minutes for twisting and pinning.

Tools Required:
Elastic, bobby pins, boar bristle brush, smoothing serum.

Maintenance Tips:
Mist with flexible hold spray for control. Tuck in any flyaways with a dab of serum.

Suitable Age/Event/Face:
Ages 28–65; universally flattering. Perfect for formal dinners, museum galas, or weddings.

Best Outfits:
Tailored strapless evening gowns, heirloom brooches, silk wraps.

Popular Color Shades:
Espresso, champagne blonde, dark chestnut.

Pro Tips:
Pin a vintage barrette or pearl comb above the chignon for a custom touch.

18. Retro Brushed-Out Glamour Waves

Retro brushed-out glamour waves evoke old Hollywood charm—smooth, perfectly aligned, and full of vintage luster. This style radiates inherited style and is made for evenings at the opera or historic mansions.

How to Cut/Style:
Medium to long hair, blunt or lightly layered. Set hair with a 1-inch iron in uniform curls, pin to cool, then brush thoroughly for soft, continuous waves.

Time to Attain:
1–1.5 hours for curling, setting, and brushing.

Tools Required:
Curling iron, setting clips, boar bristle brush, shine spray.

Maintenance Tips:
Touch up with a soft brush and re-mist with shine spray as needed. Protect with a silk scarf overnight.

Suitable Age/Event/Face:
Ages 25–65; ideal for oval, heart, and long faces. Perfect for balls, society weddings, or formal galas.

Best Outfits:
Vintage velvet strapless gowns, fur stoles, diamond earrings.

Popular Color Shades:
Golden blonde, chestnut, dark auburn.

Pro Tips:
Set every curl in the same direction for a flawless, wave-like effect.

19. Center-Parted Sleek Long Layers

Center-parted sleek long layers deliver quiet opulence. The style falls like silk over the shoulders, accentuating both face shape and high-quality fabrics—embodying the essence of “money talks, wealth whispers.”

How to Cut/Style:
Long, blended layers. Create a precise center part, blow dry with a paddle brush, and finish with a flat iron and a few drops of lightweight serum for reflective shine.

Time to Attain:
30–40 minutes for blow-drying and flat ironing.

Tools Required:
Paddle brush, flat iron, fine-tooth comb, shine serum.

Maintenance Tips:
Keep ends healthy with regular trims and deep conditioning masks.

Suitable Age/Event/Face:
Ages 18–50; best for oval, long, and heart faces. Ideal for luncheons, board meetings, or gallery strolls.

Best Outfits:
Tailored cashmere coats, wide-leg trousers, minimalist jewelry.

Popular Color Shades:
Beige blonde, mocha brown, soft balayage.

Pro Tips:
Apply serum only to the mid-lengths and ends to avoid flattening the roots.

20. Romantic Low Ponytail with Ribbon

A low ponytail tied with a silk ribbon brings a sense of feminine tradition, reminiscent of finishing schools and estate garden parties. This style is soft, subtle, and distinctly old money, especially when the ribbon is in a muted, natural tone.

How to Cut/Style:
Medium to long hair with light layering. Smooth hair into a low ponytail, tie with a silk or velvet ribbon, and curl the ends under for movement.

Time to Attain:
15–25 minutes for smoothing, tying, and finishing.

Tools Required:
Elastic, silk or velvet ribbon, curling iron, smoothing brush.

Maintenance Tips:
Replace ribbon to avoid creases; refresh ends with a curling iron if needed.

Suitable Age/Event/Face:
Ages 16–45; flattering for oval, heart, and round faces. Great for picnics, afternoon teas, or garden weddings.

Best Outfits:
Pastel strapless sundresses, ballet flats, delicate pendant necklaces.

Popular Color Shades:
Light brunette, soft blonde, chestnut.

Pro Tips:
Choose a ribbon that matches or complements your outfit’s palette for true refinement.

21. Effortless Modern Pageboy

The modern pageboy cut, with its rounded ends and precise contour, channels European legacy and taste—always sharp, always elegant, and instantly recognizable as “old money.” This look is making a comeback for those who value crisp lines and retro luxury.

How to Cut/Style:
Short to medium length, cut blunt just below the ears with slightly undercut ends. Blow dry smooth with a round brush, and tuck the sides behind the ears for a contemporary update.

Time to Attain:
25–35 minutes for precise blow-drying and shaping.

Tools Required:
Precision shears, round brush, smoothing serum.

Maintenance Tips:
Trim every 4–6 weeks to maintain the signature curve. Use serum for lasting shine.

Suitable Age/Event/Face:
Ages 25–65; best for oval, heart, and angular faces. Perfect for art museum tours, society luncheons, or private dinners.

Best Outfits:
Crisp button-up shirts, high-waisted trousers, vintage pins.

Popular Color Shades:
Rich brunette, icy blonde, classic grey.

Pro Tips:
Pair with a classic red lip for ultimate old money drama.

Conclusion

With these 21+ old money hairstyles, you’ll channel an air of confidence, heritage, and refined luxury, no matter your wardrobe or event. Each style is thoughtfully matched to classic outfits and color palettes—ensuring your hair is always as quietly powerful as your ensemble. For best results, work with a professional stylist to adapt cuts and colors to your face shape and hair type, and invest in quality care for enduring, photo-ready polish.