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One problem with old money style in menswear is that it is very easy to go two ways. One is losing direction to the point where someone looks “just pulled off of a laundry chair,” or the other where someone looks far too over the top to the point where they give off “boarding school play” energy.
Real life dressing is far more settled. Good color choice, clean materials, subtle textures, and shoes that look like they were not bought at a store with fluorescent lights. I’ve dressed my husband for a number of things, and I mean a number, weddings, school events, “casual but not that casual” afternoons, and I know the system is ridiculous, not the man.
These offer practical outfits and combinations that avoid making him look like an auditioning heir to a vineyard.
This outfit shows old money style. The navy blazer gives it structure, and the charcoal trousers keep it grounded. The trousers stop the outfit from looking too ‘preppy costume.’ This outfit works for lunches, parent meetings, travel days (with dinners), or any vague invitations.
For this outfit, it is better to go for dark brown leather loafers and belt. Also, it is good to avoid loud pocket squares unless he is ready to defend it.
A navy blazer is a very flexible clothing item that can be used in several different situations. Aside from pairing with a pale blue shirt and charcoal trousers, the navy blazer can be used with a plethora of combinations, making it a must have item in any wardrobe.
For example, using tailored khakis instead of charcoal trousers can change the outfit’s formality level in a more sophisticated direction. A nice watch can also dress the outfit up more, and give away a lot of details about the wearer’s personality.
2. Forest Green Corduroy Jacket with Gray Flannels
Forest green makes the corduroy fabric look warm and homey, as if a second home would be redundant. It is quite versatile and can be worn for a fall dinner, a getaway, or any other instance where you need to look more casual than a blazer would allow.
This jacket splits the difference: the cut is formal, and the corduroy keeps it casual. For instance, you could pair this jacket with gray flannel pants, a striped shirt, and some brown or snuff suede derby shoes.
Corduroy fabric is the most nostalgic as it reminds people of their childhood. It’s a great fabric that adds warmness and approachability to outfits. When paired with gray flannels it becomes effortlessly chic for casual get-togethers and slightly more formal events.
This outfit can be worn to a rustic dinner party or a cozy evening by the fireplace where the relaxed vibe of the corduroy shines alongside a polished appearance.
3. Charcoal Turtleneck and Dark Wash Jeans
Charcoal turtlenecks definitely get people’s attention, and they can be dressed up or down to suit any occasion. They go great with dark jeans and a wool overcoat to bring that polished look. Paired with an overcoat and dark wash jeans you will be ready to take on fancy dates and gallery openings.
The turtleneck does all the work of putting the outfit together because you can skip the blazer. It’s one of the few overcoat and turtleneck combos that looks dressy yet relaxed at the same time. So slip on your nice suede Chelsea boots, and you’ll be good to go!
A turtleneck is sophisticated and classy so it communicates elegance without being too formal. This quality is timeless and lets you make a statement, especially in work environments.
The charcoal color is good for combining with different hues and styles, especially in more casual or slightly dressy situations. In addition to this, merino wool turtlenecks are a good investment for winter since the material is warm and breathable, and allows for temperature regulation.
A tobacco suede jacket gives off an old money vibe, especially since it will age well. This is perfect for weekend lunches, casual Fridays, travel, and occasions where he wants to look put together but not to a mirror shine. The navy knit polo stops the suede from going cowboy quicker than you want to admit. To finish the look, choose gray trousers, brown loafers, and a quietly expensive watch.
5. Burgundy Rugby Shirt and Stone Chinos
Rugby shirts are great for representing old money style, and the burgundy shade makes it look not so much like it was pulled from a college dorm. This is wearable for the school run, weekend errands, casual brunch, or whenever you need to grab a dog lead and newspaper.
The rugby shirt collar and material solves the issue of cheap looking casual clothing. To complete the outfit, pair stone chinos and navy canvas sneakers with it and add a waxed jacket if it gets cold.
6. Slate Blue Linen Shirt with Olive Trousers
The slate blue linen summer shirt is relaxed, but not totally relaxed, which is more than I can say for many summer shirts. This is good for warm weather lunches, holiday dinners, and backyard get togethers when shorts feel too bare.
