Power Ranking of Prep Brands

While not the only factor, clothing is an important consideration when working to build a preppy lifestyle. From traditional ivy jackets, to New England outdoors-wear and southern beach attire, there are many forms of clothing that are considered “preppy” by different standards. This variety leads to the question; what is the most preppy brand? Well, that depends on who you ask, but if you’re asking us, then you’ll find out soon. Keep reading to see The Weekly Preppy’s official preppy brand power rankings.

Before diving into the rankings, lets discuss ranking criteria. When putting together these rankings we considered a variety of factors, and landed on 4 primary levels on which to compare brands:

With that explanation taken care of, lets dive in to our power rankings of the top 100 preppy brands.

100. Perry Ellis, 99. Atlantic Coastal Supply, 98. Dockers, 97. Hilditch & Key, 96. N. Peal, Dr. Martens,Travis Mathew, 93. Fatface, 92. The Original Penguin, 91. Gill.

These brands are associated with an element of the preppy wardrobe, such as business wear, golf, or sailing, but don’t have any strong connections to the prep lifestyle. They may be considered loosely preppy by those outside of the prep culture.

90. GAP, 89. Coastal, 88. Reiss, 87. Loeffler Randal, 86. Nautica, 85. The North Face, 84. Columbia, 83. Fjällräven, 82. Abercrombie & Fitch, 81. Bonobos, 80. Shetland Woollen Co, 79. Banana Republic, 78. Collars & Co, 77. Fair Harbor, 76. Madewell, 75. Tailor Vintage, 74. Rhoback, 73. Boden, 72. Marine Layer, 71. Mizzen+Main, 70. Draper James, 69. Clarks, 68. Eddie Bauer, 67. Charles Tyrwhitt, 66. Burberry, 65. Patagonia, 64. Dubarry, 63. Greyson Clothiers, 62. Tommy Hilfiger, 61. Wythe,

These brands should probably be considered preppy, but maybe nor universally. The produce clothing that aligns with the preppy lifestyle, and are almost certainly found in prep wardrobes, but fall short of being considered “staples”. Some may be upstart brands still working to solidify their place, some may be nostalgic brands with modern quality concerns, other walk the line between prep and designer, but fall slightly more towards the designer side.

There’s no debate that these brands are preppy, but there can probably be healthy discussion about where they fall in the power rankings, depending on your genre of prep.

60. The Black Dog - While now more tourist-oriented, the brand remains an iconic symbol of New England island life and 1980s-90s prep culture.

59. Southern Proper - A southern brand that celebrates traditions while keeping things fresh and fun for younger prep enthusiasts.

58. Quaker Marine Supply - An east coast nautical outfitter that embodies the authentic, no-nonsense approach to maritime lifestyle clothing.

57. Musto - The British sailing apparel brand founded by Olympic sailor Keith Musto creates technical gear that's been adopted by serious sailors and coastal preppies alike.

56. North Sails - Born from actual sailmaking for competitive racing, North Sails brings technical expertise and nautical authenticity to casual wear.

55. Tretorn - A prep icon through one product - the classic canvas Nylite tennis shoe.

54. Boast - Today, this is the anti-Lacoste alternative with a cult following from those who remember its heyday.

53. Duck Head - Accessible, cheerful Southern collegiate style with deep American manufacturing roots.

52. Mercer & Sons - A New York-based brand focused on American-made clothing with clean, classic lines and exceptional quality.

51. Fairway and Greene - A luxury golf apparel brand for those who want their golf attire to be as polished as their business wardrobe.

50. Collared Greens - A modern Southern brand that merges performance fabrics with preppy styling, creating golf and lifestyle wear for the next generation. 

49. Jack Rogers - Whipstitched leather sandals that can be found at country clubs and beach towns from Nantucket to Naples.

48. Hunter Boot - A preppy staple due to its association with country estates, equestrian life, and rainy New England campuses. 

47. Todd Snyder - A blend of heritage prep with contemporary styling, elevating basics with superior fabrics and thoughtful details.

46. Hill House - While newer to the scene, HH channels a cottagecore meets Palm Beach sensibility that resonates with modern prep.

W’re getting into the upper echelon. These brands carry with them a degree of icon status, but lack one or two subtle elements keeping them from being any higher on this list.

45. The Vermont Flannel Company - Since 1991, this family-owned company has been making impossibly soft flannel pajamas and robes in their Vermont factory. Their name says it all; they do one thing and they do it well.

44. Filson - Founded in Seattle during the 1897 Gold Rush, Filson created bombproof workwear for loggers and outdoorsmen that was later adopted by preppy outdoorsmen. Their Mackinaw wool jackets and tin cloth bags represent rugged American heritage that transcends workwear to become prep staples.

