50 Old Money Outfits for Men

Want to look sharp without trying too hard? The “old money outfits men” style is all about simple, high-quality clothes that never go out of style.

We put together 50 easy outfit ideas using classic pieces you already own.

Get ready to upgrade your closet using these timeless tips.

1. The Navy Blazer Look

A dark blue blazer is the king of this style. Wear it over a simple white tee or a light blue shirt. This piece instantly makes any outfit look put together and smart.

• Fit: Shoulders must fit perfectly.
• Color: Deep navy blue is best.
• Pairing: Works well with gray wool trousers.

Pro Tip: Choose a blazer with simple brass or bone buttons instead of plastic ones for a touch of class.

2. Cream Cable Knit Sweater

This thick, textured sweater is a classic look for cooler days. It shows quality and warmth. Wear it alone or layer it over a crisp collared shirt.

• Material: Look for wool or thick cotton.
• Fit: Relaxed but not baggy.
• Accessory: Pair with a simple leather watch.

Pro Tip: Always wear a thin undershirt beneath wool knits to keep the sweater clean and protect the fibers.

3. Crisp White Polo Shirt

Forget loud logos. This polo must be plain, high-quality cotton. It works tucked into chinos or worn loose with tailored shorts. Keep the collar neat.

• Fabric: Pima cotton feels the best.
• Style: Two or three buttons maximum.
• Bottoms: Navy chinos or tailored trousers.

Pro Tip: The collar should stand up slightly under a blazer, but never ‘popped’ fully up.

4. Tailored Gray Trousers

These are wool or a wool blend, offering a great texture. They should have a straight fit and break just over your shoe. They are dressier than chinos but more relaxed than suit pants.

• Detail: Look for subtle pleats.
• Color: Medium or charcoal gray.
• Footwear: Brown leather loafers.

Pro Tip: Iron a sharp crease down the center of the trouser legs; this makes them look expensive and structured.

5. Brown Penny Loafers

A simple, classic shoe that can be dressed up or down. Choose a dark brown leather that looks rich. Wear them sockless in warm weather or with dark dress socks when cold.

• Material: Polished leather is key.
• Style: Simple penny or tassel loafer.
• Maintenance: Keep them highly shined.

Pro Tip: If wearing sockless, use no-show socks to keep the shoe lining fresh and dry.

6. The Classic Trench Coat

A light beige or camel trench coat is a perfect outer layer. It adds instant drama and structure. Wear it open over a blazer or a simple sweater and trousers.

• Length: Should hit below the knee.
• Color: Light khaki or beige.
• Detail: Check for a strong lapel shape.

Pro Tip: Do not buckle the belt tightly. Instead, tie the belt loosely in a knot behind your back for a relaxed, flowing look.

7. Oxford Shirt and Chinos

This is the everyday uniform of the style. A light blue button-down shirt paired with khaki or stone-colored chinos. The look is clean, comfortable, and always appropriate.

• Shirt: Must be neatly ironed.
• Chinos: Flat front, straight fit.
• Belt: Simple woven leather belt.

Pro Tip: Roll the shirt sleeves up past the elbow, making sure the cuff is hidden in a neat roll.

8. Simple Leather Watch

A thin, classic watch face with a leather strap is essential. Avoid large, bulky sports watches. The watch should be an accent, not a statement piece.

• Strap: Brown or black leather.
• Face: Clean white or cream dial.
• Match: Match the strap color to your shoes.

Pro Tip: A vintage or heirloom watch is the ultimate accessory for this look, showing history and taste.

9. White Tennis Sneakers

These are low-profile, clean leather sneakers. They should look spotless and simple. They replace dress shoes in casual settings without looking sloppy.

• Material: Smooth, white leather.
• Style: Very minimal design.
• Rule: They must be perfectly clean.

Pro Tip: Keep a shoe cleaning brush and white polish handy. Dirty shoes ruin the entire ‘old money’ effect.

