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Style · Winter
5 Old Money Winter Outfits for 2026 That Look Effortlessly Expensive
If you’re anything like me, once the temperatures drop, you’re dreaming of cozy coats, classic boots, and outfits that give effortless elegance — not cheesy trends or logo overload. The good news? In fact, the true old money aesthetic is about timeless styling — not flashy labels. And today, I’m giving you 5 chic winter outfit formulas that perfectly capture that vibe.
Gifting for the holidays? My Early Black Friday Picks: The Western Chic Edit has the belts, fringe jackets and boots I’ve linked on LTK for the holidays.
1. Cozy cashmere and winter whites
The Look: Cashmere crewneck sweater + ivory wide-leg pants + shearling slippers or uggs. Similar style: A New Day Women’s High-Rise Wide Leg Trousers, Burgundy Similar style: Alpine Swiss Emily Faux Fur Platform Slippers, Black OAK + FORT Oversized Slouchy Off the Shoulder Sweater, Black Similar style: Wild Fable Women’s Off the Shoulder Banded Pullover Sweater, Gray Striped
2. Ivory jeans and a cashmere sweater
The Look: Creamy sweater + ivory denim + pointed-toe pumps or loafers. PRETTYGARDEN Turtleneck Long Sleeve Oversized Sweaters Similar style: Cicy Bell Cropped Wide Leg Jeans Tony Bianco Phoenix Ankle Boots, Black Como
3. Classic wool coat and leather accessories
The Look: Tailored camel coat + skinny jeans + leather riding boots + matching gloves or a structured leather handbag. Similar style: Tahari Elliot Wool Blend Wrap Coat Similar style: Wrangler Women’s High-Rise Wide-Leg Jeans, Overcast Wash Similar style: A New Day Women’s Estella Tall Boots, Black Strathberry Midi Tote, Burgundy Croc-Embossed chouyatou Winter Double Breasted Wool Coat
4. Burgundy and brown layers
The Look: Deep burgundy sweater or cardigan + chocolate wool pants or mini skirt + loafers. Similar style: A New Day Women’s Cable Knit Pullover Sweater, Cream Tory Burch Classic Platform Lug Sole Loafer Similar style: Long Wool Blend Belted Coat Similar style: Wild Fable Women’s Low-Rise Pleated Mini Skirt, Beige Plaid OAK + FORT Oversized Slouchy Off the Shoulder Sweater, Black Similar style: Wild Fable Women’s Low-Rise Pleated Mini Skirt, Beige Plaid Strathberry Midi Tote, Burgundy Croc-Embossed
5. Royal tartan jacket and elegant basics
The Look: Royal Stuart tartan jacket + black trousers + leather gloves + knee-high boots. Similar style: A New Day Women’s Long Sleeve Button Blazer, Brown Plaid Similar style: A New Day Women’s Payton Tall Boots, Black Strathberry Midi Tote, Black Hobemty Collarless Blazer Plaid Button Front
The outfits
A New Day Women’s High-Rise Wide Leg Trousers, Burgundy
— Target. Cozy cashmere and winter whites.
Similar style, not the exact piece
Shop now
Alpine Swiss Emily Faux Fur Platform Slippers, Black
— Target. Cozy cashmere and winter whites.
Similar style, not the exact piece
Shop now
OAK + FORT Oversized Slouchy Off the Shoulder Sweater, Black
— OAK + FORT. Cozy cashmere and winter whites.
Shop now
Wild Fable Women’s Off the Shoulder Banded Pullover Sweater, Gray Striped
— Target. Cozy cashmere and winter whites.
Similar style, not the exact piece
Shop now
PRETTYGARDEN Turtleneck Long Sleeve Oversized Sweaters
— Amazon. Ivory jeans and a cashmere sweater.
Shop now
Cicy Bell Cropped Wide Leg Jeans
— Amazon. Ivory jeans and a cashmere sweater.
Similar style, not the exact piece
Shop now
Tony Bianco Phoenix Ankle Boots, Black Como
— Tony Bianco. Ivory jeans and a cashmere sweater.
Shop now
Tahari Elliot Wool Blend Wrap Coat
— Amazon. Classic wool coat and leather accessories.
Similar style, not the exact piece
Shop now
Wrangler Women’s High-Rise Wide-Leg Jeans, Overcast Wash
— Target. Classic wool coat and leather accessories.
Similar style, not the exact piece
Shop now
A New Day Women’s Estella Tall Boots, Black
— Target. Classic wool coat and leather accessories.
Similar style, not the exact piece
Shop now
chouyatou Winter Double Breasted Wool Coat
— Amazon. Classic wool coat and leather accessories.