43. Southern Marsh - Founded by two college friends from the South, this brand celebrates the Southern outdoor lifestyle marked by hunting, fishing, and football Saturdays, with a preppy aesthetic. Their "authentic" collection features heritage duck cloth and field-tested functionality mixed with Southern collegiate style.

42. Sail to Sable - This women's resort wear brand brings bold prints and cheerful colors to the Palm Beach and Nantucket set, perfect for garden parties and yacht club lunches.

41. Johnnie-O - Founded by golfer and entrepreneur John O'Donnell, Johnnie-O brings California casual to preppy sportswear with performance fabrics and vibrant colors. The brand captures that laid-back West Coast country club style, achieving a level of prep without the stuffiness.

40. Smathers & Branson - Founded by two childhood friends from North Carolina, this brand became synonymous with needlepoint belts and wallets. Their hand-stitched designs featuring everything from college logos to hunting scenes are instant prep identifiers.

39. Buck Mason - This Los Angeles-based brand launched in 2013 with a focus on perfecting American menswear basics through superior fabrics and construction. Their West Coast minimalism offers a cleaner, more pared-down alternative to East Coast prep traditionalism.

38. Faherty - Twin brothers Mike and Alex Faherty created this brand in 2013 to capture the relaxed coastal lifestyle of their childhood summers at the Jersey Shore. Their soft, lived-in fabrics and easy silhouettes define modern beach prep. They’re polished enough to wear to dinner but comfortable enough for a bonfire.

37. Alex Mill - Founded by Alex Drexler (son of J.Crew's Mickey Drexler) in 2012, Alex Mill offers refined basics with a "buy less, wear more" philosophy. The brand represents a return to J.Crew's golden era—quality American sportswear without the gimmicks.

36. Nantucket Brand - A lifestyle brand built around the iconic ACK airport code and Nantucket's maritime heritage, offering casual wear that celebrates New England island culture. Their simple, logo-driven approach appeals to those who want to wear their vacation destination year-round.

35. Castaway Nantucket - This island boutique captures the breezy, effortless style of Nantucket summer living with carefully curated resort wear. Their clothing embodies that "just threw this on before boarding the ferry" ease that defines island prep.

34. Noah - Created by former Supreme creative director Brendon Babenzien, Noah blends streetwear credibility with classic prep aesthetics and progressive politics. The brand represents thoughtful, sustainable menswear.

33. Rowing Blazers - Founded by former US national rowing team member Jack Carlson in 2017, this brand revitalizes vintage prep with an archivist's eye and a collector's passion. By reissuing classic rugby shirts, rowing blazers, and collaborating with heritage brands, they've made prep cool for a new generation.

32. Southern Tide - Founded in 2006 by a University of South Carolina student, Southern Tide brought fresh energy to Southern prep with their skipjack logo and vibrant colors. The brand captures the coastal Carolina lifestyle, blending together fraternity formal and fishing trips.

31. Allen Edmonds - Since 1922, this Wisconsin-based shoemaker has been the go-to for classic American dress shoes, particularly known for their recraftable Goodyear welted construction. The Park Avenue oxford and Strand wingtip are staples in every preppy professional's wardrobe.

30. J. McLaughlin - Founded in 1977 by brothers Jay and Kevin McLaughlin, this brand serves upscale resort communities with colorful, comfortable clothing that bridges casual and polished. Their boutiques in places like Nantucket and Palm Beach cater to preppies seeking elevated everyday wear.

29. Drake's - The London-based brand founded in 1977 specializes in ties, scarves, and tailored clothing with a relaxed British elegance that American preppies have eagerly adopted. Their unstructured sportcoats and vintage-inspired prints represent a more sophisticated, grown-up take on prep style.

28. Rancourt & Co. - This Maine-based shoemaker continues the tradition of American handsewn footwear, crafting moccasins, loafers, and boat shoes in their Lewiston factory since 1967. Their commitment to domestic production and traditional craftsmanship makes them a favorite among heritage-minded preppies.

27. Kiel James Patrick - A Rhode Island-based brand that turned nautical rope bracelets into a preppy phenomenon, KJP channels New England maritime heritage with handcrafted accessories and lifestyle goods. Founded by the eponymous Kiel James Patrick and his wife Sarah, the brand embodies Instagram-ready coastal living.

26. Peter Millar - Founded in 2001, Peter Millar quickly became the uniform of upscale country clubs and resort destinations, offering luxury performance fabrics with impeccable tailoring. The brand represents modern preppy affluence. It is understated quality that signals success without screaming it.

These are tried and true preppy brands. You’d be hard pressed to find anyone objecting to them being on this list. They are staples in preppy wardrobes or hold a significant place in the history of preppy style.