10. The Burgundy Sweater Vest

A knit vest adds a layer of color and warmth without the bulk of sleeves. Wear it over a white button-down shirt and pair it with dark trousers.

• Color: Deep jewel tones like burgundy or hunter green.
• Fit: Should be slim and neat.
• Layering: Best over a light shirt.

Pro Tip: The vest should cover your belt line completely when standing up straight.

11. Dark Wash Denim

If you wear jeans, they must be dark blue, straight-leg, and have no rips or fading. They should look almost as tailored as trousers. Pair them with a sport coat.

• Wash: Deep indigo or black.
• Fit: Straight or slim-straight.
• Avoid: Distressed or ripped styles.

Pro Tip: Cuff the bottom hem once or twice if you are wearing loafers or boots to show off the footwear.

12. Cashmere Scarf (Camel)

A simple, high-quality scarf in a neutral color. This is worn draped loosely over a coat or blazer. It adds warmth and a luxurious texture.

• Material: Cashmere or fine wool.
• Color: Camel, gray, or navy.
• Style: Solid color is best.

Pro Tip: Don’t tie it in a bulky knot. Just drape it over your neck and let both ends hang down the front of your coat.

13. Linen Shirt and Shorts

For summer, a light linen shirt (white or light blue) paired with tailored shorts that hit above the knee. This is comfortable but still looks sharp.

• Shirt: Wear it slightly wrinkled, that’s the point.
• Shorts: Tailored, flat front.
• Footwear: Boat shoes or driving mocs.

Pro Tip: Linen shirts look best when the bottom hem is left untucked and hangs straight.

14. The Rugby Shirt

A thick, heavy cotton shirt with a white collar and horizontal stripes. This is a sporty, casual piece that still feels classic. Pair it with simple chinos.

• Fabric: Heavy, durable cotton.
• Pattern: Wide, classic stripes.
• Vibe: Casual weekend wear.

Pro Tip: The rugby shirt should fit slightly loose, giving a relaxed, athletic feel.

15. Suede Chelsea Boots

A simple, slip-on boot in brown or taupe suede. These are great for fall and winter. They look fantastic with tailored trousers or dark denim.

• Material: Soft, high-quality suede.
• Color: Dark brown or sand.
• Pairing: Wear with wool socks.

Pro Tip: Use a suede protector spray when you buy them, as suede is easily damaged by rain and dirt.

16. Silk Knit Tie

A tie made of knitted silk has a unique texture that looks less formal than a smooth silk tie. Choose a solid color like navy or forest green.

• Knot: Simple four-in-hand knot.
• Color: Muted, dark colors.
• Use: Perfect with a tweed sport coat.

Pro Tip: The end of the tie should hit exactly at the top of your belt buckle, never longer or shorter.

17. Herringbone Sport Coat

A sport coat made from textured wool in a herringbone or tweed pattern. This adds visual interest and depth. Pair it with solid colored pants.

• Pattern: Subtle, not overwhelming.
• Color: Brown, gray, or olive mix.
• Layering: Works over a thin turtleneck.

Pro Tip: This jacket works best when paired with fabrics that are smooth, like cotton chinos or plain wool trousers.

18. The Simple Cardigan

A fine-gauge wool cardigan that buttons up the front. Wear it buttoned up like a sweater or open over a T-shirt. It’s a softer alternative to a blazer.

• Material: Merino wool or cashmere.
• Fit: Slim, worn close to the body.
• Detail: Leave the bottom button undone.

Pro Tip: Choose a cardigan in a classic color like burgundy or light gray for versatility.

19. Boat Shoes (Leather)

A true summer staple. Leather boat shoes are perfect for casual outings. They must be worn without socks and should be kept clean and polished.

• Material: Dark brown or tan leather.
• Rule: Never wear socks.
• Pairing: Chinos or tailored shorts.

Pro Tip: If the laces look worn, replace them immediately. Fresh laces make the shoe look brand new.

