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The Modern Guide to The Thing Before Preppy

Wednesday, November 13, 2019

Reader Question: Necessary Items for a Gentleman's Wardrobe?

A Reader Question for the Community:
I’ve been a “reader” for many years, mostly I enjoy the beautiful photos! 
What are the necessary items for a gentleman’s wardrobe? Items that an ensemble can be built around and when cared for properly can be handed down to a future generation of gentleman? 
Thank you.


  1. Rest assured, here is the definitive list:

    1. Blue Blazer. Preferably from Chipp or J. Press, always three button. It is proper to have a lighter-weight worsted wool version and a heavier flannel version.

    2. Grey (or as you Yanks say "gray") flannel trousers, cuffed and creased. These too should come from Chipp or J.Press, although O'Connell's stocks decent trousers. Here to you should own a lighter and heavier pair for seasonal considerations.

    3. Blue, pin-striped suit. Three button, cuffed and creased. From J. Press or Brooks Brothers.

    4. Alden Color 8 unlined cordovan half-strap loafers.

    5. Peal & Co. black and brown calfskin belts with silver, not gold, buckles.

    6. Brooks Brothers black strap belt with engraved silver rectangular buckle.

    7. Several ribbon watch bands and a 1997 Timex automatic to pair them with.

    8. Brooks Brothers boxers, white.

    9. Generate black and brown socks. A gentlemen either wears no socks or if wearing socks desires that they be ignored.

    10. A Herringbone (Grey) Chesterfield from J. Press circa 1978.

    11. Assorted Top-Sider Gold Cup two-eye boat shoes.

    12. Assorted pastel linen blazers, three button, from the English Shop

    13. Several pair of Reds, both trousers and shorts. Trousers are NEVER cuffed but always creased.

    14. Assorted belts emblematic of one's past adventures (e.g., your college seal; your club; your gun club; your children's prep school; your yacht club).

    15. Assorted pin point (not Oxford) button down shirts, long sleeved and solid colors with the exception of blue or red banker or schoolboy stripes. J. Press makes the best pin point. After that, try Travis in London.

    16. A Barbour belonging to a college friend's father borrowed by you 24 years ago.

    17. Horn rimmed eye glass which are too small for you head.

    18. A cursive-script mustard color barn jacket from Bean's with several stains and tears.

    19. A blue and white Norwegian sweater from Beans purchased your sophomore year at Amherst.

    20. Assorted pair of Khaki's. These should be accumulated over the preceding 20 years, be identical in size and NEVER CUFFED. They may be procured from appropriate retailers or from hosts or relatives during a visit. It is very acceptable to allow the oldest among these trousers to bear small stains and tears.

    21. Signet ring. Solid gold, real crest. Worn on ring finger of left hand (gentlemen do not wear wedding bands, even in the event they marry).

    22. NO vulgar dress slacks with whales, boats or other adornments.

    23. NO 'jackets' other that described above.

    24. NO athletic attire of any kind other than all white for tennis and golf spikes.

    25. Nothing rayon or polyester except, perhaps, for the elastic in one's boxers or socks.

    1. Golf spikes? When was the last time you were on a golf course-😂😂😂

    2. Golf spikes? When was the last time you were on a golf course-😂😂😂 Definitely satire!

    3. Gentlemen don't wear wedding bands?

    4. One blue blazer and no tweed jackets?

      Old Trad

    5. Dearest Anonymous November 13, 2019 at 12:34 PM,
      wait... what movies was this in?

    6. Anonymous November 13, 2019 at 12:34 PM...
      Dang! You had me till # 17 then I burst out laughing. Very good! Kudos to you and the well thought out effort entailed here!

