Photo by Muffy Aldrich
The Modern Guide to The Thing Before Preppy

Sunday, November 7, 2021

Core Items for a Classic Male and Female Preppy Wardrobe for 20-30 Year Olds?


What are core items for a classic wardrobe for males and females in their twenties to avoid looking like preppy/trad cosplay?

The following question was left as a comment:

I’d love to ask, as someone in the earlier twenties, I have a very similar aesthetic to yourself preppy, classic and timeless quality clothing. But I am self conscious I stand out, even wearing an oxford shirt people would ask “Why are you dressed up” “What’s happened?” Or make jokes or draw unwanted attention. Even wearing boat shoes has garnered comments such as “Old man”. Interested to hear others thoughts.



  1. My husband and I had a very similar experience in our mid twenties. We had to move often due to his job and our classic/timeless style looked very out of place in many of our new communities (this was also the dawn of athleisure). Our problem was solved when we moved overseas for 8 years (to Europe) where our style was much more common and we never felt out of place. Now, back on the Eastern Seaboard (of the US), we still dress in a classic style (and still have not bought into the athleisure thing) but have grown into it so much so that weird looks or off comments aren't taken personally but instead, we find, are a good conversation starter. In fact, last week someone made a comment about my husband's colorful Fair Isle sweater and he used it as an opportunity to tell the story of how we took a boat to the Shetland Islands where he had purchased the sweater. Turns out the commenter had spent some time in Ireland and we had a lovely conversation. My advice is to stick with your style and respond to all perceived off comments and looks with kindness. Often they are not what you think and eventually you become so comfortable looking a little bit nicer that the self consciousness fades away.

  2. You draw attention and comments because you DO stand out, and the reason you stand out is that you look better than those around you. Hat tip Martha, that's a good thing. I read a book back in I think the 70's called "Dress For Success," and decided a good clothing rule to live by is that there is no such thing as overdressed. No one has ever been thrown out of the dining room at the Ritz, asked to leave a golf course, or been denied admittance to a club because they were OVER dressed.

    1. Probably true. But you CAN look ridiculous if your dress is too far out of line with commonsense. Wear a dinner jacket to go golfing??

      Having said that, I wear long-sleeve sport shirts and OBDCs with tan travel slacks and Clark's shoes — pretty much everywhere, every day. For example, that's what I was wearing while blowing & shredding leaves in the yard this morning. Before that I was on the roof with a leaf-blower cleaning out the gutters (tons of fun blasting them out, by the way!).

      I guess it depends on how far out of joint your dress is with the situation you're in — and how much that disjuncture bothers you. For people in careers where you'll be seen and other peoples' opinions matter, well, you probably shouldn't be too far out of joint.

      It's always a good idea NOT to dress down compared to your boss, but it's also not good to dress too far above him/her, either.

      Gotta say, it's a helluva lot easier once you retire.

    2. I disagree with the idea that there's no such things as being overdressed. The initial question is a good one. In certain areas of the US (e.g., parts of the west coast) preppy dress can end up looking like a costume. It's not seen as stuffy, old-soul, heritage, or respectable but outdated. It's perceived as fake, costume-y, and try-hard.

      If OP is in this situation, the preppiest attitude is to truly not care (but they asked the question, so they do seem to care), or alternatively, inch back on the preppy scale just a little bit to avoid the costume impression.

      If my read of this situation is correct, the OP should focus on classic items that are borderline preppy, borderline not preppy, but still classic. Levi's jeans are a great example. "True" preppies won't wear jeans except for manual labor. But for someone in their 20s, they probably do want to wear jeans to fit in with peers, since 99% of people in their 20s wear jeans. In this case, it's not a question of jeans vs no jeans. It's a question of finding the most timeless, classic jeans. Hence my suggestion for Levi's.

      I can suggest similar small adjustments: instead of hoodies, wear crew neck sweaters or sweatshirts. Classic crew neck, college logo sweatshirts are a great idea for people just out of college. They're preppy but clearly not a costume. Instead of black clothing, try navy. Instead of brand logos, no logos. etc.