Olive trousers make the outfit more interesting than the usual khaki and white. Finish with a woven belt, some suede loafers, and sleeves rolled down, not like he lost a fight with them.
7. Olive Field Jacket over a Denim Shirt
The olive field jacket is practical old money; it shows he knows where the good flashlight is. It’s good for rainy weekends, travel, markets, and casual family outings. The denim shirt makes it approachable, and the dark brown cords add warmth and texture. Finish off with rugged leather boots, and keep the fit tidy since utility clothing has its boundaries.
8. Chocolate Brown Suit with Pale Pink Shirt
Chocolate brown suits have a richer, softer tone than black, and it conjures up confidence at dinner dates. Optimal for fall weddings, anniversary dinners, festive holiday parties, or as an evening out alternative where navy may feel too safe.
The pale pink shirt introduces a little brightness to the ensemble and brown won’t get too weighty, as if opening a window in a very serious room. Oxblood loafers and a dark silk tie can be worn as well should the occasion call for added refinement.
I really appreciate this weekend formula. It’s reliable and good for family lunches, easy church services, trips, and everything else. It also suits jobs that are too casual for jeans but not for tailoring.
The peak of the Oxford collar gives the sweater some shape, and the chinos will always be classy. Boat shoes, penny loafers, and clean canvas sneakers are good to finish the look depending on the polish level you want.
You can wear this outfit in lots of settings. The pale blue Oxford shirt and navy sweater look good together. Khaki chinos also look good, and are neutral, so you can try different shoes and accessories. A solid colored pocket square and leather strap watch is a nice little touch that can elevate the look. You can wear this outfit for a variety of settings, from a casual brunch to a spontaneous meeting.
10. Camel Topcoat with Black Knit and Gray Trousers
There are only a couple beige things I plan to defend publicly, and one of them is a camel topcoat. Topcoats are great for putting outfits together. You can wear one over dinner outfits, office outfits or even travel outfits. It’s especially nice when people can see the coat before they see the rest of the outfit.
The coat makes the outfit look sharp and the gray trousers stop the outfit from looking too formal. To complete the outfit you can go for black loafers or dark brown lace-up shoes depending on the leather items he has.
The camel topcoat is a classic, stylish piece that can be worn anywhere. You can wear it to the city or the country. Because of the neutral color, the coat goes with almost any outfit. In the winter, a thin knit under the coat provides warmth. Trim gray pants add sophistication to the outfit and pair beautifully with the coat. To finish the look, add a scarf that has some colors that match the coat.
11. Deep Teal Blazer with Ecru Knit and Brown Trousers
If you want to achieve an old money style with a little more flair than navy, then deep teal is a smart idea. This is great for date nights, winter parties, and dinners where a suit would be too formal.
The ecru knit top softens the face without washing the entire outfit out in cream. Now for the rest of the look, wear brown wool trousers and chestnut loafers, and a pocket square only if it looks like an afterthought.
This rust cardigan is great for that charming ‘professor-at-the-good-table’ look, and that’s exactly the kind of vibe men’s knitwear should go for. It’s perfect for casual dinners, holiday mornings, and even days when you want to dress down at the office and a blazer feels too corporate.
This cardigan fixes the issue of sweaters looking like bags with its shawl collar which gives a nice frame to the shirt you wear underneath. Pair with navy trousers, a striped shirt, and brown suede loafers for a complete look.
13. Black Cashmere Crewneck with White Jeans
White jeans can be a little bit daring on guys, but a black cashmere sweater brings a little more refinement to the look. This option also works for resort dinners, spring evenings, and other polished casual occasions where dark denim feels a bit too expected.
The contrast is crisp and avoids the nautical look, which is a lesson I’m proud to say I’ve learned the hard way. Black suede loafers and for the jeans, I’d recommend straight, clean, and definitely not distressed.
14. Moss Green Tweed Sport Coat with Tan Corduroys
Moss green tweed might have some thoughts on fireplaces. You can wear this to autumn lunches, countryside wedding celebrations, Thanksgiving, or other events that require more texture than shine. Tan corduroys add to the casual look and the blue check shirt keeps the ensemble from becoming too brown and earnest. If the invitation is on the formal side, wool ties and mahogany brogues will do the trick.