25. G.H. Bass - Founded in Wilton, Maine in 1876, Bass created the iconic Weejun loafer in 1936, adapting Norwegian moccasins into the slip-on shoe that would define preppy footwear. The penny loafer (named for the practice of placing a penny in the saddle slot) remains the most recognizable prep shoe silhouette ever created.

24. Sid Mashburn - Founded in 2007 by former J.Crew men's fashion director Sid Mashburn, this Atlanta establishment offers a Southern gentleman's take on classic menswear with impeccable tailoring and personal service. The brand represents sophisticated, grown-up prep.

23. Baracuta - This British outerwear brand, founded in 1937, created the G9 Harrington jacket that became a preppy essential thanks to its adoption by Steve McQueen. The tartan-lined jacket represents British mod style that seamlessly integrated into American prep.

22. Land's End - Founded in 1963 in Chicago as a sailing equipment catalog, Land's End evolved into a reliable source for American casual classics such as oxford shirts, chinos, and sweaters at honest prices. The brand walks a fine line in the prep world, attempting to produce quality basics without pretension or exorbitant pricing.

21. Sperry - In 1935, sailor Paul Sperry invented the boat shoe with siped rubber soles after studying his dog's paws on ice, creating an icon of American prep. The Original Boat Shoe, particularly in brown leather with white soles, became as essential to the preppy uniform as the oxford shirt.

20. Pendleton - Operating woolen mills in Oregon since 1863, Pendleton became famous for their blankets and wool shirts featuring Native American-inspired patterns and bold plaids. Their rugged Pacific Northwest heritage crossed into prep through Ivy Leaguers who appreciated quality woolens, making the board shirt a staple.

19. J.M. Weston - Since 1891, this French shoemaker has crafted shoes in Limoges using traditional techniques, with their #180 loafer becoming a preppy favorite for its elegant last and substantial construction. American preppies embraced Weston as a more refined European alternative to domestic loafers, serving as proof that prep appreciates Old World craftsmanship.

18. GANT - Founded in 1949 by Ukrainian immigrant Bernard Gantmacher, GANT revolutionized the button-down by adding a locker loop and perfecting the collar roll for Yale's campus shop. Their technical innovations and Ivy League origins make them fundamental to American prep, even as the brand is now Swedish-owned.

17. Tuckernuck - Founded in 2012 as a curated boutique for classic American style, Tuckernuck (named after a tiny island off Nantucket) offers a carefully edited selection of preppy brands and their own private label. The shop represents modern prep curation, helping customers navigate the aesthetic without the gatekeeping.

16. Vineyard Vines - Founded in 1998 by brothers Shep and Ian Murray after they quit their corporate jobs, Vineyard Vines captured modern Martha's Vineyard style with their signature whale logo and "Every day should feel this good" motto. Early 2000’s prep was in part defined by their democratization of the style.

15. Anderson & Sheppard - Established on Savile Row in 1906, this bespoke tailoring house became the choice of discerning American preppies who appreciated their "soft tailoring" approach with draped shoulders and comfortable elegance. Having dressed everyone from the Duke of Windsor to American captains of industry, they represent the pinnacle of understated British craftsmanship.

14. Ben Silver - This Charleston-based haberdashery founded in 1967 specializes in British-influenced Southern elegance, from bespoke neckties to their iconic needlepoint belts featuring club crests and whimsical designs.

13. The Andover Shop - Opened in 1949 across from the Harvard Yard in Cambridge, The Andover Shop became the epicenter of American Ivy style under Charlie Davidson's leadership. This small shop defined what prep meant during its golden era, outfitting generations of Harvard men in natural shoulder suits and repp ties.

12. Orvis - Founded in Manchester, Vermont in 1856 as America's oldest mail-order retailer, Orvis began with fly-fishing tackle before expanding into sporting apparel and country lifestyle goods. The brand represents old money New England sporting.

11. O'Connell's Clothing - This Buffalo institution, founded in 1960, remains one of the last true purveyors of authentic Ivy League style, refusing to compromise on traditional cuts and natural shoulders. Their unwavering commitment to trad principles makes them a pilgrimage destination for serious prep devotees seeking clothing exactly as it was worn in the 1960s.

These are the brands that truly define the preppy style. Every brand on this list plays a role, but these ten are the quintessential brands the represent prep culture and style. They may not all be large today, but their influence is undeniable.

Founded in 1909 in Perry, Maine, Quoddy continues the Native American tradition of handsewn moccasins, with each pair still crafted by individual artisans in their Maine workshop. The brand represents the ultimate in American craft heritage; shoes made the same way for over a century, with leather hand-stitched using techniques passed down through generations. Quoddy's moccasins, boat shoes, and boots achieve that perfect preppy combination of casual refinement and genuine utility, whether worn sockless in summer or with wool socks in fall. The brand's commitment to American manufacturing and traditional methods, even as competitors moved production overseas, earned them cult status among heritage-obsessed preppies. In a Quoddy loafer or moccasin, you're wearing a piece of Maine history. Honest, handmade, and quintessentially New England.

