Town & Country Preppy Essentials

Town & Country Preppy Essentials: Splurge vs. Steal


preppy wardrobe essentials

Last week Town & Country magazine published a list of preppy wardrobe essentials. Since I have lived in what are considered to be some of the most preppy areas of the country (Palm Beach Gardens, Connecticut, D.C., and now a very preppy area of Dallas), I thought it would be fun to review this list and add some less-expensive preppy alternatives.

Of all the places I have lived, I believe New Englanders have mastered the preppy look more than any others, as they have been doing since long before the Kennedys arrived on the scene. What I learned during my time on the East Coast is that the preppy look has to appear effortless. In other words, head-to-toe Vineyard Vines is trying way too hard.

So what is a true preppy look?  My husband and I joke that it is the art of looking like you have a lot of money without looking like you have a lot of money. Achieving the classic New England look is almost an art form. It’s the crazy juxstaposition of wearing $400 jeans with $80 ugly boat shoes from L.L. Bean. But it works, as it has for generations.

Below I’ve detailed the list, with less expensive alternatives. See what you think:

Barbour Beaufort Coat


Pretty much a winter staple among the upper crust. Rugged, but classic. The L.L. Bean one on the right is a less expensive version of the original. I love this coat because just about any guy can pull it off, young or old.

Duck Shoes


My dad and husband are hunters so these shoes have been a presence in my life for a long time. So it was stange to me when I noticed people wearing them on rainy days with their cute jeans. Funny how trends work. Really the original L.L. Bean duck boots are not that expensive (since they last forever) so I would say go with the original!

Brooks Brothers Navy Blazer


When we first got married, I told my husband (who hates all things navy) that he needed a blue Brooks Brothers blazer. After much coaxing, I finally talked him into one a few years later and he still has it to this day. Every man needs a navy blazer, no matter what your fashion sense. Of course, I love the Brooks Brothers classic with its brass buttons, but if you don’t want to spend that much, the Michael Kors blazer on the right is 50% off right now so it would only be $150!

Cartier Tank Watch and Juste un Clou bracelet


Even if I had a Cartier watch or bracelet, I don’t think I’d wear it; I am too scared of losing expensive things! These cheaper versions come pretty close if you like that Cartier look.

Needlepoint Belt


A Smathers and Branson needlepoint belt was another accessory on the list. What a beautiful gift to give your husband or dad! But if you want that same look, Vineyard Vines has some similar styles for around $50. It’s not needlepoint though (and it’s all in the details for a true preppy look!).

Plaid Pants


Town and Country chose these LOFT plaid pants as their example of the perfect preppy pants for women. Both are super cute and well-priced.

New Balance 991’s


I forgot to mention that I also lived in Memphis, home of MUS all-boys school where everyone wears gray New Balance shoes or Wallabees (or used to at least!). In college, I could always pick out those preppy MUS boys from across the quad! I didn’t even know there were different types of gray New Balance sneakers, but apparently the ones on the left are the more classic look.

Lilly Pulitzer Wrap Dress


While I love this wrap dress, I will have to respectfully disagree with Town & Country on this one. I used to work at a Lilly store and I would say with full confidence that the true embodiment of the preppy look is a Lilly Pulitzer shift dress.


Stubbs and Wootton Slippers


Smoking slippers have made a recently comeback. The C. Wonder ones on the right are so cute and 50% off right now so they are actually $74. I want some!

Sperry Boat Shoes

A classic shoe that’s not just for boating. I can’t stand fake leather shoes so I’d go with the originals on the left.

Tory Burch Tunic


Tory Burch didn’t create the tunic, she just perfected it. But I love the price of the J. Crew Factory one on the right!

T. Anthony Classic Duffle Bag


I think it’s obvious the one on the right looks almost identical to the more expensive version. How perfect for a casual weekend away (and a great gift!).

Patagonia Snap T Pull-Over


If you’ve had a Patagonia,  you know that it looks pretty much the same year after year, which is perfect for the classy look. But L.L. Bean is very similar in that way. Hard to choose on this one!

Acqua di Parma Cologne


Worn by Carey Grant and Audrey Hepburn, this cologne is a preppy essential. Since you can’t be cheap when it comes to fragrances, I’ve shown the cologne on the left and the shower gel on the right, which might be better anyway in just giving off a hint of classiness.

Anything Nantucket Red

Nantucket Red means “it looks like I’ve worn this shirt for years” red. Again with the not trying too hard thing. I picked various Nantucket red items that your guy might enjoy this Spring/Summer.


What do you think of the Town & Country Preppy Essentials list? Would love to know.

Happy Boating!





More Practical Preppy Looks


More Tory Burch Tunics



 Photo Source: Town & Country on Instagram 
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