Five Tips on How to Dress Classy

But how can you dress classy in this old-money way without, well, old money? Here are some tips and observations from my own experimentation and research, tailored for college students and teenagers trying to capture that timeless look.

1. Start with Timeless Staples (Quality Over Quantity)

The old money wardrobe doesn’t require a closet the size of a yacht club. It actually thrives on owning just a few classic pieces and wearing them in rotation. The goal is to build a small collection of versatile, high-quality staples – things you can mix-and-match for years. Every classy wardrobe starts with the essentials. For guys, that might be a pair of tailored trousers (a good pair of chinos or flannel pants), some Oxford shirts, and leather loafers. For girls, perhaps a little black dress or a classic midi dress, a cozy cardigan or tweed blazer, and maybe a strand of pearls or simple studs. Neutral colors like beige, navy, white, and black form the foundation of this style, allowing you to combine outfits without ever clashing.

• Oxford Shirts & Button-Downs: A crisp white or blue Oxford shirt is a must – it’s the kind of shirt that instantly classes up your look when paired with anything. Roll up the sleeves for a relaxed study session or button it to the neck for a presentation. (You can find plenty of these in thrift stores or in curated collections of old money shirts that focus on quality fabrics and classic cuts.)
  
  

• Trousers with Tailoring: Swap out the distressed skinny jeans occasionally for well-fitted chinos or high-waisted tailored pants. They don’t have to be expensive; even a thrifted pair of trousers can look sharp after a trip to the tailor for adjustments. A pair of flat-front khaki chinos or wool slacks in grey/navy can anchor dozens of outfits. Fit is key – classy pants should skim your legs, not squeeze or sag. A pro tip I learned: if the pants fit your waist and hips but are too long, spend a few dollars to hem them. That transformation from sloppy to sharp is worth it. (Check out old money pants selections for inspiration on classic cuts and materials.)
  
  

• Blazers or Structured Jackets: One well-structured blazer (navy is a safe bet) can be thrown over just about anything and instantly elevates your look. Throw it over a t-shirt and jeans and you go from casual to “casually classy.” Look for blazers with minimal shoulder padding and a trim fit. You might find a vintage Ralph Lauren navy blazer in your dad’s closet or at Goodwill – and if it has brass buttons, even better. The patina of age, those little nicks and wear marks, can actually add to the charm in this aesthetic (the old money look welcomes well-worn pieces with open arms).
  
  

• Classic Shoes: Finish off with shoes that have stood the test of time. Loafers are a favorite – penny loafers or hose bit loafers in brown or black leather. They’re comfortable enough for campus treks but always look polished. Low heels or ballet flats for women, clean white sneakers (think classic Reeboks or Stan Smiths) for a modern twist – as long as they’re simple and logo-free, you’re good. I once splurged on a pair of brown leather loafers at a second-hand shop; they had a little crease and a story behind them, and they quickly became my go-to “dress-up” shoes with jeans. If thrift hunting isn’t your thing, you can also find new options that capture the vibe in old money shoes collections online. Just remember, quality leather and comfort matter more than a flashy brand name emblazoned on the side.
  

The beauty of focusing on staples is that fewer (better) clothes actually make life easier (and can save money in the long run). A well-constructed navy peacoat or trench will last you through college and beyond, whereas a cheap trendy jacket might fall apart by midterms. As one style writer notes, building a wardrobe on old money principles often means “fewer but better-quality items, saving both time and money in the long run”. And don’t shy away from second-hand shops—thrifting is your secret weapon for this aesthetic. You’d be amazed how often you can snag a pure wool coat or a silk scarf for the price of a campus latte. These secondhand gems keep the look authentic and budget-friendly.

2. Stick to Neutral Colors and Subtle Patterns

If you peek into an old-money wardrobe, you won’t be blinded by wild prints or garish colors. The palette is decidedly understated. Think of the colors of a country club lounge: navy blues, hunter greens, camel beige, cream, soft white, charcoal gray. These colors all play well together, layering up in pleasing harmony. A camel coat over a white shirt and jeans already speaks volumes quietly. A pair of white pants with a light blue sweater gives a fresh, moneyed look without any logos in sight.