  3. There is an ethos of traditional dress that is easy to spot. It centers on natural materials used in comfortable and well constructed clothing. Over the years the standard wardrobe for a prep or ivy type has enabled an industry, albeit a small one, to endure, but finding clothing that embodies that ethos while being better suited to a person from a younger generation is hard. I see people in their twenties who are drawn to such clothing but would find dressing like older generations awkward. They are wearing things like unironed all cotton khakis or jeans, shirts from such brands as Filson, Columbia (especially PFG), and Patagonia, trim fit polos, and footwear ranging from round toed work boots or ropers to desert boots to camp mocs from brands like Rancourt. When it is hot they shift to athletic shoes like Asics or to leather flip flops. They like half zip pullovers when it gets cool, topped with a quilted Patagonia when it is cold. They favor plain front khaki shorts when it gets hot and, for summer casual, a fair amount of Vineyard Vines items. They tend to avoid the professionally laundered look for anything. Most outfits are topped with a gimme cap. I know these things because I am in a college town and have a young son in law.

  4. You dress for your own pleasure, not for other's. PBH

  5. You do stand out in the sense you are well dressed. There is nothing wrong with being overdressed and you should not feel self conscious about it. I started dressing well at 19. My ex used to make negative comments and once overheard another student making a negative comment to another about my outfit (something along the lines of that’s what old ladies wear). Those comments from a very small handful of individuals never bugged me. I’m in my early thirties today and everyone is used to seeing me wearing oxfords, wool and cashmere sweaters, blazers, sheath dresses, skirts, trousers, tartan, heels and loafers.

  6. I understand being timid and not wanting to draw attention to yourself. That's fine and it's a sign of humility and good character. I never wanted anyone to feel uncomfortable around me but I wouldn't insult them by being less than I am for their benefit. You should always dress appropriately ( don't wear black tie to a pizza shoppe) modestly and humbly but never dress down for anyone. Be yourself and be authentic. If someone believes that an oxford shirt is over-dressing, then perhaps you should consider why they feel the need to belittle and disrespect you.

    "Birds of a feather flock together"

    When I was young, my mother frequently used that phrase to encourage me to be more selective in choosing my friends. I thought it was so unfair and snobby. As I matured, I realized the truth in that statement and why it is so important not to surround yourself with people who need to dim your light in order to feel worthy. You were born to shine.

  7. Early twenties, and having people criticize your (correct) clothing choices? I’m not surprised.

    I’m sorry, but through no fault of your own, you just happen to belong to the “Dumbest Generation.” It’s called Gen D (for Dumb). Yes, the exact opposite of the “Greatest Generation.”

    To prove this point is easy – next time a contemporary makes fun of your tasteful civilized attire, ask them the following questions: 1) Who was the first US President? 2) Who was Senator Joseph McCarthy?

    If they respond with a clueless stare - then you know you’re dealing with idiots who have no right to criticize anyone about anything. (To be fair, George Soros, Saul Alinsky and George Orwell never considered those questions to be important either, so your critics can be excused in their ignorance. And, besides, they didn’t spend $70K a year attending Kolidges to actually learn how to think independently when orthodox GroupThink is all they’ll need once they graduate.)

    At your tender age, there’s no sense in advising you to just ignore the flack because I know it’s impossible. Believe it or not, I was once your age (I think it was back during the Peloponnesian War?) and understand how difficult it is not to conform. There’s a Russian proverb that states that the nail that sticks up is always hammered down. You can at least try to be that nail, and I wish you luck.

  8. Just say this: "It's the style I prefer and I think it's far superior to today's fashion."

    1. And then there is the ever popular "I don't take clothing advice from someone who looks like he(she) sleeps under a bridge."

    2. Let him stand his ground in a positive, non-provoking way -- not that I wouldn't do the opposite myself. Let's get the young man off to a good start.

  9. When my brother was younger, he was occasionally teased for his classic style. Smiling sweetly, he would just answer, "I'm an old soul," and he really embraced it.

  10. I'm 28 and and have definitely had similar concerns in the past. I've also fielded my fair share of these questions over the years. I have largely moved past both of these issues and offer three pieces of advice. First, just be honest with people who say anything. I normally just respond along the lines of "this is just how I always dress" or "I tend to skew a bit dressier than most people our age." Second, the best way to avoid comments/judgement from others is to be consistent in the way you dress. I've found that it I just wear my typical traditional attire every day, people adjust to it quickly and rarely say anything within a few days of meeting me. Third and regarding your preppy/trad cosplay concerns, I actually think that leaning even harder into true traditional style is the best way to be viewed as authentic. For example, wearing Vineyard Vines or overly vibrant pastels is likely to come off as out of touch and overdoing it. Conversely, more conservative, timeless outfits like a high-quality white OCBD underneath a neutral-colored shetland paired with well fitting chinos signal a more genuine commitment to traditional style.