20. Turtleneck Sweater (Thin)

A thin, high-quality wool turtleneck in black or navy. This is a sharp look when worn under a blazer or sport coat. It replaces the need for a collared shirt.

• Material: Fine merino wool.
• Fit: Neck should be snug.
• Color: Dark and solid.

Pro Tip: Make sure the turtleneck is thin enough that it doesn’t bunch up awkwardly under your jacket collar.

21. White Dress Shirt

Every man needs several crisp white dress shirts. They are the foundation of almost every smart look. Ensure they are always perfectly ironed.

• Collar: Choose a spread or semi-spread collar.
• Fit: Tailored, not too billowy.
• Use: Wear under everything.

Pro Tip: Starch your collars lightly for a sharper, more structured look that holds up all day.

22. Khaki Chino Shorts

Shorts should be flat-fronted and hit just above the knee. Avoid cargo shorts or anything too baggy. Keep the color light and neutral.

• Length: 7-inch or 9-inch inseam.
• Color: Stone, khaki, or light blue.
• Detail: Ironed cuffs look best.

Pro Tip: Pair khaki shorts with a navy polo or a light blue button-down shirt for a classic summer outfit.

23. The Pocket Square

A simple accessory that adds a lot of polish. A white linen square is the easiest choice. It should complement the shirt, not match the tie.

• Color: White linen is timeless.
• Fold: Simple straight line or a puff fold.
• Placement: Only in a blazer or sport coat pocket.

Pro Tip: The pocket square should never be the same fabric or pattern as your tie. They should contrast.

24. Navy Pinstripe Suit

A subtle pinstripe adds a layer of formality and texture. The stripes should be thin and barely noticeable. Wear with a solid tie and simple shoes.

• Stripe: Very thin and light.
• Fit: Must be perfectly tailored.
• Shirt: Light blue or white.

Pro Tip: Never wear a pinstripe suit jacket as a standalone blazer; it only works as a full suit.

25. Driving Moccasins

A very comfortable, casual shoe often made of suede or soft leather. They are perfect for driving or relaxed summer days. Choose a muted color.

• Material: Suede or soft leather.
• Color: Tan, navy, or gray.
• Wear: Only in dry weather.

Pro Tip: These shoes are meant to be worn without socks, just like boat shoes.

26. The Harrington Jacket

A simple, lightweight zip-up jacket, usually in beige, navy, or green. It’s a great casual layer that is much cleaner than a hoodie or bomber jacket.

• Style: Simple collar, simple zipper.
• Color: Beige or stone.
• Pairing: Jeans or chinos.

Pro Tip: Keep the jacket unzipped over a nice shirt or sweater to show off the layer underneath.

27. Wool Overcoat (Long)

A heavy, structured coat that goes past the knee. This is worn over your entire outfit in cold weather. Charcoal gray or camel wool are the best choices.

• Length: Below the knee for maximum impact.
• Material: Heavy wool or cashmere blend.
• Color: Charcoal gray or camel.

Pro Tip: Ensure the coat is large enough to fit comfortably over a blazer without pulling or bunching.

28. Gingham Check Shirt

A shirt with a small, subtle check pattern. This adds visual interest without being loud. Pair it with solid trousers or a navy sport coat.

• Pattern: Small scale check is key.
• Color: Blue and white or pink and white.
• Fit: Worn tucked or untucked.

Pro Tip: If wearing a patterned jacket, choose a very small gingham check to avoid clashing patterns.

29. Simple Leather Belt

A thin, high-quality leather belt with a simple, small buckle. The belt should always match the color and finish of your leather shoes.

• Buckle: Small and plain metal.
• Color: Match your shoes exactly.
• Width: Thin, not too wide.

Pro Tip: Avoid large, flashy logo buckles. The buckle should be subtle and functional.

30. Monochromatic Gray Look

Wearing different shades of the same color, like light gray trousers with a darker charcoal sweater. This looks clean and intentional.

• Rule: Use different textures.
• Colors: Gray, navy, or cream.
• Effect: Looks instantly expensive.