Why neutrals? They’re timeless and versatile. You can mix almost any neutral piece with another and it will look coordinated and elegant. Neutrals also have this magic of looking “expensive” even when they’re not. As a fashion commentary noted, a palette of camel, navy, cream, and crisp white creates depth and dimension “without ever needing to raise their voice”. In other words, your outfit stands out for its simplicity and cohesion, not because it’s shouting in neon.

Patterns aren’t off-limits, but keep them classic: a subtle windowpane check on a blazer, thin stripes on your shirt, maybe a touch of houndstooth or tweed. Avoid anything too loud or busy. A tip I got from a style-savvy friend: if you do wear a bolder pattern (say, a tartan plaid skirt or a vibrant paisley tie), make sure the rest of your outfit is simple and solid to balance it out.

Crucially, ditch the conspicuous logos or flashy branding if you want the true old money look. Wearing a shirt with a giant logo or a handbag plastered in monogrammed print kind of defeats the “classy, not showy” principle. Remember Tom in Succession joking about a guest’s “ludicrously capacious” Burberry bag – it stood out (in a bad way) because it was so loud. The quiet luxe approach prefers logo-less quality. Instead of a T-shirt screaming a designer name, go for a plain solid knit that whispers good fabric. In practical terms, this might mean choosing a $30 plain sweater made of decent cotton over a $300 sweatshirt covered in logos. You’re paying for material and cut, not the brand’s billboard. High-end fashion commentators observed that “quiet luxury doesn’t have to mean expensive – focus on simple, versatile pieces… rather than clothing with a giant logo, opt for tailored pieces in quality materials like cotton, cashmere, wool, or silk to bring an expensive feel without shouting”. The college version of this: your outfit shouldn’t rely on a Nike swoosh or Gucci print to look good. It should look good because of the colors, the fit, and the confidence of the person wearing it.

3. Nail the Fit: Tailoring Makes the Difference

One thing I noticed about that classmate with the blazer was how well everything fit him. Not too tight, not baggy – just well-proportioned, like the clothes were made for him. Fit is everything when you want to dress classy. You can have an inexpensive outfit and if it’s tailored well to your body, it will still look like a million bucks. Conversely, a pricey designer dress worn two sizes too big will just look sloppy.

Old money style has its roots in bespoke culture – clothes that were often custom-made or at least adjusted for the wearer. You don’t need a personal tailor to get this effect. Many dry cleaners offer basic alterations, or you might have a relative who’s handy with a sewing machine. Little tweaks can elevate your look instantly. Hem those pants so they don’t drag. Bring in the waist of that thrift-store blazer a touch so it doesn’t box out. Even rolling up sleeves or tucking in shirts properly makes a huge difference to the silhouette.

This aesthetic “hinges on impeccable tailoring,” as one style writer notes – structured blazers, pleated trousers, and skirts that fit like they were made just for you. The goal isn’t to look formal or stiff, but to appear effortlessly put-together. When your clothes fit well, you naturally stand straighter and feel more confident. (I’ll admit, the first time I had a dress shirt darted in the back to taper to my shape, I walked a little taller around campus that day.)

If you’re a student, you might be mostly buying off-the-rack, and that’s totally fine. Choose slim or straight cuts for a more tailored look rather than ultra baggy or super skinny. Classic fit jeans or chinos can always be cinched with a belt or nipped at the waist if needed. Women’s clothing nowadays often has stretch, which helps with fit, but even so, look for clean lines – not too much bunching or gaping. And for the love of style, avoid overly distressed or ill-fitting pieces if you’re aiming for classy. That means saying no to pants that drag on the ground, jackets that swallow you, or shirts where the seams are hanging off your shoulders. A little structure goes a long way toward that polished old-money vibe.