  2. Always start with the best blue blazer you can afford; skip Brooks and go to J Press for the real 3-2 roll example.

  3. Is this a serious list or satire (see No. 20)?

  4. List is pretty serious. With exception of the red pants and my Chesterfield is brown not grey, that is what I wear.

    1. I stand corrected. I do wear a wedding band. Have for 38 years.

  5. I took it as a useful satire. However, with regard to No. 20: no grocer's apostrophe's on your "khaki's," ever.

  6. List reminds me of something I read in The Preppy Handbook.

  7. No one mentioned handkerchief.preferably washed before handing down to future generations.

  8. Cuffs, toujours, cuffs.

  9. Blue blazer! The finest available.

  10. There was a list, or rather, lists, published in some magazine back in the early 1960s of what college men needed. It was fairly close to what most businessmen would need for any occasion. No mention of brand names was made and the lists varied quite a bit from one part of the country to another. California was the most casual, not surprisingly, but apparently college men dressed up more than seems to be the case now. It was certainly true when I started college in 1964. Things had changed a lot by the time I graduated.

    There was also a time when gentleman (as well as some who were not) would have his suits, at least, made to measure. That is probably rare these days, like having two pair of pants with a suit. Alas, if suits are actually worn everyday (probably rare these days), they will not last long enough to become hand-me-downs, unless you have a lot of suits. But things like tweeds and formal wear probably will. This all assume that the next generation is reasonably close in size--as well as the same gender.

    Table linens can be passed down through several generations. The one on my lap now is about a hundred years old, I'm told. It's from my wife's side of the family, naturally.

  11. A study in gentleman's clothing:

    The two state department officials testifying yesterday presented themselves "perfectly" from a sartorial point of view. A glen-check, three-piece suit, topped with a bow tie; and a nice, dark suit with understated tie.

    Others, some even without a suit jacket, looked like they were attending a World Wrestling Federation event, and acted like it, too.

    Now I don't know if one's clothing influences one's inner convictions and outward behavior--that's deeper than my pay grade, but I'll go with the well-dressed man any day.


    1. Books bound in calfskin are the only ones worth reading.

    2. Agrée with Aiken.

      I still think bow ties are prententous.

    3. Aiken - you just made my day! More, please!

    4. Aiken, you always makes me smile. Thanks for that.

  12. Okay, ladies and gentlemen, I found the list. This is only the part for the Northeast, where everyone here lives, except for me. The list is only slightly dated but would do very well for a complete outfit.

    Two suits, one medium to dark gray, the other a glen plaid. All natural shoulder three-button models.

    Two or three sport jackets, Shetland or tweed in dark tones, blue flannel blazer, Madras or patterned cotton for early fall and spring.

    Six or seven pairs of slacks; two dark gray flannels, one olive, the rest tan chinos, cords or poplins.

    A topcoat plus a raincoat in tan poplin.

    A duffel coat in navy, green, camel or coat in loden; a casual jacket or warm-up jacket.

    Three hats; a dressy felt with narrow brim, a Tyrolean hat and a rain hat.

    Two sweaters; a crew neck Shetland and a bulky crew or boat neck.

    Eight dress shirts; assorted button-downs and tab collars in oxford and broadcloth, mostly white, plus blues and stripes.

    Four sport shirts; Cotton button-down collar in Madras, checks, etc.

    Eight ties; wool challis, reps, foulards, etc.

    Shoes; one pair plain toe blucher, one pair wing tips, one pair sneakers (plus slippers).

    Formal wear; one tuxedo with all the accessories, including shoes.

    Other items; eight pair socks, muffler, two pair walk shorts (Madras, poplin), tie clasps, collar pins, odd vest, silk or rayon ascot, handkerchiefs and gloves.

    That's just the starting point, of course. Hardly anyone wears dress hats and collar pins these days and curiously, there is no mention of polo shirt or boat shoes (moccasins and desert boots in other regions, however). And not one single brand name was mentioned.

    The suggestions for the West Coast, meaning Southern California, was very up to date, with mention of t-shirts being worn alone with wash slacks and how the in crowd sometimes chop off the sleeves of their sweat shirts.

    I think everything here will fit into a large rolling duffel when you go off to school next year or to your new job in the city.