    1. Anon 4:58—genius. Well said.

  11. Tell them you are allergic to polyester.

  12. I'm 33 and think it's a matter of leaning more into the Ivy/Trad side. The prep might use loud colors and patterns to attract attention, but the trad uses texture and detail to build intrigue instead.

    So, here are some staples for a well-rounded Trad/Ivy guy's wardrobe: (Easily adapted for gals, too!)

    1) A solid navy or grey suit for interviews, weddings, funerals, etc. If you need more suits, whichever color you didn't start with is #2.

    2) A classic navy blazer, but in hopsack with patch pockets and non-brass buttons to dress it down.

    3) For colder climates, a grey/brown (Harris) tweed herringbone sport coat. For warmer climates, a brown/olive corduroy.

    4) A plain white dress shirt. If you wear suits more often, a plain light blue is next, followed by simple graph checks and bengal stripes.

    5) OCBD's. (My starting four -- 1: solid white, 2: white and blue uni stripe, 3: solid blue, and 4: either solid pink or white with a navy graph check.)

    6) Plaid flannel shirts in muted primary colors for cold weather.

    7) Lightweight sport shirts for warm weather. I have a navy linen gingham and a green madras.

    8) Plain polos in solid neutrals with minimal logos for warmer weather - start with white & navy, then go from there.

    9) Crewneck / v-neck sweaters, starting with navy & medium grey. The material depends on your climate and budget. Once you've got the basics covered, look into textured weaves like cable knits and/or interesting collars like shawl collars or quarter-zips next.

    10) Plain, dark, slightly fitted (but not super-skinny!) jeans. I like Levis 502s. If the dark jeans are too hot in warmer weather, a second medium- or light-wash pair is appropriate.

    11) Tan khakis, dressed down (e.g. no permanent creases, pleats, or cuffs, etc.) I've heard grey wool trousers are also essential, but rarely find a time when I'd wear them with a blazer instead of a suit.

    12) Tan khaki shorts for warmer weather. It's best to leave the Nantuckets and madras shorts behind.

    13) Plain or cap-toe black leather dress shoes, plus brown leather wingtips and/or burgundy loafers.

    15) A few pairs of casual shoes. I can get by with a simple pair of grey New Balance sneakers in nice weather and LL Bean duck boots in gross weather. But, I also have Sperry boat shoes for warm weather, and I'm considering getting a pair of chukkas for cold weather, too.

    16) A navy peacoat is the easiest outerwear to dress up & down. If the peacoat is too warm in summer, look for a khaki mackintosh next. If colder temps demand it, a large winter coat. Rounding things out, a brown leather jacket and/or a dark green Barbour coat.

    17) A navy grenadine tie, which will go with anything and perfectly displays the value of texture. If you want to branch out to more ties, a wine/burgundy grenadine is next, followed by some classic Brooks repp stripes. Steer clear of non-tux bowties, though -- too preppy!

    18) 1-2 leather belts. I have a plain black dress belt to go with my black dress toes and a brown braided leather belt to go with everything else.

    19) A pair of shades. Aviators and wayfarers are the two classic archetypes.

    20) A dress watch or two to wear with the suit + a more casual watch or two to wear with anything else.

    21) BONUS: As mentioned above, a healthy nonchalance about what others think or say. (It often says more about them than you!)

    That said, by sticking to the classics in a muted color palette, you'll create a very versatile and classic wardrobe that suits almost any occasion from a more limited number of items...

    ... which, at its core, is kinda what the Ivy/Trad style is all about!