4. Mind the Details: Accessories, Grooming, and Attitude

Dressing classy isn’t just about the main items of clothing – it’s also the little details that pull everything together (or conversely, the details that can ruin an otherwise great outfit). The old money aesthetic is big on “polish.” Not in a glossy, all-that-glitters way, but in a quietly meticulous way. Here’s how you can mind the details:

• Minimal, Meaningful Accessories: In the world of quiet luxury, less is more when it comes to add-ons. Rather than layering on six trendy necklaces or flashing a logo-covered belt, pick one or two subtle pieces that mean something to you. Maybe it’s a classic watch your parents gave you for your birthday, or a pair of small gold hoop earrings you wear every day. Perhaps it’s a simple silk scarf knotted to your tote bag strap for a pop of personality. Men might opt for a leather belt that matches their shoe color (a sign of sartorial thoughtfulness), or an understated navy tie for that presentation in class. The key is understated elegance: accessories that “enhance the outfit without overpowering it.” A style guide for students suggests men go for leather belts, understated watches, and cashmere scarves, while women choose things like structured handbags, dainty necklaces, or elegant headbands. Jewelry should be minimal and timeless: think a single strand of pearls or a modest signet ring – pieces that whisper elegance rather than shout for attention.
  
  

• Grooming and Cleanliness: Old money style also implies taking care of your clothes and yourself. You could be wearing a $5 thrifted shirt, but if it’s clean, neatly pressed, and lint-free, you’ll still outshine the guy in a $500 designer tee that’s wrinkled or stained. Pay attention to the basics: keep your whites white (a little bleach or baking soda in the wash works wonders), polish your shoes now and then (yes, even sneakers can be cleaned), and replace those cracked buttons or fraying laces. As for personal grooming, you don’t need a Wall Street haircut or a salon blowout; just keep your look neat. Trimmed nails, hair kept in whatever style suits you but maintained, a light touch of fragrance or deodorant so you smell fresh but not overpowering. The idea is effortless sophistication – you want to look like you naturally woke up put-together, even if in reality it took a bit of planning. I’ve noticed that the folks who pull off classy on campus often have a kind of fresh-faced simplicity: maybe a basic hairdo, clean skin, nothing too obviously “done” or heavy. It’s that whole Sofia Richie quiet luxury makeup vibe: natural and glow rather than a face full of sharp contouring. In practical terms, it might mean choosing a clean moisturizer and a bit of sunscreen instead of layers of heavy makeup, or a classic haircut over the trendiest dye-job. When your clothes and grooming are clean and cohesive, you radiate a quiet confidence.
  
  

• Posture and Attitude: This one might sound cliché, but it’s real: the way you carry yourself completes the classy look. Imagine someone walking into a room in a tailored suit but slouching and fidgeting nervously – the charm drops a notch. Now imagine someone in a simple sweater and slacks, shoulders back, with an easy smile as they hold the door open for others. Who comes off classier? The old money aesthetic has an aura of confidence and courtesy around it. Good posture, a calm demeanor, and polite manners are free to acquire, and they instantly elevate whatever you’re wearing. When I first wore a blazer to a study group, one of my friends jokingly asked if I had a job interview that day. In that moment I realized I did feel a bit like I was about to give a presentation – I was sitting up straighter, I was more aware of my presence. It’s funny how dressing a bit nicer can put you in that mindset of composure. Embrace that. Even if you’re just wearing a nice sweater and jeans, carry it with confidence. As the saying goes, “wear the clothes, don’t let the clothes wear you.”
  
  

Finally, remember that classy doesn’t mean stuffy. You’re young, and this is supposed to be fun – a form of self-expression. The old money style isn’t about pretending to be a 70-year-old millionaire; it’s about finding beauty in classic, well-made things and making them your own. You can absolutely put a contemporary twist on it. Pair your vintage blazer with clean white sneakers, or your elegant blouse with high-waisted denim. The mix of modern and classic can create a very cool contrast. Fashion writers have noted that modern old money fashion allows for a bit of experimentation – like swapping loafers for minimalist sneakers or pairing a tailored jacket with jeans – “adapting the look to personal taste while maintaining its core quality and elegance”. So don’t feel like you’re stuck in a rigid dress code from the past. Make it yours.

