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Old Money Seasonal Style Guide for Modern Gentlemen

With its timeless elegance and understated sophistication, the Old Money aesthetic has captivated fashion enthusiasts for generations.

However, to master the Old Money look, you must know how to adapt your wardrobe to different seasons and weather conditions.

In this guide, we’ll introduce you to the seasonal secrets of Old Money style, tips on wardrobe essentials, layering techniques, and key accessories for mastering the look.

Before diving into each season’s specifics, do your seasonal color analysis and find your unique color profile.

That’s to ensure that the recommended colors in this article match your seasonal color palette and your wardrobe harmonizes with your skin, hair, and eye color.

Old Money Spring Style

Spring’s Old Money aesthetic embraces soft hues and lightweight fabrics.

The palette includes pastel shades like blush pink, pale yellow, mint green, and light neutrals like beige, ivory, and light gray.

Cotton, linen, and seersucker fabrics offer breathability and comfort in warmer weather. Spring style balances semi-formal and casual, depending on the occasion.

Emulate John F. Kennedy’s iconic Nantucket look with a white cotton cable-knit sweater from Aran Sweater Market and well-fitted khaki chinos from Brooks Brothers.

Complete the ensemble with classic Sperry Authentic Original boat shoes in Sahara leather. For a classic layered look à la Ralph Lauren, pair a lightweight navy Harrington jacket from Polo Ralph Lauren with a pale blue gingham shirt from Turnbull & Asser.

Accessorize with a timeless stainless steel Rolex Datejust 41 with a white dial, a Jubilee bracelet, tortoiseshell Persol PO3019S sunglasses, and a woven leather belt in tan from J.Crew.

Spring Details
Colors Blush pink, pale yellow, mint green, beige, ivory, light gray
Garments White cable-knit cotton sweater (Aran Sweater Market), khaki chinos (Brooks Brothers), pale blue gingham shirt (Turnbull & Asser), lightweight navy Harrington jacket (Polo Ralph Lauren)
Footwear Sperry boat shoes in Sahara leather, Gucci Jordaan horse-bit loafers in brown leather
Accessories Rolex Datejust 41 (stainless steel, white dial, Jubilee bracelet), Persol PO3019S Havana Green tortoiseshell sunglasses, J.Crew woven leather belt.

Old Money Summer Style

Summer Old Money aesthetic features breathable fabrics and a vibrant color palette.

Bright whites, classic French blue, nautical navy, and bold red dominate the wardrobe. Linen, cotton, and lightweight wool blends are the fabrics of choice.

Summer style tends to be casual, with occasional semi-formal events.

Channel Gianni Agnelli’s effortless summer style with a cream linen suit from Brioni, a light blue linen shirt from Charvet, and Fratelli Rossetti Brera tassel loafers in tobacco suede.

For a classic Hollywood summer look inspired by Cary Grant, don a navy linen blend suit from Brunello Cucinelli, a white linen shirt from Orlebar Brown, and an ivory Panama Quito hat from Borsalino.

Complete your summer ensemble with Amber tortoiseshell sunglasses from Cutler and Gross, a navy and white NATO watch strap from Tudor, and Swims Breeze loafers in white.

Summer Details
Colors Bright white, French blue, nautical navy, bold red
Garments Cream linen suit (Brioni), light blue linen shirt (Charvet), navy linen blend suit (Brunello Cucinelli), white linen shirt (Orlebar Brown)
Footwear Fratelli Rossetti Brera tassel loafers in tobacco suede, Swims Breeze loafers in white
Accessories Borsalino Panama Quito hat in ivory, Cutler and Gross Amber tortoiseshell sunglasses, Tudor navy and white NATO watch strap

Old Money Fall Style

Fall Old Money aesthetic embraces rich, warm tones and medium-weight materials. Burgundy, olive green, burnt orange, and camel dominate the palette.

Wool, cashmere, and corduroy add texture and depth to your wardrobe. The level of formality shifts towards semi-formal and formal, with occasional casual events.

Emulate Steve McQueen’s rugged yet refined fall style with a chunky cream Aran knit wool sweater from Peregrine, olive corduroy trousers from Brooks Brothers, and a brown leather bomber jacket from Valstar.

For a classic layered look inspired by Paul Newman, pair a dark green lambswool turtleneck from John Smedley with a brown houndstooth tweed sport coat from J.Press.

Accessorize with a burgundy cashmere scarf from Begg & Co., a stainless steel Cartier Tank Solo XL watch with a black alligator leather strap, and Tricker’s Stow country boots in marron antique calf leather.