  13. Susan, your brother sounds like someone I would enjoy meeting, and emulating.

  14. I'm in my early thirties and while I do tend to wear jeans, I've always dressed "nicer" than others my age (e.g. no athleisure in public unless I'm on my way to play tennis or squash, and then that's not really athleisure, anyway!) In the town where we live now, which has always been a very traditionally "preppy" town, a lot of the other mothers at the toddler programs we attend ripped jeans, yoga leggings, and other items of that ilk. I don't, and I definitely stand out in my khakis and Barbour. I do feel that I stand out, but these are the clothes I'm comfortable in. My entire family dresses more formally than most people, I suppose, and the majority of my friends do as well. I think that dressing more carefully is a sign of respect to yourself and to others, and that's something to be proud of, and take confidence from!

    For me, my key items are: slim cut pants (but not skinny), Belgian Shoes, turtlenecks, good sweaters (vintage or handmade are best, though I'm planning to try Le Tricoteur and Bosie based on Muffy's recommendations!), a good overcoat, and a well-fitting blazer or tweed jacket.

  15. My late mother used to instruct about others' negativity, "Just let roll off your back, like water off a duck." Ignore questions/comments (with kindness) in other words. If you dress well long enough, the comments will go away as your attire becomes part of the scenery.

    Kind Regards,


    1. I love that sentiment. My grandmother and mother would say: "in one ear and out the other, water off a duck's back"

  16. "even wearing an oxford shirt people would ask “Why are you dressed up”"

    Don't iron it. Wear it 'freshly laundered'.

    "Even wearing boat shoes has garnered comments such as “Old man”"

    Boat shoes are classics and it's weird to think someone can call them "old man" shoes. If you find wearing traditional colours an issue go for bright coloured boat shoes. Over the years, as well as having classic brown and navy, I've had money green leather, tri-tone grey leather, cobalt suede, and lavender nubuck, all with white or cream soles.

  17. There are some great suggestions here.
    As a forty-something year old father of children entering their teens, I understand your dilemma.
    Trying to stick to a wardrobe of modest clothing, of natural fibres and timeless designs is a full-time hobby!
    The first thing I would say is that people WILL judge you on what you wear. This is a particular issue in your 20’s, when you are trying to make your way in a career, finding a potential partner and making your way as an independent adult. As much as people like to say “be yourself” or “who cares what others say?”, you do need to tread a little carefully. It can really affect your career prospects if you are known as “the bow tie guy” or are the only one in the office that wears tweeds with elbow patches. You will be noticed (and perhaps not in a good way).
    The second thing is while we like to dress trad, there is a spectrum. There is “old person trad” and there is a younger style of trad. You want to avoid the older style if you can possibly help it.
    There are some general comments on style that you still need to adhere to. In no particular order:
    FIT: This one is crucial. No matter what style you prefer, it always looks better when it is well fitted. Nothing will age you faster than oversized clothing and shoes. Choose slimmer cuts and well-fitted pieces. Girls, keep your hemlines modest but not frumpy. Guys, if you have a slim figure, wear properly tailored shirts.
    KNOW THE TRENDS: While you don’t want to be captive to the winds of fashion, you should show that you have some knowledge of the world around you. If you wear a tie, don’t have it too wide. 4 inch ties might have been normal in the 90’s, but please don’t wear them today. Likewise, if there is an in-season colour you like, don’t be afraid to introduce it into your rotation. It will show that your style is a conscious choice, not a costume.
    MIX IT UP: depending on how totally dedicated you are to the traditional palette, you can introduce other pieces in a “shandy”. As an example, you could introduce a denim trucker jacket. It fits the bill of natural fibres in a classic fit. It goes well with OCBDs and chinos. Likewise, a modest baseball cap might suit you better than a Panama hat at times. Instead of a Barbour, consider a Harrington.
    PAY ATTENTION TO SHOES: Be careful what shoes you wear. You really want to avoid looking like you are wearing bulky orthopaedics. There are plenty of well-constructed shoes in younger styles.
    USE COLOUR TO YOUR ADVANTAGE: younger people can get away with brighter colours, so use that to your advantage. Don’t overdo it, but avoid going all-beige.....
    GO EASY ON THE ACCESSORIES: while we often get excited about clothes in our younger years, go easy on the extras. Pocket handkerchiefs and watch chains can look great in a movie, but may not win you many friends on the bus.
    We all wish you the very best!

  18. It's not just the young. I was in our town center yesterday, wearing wrinkled cotton khakis, a pale yellow Shetland sweater, a blue oxford slightly frayed at the collar, and blucher moccasins. I had not shaved. An acquaintance asked me where I was "all dressed up" to go. And I am, as Dame Edna Everage observed, "Approaching 60, but unfortunately approaching it from the wrong direction."