5. The Classy Mindset: Confidence Over Cash

One of the biggest things I’ve observed is that dressing classy is more about mindset than money. Sure, having a limitless budget could deck you out in $2,000 coats and bespoke suits, but I’ve seen plenty of genuinely classy looks assembled from H&M sales racks, thrift store finds, or just creative re-combinations of basic pieces. The difference comes in the attitude and care behind it.

The old money aesthetic resonates with so many students now partly because it represents a shift toward sustainability, simplicity, and confidence. It’s almost a backlash to the loud, throwaway fashion culture. Instead of chasing every micro-trend (and exhausting ourselves in the process), adopting a classy, timeless style is like saying: I’m going to wear what I feel good in, what lasts, and what represents me best. There’s a quiet rebellion in that decision, especially for young people. We’re often told to constantly update, upgrade, consume – but choosing a pair of sturdy leather shoes that you’ll resole over and over, or a vintage coat that carries history, that’s choosing character over hype.

And speaking of history and character – don’t be afraid to weave your own story into your style. Maybe it’s a hand-me-down watch from your grandparent, or a pin from your hometown on your bookbag. Classy doesn’t mean plain. It means intentional. It means every piece you put on has a purpose or a story, even if that story is simply “this sweater makes me feel like a young Hemingway sipping coffee by the Seine.” If you love something quirky – a patterned pocket square, a pair of funky socks – you can still make it work in a classy outfit by letting it be the one pop of playfulness against a clean backdrop.

In the end, dressing classy in that old money way is about respect – respect for the clothes (their craftsmanship and longevity), respect for the occasion (showing you care how you present yourself), and respect for yourself. You’re signaling that you value timeless quality, and that you don’t need to peacock around in wild outfits to feel important. There’s a kind of quiet confidence in that which, frankly, no Supreme hoodie or designer sneaker can replicate.

Oddly enough, the true “old money” look isn’t really about money at all – it’s about taste. And taste, my friends, can be cultivated at any budget.

In a final picture from that rainy morning on campus, I remember walking into my lecture after the blazer-clad classmate. The professor actually paused mid-sentence to quip, “Looking sharp, you two. Are we discussing philosophy or heading to a business meeting?” The class chuckled. I was a little embarrassed (I had on a thrifted tweed jacket that day, stepping up my game), but I also felt a swell of pride. Dressing classy had subtly changed the mood – for me, and apparently even for my professor. It was proof that this old-school elegance can still turn heads and open doors, even in our casual modern halls.

So next time you’re deciding what to wear to class or a low-key Friday night hangout, consider reaching for one of those timeless pieces in your closet. You don’t need a trust fund or a yacht club membership to channel the old money aesthetic. With the right staples, a keen eye for detail, and the confidence to buck the fast-fashion frenzy, you can dress classy and make every day feel a touch more special – like you’re living in a black-and-white movie, but in full color.

1. Richard Thompson Ford’s definition of the “old money” aesthetic emphasizes classic, durable clothing reminiscent of mid-20th century Ivy League elites. In other words, timeless pieces that could be worn today or 100 years ago without looking out of place.
   
   

2. Old money fashion prioritizes “refined, high-quality pieces” and durable fabrics, steering clear of flashy logos or fast-fleeting trends. It’s more about subtle elegance and heritage than about showing off brands.
   
   

3. Gen Z’s revival of this aesthetic, often termed “quiet luxury” or “stealth wealth,” revolves around preppy staples (blazers, Oxford shirts, loafers, etc.) that whisper elegance rather than shout. The focus is on quality, discretion, and longevity in style.
   
   

4. Building a classy wardrobe on a student budget is achievable by investing in fewer but better pieces. Style experts note that a capsule of neutrals and classics can save money in the long run and outlast seasonal fads. Thrifting and second-hand shops are valuable resources for finding authentic, affordable staples.
   
   

Accessories and finishing touches in an old money look should be understated and meaningful. Go for a minimalist approach – for instance, a classic watch or simple jewelry – to enhance an outfit without overpowering it. This “less is more” philosophy helps keep the overall look polished and elegant.