Tweed brings out a strong sense of made-up traditions. You’d think the first people to wear tweed lived in a castle in the countryside or some old-timey university. This outfit, made of tweed in a soft green color, is a good fit for woodlands and cities.
Wearing tan corduroys also brings the outfit together. You can also base the entire outfit off of the color of your shirt. The blue checkered shirt is a good selection for this outfit, and, while in style, is not too flashy and tones down the entire outfit.
15. Plum V-Neck Sweater with Gray Suit Trousers
Plum is a more subtle shade which is exactly what makes it work for this outfit. This looks good for office-adjacent events, smart breakfasts, and dinners where the jacket is likely to come off.
The V-neck is intentional, not accidental, and the gray trousers are a tailored bottom to finish off the look. Pair the outfit with black penny loafers or dark brown derby shoes, and leave the fun socks at home, as plum has done the interesting part.
16. Tan Suit with Blue Chambray Shirt
With the right outfit choices, the tan cotton suit can complement the occasion rather than distract from it. Great for garden parties, outdoor weddings and dinners, warm weather dinners, and outdoor business casual work events.
The blue chambray shirt pairs nicely with the suit, adds some casual flair to the outfit, and provides the antidote to being too dressed for daylight. Brown leather loafers and a woven belt finish the look. No tie unless the host is super serious about it.
A tan suit can be worn on countless occasions, and its ability to blend formal and casual settings makes it the ideal option when you need to look neat, yet still want to be relaxed, or when the event calls for a more laid back atmosphere.
The blue chambray shirt balances the outfit nicely while keeping the look light and airy, a perfect complement for summertime events. Finish this outfit off with some accessories, like a light scarf, for some added comfort and a look of class, and maybe some fashionable sunglasses.
17. Maroon Velvet Dinner Jacket with Black Trousers
A maroon velvet dinner jacket isn’t something you wear every Tuesday and that’s what makes it perfect for the right occasion. Throw it on for Christmas parties, formal dinners, New Year’s, or weddings with some real bling.
The black pants stop the velvet from getting too theatrical and a crisp white shirt really finishes it off. Patent loafers or shiny black dress shoes complete the look, and don’t overdo it on the accessories.
18. Medium Gray Suit with Denim Blue Tie
A medium gray suit is similar to a man’s diplomatic passport, as it is acceptable for use at any event that requires a strict dress code. Weddings, interviews, funerals, and other situations where looking respectable is required but looking self-important is not appropriate.
The denim blue tie adds some cheer to the suit and helps it to feel more friendly by lessening a bit of the corporate feel. Top off the look with black oxfords, and finish the ensemble with a white shirt and a clean pocket square that is folded in a simple style like an adult made the decision.
A medium gray suit is a smart choice for any man’s wardrobe. It shows maturity and sophistication, and allows the wearer to show poise in different social situations. The denim blue tie even offers a little pop of color while still being formal and professional.
This suit and tie combo would be perfect for someone who wants to stand out just a little, without being too flashy. Plus, well tailored suits give a sharp silhouette and really enhance the height and presence of the wearer.
Men’s summer clothing tends to look a bit flimsy, but this can be avoided with a knit polo. The sea green color is fresh and avoids the sweeter pastel tones. The navy linen trousers give the pairing a little authority.
The outfit is great for multiple occasions whether it be lunch on holiday, evenings at a resort, outdoor smart casual dinners, or summer birthdays. To finish the outfit, choose woven loafers and some shades, unless the glasses are from a speedboat salesman.
During warmer months, you can stay looking classy by wearing knit polos. The knit fabric provides sophistication that cotton polos do not offer. Also, the sea green color is refreshing and can be easily matched with many different colors and styles.
The sea green knit polo and navy linen trousers combined create a look that is casual yet polished, so you can wear it to upscale events and to casual outings. This outfit is a perfect choice for summer when you want to avoid the heat and stay stylish. Just remember, summer makes both comfort and style pretty demanding.
The chestnut quilted vest (not black) is an example of old money style. It is perfect for cool morning walks, casual outings, outdoor dining, or family outings involving coffee and mud.