Pro Tip: If going monochromatic, ensure one piece (like the shirt) is a very crisp, contrasting white.

31. Tailored Swim Trunks

Swimwear should look like tailored shorts. They must be shorter, hit above the knee, and be a solid color or a subtle pattern.

• Length: Mid-thigh is ideal.
• Pattern: Solid navy or light blue.
• Avoid: Baggy board shorts.

Pro Tip: Pair your tailored trunks with a crisp white polo shirt when walking to and from the pool or beach.

32. The Light Blue Suit

For summer events, a suit in light blue or stone cotton or linen. This is sharp but feels relaxed. Wear it with a white shirt and no tie.

• Fabric: Cotton or linen blend.
• Style: Unstructured jacket is best.
• Footwear: Brown loafers.

Pro Tip: An unstructured jacket has less padding, making it much cooler and more comfortable in heat.

33. Wool Pleated Trousers

Trousers with a single or double pleat at the waist. This gives a more classic, slightly roomy fit that looks great when the shirt is tucked in.

• Fit: Roomier through the thigh.
• Color: Dark brown or navy.
• Detail: Cuffed hem.

Pro Tip: Pleats work best on taller men or those with a slim frame. Avoid them if you carry weight around your middle.

34. The Breton Striped Shirt

A long-sleeve cotton shirt with thin, horizontal navy and white stripes. This is a French classic that works perfectly for casual weekends.

• Stripes: Thin and even.
• Color: Navy and white.
• Pairing: Khaki chinos or white jeans.

Pro Tip: This shirt looks best when worn untucked and slightly loose, giving a nautical feel.

35. Suede Bomber Jacket

A simple, elegant jacket made of suede. It’s a casual piece but the material keeps it looking rich. Choose a dark color like navy or forest green.

• Material: High-quality, soft suede.
• Style: Minimalist zipper and collar.
• Avoid: Patches or logos.

Pro Tip: Suede is a great way to add texture to an outfit that is otherwise all smooth cotton or wool.

36. The Simple Duffel Bag

For travel or the gym, ditch the nylon backpack. Use a high-quality leather or heavy canvas duffel bag. It is a subtle sign of quality.

• Material: Thick canvas or leather.
• Color: Brown, tan, or navy.
• Size: Medium, not oversized.

Pro Tip: A canvas bag with leather trim offers a classic, durable look that ages well.

37. Dark Green Polo

A long-sleeve polo in a deep, rich color like hunter green. This is a great alternative to the standard navy or white polo and looks sharp with gray trousers.

• Sleeve: Long sleeves look dressier.
• Color: Deep, saturated green.
• Pairing: Light gray wool pants.

Pro Tip: Choose a polo made of merino wool for a softer feel and better drape than standard cotton.

38. White Jeans (Clean)

White denim is a strong summer look, but they must be perfectly clean and stain-free. Wear them with a navy blazer and brown loafers.

• Fit: Straight leg only.
• Rule: Must be spotless.
• Season: Best worn between Memorial Day and Labor Day.

Pro Tip: White jeans look best when worn with dark tops or jackets to create a strong contrast.

39. The Field Jacket

A structured cotton jacket with four front pockets. Usually in olive green or navy. This is a practical, durable jacket for casual outdoor activities.

• Material: Heavy waxed cotton.
• Color: Olive green or dark navy.
• Use: Great for rainy or cool days.

Pro Tip: Keep the collar up slightly when wearing a field jacket to protect your neck from the wind.

40. Simple Gold Cufflinks

If wearing a French cuff shirt, choose small, simple gold or silver cufflinks. Avoid novelty or large, flashy designs.

• Design: Knot or simple rectangle.
• Color: Gold or silver metal.
• Use: For formal or business events.

Pro Tip: Cufflinks should match any other metal you are wearing, like your watch case or belt buckle.

