Ever wondered how to nail that effortlessly polished, sophisticated look that screams wealth and class without trying too hard? Welcome to the world of men’s old money outfits—a style that’s all about timeless elegance, understated luxury, and a touch of that “rich boy aesthetic” charm. Whether you’re tired of fast fashion trends or just want to elevate your wardrobe with pieces that exude confidence and refinement, this guide has got you covered.
Also, achieving the old money style men dream isn’t as complicated (or expensive) as it sounds. From office old money looks to casual old money fits, this article is packed with ideas to help you channel that old wealth aesthetic effortlessly.
So, whether you’re dressing for a formal event, a casual outing, or just want to upgrade your everyday style, you’re in the right place. Let’s dive into the world of old money fashion and discover how to dress like a modern gentleman with a timeless edge.
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Effortless Elegance: Knit Polo + White Trousers
@manuel.fiori
This old money outfit is all about understated luxury. A knit polo paired with tailored white trousers creates a polished yet relaxed vibe. The addition of loafers and a sleek belt ties the look together, making it perfect for a summer brunch or a casual garden party. It’s a timeless choice for the old money aesthetic men.
Classic Cool: White Polo + Khaki Trousers
@iman.soly
This old money style men look is all about effortless sophistication. A crisp white polo tucked into tailored khaki trousers creates a clean, polished vibe. The leather belt and watch add subtle luxury, while the sunglasses complete the look. Perfect for casual outings or a relaxed business lunch.
Urban Sophistication: Grey Sweater + White Trousers
@julianpiket
This old money aesthetic outfit pairs a sleek grey sweater with white trousers for a refined yet approachable look. The layered shirt collar adds depth, while the camel coat and suede loafers elevate the ensemble. Ideal for city strolls or upscale casual events, this look is timeless and versatile.
Minimalist Cool: Black Tee + White Trousers
@itsohrab
This rich boy aesthetic look is all about simplicity. A fitted black tee tucked into tailored white trousers creates a sleek, modern vibe. Chunky black shoes and a leather backpack add a contemporary edge, making it perfect for casual office days or city adventures.
Coastal Charm: Blue Linen Shirt + White Shorts
@aryannnsingh.a
For a breezy, coastal-inspired old money fashion, pair a light blue linen shirt with white shorts. The relaxed fit and soft textures exude effortless luxury. Add a beaded necklace and a canvas bag for a laid-back yet stylish vibe, perfect for beach days or summer getaways.
Laid-Back Luxe: Navy Henley + White Pants
@oldmoney_men
A navy henley paired with white pants is the perfect blend of casual and refined. This old money style men outfit is ideal for relaxed afternoons or outdoor gatherings. The neutral loafers and sunglasses add a modern touch, making it a versatile choice for any occasion.
Cozy Sophistication: Wool Coat + Beige Sweater and Dark Trousers
@oldmoney.heiress
This old wealth aesthetic look features a wool coat layered over a beige sweater and dark trousers. The black scarf adds warmth and elegance, while the relaxed fit keeps it comfortable. Perfect for chilly days when you want to stay stylish and cozy.
Edgy Elegance: Leather Jacket + Pleated Trousers
@cabigaobrian
For a bold twist on old money style men, pair a classic leather jacket with pleated trousers and a tucked-in henley shirt. The mix of textures creates a striking balance between edgy and sophisticated. Add black boots to complete this versatile look, perfect for evenings out or casual gatherings.
Minimalist Cool: Navy Shirt + Black Joggers
@mystreetkit
This rich boy aesthetic outfit is all about simplicity with a modern edge. A navy short-sleeve shirt paired with black joggers creates a relaxed yet polished vibe. White sneakers and dark sunglasses add a contemporary touch, making it perfect for casual weekends or travel days.
Monochrome Sophistication: Grey Peacoat + Slim-Fit Trousers
@yohansimplement
A grey peacoat layered over a turtleneck and slim-fit trousers is the ultimate old wealth aesthetic look. The monochrome palette exudes timeless elegance, while black Chelsea boots and sunglasses add a sleek finish. This outfit is perfect for winter outings or formal occasions.
Modern Gentleman: Camel Coat + Brown Turtleneck
@mauro.littera
Channel the ultimate old money style men with a camel coat layered over a brown turtleneck and tailored trousers. This look is perfect for cooler weather, offering warmth without compromising on style. Pair it with polished leather shoes for a sharp, professional vibe that’s both timeless and versatile.
Casual Luxe: Polo Shirt + White Shorts
@nachoyanes
A light blue polo shirt paired with white shorts is the epitome of casual luxury. This rich boy aesthetic look is perfect for a sunny day out or a relaxed lunch. Add black sandals and sunglasses for a laid-back yet refined vibe that’s effortlessly cool.
