Old Money Style: How to Dress the Casual Way

Casual old money style means quiet, well-fitted basics in natural fabrics and a muted palette: a crewneck knit, a crisp shirt, straight trousers, loafers. Nothing has a visible logo, and nothing looks new for the sake of it.

If you want the short version of how to dress old money, buy fewer pieces, choose fabric and fit over labels, and keep your colors close together.

Section 01

What is old money style?

Stanford law professor Richard Thompson Ford describes old money aesthetics as "anything that evokes mid-20th century East Coast elites—think clothing that would be worn to prep schools or Ivy League college quads." So it is a look, not a price bracket. You can build it with thrifted knits and a good pair of chinos.

Much of it grew out of campus sportswear. The Harvard Gazette notes that preppy style can be traced back to Ivy League campuses, where students wore pleated tennis pants and skirts, rugby shirts and sweaters to class, to practice and to dinner afterwards. The same article says the button-down and polo shirt have outlasted trend cycles.

Dressing for the occasion is an older idea too. James Laver wrote that "Even rich women wore tailor-mades in the country or when traveling". Practical, well-cut clothes for real activities have long been part of the look.

Section 02

What is the old money color palette?

Stay in a narrow range: navy, camel, cream, olive, soft gray, stone and the occasional deep green or burgundy. Pick ivory over stark white and navy over harsh black. The softer contrast keeps the outfit calm.

Through the lens of evidence-based design, I'd think about texture before color. A matte wool and a shiny synthetic in the same navy do not read as the same navy, because the surface changes how light reaches the eye. Matte, brushed and woven surfaces tend to look more settled.

Good pairings to try:

• Navy and camel
• Olive and cream
• Soft gray and blush
• Stone and white with a navy accent

Cool undertones (pink or blue) often look good in navy, stone and gray. Warm undertones (golden or yellow) usually suit camel, olive and cream. Hold a sweater up to your face in daylight and see whether it brightens or flattens you.

If you like color with your classics, see old money bright colors styling tips.

Section 03

Old money outfit essentials

You need surprisingly little. A short list covers most days:

• A crewneck or V-neck sweater in wool, merino or cashmere
• A white or pale blue button-down in cotton or linen
• A polo shirt in a plain color
• Straight chinos or wool trousers
• A navy blazer
• A beige trench or a simple wax or wool coat
• Loafers, leather sneakers or simple flats
• A leather belt and a plain watch

Skip visible logos and heavy embellishment. The point is that the quality shows up in the drape and the stitching, not on the chest.

Want to go deeper on building a set? The old money capsule wardrobe and the comfy version lay out full combinations.

Section 04

Old money style casual: how to wear it day to day

Casual means relaxed, not sloppy. Swap the blazer for a cardigan, the trousers for clean chinos or pleated shorts, and keep the shirt crisp. A sweater over the shoulders or a tucked polo reads as easy and put together.

Layering helps. Try a linen shirt under a lightweight merino knit, with a scarf in a muted tone if the weather asks for it. Each layer should sit close to the next without pulling.

Old money style for summer leans on breathable fabrics: linen shirts, cotton polos, light chinos, leather sandals or canvas shoes. Stick to cream, pale blue, sage and sand so the heat does not push you into loud colors.

For more everyday ideas, browse casual old money fashion trends.

Section 05

Old money style for women and men

Women

Think A-line or midi skirts, silk or cotton blouses, tailored trousers, ballet flats and a structured bag. A fitted knit with high-rise trousers works on most body types. If you have broader shoulders, wide-leg trousers and a simple top balance the line. If you want more definition at the waist, a belted coat or a nipped-in jacket does the job.

For dressier days, romantic old money outfit ideas show a softer take.

Men

Start with an oxford shirt, a shawl or crewneck sweater, flat-front chinos and loafers. Keep the trouser break slight and the shoulder seam on the edge of your shoulder. A navy blazer with gray trousers covers almost any smart-casual invitation.

Section 06

How should old money clothes fit?

Fit does most of the work. A jacket that pulls at the shoulders is a fit problem, not a you problem, and a tailor can often fix sleeve length and trouser hems for a modest fee.

• Shoulder seams should sit where your shoulder ends.
• Sleeves should show a little shirt cuff under a jacket.
• Trousers should skim, not cling or pool.
• Knits should lie smooth over the torso without stretching.

I'd treat the neckline as the first thing the eye reads, so a clean collar or crew neck that sits flat matters more than an extra accessory.

Section 07

Do's and don'ts

• Do choose natural fibers like wool, cotton, linen, silk and cashmere when you can.
• Do wash knits sparingly and hang jackets on wide wooden hangers to keep their shape.
• Do buy secondhand. Well-made pieces often outlive new ones.
• Don't wear head-to-toe trend items. One current piece, such as wide-leg trousers, is plenty.
• Don't let logos, heavy distressing or glossy synthetics lead the outfit.

Trends do come and go. The FIT fashion timeline records that skinny jeans were introduced in 2005 and were commonplace by 2006, and plenty of people have since moved on to straighter cuts. Cuts that stay close to classic age better.

Heading to an event? See the wedding guest guide or the office outfits page.

Backstage Q&A

Frequently asked questions

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