🧥 14 Old Money Casual Outfits Men

ByJonathan Biggins

Old money casual is quiet confidence with great fabrics. No logos, no shouting, just clean lines and pieces that age like a good Scotch. Think timeless, slightly lived-in, and very intentional. Let’s build that wardrobe without looking like you tried too hard.

1. Oxford Shirt and Chinos

Simple, crisp, unbeatable. A white or blue Oxford with khaki chinos screams understated polish. Roll the sleeves and relax.

  • Choose a button-down collar for structure.
  • Stick to flat-front chinos, not skinny.
  • Finish with brown loafers or clean white sneakers.

Pro tip: Wash-and-wear Oxfords look better slightly rumpled. Ironing optional. It works because it’s classic, comfortable, and quietly sharp.

2. Cashmere Crewneck and Denim

Soft sweater, sturdy jeans, perfect balance. A cashmere crewneck over dark straight-leg denim delivers warmth without bulk.

  • Go for navy, camel, or grey knit.
  • Denim should be minimal fade, no whiskers.
  • Add suede chukkas to keep it elevated.

Pro tip: Size the sweater just relaxed, not slouchy. This works because luxe texture meets rugged simplicity.

3. Polo and Pleated Trousers

Preppy, but not precious. A pima cotton polo paired with single-pleat trousers feels effortless.

  • Choose a spread or Johnny collar polo.
  • Stick to cream, navy, or olive pants.
  • Slip on penny loafers for the win.

Pro tip: Tuck the polo and add a braided leather belt. It works because proportions stay relaxed yet refined.

4. Rugby Shirt and White Jeans

Weekend sporty with heritage vibes. The rugby stripe brings character, and white denim keeps it crisp.

  • Pick muted stripes like navy-cream.
  • Choose straight or slim-straight white jeans.
  • Anchor with desert boots or canvas sneakers.

Pro tip: Cuff the jeans slightly to show some ankle. It works because it’s playful, nautical, and clean.

5. Tweed Sport Coat and Knit Tee

Grandpa core, but make it chic. A tweed blazer over a fine-knit tee nails casual-tailored.

  • Go herringbone or houndstooth.
  • Keep the tee crewneck, solid, and fitted.
  • Team with grey flannels or dark denim.

Pro tip: Pocket square optional, but keep it subtle. It works because texture does the talking.

6. Linen Shirt and Tailored Shorts

Warm-weather aristocrat mode. A linen button-up with 7–8 inch shorts feels breezy and grown-up.

  • Stick to white, stone, or sky blue.
  • Shorts should be tailored, not tight.
  • Wear espadrilles or leather sandals.

Pro tip: Half-tuck the shirt and add a webbed belt. It works because it’s relaxed without being sloppy.

7. Cable Knit and Oxford Cloth

East Coast campus energy. A cable-knit sweater layered over a button-down always lands.

  • Choose cream or forest green knit.
  • Let the collar and cuffs peek out.
  • Pair with twill trousers or chinos.

Pro tip: Keep logos tiny or nonexistent. It works because heritage layering never dates.

8. Harrington Jacket and Knit Polo

Clean jacket, refined base. A Harrington over a knit polo gives casual structure.

  • Pick tan, navy, or olive jacket.
  • Go merino or silk-cotton polo.
  • Wear with grey jeans or chinos.

Pro tip: Zip halfway and pop the collar slightly. It works because it’s sleek without trying.

9. Chambray Shirt and Wool Trousers

Workwear meets gentleman. A chambray button-up with lightweight wool pants blends textures.

  • Chambray in mid-blue looks best.
  • Choose high-twist wool for drape.
  • Add tassel loafers or derbies.

Pro tip: Unbutton one extra and skip the tie. It works because soft and sharp balance out.

10. Cricket Sweater and Relaxed Denim

Sports club chic. A cricket V-neck with straight-leg denim is retro-right.

  • Keep trims navy or green.
  • Denim in mid-wash feels lived-in.
  • Finish with white leather sneakers.

Pro tip: Layer a poplin shirt underneath for extra polish. It works because it’s playful tradition.

11. Suede Overshirt and Tee

Luxury layer, simple base. A suede shacket over a high-quality tee hits that quiet-luxe note.

  • Colors: tobacco, chocolate, sand.
  • Tee should be heavyweight cotton.
  • Pair with tailored cargo trousers or chinos.

Pro tip: Keep accessories minimal and leather. It works because texture elevates basics instantly.

12. Barbour and Shetland Wool

Country weekend, city approved. A waxed jacket with a Shetland sweater feels rugged but refined.

  • Jacket in olive or brown.
  • Knit in heathered tones.
  • Team with corduroys or denim.

Pro tip: Let the jacket age. Patina is the point. It works because heritage gear has charm.

13. Tennis Sneakers and Flannel Trousers

Sporty base, tailored legs. Minimal leather sneakers with grey flannels feel modern-classic.

  • Choose low-profile sneakers.
  • Flannels with medium rise.
  • Top with a lightweight cardigan or tee.

Pro tip: Keep socks tone-on-tone. It works because comfort meets polish.

14. Navy Blazer and Knit Hoodie

Yes, the hoodie made the list. A fine-knit hoodie under a navy blazer reads relaxed-smart.

  • Hoodie in merino or cashmere.
  • Blazer with soft shoulders.
  • Wear with tan chinos and loafers.

Pro tip: Keep the hoodie thin so it layers clean. It works because it’s unexpected but tasteful.

Conclusion

Old money casual isn’t a costume. It’s good fabrics, easy fits, and quiet details doing heavy lifting. Build around timeless pieces, keep colors muted, and let quality speak. Understated is the flex.

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