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

Wednesday, June 26, 2024

Some nice preppy shirts and trousers for a 20 year old male?

 A reader question:

I am looking for suggestions for a young man (20 years old) to buy some nice shirts and trousers. Preppy look perfect.   What are options for as cheaply as possible and as classic as possible? 

Thank you!

27 comments:

  1. L.L. Bean and J. Crew aren't very expensive.

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  2. Inexpensive and classic aren't mutually exclusive but can be.

    Inexpensive, try Uniqlo or LL Bean.

    Classic khaki trousers, 'you get what you pay for,' Jack Donnelly. They're not cheap. They offer different cuts to fit different-sized people, the fabrics are excellent, and they're high-quality - will last a long time and still look great.

    Best compromise on dress shirts and button-downs, Proper Cloth. Again, not cheap, but excellent quality, made to measure, and a very large choice of fabrics.

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  3. Lands End has all you need

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  4. A twenty year old ( obviously not a trust fund baby) is looking for some new classic but affordable clothes. I can’t wait to see how many responders tell him to go to Jack Donnelly, JPress, O’Connell’s, Mercer etc. Maybe if he needs shoes he could go to John Lobb or Edward Greene or pick up a nice new duffel bag from Lotuff.I know that everyone likes to show off their knowledge of the finest products and of course support Muffy’s benefactors, but give the kid a break and some real world recommendations.

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    1. Exactly. It doesn't seem very preppy to begin building debt.

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  5. LL Bean and Lands’ End will cover it. If you’re not actually from that background, though, ease into it very slowly, or you will look like a clown and Avril Lavigne will mock you.

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  6. Frederick J JohnsonJune 26, 2024 at 4:03 PM

    When its all said and done your best value may be J Press. Their khakis are a bit cheaper that JD's but, in my opinion, every bit as good. Their shirts are cheaper than Mercer and come in exact neck/sleeve sizes.

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  7. Have a look on ebay. You can often find e.g. new Brooks brothers shirts and khakis (and lands end) at a fraction of the list price. Other preppie items too. Ideal if funds are limited.

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  8. Echoing the recommendations for L.L.Bean and Lands End. I prefer Bean for chinos and Lands End for shirts.

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  9. You can also take a look on Poshmark for some good deals on barely used items. However I do agree with Anonymous @2:22. Classic and inexpensive versions of both shirts and trousers are not to be found at places normally suggested for people with a little more in their bank account.

    L.L. Bean have really nice, classic chinos with different lengths and are 100% cotton. When looking for shirts, take care not to buy shirts with any kind of wrinkle-free coating - they undo all the breathability of cotton, as well as the softness. J.Crew, L.L. Bean, Gap, Lands End all have some really nice shirts - just read the small print.

    Again, many of these can be found on Poshmark, but they won't break the bank if you buy brand new.

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    1. Sadly, the vast majority of shirts at this price point are now "wrinkle free" or "performance stretch"... but, yes, 100% cotton can be found. The Lands End Sail Rigger Oxford is a decent example.

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    2. The LE Sail Rigger does not have exact sleeve lengths, and the collar points are too short. While LE's stuff is still well made, its designs have strayed from the traditional stylings it embraced in the '70s and '80s. It has fallen in love with the "no iron" thing. It continued to sell a must-iron Hyde Park 100 percent cotton dress shirt with exact sleeve lengths until the last year or two, but I can no longer locate that product on its website. "No iron" makes sense for travel, but nothing beats "must iron" for comfort. Untreated must-iron fabric also seems to last longer, especially if laundered at home.

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    3. I stocked up on those Hyde Park shirts before they disappeared a couple of years ago. Some time before vanishing they had downgraded to alpha sizing.

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  10. Good heavens, go to Good Will or similar. No need to buy new/full price.

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    1. Thrift stores are great, but hit-or-miss. If you have to outfit a young man for school or work, good luck. I did, however, snag a 100 percent linen casual button-up shirt, freshly laundered, at a local thrift shop this past Sunday for $7 (less my 10 percent senior discount). Frugality is not exclusive to New England.

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    2. Yankee thrift!

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    3. The thrift stores here in Maine are littered with L.L. Bean rejects, especially the stores closest to Freeport.

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  11. My son does will with L.L. Bean, J. Crew and Lands End. He also has had good luck with Banana Republic for khakis--they have various fits he finds the ones with a bit of stretch extremely comfortable. Plus, they run some great sales.