Shop now
A New Day Women’s Cable Knit Pullover Sweater, Cream
— Target. Burgundy and brown layers.
Similar style, not the exact piece
Shop now
Tory Burch Classic Platform Lug Sole Loafer
— Nordstrom. Burgundy and brown layers.
Shop now
Long Wool Blend Belted Coat
— Amazon. Burgundy and brown layers.
Similar style, not the exact piece
Shop now
Wild Fable Women’s Low-Rise Pleated Mini Skirt, Beige Plaid
— Target. Burgundy and brown layers.
Similar style, not the exact piece
Shop nowWild Fable Women’s Low-Rise Pleated Mini Skirt, Beige Plaid
— Target. Burgundy and brown layers.
Similar style, not the exact piece
Shop now
Strathberry Midi Tote, Burgundy Croc-Embossed
— Nordstrom. Burgundy and brown layers.
Shop now
A New Day Women’s Long Sleeve Button Blazer, Brown Plaid
— Target. Royal tartan jacket and elegant basics.
Similar style, not the exact piece
Shop now
A New Day Women’s Payton Tall Boots, Black
— Target. Royal tartan jacket and elegant basics.
Similar style, not the exact piece
Shop now
Strathberry Midi Tote, Black
— Strathberry. Royal tartan jacket and elegant basics.
Shop now
Hobemty Collarless Blazer Plaid Button Front
— Amazon. Royal tartan jacket and elegant basics.
Shop nowProduct photos are from the retailer and show the exact items linked; a similar style is labeled as one. Prices and availability are set by the retailer and can change.
Splurge Option: Ralph Lauren or House of Bruar always have Jackets like this around the holidays. Style Tip: Keep the rest of your outfit sleek to let the jacket shine. Tartan is old money holiday code — festive, preppy, and timeless. Perfect for tree lightings or holiday dinners.
Shopping for a Western-chic girl too? My Western Chic Gift Guide has the buckle belts, boots and cozy layers I’ve tagged on LTK this season.
(I’m also the founder of American Darling, Western chic loungewear. Nothing from it is linked in this post.)
20 picks · All
Target
A New Day Women’s High-Rise Wide Leg Trousers, Burgundy
Similar style, not the exact piece
Shop nowTarget
Alpine Swiss Emily Faux Fur Platform Slippers, Black
Similar style, not the exact piece
Shop nowOAK + FORT
OAK + FORT Oversized Slouchy Off the Shoulder Sweater, Black
Shop nowTarget
Wild Fable Women’s Off the Shoulder Banded Pullover Sweater, Gray Striped
Similar style, not the exact piece
Shop nowAmazon
PRETTYGARDEN Turtleneck Long Sleeve Oversized Sweaters
Shop nowAmazon
Cicy Bell Cropped Wide Leg Jeans
Similar style, not the exact piece
Shop nowTony Bianco
Tony Bianco Phoenix Ankle Boots, Black Como
Shop nowAmazon
Tahari Elliot Wool Blend Wrap Coat
Similar style, not the exact piece
Shop nowTarget
Wrangler Women’s High-Rise Wide-Leg Jeans, Overcast Wash
Similar style, not the exact piece
Shop nowTarget
A New Day Women’s Estella Tall Boots, Black
Similar style, not the exact piece
Shop nowAmazon
chouyatou Winter Double Breasted Wool Coat
Shop nowTarget
A New Day Women’s Cable Knit Pullover Sweater, Cream
Similar style, not the exact piece
Shop nowNordstrom
Tory Burch Classic Platform Lug Sole Loafer
Shop nowAmazon
Long Wool Blend Belted Coat
Similar style, not the exact piece
Shop nowTarget
Wild Fable Women’s Low-Rise Pleated Mini Skirt, Beige Plaid
Similar style, not the exact piece
Shop nowNordstrom
Strathberry Midi Tote, Burgundy Croc-Embossed
Shop nowTarget
A New Day Women’s Long Sleeve Button Blazer, Brown Plaid
Similar style, not the exact piece
Shop nowTarget
A New Day Women’s Payton Tall Boots, Black
Similar style, not the exact piece
Shop nowStrathberry
Strathberry Midi Tote, Black
Shop nowAmazon
Hobemty Collarless Blazer Plaid Button Front
Shop nowLinks go to the retailers. Product photos are from the retailer and show the items linked. Prices and availability are set by the retailer and can change, so I don’t list them here.
What is old money winter style?
Classic, quiet pieces: cashmere knits, wool coats, ivory denim, tartan and leather accessories in neutral or rich colors.
How do you make a winter outfit look expensive?
Keep to a few colors, choose wool or cashmere, and add leather boots and a structured bag.
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