Old Money Outfits For Men: How to Look Timeless

Step into the world of timeless elegance and sophistication as we delve into the captivating realm of Old Money Outfits for Men. Discover the secrets behind crafting a polished and distinguished look that exceeds trends, celebrating the timeless allure of classic style.

Turnbull Asser Shirt Collection

Discover the art of dressing in old money style with our guide to timeless outfits for men. Embrace the classic aesthetic and ageless style that exudes sophistication, whether you’re in your twenties, thirties, or forties. You’ll find old money outfits for men that have already stood the test of time and will be just as stylish years from now.


At Midway Gentleman, we independently research, review, and recommend products we like and believe you’ll find appealing. Our recommendations are rooted in genuine belief, giving you confidence when purchasing any suggested item. We may earn a commission if you make a purchase through our links – at no extra cost to you.

How to Dress Old Money?

Dressing Old Money as a man involves timeless, classic, and understated styles. Opt for high-quality, tailored clothing in neutral colors with brands known for heritage and craftsmanship. Brands like Ralph Lauren, Loro Piana, or Brioni offer timeless pieces that will last you a lifetime if you care for them.

Choose elegant accessories and avoid flashy logos, reflecting a sense of refined taste and sophistication.

Old Money Outfits for Men: White T-Shirt

Old Money Outfits

Old Money outfits exude timeless elegance and sophistication. Think tailored suits, luxurious fabrics, and classic accessories. With a focus on high quality pieces over trends, these ensembles convey a refined and distinguished sense of style that transcends generations.

1. The Navy Blazer

The outfit consists of a navy blazer, a light-colored dress shirt, khaki or gray dress pants, brown leather loafers, and optionally, a patterned silk tie and pocket square. For a more casual look, you can unbutton the top two buttons and drop the tie.

Old Money Outfits for Men: Navy Blue Blazer
Navy Blue Blazer Outfit © Hocketry

2. The Tweed Suit

The outfit features a tweed suit jacket paired with tweed suit pants, complemented by a burgundy dress shirt, and completed with a pair of brogues or leather oxfords. It’s a versatile outfit that can be worn on many occasions.

Old Money Outfits for Men: Tweed Suits

3. The Camel Hair Overcoat

The outfit features a camel hair overcoat elegantly matched with a beige turtleneck and light-washed denim jeans and a pair of Chelsea boots. It portrays timeless sophistication, capturing the essence of refined taste and ageless fashion. Prepare to make a bold and lasting impression with this captivating look.

Old Money Outfits for Men: Camel Hair Coat Men Outfit

4. The Traditional Tuxedo

The king of formal attire. This look features a black tuxedo jacket with satin lapels paired with matching black tuxedo pants adorned with satin stripes, accompanied by a pleated white tuxedo shirt, a classic black bow tie, and polished off with sleek patent leather shoes.

Old Money Outfits for Men: Black Tuxedo Outfit

5. The Preppy Polo Look

This outfit presents an array of options, featuring a stylish polo shirt in either white, pastel colors, or classic navy, paired with khaki or gray chinos, or dress pants.

The outfit usually includes a brown leather belt, but for this particular instance, the belt was skipped. The outfit could be completed with a choice of boat shoes, loafers, or even white sneakers.

Old Money Outfits for Men: White Polo Summer Outfit

6. The Country Club Casual

For this outfit, combine a cable-knit cashmere sweater in either a v-neck or crewneck style, paired with light-colored chinos, and completed with a choice of penny loafers or suede driving shoes. Additionally, you can throw on a pair of shades and your favorite wristwatch.

Old Money Outfits for Men: V-Neck Sweater and Pants

7. The Classic Oxford Shirt

Pair a crisp white Oxford shirt with charcoal gray wool trousers, add a brown leather belt, and complete with classic wingtip brogues – or, skip the belt, go for side adjustable pants and a patterned necktie.

Old Money Outfits for Men: Oxford Shirt with Gray Pants

8. The Houndstooth Check

To achieve this look, pair a houndstooth sport coat or blazer with gray flannel trousers, and complement it with a light blue or plain white dress shirt, a tasteful paisley or striped tie, and complete the ensemble with polished leather dress shoes.

For a more relaxed appearance, skip the tie and add a stylish pocket square. This outfit will be perfect for casual and formal events during summer.

Houndstooth Sport Coat Outfit

9. The Summer Seersucker Suit

The outfit exudes a timeless charm with a seersucker suit jacket and matching seersucker suit pants, elegantly combined with a light-colored linen dress shirt.

Optionally, you can add a necktie for a touch of sophistication. For sunny summer days, you can choose to leave the necktie at home. The outfit is completed with a pair of brown leather loafers.

Old Money Outfits for Men: Linen Suit Outfit
Old Money Outfit by Carlos Roberto and Amanda Roya

10. The Timeless Trench Coat

The perfect outfit for those gloomy autumn days. The outfit features a black or khaki trench coat layered over a navy blue suit, elegantly paired with a white dress shirt. The look was completed with sleek black leather dress shoes, adding a touch of refinement and sophistication.

Old Money Outfits for Men: Black Trench Coat Outfit


Keep in mind that these outfits draw inspiration from old-money aesthetics, which feature classic and refined styles. Feel free to mix and match them according to your personal preferences and the occasion you’re attending.

Nevertheless, remember that to embody the old money style, prioritize quality over quantity and opt for muted colors rather than bold flashy ones.

Old Money Outfit Including Light Blue Shirt and White Pants
Old Money Outfit Inspiration

With a versatile wardrobe, you can mix pieces and the results will still look good, only look out for certain rules that we talked about in a previous article: How to Look Old Money on a Budget

Old Money Outfits For Men: How to Look Timeless
Article Name
Old Money Outfits For Men: How to Look Timeless
Discover the art of timeless elegance with Old Money outfits for men. Unveil the secrets of classic style and sophistication in our comprehensive guide.
Publisher Name
Midway Gentleman
Publisher Logo