Want to channel that timeless, luxurious vibe without actually raiding a trust fund? These 32+ old-money winter outfits are your ticket to looking effortlessly expensive, even if you’re shopping on a budget.
From perfectly tailored coats to sophisticated layering pieces, we’re breaking down the essential looks that’ll have everyone thinking you summer in the Hamptons and winter in Aspen!
1. Slip-on Dress and Trench Coat
Slip-on dresses speak the old money language best when paired with classy trench coats! With black court heels and dainty gold jewelry, you have a unique fall/winter ensemble to try!
2. Loose Fit Sweater and Slip-On Pattern Mini Dress
Nail that sophisticated look for fine dining in winter, with this old-money outfit combo! Have fun accessorizing this fit with any black-toned floppy hats, sunglasses, and dangler earrings!
3. Loose Fit Sweater and Textured Mini Skirt
Need an old money fall outfit to rock at your campus? Try this textured look with silver pendants, mesh tights, and loafers!
4. Lace Top, High Waist Trousers and Long Coat
Fine lace tops are timeless old money garbs that you can layer with these trousers and a longline coat for a classic winter look! For footwear, ankle boots are a stellar pick!
5. Long Sleeve Velvet Dress and Longline Coat
An old money winter outfit that looks like a million bucks! This one looks even more glamorous with pearl accessories, statement sunglasses, and mesh tights!
6. Maxi Bodycon Dress and Trench Coat
Bodycon dresses make for classy old-money fall outfits when you’ve got chic pattern scarves and a long coat to style them! Add in minimal gold jewelry and court heels and you’re all set!
7. Ribbed Knit Maxi Dress
Nail a minimal old money winter look for the winter with this fall outfit in neutral hues! Add in dainty gold jewelry plus mid-calf tan boots and you have a classy fit to don!
8. Tweed Maxi Dress
These tweed dresses aren’t just warm old money fits to try out in fall/ winter, they make for statement looks with a pair of sunglasses and ballet pumps to match!
9. Ribbed Top and Pants Set + Longline Coat
If you’re aiming for a wild touch with your old money fall outfit, try on this stellar combo with matching fedora hats and court heels! The look is a great pick for family brunches in tan hues!
10. Flared Top, Straight Leg Trousers and Leather Jacket
A vibrant leather jacket can give any basic winter old money outfit an eclectic look. While it won’t need much jewelry, add a charm necklace for the win!
11. Ruffle Sleeve Tiered Dress and Trench Coat
This one is perfect for chilly days with glove details and pearl accents to match old money aesthetics but with an airy and comfy feel! Add in a floppy hat and neutral pumps as well!
12. Strap Top, High Waist Jeans and Trench Coat
Channel that sophisticated yet casual energy for your coffee dates with this stellar old-money winter fit! For cold weather, opt for a longline fur coat along with contrast berets and ankle leather boots!
13. Fur Lined Long Coat, Turtleneck Sweater and Leggings
Make your holiday dinner fit extra classy with this old-money-style outfit! Add in mid-calf boots + fedora hats and you have a look that can turn heads!
14. Textured Sweater Dress and Longline Coat
Look natural while pulling off old money winter outfits with elegant sets like these! Top the look off with a matching beret, lace stockings, and buckle shoes!
15. Fitted Sweater, Pattern Jacket, and Thermal Leggings
Pattern jackets in neutral hues make you stand out from the regular winter looks with an old-money vibe! So, this season, try pairing one with this combo, leather boots and a contrast beret!
16. Knit Sweater, Plaid Skirt and Double Breasted Coat
If you have a knit sweater and plaid skirt, you can effortlessly pull off this old money fall/ winter look! Add in pattern stockings and loafers and you’re set to walk the cityscape!
17. Turtleneck Sweater and Maxi Knot Skirt
Sometimes, simplicity works a clean winter old money outfit and this contrast combo achieves that right! With ivy hats and new balance sneakers, you have a stylish yet practical fit!
18. Pleated Mini Skirt and Fitted Sweater and Textured Long Coat
An elegant campus fit matching the old money aesthetics, this look achieves the perfect fall balance with leather belts and slouchy knee-high boots!
19. Vinyl Pants, Sweater and Longline Coat
Looking for a classy old money winter outfit but in ranch style? With cowboy hats and fringe boots, this look is one stellar pick that gets the country vibe just right!
20. Vinyl Pants, Turtleneck Sweater and Plaid Longline Coat
This preppy-style old-money winter outfit combo is perfect for offices as well as universities! For footwear, any chunky boots in black, work naturally!
21. Turtleneck Sweater, High Waist Jeans and Trench Coat
Try on this laid-back old money outfit this winter with heeled leather boots to match! If you prefer to increase the casual edge of the fit, try swapping the boots for sneakers instead!
22. Turtleneck Top, High Waist Pants, and Leather Long Coat
Your casual turtleneck and pants combo can be elevated to old money aesthetics with a classy leather coat! A touch of gold jewelry and block-heeled boots are perfect for this look!
23. Long-Sleeved Dress and Longline Coat
This bold red and tan combo pairs well with white ankle boots for that rich-looking old money outfit! With a scarf detailing to add, you have a look to don throughout the fall season!
24. Turtleneck Sweater, Straight Leg pants and Longline Coat
Keep up the old-money aesthetics on snowy days with this neutral fit! Instead of the usual boots pairing, try adding UGGs to this fit for that hint of casual glam!
25. Cropped Jacket, Sweater and High Waist Straight Leg Trousers
Channel that old money energy in your winter-time client dinners with this stellar fit! Neutral pumps are great footwear additions to this combo!
26. Ruffle Top, High Waist Jeans and Trench Coat
Craving an old money fall/winter fit but with your favorite pair of jeans? Add a ruffle top along with a longline coat. Pearl earrings and pointed-heel boots match the look effortlessly!
27. Plaid Sweater & Cropped Turtleneck and High Waist Jeans
For a street-style old-money winter outfit that still has contemporary elements, try on this look in all neutrals! For extra cold, add a puffer jacket! Add in ankle boots and you have a neat fit!
28. Pleated Skirt, Fitted Sweater, Solid Shirt and Longline Coat
Bring a touch of playful energy to your old money fall outfits with this combo! Add in knee-high socks + loafers and you have a classy fit to don for semi-formal events in the season!
29. Cropped Jacket, Midi Dress and Mesh Tights
Perfect old money winter outfit for less chilly days! A pair of tinted sunglasses and textured boots are plenty, to balance the fit out!
30. Solid Shirt, Tweed Blazer and Skirt Set
These tweed sets never miss to bring in the old money energy! With a beret and mid-calf boots to add, you have a relaxed yet posh daytime look!
31. Lace Top and Plaid Mini Skirt
A romantic old money fall/winter outfit in black tones perfect for every date! Add in an extra fedora hat and mesh stocking with moccasins for some drama with the fit!
32. Wrap Cardigan and Slip On Dress
Try on this iconic old money outfit for your formal winter/ fall parties with pointed-toe heels in neutrals! Try getting your hands on silk dresses though as they give off luxurious vibes naturally!