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  12. The trick to building a wardrobe is taking your time, finding your style and size, and buying quality once rather than junk several times. That's tough when starting out, but it's worthwhile to exercise patience.

    Try different brands, fits, and sizes on and find what fits and looks best for you. It may be helpful to go to a store and spend time with different brands or different stores looking at and trying on different items. Educate yourself why some brands are more expensive than others.

    Get to know a tailor, as proper fitting "cheap" clothing looks 10x better than "fancy" but sloppy clothes. Take advantage of sales on things you need and know you will wear.

    Build your wardrobe to be interchangeable: Keep everything within a palette so all your shirts coordinate with all your pants, etc.

    If you splurge, do it on shoes and a nice belt (that matches the shoes). You don't need to spend $700 on Aldens to have nice shoes, but a decent pair of comfortable, Goodyear weld loafers can last a long time and be resoled -- which will save you money over time (but they will still be $200 to $300 a pair).

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  13. Most gentlemen will find that they look best when the widest part of the collar on their button down shirt (at the front, near the button) is the same width as their tie and lapels at their widest points. Something around 3 1/4 to 3 1/2 inches looks best, even when one is not wearing a tie and jacket. Unfortunately, I don't know of any store that offers an all cotton, untreated shirt with the correct collar width for less than about $140. Ebay is the way to go if looking to save.

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  14. Fit, fabric, color, but the greatest of these is fit.

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  15. L. L. Bean, J. Press!

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  16. The Pennant line at JPress is geared toward younger buyers with the same JPress quality at a lesser price. Most Chinos are just under $100 and if you sign up at their website you get 10% off your first order.

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  17. At the moment Eddie Bauer has nice khakis for $30-40. For shirts, jackets, and more, search Etsy and eBay. NWT in your size is quite often on both sites. The sales at Orvis are often a good source for more casual items.

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  18. Most stores have a section which includes end of season and discontinued items. You can find some great deals but not all sizes.

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  19. *Tailoring:*
    What to get: A solid navy or grey suit, a navy blazer, and maybe either a brown corduroy (for temperate climates) or a grey tweed (for colder climates) sport coat.
    Where to get it: Spier & Mackay or Brooks Brothers & J.Press Pennant (when on sale.) If you know your size / measurements, good deals can also be found on eBay or your local thrift shop!

    *Shirts:*
    What to get: 2 dress shirts (white & light blue), 4 oxford shirts (white, blue & white striped, light blue, and pink), 4 seasonal sport shirts (2 fall/winter - think plaid flannels, and 2 spring/summer - think gingham and madras), and 2-4 polos (start with navy and white, then branch out to more colors.)
    Where to get it: Lands End & L.L. Bean, or J.Crew & J.Press Pennant (when on sale)

    *Pants & Shorts:*
    What to get: Grey wool trousers, tan khakis, dark blue jeans, and khaki shorts
    Where to get it: Levis for jeans, J.Crew for trousers, khakis, and shorts (when on sale)

    *Sweaters*
    What to get: 2+ shetland crewneck sweaters (in navy and grey)
    Where to get it: J.Crew or Brooks (when on sale), or at your local thrift store. The J.Press "Shaggy Dog" version of this is iconic, though -- and makes a great gift!

    *Outerwear*
    What to get: A raincoat, plus a wool overcoat or peacoat
    Where to get it:

    * Shoes*
    What to get: A pair of brown/burgundy penny loafers, classic sneakers, brown/tan desert chukka boots, and brown boat shoes
    Where to get it: Bass Weejuns are the classic penny loafer, but they're hell to break in. If you can wait/save up a bit, Jay Butler makes far better ones and they're close to the same price when on sale. Grey New Balance, white Nike killshots, or white Adidad Stan Smiths would all be classics. Clarks makes good desert boots. Sperry for boat shoes.

    *Accessories:*
    What to get: A navy grenadine tie, a burgundy grenadine tie, a repp striped tie, and a guard striped tie. A brown dress belt. Sunglasses (either aviators or wayfarers). Gloves, scarves, and an umbrella.
    Where to get it: TheTieBar has the best cheap, new ties. But, a local thrift shop or eBay may have Brooks' Makers ties (a far better quality) at a similar price.

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