    1. I hear you, more or less my weekend wardrobe.

    2. Love Dame Edna! Thanks for the quote!

    3. Just turned 60 myself. Love your "Approaching 60..." quote.

    4. One of my favorites -- appearance on Parkinson

  19. I'm in my thirties and have likewise always 'dressed up' compared to my peers. I think anyone these days who doesn't wear fast fashion is going to be perceived as dressed up. Good garment construction and natural fibers really do stand out. One's early 20s is the most difficult time to wear classic dress in terms of comments from others (and the urge to compare oneself to others). Avoiding anything loud (vineyard vines, brightly colored Sperrys) is good advice. I would also avoid things like a lot of argyle, sweater vests, and tennis sweaters at that age, too. They all tend to give off that 'cosplay' vibe in younger wearers. Stick with more muted or darker solid colors for now.

    1. Good shout with fast fashion. People who buy bags full of fast fashion every month just don't know what quality fabrics and clothes are.

    2. I have never followed a fashion trend in my life. But I will say, those who want fast fashion have that right and privilege. If it makes them happy good for them. If we all could do what makes us happy and we didn’t worry about what others were saying or doing what a pleasant life that would be.

  20. Interesting question, and very interesting and some beautiful responses. I would be intrigued to hear what Muffy thinks in regard to the question

  21. I prefer to wear dresses or skirts daily- it is who I am and how I feel comfortable. It’s rare now at my age, but when people on occasion ask me why I am “dressed up” I just look them square in the eye and say “this is how I dress.” No one has ever asked twice.

  22. Having attended parochial and private schools in the '40s and '50s I was used to wearing shirts and ties from early on and not to soon sport jackets so it came as natural when attending college that that was how to dress. After years in the corporate world of NYC and later in academe, dressing in the preppy way, though it was hardly spoken of as that was a natural - it was a "trad"itional for me, and most of my cohort. To this day, (I'm 82) it's still OCBDs, khakis, Topsiders, Old Brooks Brothers, and once in a while in summer, besides khaki shorts, a pair of old Madras shorts, bought years ago for a college re-union. If neighbors or my kids see me puttering around in old painter's pants and a sweatshirt they ask if everything's alright. HA! Old habits die hard.

  23. Looks like it's time to read or reread Stephen Potter's One-Upmanship. Good advice on how to deal with the fashion police who try to run one's life. Very amusing material.

  24. Our son is in his mid-20s, lives in New York City, and is a bit of a mix between prep/traditional and more modern. Wear what you like, and you don't need to worry about what other people think or say.

  25. In your 20’s you’re still kinda feeling out what works for your wardrobe.
    Part of the reason you might be getting comments is because it comes off as a costume. Wear those OCBDs around your house while lounging to break them in and get them feeling like a second skin. Put on that sport coat everyone you head out the door. They’ll start to feel more natural.
    Unconstructed has been key for me with blazers (not only to deal with Florida heat, but also decreasing formality).
    Color can also play into it. The boat shoes coming off as “old man” might be because they’re light brown/dark brown or brand new. Don’t run out and get new ones, just beat them up a bit and they’ll look less formal.
    Sometimes I’d overreach and dress too nicely for the occasion, but you’ll sort that out. Now when people comment it’s more “dammit why do you always look so good?!”

  26. 15 years ago at 20 at least J. Crew and Brooks were around and still constructing half decent garments which fit the youthful male form. A lot of my friends back then dressed similarly. Coworkers were mostly older than myself and well dressed. Now I show up to work and am one of the only guys not in sweatpants. I don’t know where these kids shop or how they can walk in public that way. No wonder they’re all on antidepressants. We can thank Zuckerberg & Co.

    “Why are you so dressed up?” They ask.
    I’m wearing old khakis and OCBD.
    My reply, “This isn’t dressed up”

    1. There was a time, probably more than 20 years ago, when every town, even small towns, had decent men's shops and lady's shops where nice clothes could be found. After all, not everyone used to shop at Brooks Brothers, unless they happened to be passing through New York. The clothes were not necessarily all that conservative but they were usually what would now be considered rather dressy, judging from previous comments here. They were certainly things that were in style. They were mostly all independent, too, and still would be, if any still exist. Of course, that was all before the internet and perhaps more significantly, before casual Friday. Moreover, the clothing would have been American-made, for what it's worth. I've mentioned all this before.