    1. I'm curious as to where you found this list.

    2. I don't know which magazine it was published in but it's from 1962. Here is a link:

      I have also seen a similar list from the fall of 1948. It featured more hats and double-breasted suits. It goes without saying that college campuses were very different before the mid-1960s. These things are all a little idealized, of course, but not far off the mark. Among other differences, well-dressed men and women would more likely have obtained their wardrobe from small, locally owned shops catering to men or women or both, which I suppose included the likes of J. Press. And even small colleges probably had a local store specializing in campus fashions.

    3. Going "Commando?"

  13. Here is a list from Sid Mashburn:

    Here's what I'd get as a starter kit, from head to toe:
    •1 navy suit (that can be split up into separates)
    •1 pocket square
    •1 light blue stripe dress shirt
    •1 white dress shirt
    •1 patterned sport shirt
    •1 navy knit tie
    •1 pair of grey dress trousers
    •1 pair of dark jeans (this means no rips or heavily distressed)
    •1 dark brown belt
    •1 pair of dark, over-the-calf socks
    •1 pair of dark brown lace-up calfskin shoes

  14. I would love to see similar lists for women.

  15. This won't work for everyone, but here is what I find the most useful in my wardrobe.

    1) OCBDs. Blue is the most useful color. White is also helpful. I really like Mercer's Crimson and White Stripe: it is surprisingly versatile, goes really well with navy and green (better than blue), and isn't as severe or formal as white. Blue and white stripe is also good. Oxfords are a good base, they go with most things. When deciding whether I should purchase something, one of the main questions I ask is whether it goes with my OCBDs.

    2) A navy blazer/sport-coat for the summer in a hopsack or similar. Should be sufficiently textured so it doesn't look like a suit. Natural shoulders are good. Mine is a model 3 from the Armoury in a dark navy balloon fabric. I recommend it highly.

    3) A grey herringbone tweed sportcoat for the winter. You could do another navy sportcoat, but I think the grey herringbone provides nice variety and goes well with everything the navy goes with. It looks really good with a lot of things, especially with charcoal trousers.

    4) Chinos and khakis. Khakis can be a bit hard to pair with shoes that aren't tennis shoes, they go well with loafers, because you get some sock in between, but otherwise, the khaki shade clashes with a lot. A greyish olive color for cotton is probably more versatile (goes a lot better with brown shoes and is subtler) but is less traditional. Chinos work better if they are a little slimmer toward the bottom, otherwise they tend to flail about wildly at the bottom because they don't drape too well. With heavier cottons this isn't as much a problem.

    4) Charcoal grey trousers. They just work well with a lot. Cavalry twill, whipcord, and flannel for the winter, high twist wools for the summer.

    5) Shetland sweaters for fall-spring. Neutrals and less bright colors. Can still do a variety of exciting colors, the colors should just be less saturated so that they are more versatile.

    6) Repp stripe ties in darker colors.

    7) Suede loafers. Aldens are nice. Rubber soled dress-shoes for the rain.

    8) A navy suit. I have a double-breasted for variety.

    9) A coat or two of some sort. Waxed cotton is good for more casual. A double breasted coat is good for other times. I think a polo in grey herringbone is nice. Camel is also nice, but is less versatile. I also like tweed balmacaans. Make sure the coat reaches your knees.

    This provides a good foundation. Things are pretty interchangeable, which allows for a lot of combinations. For example, you can use khakis for less formal and charcoal for more. Remove the jacket for less. I left out more niche single use items like black oxfords, which you should have, but which--unless your job demands it--you will only wear rarely.

    You can expand this wardrobe in all sorts of ways, and that it how you put personality into things. For example, you may choose to add green cords, or a few more tweed jackets in various checks, or a linen jacket, or a turtleneck. But when you wear these extra items, you will likely wear them with these core items, e.g. with ocbds or charcoal trousers, or khakis.

    Hope this helps.