Autumn Details
Colors Burgundy, olive green, burnt orange, camel
Garments Cream Aran knit wool sweater (Peregrine), olive corduroy trousers (Brooks Brothers), brown leather bomber jacket (Valstar), dark green lambswool turtleneck (John Smedley), brown houndstooth tweed sport coat (J.Press)
Footwear Tricker’s Stow country boots in marron antique calf leather, Crockett & Jones Coniston in tan scotch grain leather
Accessories Begg & Co. burgundy cashmere scarf, Cartier Tank Solo XL (stainless steel, black alligator leather strap), Ghurka Examiner No. 5 leather briefcase in chestnut

Old Money Winter Style

Winter Old Money aesthetic prioritizes warmth and sophistication with deep, rich hues and heavy, warm materials.

Navy, forest green, charcoal, and burgundy dominate the color palette. Wool, cashmere, and flannel keep the cold at bay.

Winter style focuses on formal and semi-formal dressing, with occasional casual events.

Channel John F. Kennedy Jr.’s timeless winter elegance with a navy wool overcoat from Polo Ralph Lauren, a cream Aran knit wool sweater from Inis Meáin, and charcoal flannel trousers from Cordings.

Emulate Prince Charles’s regal winter style with a double-breasted navy cashmere overcoat from Crombie, a light blue herringbone shirt from Turnbull & Asser, and a burgundy cashmere scarf from Johnstons of Elgin.

Complete your winter ensemble with Crockett & Jones Molton chukka boots in dark brown suede, a stainless steel Omega Seamaster Diver 300M with a blue dial and steel bracelet, and a pair of Dents Flemming cashmere-lined leather gloves in black.

Winter Details
Colors Navy, forest green, charcoal, burgundy
Garments Navy wool overcoat (Polo Ralph Lauren), cream Aran knit wool sweater (Inis Meáin), charcoal flannel trousers (Cordings), double-breasted navy cashmere overcoat (Crombie), light blue herringbone shirt (Turnbull & Asser)
Footwear Crockett & Jones Molton chukka boots in dark brown suede, Edward Green Galway in dark oak antique calf
Accessories Johnstons of Elgin burgundy cashmere scarf, Omega Seamaster Diver 300M (stainless steel, blue dial, steel bracelet), Dents Flemming cashmere-lined leather gloves in black

Old Money Seasonal Styling Tips

When mastering the Old Money style across different seasons, there are certain do’s and don’ts to remember.

Follow these guidelines to keep your wardrobe timeless, elegant, and adaptable.


  • Adapt your Old Money style to your climate, region, and the modern world
  • Choose fabrics and weights appropriate for local weather conditions
  • Consider cultural norms when selecting garments, footwear, and accessories for your outfits
  • Incorporate contemporary aspects into your wardrobe – modern accessories or trendy colors to keep your look current and relevant
  • Focus on well-fitted, high-quality garments that exude timeless elegance
  • Focus on classic silhouettes from premium materials and impeccable tailoring
  • Craft a wardrobe that transcends seasons and stands the test of time


  • Ignore the influence of your climate and region on your style choices
  • Wear fabrics or weights that are unsuitable for the local weather conditions
  • Disregard cultural norms when selecting outfits
  • Stick solely to traditional Old Money style garments without incorporating trendy fast-fashion
  • Settle for ill-fitting or low-quality garments that lack timeless elegance
  • Skimp on investing in classic silhouettes, premium materials, and impeccable tailoring
  • Build a wardrobe that is limited to a single season or fails to stand the test of time

Old Money Mastery with The VOU

Crafting an Old Money look that adapts to the changing seasons requires attention to detail and a keen understanding of timeless elegance.

The VOU’s expert stylists can guide you through the intricacies of seasonal Old Money style – wearing correct garments, footwear, and accessories for every occasion.

Our stylists will help you incorporate contemporary elements while maintaining the essence of the old-money aesthetic, ensuring your look remains current and relevant.

Whether you’re attending a formal event, a business meeting, or a casual gathering, The VOU will help you curate a wardrobe that reflects your unique personality and aspirations.

Take our Fashion Style Analysis to embark on a journey of sartorial discovery with The VOU’s expert guidance and uncover your signature Old Money style.

With over twenty years of front-row fashion and styling events, collabs with haute-couture houses, and a PhD in Luxury Fashion, Laurenti is an expert in crafting personalized looks that depict old-money sophistication.

With years of expertise in high-end fashion collabs and a PhD in Sustainable Fashion, Ru specializes in curating eco-luxe wardrobes for the modern gentleman seeking understated refinement.

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