Smart-Casual Charm: Cream Blazer + Burgundy Trousers
For a smart-casual take on the old money fashion, pair a cream blazer with burgundy trousers. The muted tones create a sophisticated palette, while the tailored fit keeps it sharp. Finish with black leather shoes for a look that’s perfect for semi-formal events or a stylish day in the city.
Relaxed Sophistication: White Shirt + Beige Trousers
@robo_13
This look is a masterclass in old money style men. A crisp white shirt tucked into beige trousers creates a clean, polished aesthetic. The sweater draped over the shoulders adds a touch of effortless charm, while neutral sneakers keep it casual. Perfect for a stroll through the city or a relaxed lunch date.
Rainy Day Chic: Navy Puffer + White Pants
@byazzamjamil
For a refined yet practical outfit, pair a navy quilted jacket with white pants. The dark polo shirt adds depth, while brown loafers and a leather belt complete the old money aesthetic men vibe. This look is ideal for rainy days when you want to stay stylish without sacrificing comfort.
Earthy Elegance: Brown Shirt + Wide-Leg Trousers
@aryannnsingh.a
Channel the old wealth aesthetic with this earthy-toned outfit. A relaxed brown shirt paired with wide-leg trousers creates a vintage-inspired yet modern look. The soft textures and warm tones make it perfect for casual outings or evening gatherings. Add leather shoes for a polished finish.
Vintage Luxe: Trench Coat + Brown Vest + Wide-Leg Trousers
@moritz.taylor
This look is a nod to classic old money fashion. A tailored trench coat layered over a brown vest and wide-leg trousers creates a vintage yet sophisticated vibe. The tie and cap add a playful touch, making it perfect for formal events or stylish city strolls.
Sleek Professional: Black Blazer + Blacl Turtleneck + Grey Trousers
@gentlemansthing
For a modern take on the old money aesthetic men, pair a fitted black blazer with grey trousers and a black turtleneck. The structured silhouette exudes confidence, while the leather bag and polished shoes complete the look. Ideal for business meetings or upscale gatherings.
Timeless Charm: Camel Coat + Black Trousers
@ilyes_gherissi
A camel coat over a crisp white shirt and black trousers is the epitome of old money style men. This outfit is effortlessly elegant, with the neutral tones creating a refined palette. Add black leather shoes and sunglasses for a polished, versatile look that works for any occasion.
Bold Sophistication: Burgundy Shirt + Charcoal Pants
@mohammadpouralli
This rich boy aesthetic look is all about making a statement. A deep burgundy shirt paired with charcoal pants creates a bold yet classy vibe. The rolled-up sleeves and sleek watch add a touch of casual elegance, perfect for evening events or date nights.
All-White Elegance: White Suit + Open Collar White Shirt
@oldmoney
Nothing says old wealth aesthetic like an all-white suit. This look is effortlessly luxurious, with the open-collar shirt adding a relaxed yet refined touch. Perfect for summer parties or exclusive events, this outfit is a true standout in the world of old money outfits.
Relaxed Luxury: Oversized Shirt + Wide-Leg Trousers
@najibasma
This old money aesthetic look combines an oversized cream shirt with wide-leg brown trousers for a relaxed yet refined vibe. The tucked-in tank top adds a modern touch, while leather loafers and a sleek black bag complete the ensemble. Perfect for casual outings or a stylish coffee run.
Coastal Sophistication: Striped Linen Shirt + Grey Trousers
@old_money_royalty
A striped linen shirt paired with tailored grey trousers is a breezy take on old money fashion. The lightweight fabric and neutral tones make it ideal for warm weather, while the open collar adds a touch of effortless charm. This look is perfect for summer vacations or rooftop brunches.
Urban Edge: Black Peacoat + Slim-Fit Jeans
@yohansimplement
This old money aesthetic men look combines a black peacoat with slim-fit black jeans and a textured sweater for a sleek, urban vibe. The monochrome palette is effortlessly stylish, while suede boots and sunglasses add a touch of sophistication. Perfect for casual city strolls or evening outings.
Rustic Elegance: Tan Blazer + Cream Trousers
@romuloozolio22
A tan double-breasted blazer paired with cream trousers is a classic old money style men outfit. The crisp white shirt adds a clean touch, while brown leather shoes complete the polished look. Ideal for outdoor events or countryside gatherings, this ensemble exudes timeless charm.
Modern Casual: Grey Blazer + Black Trousers
@_nikolovski_1
This rich boy aesthetic outfit features a grey blazer layered over a black tee and paired with black trousers. The yellow pocket square adds a pop of color, while Chelsea boots and sunglasses keep it sharp. Perfect for casual business meetings or stylish weekend outings.