  27. What I Learned In My 20's About Dressing Well
    1) Wear what you want.
    2) Whatever you wear, one thing tops brand, style, or cost. Fit. Early in my corporate career, I became good friends with a gentleman whose fondest desire was a Ralph Lauren suit. On the occasion of his first raise, he bought the best one he could afford. Unfortunately, it was from RL briefly available (thankfully) line of skinny, minimalist suits made to compete with Thom Browne. My friend went to college on a scholarship as a guard for a fairly good Division 2 program. Beautiful suit. Grey pinstripe. He looked as though he was trying to emulate Chris Farley's "Fat Guy in a tiny jacket" comedy routine.
    3) Know what to spend your money own. There is no need to spend more for underwear than you would spend at Target or Old Navy.
    4) Likewise, build your wardrobe around a few quality items and work out from there. For most of my twenties, the most expensive things in my closet were a Hart Shafter Marx Charcoal Suit and a Brooks Brothers Navy Blazer. This is probably heresy at this site but a good pair of Dockers is perfectly acceptable if you save enough money to buy a better pair of business shoes. You can replace them with Donnelly's when you put a couple of raises under your belt.
    5) Learn what makes a quality artisan and make friends with one of each of the following: tailor, cobbler, dry cleaner and hair stylist.
    6) Likewise, make friends with a good salesperson at a retail store who carries clothes you like. Much of what I include in this post was taught to me by Paul Chance of Pennick and Chance and Herman Massad at Massad's menswear in Tyler Texas. Mr. Chance was friends with my father and I had the honor of getting the first crack at the clearance clothing the day before the actual sale began.
    6) Never pay retail. Don't be afraid to pop into a thrift store. The HSM suit may have been my most expensive item but I got just as many compliments on the JCrew suit I found at Goodwill Store in Dallas.
    7) Learn how to properly care for clothes. Shoe trees and quality polish and cleaner will make a pair of comfortable mid-range shoes last a decade.
    8) I suspect that the next Brooks Brothers or J Press will be or, at least begin, online. I just bought my first pairs of men's dress shoes from the online retailer Becket and Simonon. The shoes are classic, well crafted and of a higher quality than the Cole Hahn and Johnston and Murphy shoes that have been my go to shoe brands for 20 years and cost 15 to 20% less.
    Dress appropriately for the setting but never be afraid to be the best dressed person in the room. In the immortal words of the late Glenn O'Brien, GQ magazine's former menswear consultant "If you show up at a party overdressed, just leave early. Everyone will think you had someplace better to go."

  28. I think if somebody said something about what I was wearing, I would put on a slightly taken aback expression, look down at what I had on (as if to remember exactly what it was--to convey the impression that clothes are so unimportant that I had already forgotten what I picked that morning) and then say, "Why, I don't know...I never thought much about it." Then go silent. This will throw the conversation back to the other person and they will either be forced to defend the reason they criticized your clothing (and if they can't think fast they will look like fools) or if they say nothing they will come across as rude. I believe at this point anybody else in earshot would be sympathetic to the person who was picked on and that might be the awkward end of that.

    If you were really cruel you could say something like "Oh, I know! I agree, but my grandmother got this for me and she died just lately (or something along those lines--make sure it's true) so every time I drag it out I think of her....sorry!"

  29. I’m in your same boat, though I think I have mastered it. As another comment suggests, you tone down some of the more outlandish elements of the style. Muffy’s blog is great because she already does this for the most part. For instance, drop the bright colored pants, the pants with little icons sewn into them, the “fun” shirts, etc. wear your blue/white/blue and white OCDBs, your solid colored sweaters, your khaki chinos (or jeans), and brown ranger mocs or boots — completely inoffensive pretty much everywhere. You end up with a modification of what is now referred to as “smart casual.”

    I recommend incorporating some chambray shirts as well. I’d in your 20s there are places you’ll go wear even the above doesn’t make sense — a Brooklyn punk bar for instance. The chambray will keep you relatively classic but not over dressed — and you can definitely be overdressed.

    The answer, in other words: simplify.


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