  16. A gentleman simply knows what is appropriate and dresses as such, as does a lady. Plain classic and basic styles. You wear the clothes -- they do not wear you. You don't want to get into what is "stylish" you just need the clothes to cover your body. Plain basics are always best, but now you can get them anywhere. Don't get ruled by only certain stores. Slowly you will learn that many stores do not provide the quality that you seek, but sadly many of the stores once considered great are not of the same quality. What does a "gentleman" do with this dilemma? He grandly moves on. It's more than clothes. It's spirit although the clothes are the entry.

    1. I understand what you're saying but some of us, myself in particular, were born into very modest circumstances. My father was a truck driver and spent the last twenty years of his working life as a rural mail carrier. Though he was not well educated, he was nevertheless very much the gentleman in that he was kind, considerate, had excellent manners and was discreet. He was not to the manor born; he was born on a farm in Virginia.

      I, on the other hand, managed to finish university and marry into a family with some local historical connections, not all of which I have straight, even after 40 years of marriage. Along the way, I had made the acquaintance of several understanding gentlemen who gladly helped me learn a few social skills that I missed out on when the rest of you were either in prep school or finishing school, little of which had anything to do with clothing. Choose your friends carefully and don't worry about the stores.

      There is chance involved in making friends, I will admit. Once upon a time, I had the occasion to drive up and down a certain street in Alexandria, Virginia, where I was living. I happen to notice a certain rare car, just like one that I had. It was a Rover, from when Rover still existed and made cars. So, one day, I decided I just had to stop and find out who owned it. After knocking on a couple of doors, the man who owned the car very graciously invited me in and we chatted for a while. It turned out that I had actually seen him before at a dance in D.C. (small world). Anyway, he was a former foreign service officer and very much the gentleman. A few years later, he was my best man when I got married. So, based entirely on my own experiences, clothes aren't so important but having an interesting car can be critical.

    2. I will occasionally drive down the block of Princess Street in Alexandria with the vintage Land Rover simply to stare at it.

    3. I lived on North Pitt Street. That was over 40 years ago. My wife had lived up near the seminary, next to her grandparents, on land that had been in the family since before the war (the Civil War, that is) and still is.

  17. Being a gentleman has nothing to do with clothes.


    1. AnonymousNovember 16, 2019 at 8:13 AM
      May I ask, would you be considered a "gentleman" wandering about in your birthday suit?

  18. The above lists are notable for their omissions. It seems that preppy New Englanders go to bed naked even in the winter. There is no mention of pyjamas, dressing gowns or slippers. They must go skinny dipping too as it seems that no one has swimwear! And I did not spot any polo shirts, my spring and summer staple.

    My standard kit for the cold weather is a tattersall shirt, shetland jumper, heavy moleskin trousers, a tweed shooting jacket, flap cap and country shoes with a thick rubber sole. For meeting up with friends in town or going to a party, it's an Oxford cotton shirt, wool tie, cavalry twill or flannel trousers, a sports jacket or barathea blazer, wing tip/brogue shoes, trilby and a covert coat.

    A big NO to anything with animals or fish on them or made from nylon and polyester! Denim jeans, cargo shorts, sneakers, flip-flops, Crocs, hoodies and baseball caps should stay home as they are unacceptable in public.

  19. One more thought and I'll leave it. Even if you follow the lists of wardrobe basics, you must still make sure they all fit you properly. Sizes are not the same between different makers, since each cuts its clothes to its own patterns, like shoes built on different lasts. So, the first step is to find makers whose clothes fit your shape as closely as possible to begin with. The next step is to find a real tailor (getting harder and harder to find) and have him fine tune the fit. Don't rely on the person provided by the store, who likely will not know how to remove a collar to properly eliminate the bubble in the back of a suit coat. The most expensive suit or jacket or pants may still look clownish if they do not fit you properly.

  20. Anyone have a similar list for teenaged boys? F

  21. Haven't read all the comments yet, so apologies for the duplication if already noted. One should have at least one, and if possible, two sets of good cuff links. They will, with care, last a lifetime.

  22. I find Bruce's guidance quite acceptable although my footwear choice is Birkenstock's Alden Loafers or Bean boots and running shoes


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