Refined Layers: Beige Sweater + White Pants
@miguel_label7
For a sophisticated yet approachable look, pair a beige sweater with crisp white pants. This combination exudes the old wealth aesthetic, blending comfort and elegance effortlessly. Add loafers or moccasins to complete the ensemble, making it ideal for a day at the office or a classy dinner outing.
Vintage Charm: Navy Overcoat + Grey Trousers
@murray_bm
A navy overcoat paired with grey trousers and a tie creates a refined old wealth aesthetic look. The flat cap adds a vintage touch, while polished black shoes complete the ensemble. This outfit is perfect for formal occasions or a day at a historic venue.
Sophisticated Neutrals: Camel Coat + Plaid Trousers
@lebeaugustave
This old money fashion look features a camel coat layered over a beige zip-up sweater and plaid trousers. The neutral tones create a sophisticated palette, while sunglasses and a leather bag add modern flair. Perfect for winter outings or upscale casual events.
Preppy Charm: White Polo + Cream Trousers
@classic_elegance._
This old money aesthetic look is effortlessly preppy. A fitted white polo tucked into cream trousers creates a clean, polished vibe. The sweater draped over the shoulders adds a touch of sophistication, while a brown belt and gold watch complete the ensemble. Perfect for casual outings or a day at the yacht club.
Retro Cool: Beige Jacket + Grey Trousers
@leonlund.pictures
This rich boy aesthetic outfit is all about vintage-inspired charm. A beige jacket layered over a white polo and paired with grey trousers creates a relaxed yet polished vibe. The loafers and minimal accessories make it perfect for casual drives or weekend getaways.
Ivy League Vibes: Cable Knit Sweater + White Trousers
@gentlemens.order
A cream cable knit sweater paired with white trousers is the epitome of old money fashion. The V-neck detailing adds a preppy touch, while the brown leather shoes and watch complete the look. Ideal for brunch at a high-end café or a day at the country club.
Nature-Inspired Elegance: Olive Shirt + White Linen Trousers
@michaelzusolms
This old money aesthetic look is perfect for a relaxed day outdoors. The olive button-up shirt paired with white linen trousers creates a breezy, sophisticated vibe. The neutral tones and lightweight fabrics make it ideal for warm weather, while aviator sunglasses add a touch of effortless cool.
Playful Casual: Patterned Co-Ord Set + White Sneakers
@benimino.fr
For a modern twist on old money fashion, this patterned co-ord set paired with white sneakers is both stylish and comfortable. The relaxed fit and subtle design make it perfect for casual outings, while the white socks and accessories add a polished touch. A great choice for summer days or laid-back events.
Retro Formal: Black Sweater + High-Waisted Trousers
@arnald.lagji
This old money style men outfit channels retro sophistication. A black sweater layered over a white shirt and tie, paired with high-waisted trousers, creates a sharp, vintage-inspired look. The belt and sunglasses add a modern edge, making it perfect for formal occasions or stylish city strolls.
Monochrome Luxe: Camel Coat + Beige Turtleneck
@peterabat
This rich boy aesthetic look is all about tonal elegance. A camel coat layered over a beige turtleneck and slim-fit trousers creates a sleek, monochromatic outfit. The brown belt and loafers complete the ensemble, making it ideal for winter outings or upscale events.
Classic Preppy: Black Sweater + Grey Jeans
@arnald.lagji
For a timeless old wealth aesthetic, pair a black sweater with grey jeans and a crisp white shirt. The tucked-in tie adds a preppy touch, while the sunglasses and leather belt keep it modern. This versatile look is perfect for casual office days or weekend brunches.
Coastal Elegance: Suede Jacket + White Pants
@vistavast
For a breezy old wealth aesthetic, pair a light suede jacket with white pants and a mandarin-collar shirt. The soft textures and neutral tones exude understated luxury, while the loafers add a relaxed charm. Perfect for a coastal drive or a weekend getaway, this look is effortlessly chic.
Minimalist Charm: Ribbed Polo + Black Trousers
@tradition_wardrobe
This rich boy aesthetic outfit is a masterclass in simplicity. A ribbed white polo paired with tailored black trousers creates a sleek, modern silhouette. The clean lines and neutral palette make it perfect for casual dinners or stylish coffee dates. Add a watch for a touch of elegance.
Embracing men’s old money outfits is all about timeless elegance, understated luxury, and crafting a wardrobe that speaks sophistication without saying a word. Take inspiration from our curated list of men’s old money outfits and start building a wardrobe that exudes timeless elegance and effortless sophistication.