41. The Wool Vest (Waistcoat)

A wool waistcoat worn without the matching suit jacket. Layer it over a simple button-down shirt and pair it with contrast trousers (e.g., gray vest, navy pants).

• Fit: Snug and tailored.
• Fabric: Wool or tweed.
• Rule: Leave the bottom button undone.

Pro Tip: This look is best for smart casual events where you want to stand out slightly without wearing a full jacket.

42. Suede Bomber Jacket

A simple, elegant jacket made of suede. It’s a casual piece but the material keeps it looking rich. Choose a dark color like navy or forest green.

• Material: High-quality, soft suede.
• Style: Minimalist zipper and collar.
• Avoid: Patches or logos.

Pro Tip: Suede is a great way to add texture to an outfit that is otherwise all smooth cotton or wool.

43. Corduroy Trousers

Trousers made of fine-wale corduroy in a deep color like brown or moss green. This adds a warm, classic texture to cold weather outfits.

• Texture: Fine wale (thin ribs).
• Color: Earth tones (brown, green).
• Pairing: Leather boots or loafers.

Pro Tip: Corduroy is naturally heavier. Ensure the fit is straight and not too wide at the leg opening.

44. The Newsboy Cap

A classic wool or tweed cap for cold weather. This is a subtle nod to vintage style. Only wear this with other textured fabrics like tweed or wool.

• Material: Wool or tweed.
• Pattern: Subtle herringbone or solid.
• Use: Outdoor casual wear.

Pro Tip: The cap should match the general color palette of your coat or jacket.

45. The Solid Crewneck Sweater

A simple, fine-gauge crewneck sweater in wool or cotton. Choose colors like deep burgundy or navy. Layer it over a collared shirt or wear it alone.

• Material: Fine merino wool.
• Fit: Neat and close to the body.
• Layering: Collar should peek out neatly.

Pro Tip: If wearing it over a shirt, make sure the shirt collar is tucked fully inside the sweater neck opening.

46. Leather Driving Gloves

Thin leather gloves, often perforated, that are a detail of classic luxury. They are worn for driving or as a stylish cold weather accessory.

• Material: Thin, soft leather.
• Color: Dark brown or black.
• Detail: Subtle stitching.

Pro Tip: These are an accessory of intent; wear them when you are actually driving or traveling.

47. The Simple Umbrella

A high-quality umbrella with a wooden handle and a dark canvas. Treat your umbrella like an accessory, not just a tool. It speaks to preparedness.

• Handle: Curved wooden handle.
• Color: Black, navy, or dark green.
• Quality: Should open smoothly.

Pro Tip: Avoid cheap, folding umbrellas. A classic stick umbrella is the only choice for this look.

48. Suede Derbies

A lace-up shoe in suede (instead of smooth leather). This is a smart-casual shoe that pairs well with chinos and tweed jackets.

• Material: Dark brown suede.
• Style: Simple, round toe.
• Pairing: Works well with textured socks.

Pro Tip: Suede shoes dress down an outfit slightly while still looking polished and expensive.

49. The Light Pink Shirt

A light pink or salmon colored button-down shirt. This is a subtle way to add color without being loud. It looks great under a navy blazer.

• Color: Very pale, not bright.
• Fabric: Oxford cloth or linen.
• Pairing: Navy or gray trousers.

Pro Tip: Pink is a classic color that complements all skin tones, especially when paired with dark blue.

50. The Navy Raincoat

A simple, tailored raincoat in dark navy or black. It should be waterproof but still look sharp and structured. Worn over any smart outfit.

• Material: Waterproof cotton or technical fabric.
• Length: Mid-thigh or knee-length.
• Fit: Straight and neat.

Pro Tip: Choose a coat that is unlined or lightly lined for year-round use and easy layering.

These ‘old money outfits men’ ideas prove that great style doesn’t have to be complicated.

Focus on quality fabrics, clean lines, and simple colors.

Now go put these tips to use! Comment below and tell us which outfit you are trying first, and don’t forget to Pin this post!