Paired with navy corduroy pants, it feels more intentional than if it were paired with jeans; a green check shirt boosts the country look. For when the weather gets a little prickly, country brown boots and a sweater will complete the look.
The chestnut quilted vest will be your go-to layering piece for every season. Its rich hue allows you to style it with different outfits and also elevates your casual outfits for a sophisticated touch.
The vest is bulk-free and allows ease of movement to keep you warm while you are walking or eating outside. When you wear it with navy corduroy trousers, it gives a classic contrast and a green check shirt on top introduces an element of playfulness while keeping it refined.
21. Indigo Shawl-Collar Cardigan with Cream Trousers
An indigo shawl collar cardigan is a nice option for a jacket and is a great go-to when comfort is needed. Think casual dinners, travel days, family gatherings and weekend trips.
The cream trousers definitely work here as the indigo cardigan really does anchor them to the outfit and prevents it from floating away like a linen napkin. A pale blue shirt and brown loafers will finish off the look softly and cleanly and will keep it looking quite grown up.
The cardigan has a shawl-style collar which looks classy and adds some warmth. Indigo is a confident and sophisticated color while the cream trousers provide a nice contrast and brighten the look. This outfit works for daytime occasions, and evening ones just take a change of shoes. The mixture of colors and textures shows thoughtfulness in dressing and provides a good comfort and style balance.
22. Mustard Crewneck with Charcoal Overcoat
Mustard is a little quirky (in a good way) like a brass lamp in a serious room. It is also good for warming an outfit for winter and preventing charcoal from getting too serious. This is good for casual lunches, walks with coffee, trips and city weekend days when you want color without screaming. Wear with dark rinse jeans and brown boots, plus a charcoal overcoat that fits through the shoulders.
The mustard crewneck sweater adds fun and color to an otherwise dull winter wardrobe, full of muted outfits. The color of this crewneck makes it different in a good way, and will not clash with any other colors in your outfit.
Warmth and style are achieved when paired with a charcoal overcoat, making it suitable for chilly city walks or easygoing weekend strolls. Because of the modern appearance when this sweater is paired with dark rinse jeans, any footwear can be worn. This includes casual shoes or even genuine leather boots.
23. Wine Merino Zip Neck with Taupe Trousers
A merino zip neck is a great versatile layer that doesn’t immediately read as golf merch. The wine tone gives a more put-together option, and the taupe trousers offer a more cohesive color palette.
This piece is great for traveling, casual days in the office, long lunches, and weekends when a hoodie is too soft. Depending on how much walking is involved, pair this with some suede loafers or clean leather sneakers.
With a zip neck design, you can adjust based on how hot or cold it is. Merino wool has great breathability and temperature regulating features, which is ideal for a wide range of climates. The wine color is rich and gives an understated pop to the outfit.
Paired with the zip neck, the taupe trousers complement and create a look that is appropriate for business and casual occasions. This outfit is a great example of how simply, yet effortlessly someone can dress well.
Midnight navy is a softer option than black which can actually appear more compelling in low light situations. This suit is intended for formal receptions, weddings, galas, and other serious dinners with a more business like dress code.
The silver grenadine tie adds texture without shouting and that’s the aim of this lane. Finish the look with black cap-toe shoes, a white shirt, and good tailoring that doesn’t pool at the ankles.
For every guy’s closet, the midnight navy suit is the best pick because of how cool it is. The deep color of the suit helps it keep a sophisticated look, while also being flexible for how you want to style it. The silver grenadine tie adds some texture to the look and enhances how it looks overall without taking away some of the suit’s class.
This is a really good combo for events that are really important and it needs a good impression. The well-fitted white shirt gives off a really good contrast and the black cap-toe shoes really pull the whole thing together to achieve a polished look that is modern as well as timeless.
About the Author
Allena Rissa
Founder & Editor
Allena Rissa is the founder and editor of The Better Fit. She has been writing about clothes since she was twenty-two, and for nine years she has been the one dressing her husband, her kids, and herself for family photos, fall weddings, work conferences, and Christmas cards that had to land. On the site she covers five pillars: Her Style, His Style, Together, Occasions, and Foundation, the bras and fit mechanics that started it all. Her advice has been featured in Cosmopolitan, Better Homes & Gardens, Insider, and NBC.