Looking to dress with that timeless old money aesthetic but not sure where to start? These 30+ outfit ideas will help you master sophisticated fashion, whether you’re building your professional wardrobe or upgrading your everyday style.
From crisp blazers and well-fitted trousers to quality loafers and statement accessories, we’ve curated 30+ essential outfits that bring that refined old money look into your modern wardrobe.
1. Textured Long Coat and Two Piece Suit
Elevate your winter office style with this neutral old money-style combination! Go for metal watches in gold and dark Oxford shoes for a preppy finish!
2. Solid Two Piece Suit
Style your formal suits in neutral hues for a sleek-looking old money fit! Skip ties and rock the look in white sneakers for a modern finish or opt for classic Oxfords instead!
3. Solid Sweater, Long Coat, and Solid Trousers
Upscale your street looks from basic to edgy ‘old money’, with this neat monochrome find! Add in leather gloves, belts, and dress shoes for a refined appeal!
4. Striped T-shirt, Solid Trousers, and Trench Coat
Make your hangout looks scream old money elegance with this striped combo, dress shoes, and layered bracelets in gold or silver!
5. Casual Shirt and Loose Fit Trousers
Pull off this minimal old money look in neutral hues, ankle boots, and dainty metal jewelry for effortless cool!
6. Solid Shirt, Slim Fit Pants, and Trench Coat
Exude effortless old money elegance for your winter hangouts with this tailored trench coat combo, ankle boots, and dark sunglasses!
7. Full Sleeve T-shirt, Bootcut Jeans, and Fleece Lined Leather Jacket
Try this country-style old money look for your summer getaways in tan and neutral hues! Finish off the look in leather boots and silver pendants for a vintage touch!
8. Hoodie, Slim Fit Jeans, and Long Coat
Mix casual with classy for your winter outings in this stellar old money find! Go for black and tan hues with the outfit alongside high ankle boots and clubmaster sunglasses as add ons!
9. Solid Shirt, Sweater Vest, Plaid Blazer, Fit Trousers and Trench Coat
An old money-style winter outfit perfect for formal meetings and dinner parties! Add patterned scarves, fedora hats, and leather gloves for a dramatic finish!
10. Turtleneck Sweater, Slim Fit Pants, and Alpaca Coat
Layer a tan Alpaca coat over neutral or white turtleneck sweaters for a casual look that is relaxed yet refined! With the pants, try styling Oxford shoes in black alongside dark sunglasses!
11. Solid Shirt and Shorts
Keep it light and classy for your summer cruises in this pastel combo paired with midsole sneakers and dainty neck chains! Add Clubmaster sunglasses for a refined finish!
12. Striped Casual Shirt and Slim Fit Trousers
Blend tropical with elegance in this relaxed old money combo! Go for linen textures with the trousers and muted hues while the footwear can be kept minimal neutral loafers!
13. Flat Knit Shirt, Slim Fit Trousers, and Cropped Coat
Bring in a laid-back old money appeal into your fall/ winter hangouts with knit shirts in light hues! Add in a metal watch in silver with leather slip-ons for a classy finish!
14. Polo T-shirt and Slim Fit Trousers
Pull off this refined casual combo in neutral hues in classic old-money fashion! Go for beret hats and leather Oxford shoes for an opulent touch!
15. Turtleneck Sweater, Slim Fit Trousers, and Trucker Jacket
A preppy but casual old money look to don this winter, rock the look in dainty silver jewelry and ankle boots if you’re headed out during the day!
15. Knit Polo Shirt and Slim Fit Trousers
Simple and classy, don this old money combo for your summer hangouts with leather belts, metal watches, and contrast slip ons!
16. Solid Shirt, Cardigan, and Tapered Trousers
A vintage old money combo to pull off in neutral hues, go for tan slip-ons for a minimal finish, or swap them with white sneakers for a more modern appeal!
17. Turtleneck Sweater, Gurkha Pants and Long Coat
Rock this minimal old-money winter combo in black and tan hues with Chelsea boots and dainty silver jewelry for a powerful hangout look!
18. T-shirt, Slim Fit Trousers and Bomber Jacket
Create a relaxed outfit with old-money aesthetics with this combination! Go for leather textures with the jacket alongside gold chains along with casual sneakers!
19. Striped Shirt and Slim Fit Trousers
A classic club-style old money combo to rock in the summer, go for minimal styling with this one using leather belts and casual sneakers!
20. Solid Shirt, Sweater, and Mac Coat
Add this layered old money combo to your winter workwear or hangout wardrobe in somber hues alongside Chelsea boots in leather!
21. Turtleneck Sweater, Slim Fit Trousers, and Overcoat
Rock this corporate old-money combo in navy blue and dark hues with classic Oxford shoes and a metal watch for sophistication!
22. Contrast Three Piece Suit and Solid Top Coat
Bring original prep school energy into your formal looks with this old-money combo! Go for silk ties with Derby shoes in black or tan and a vintage watch!
23. Cropped Trench Coat, Turtleneck Sweater and Trousers
A minimal old-money combo for your wintertime casual dates or hangouts outs, style this one in metal-rimmed sunglasses and bracelets in gold!
24. Solid Shirt and Slim Fit Trousers
Pull off this semi-formal old money combo in pastels for your summer outings with tan Oxford shoes and a metal watch for a refined edge!
25. Two Piece Suit and Overcoat
Create old money finesses with this all-black formal combo, dark loafers, and a gold metal watch! For the glasses, go for wayfarers with a dark tint!
26. Turtleneck Sweater, Slim Fit Trousers and Top Coat
Achieve a relaxed yet timeless casual appeal with this old money combo and leather belts! A blend of blue, black, and tan tones works well. For footwear, pick leather Chelsea boots!
27. Sweater, Slim Fit Trousers and Overcoat
Go bold with your winter looks in this old money pairing! Give the outfit a preppy finish with matching French berets and Oxford shoes!
28. Suit Jacket, Gurkha Pants, and Crisp Button Down Shirt
Look effortlessly elegant for your formal parties in this sleek old-money outfit! Top the look off in Clubmaster sunglasses and tan loafers!
29. Sweater Vest, Button Down Shirt, and Slim Fit Trousers
A stylish old-money winter look to don in professional or campus settings, amp up this one’s relaxed appeal with white sneakers and a metal watch!
30. Oversized Suit-Pant
While oversized clothes are considered streetwear, you can transform a baggy suit-pant into an old-money look pairing it with classy sunglasses and chunky shoes.