Lilly Pulitzer, born into a prominent New York family and married to publishing heir Peter Pulitzer, created her brand almost by accident in 1959 when she designed bright shift dresses to hide juice stains while running a citrus stand in Palm Beach. Her vibrant prints and simple silhouettes captured the elegance of southern living. The brand became synonymous with a specific slice of preppy life: Palm Beach winters, country club lunches, and the confidence of women who summered in the right places. After Lilly's death in 2013, the brand continues as the uniform of Southern sorority girls, Junior League members, and anyone channeling that carefree, colorful Palm Beach spirit.

Founded in 1983 as a catalog company, J. Crew hit its cultural peak under Mickey Drexler's leadership (2003-2017), when it became the uniform of aspirational young professionals and Obama-era style. The brand made prep accessible and cool, introducing slim fits, collaborations with heritage brands, and styling that felt fresh rather than stuffy. Jenna Lyons' tenure as creative director elevated J. Crew into a fashion force, mixing preppy classics with unexpected elements and creating the "preppy but make it interesting" aesthetic. Financial troubles, overexpansion, and quality decline tarnished the brand's reputation, but its cultural impact remains enormous. An entire generation learned about Alden, Barbour, and Red Wing through J. Crew collaborations. At its best, J. Crew proved that prep could evolve while honoring its roots.

Founded in 1894 in South Shields, England, Barbour created waxed cotton jackets for fishermen and sailors before the British country set adopted them for field sports and country pursuits. The Beaufort and Bedale jackets, with their distinctive waxed cotton, corduroy collars, and tartan linings, crossed the Atlantic and became essential preppy outerwear by the 1980s. Barbour represents functional British heritage that aligned perfectly with preppy values like country living, field sports, and clothing that improves with age and repair rather than replacement. The jackets' ability to be rewaxed and repaired by Barbour exemplifies the prep mindset of buying well and maintaining forever. Equally at home on English moors and New England campuses, Barbour became the jacket of choice for preppies who valued authenticity and British country style.

Founded in 1884 in Middleborough, Massachusetts, Alden remains one of the last American shoe companies crafting Goodyear-welted dress shoes domestically, maintaining standards of construction that most competitors abandoned decades ago. Their cordovan shell leather shoes, particularly in the #8 burgundy color, achieve cult status among menswear enthusiasts who appreciate the way cordovan ages and develops character over years of wear. The legendary collaboration with Brooks Brothers on various models cemented Alden's place in prep history, while limited production and traditional methods keep demand eternally high. From tassel loafers to cap-toe boots, Alden represents American craftsmanship at its finest, making shoes that cost significantly but last decades. For serious preppies, owning Aldens isn't just about footwear; it's about participating in a tradition of quality and supporting domestic manufacturing.

It would be difficult to place the inventor of the polo shirt outside the top ten on this list. French tennis champion René Lacoste revolutionized sportswear in 1933 with his creation. The short-sleeved, soft cotton piqué shirt with a ribbed collar was a more comfortable alternative to the woven long-sleeve shirts worn on tennis courts. The iconic crocodile logo (a nickname earned for Lacoste's tenacity on court) made it one of the first designer logos, and American preppies immediately embraced it as leisurewear perfection. The polo shirt in white, navy, or pastel colors became as essential to the preppy uniform as khakis and loafers. Lacoste represents the athletic side of the prep lifestyle; tennis, golf, and country clubs.

Leon Leonwood Bean founded his mail-order company in Freeport, Maine in 1912, creating the iconic Maine Hunting Shoe (Bean Boot) when he combined leather uppers with rubber bottoms for his own hunting expedition. That commitment to functional, honest products for outdoor pursuits became the foundation of a brand that epitomizes New England practicality and durability. The Bean Boot remains virtually unchanged and completely iconic. It’s a preppy status symbol that's actually earned through genuine utility. Beyond the boots, LL Bean's canvas totes, Norwegian sweaters, and chamois shirts became campus staples, representing a democratic prep that valued quality and function over pretension. The brand embodies the Maine character: unpretentious, hardworking, and built to last generations.

Ralph Lauren didn't just participate in preppy culture, he represented it. Starting with wide Polo ties in 1967, Lauren built an empire by romanticizing the American upper class, from the Hamptons to the hunting lodge, making preppy style accessible to anyone who could afford it. His genius was understanding that prep wasn't just clothing but a complete lifestyle, a mythology of old money, country clubs, and effortless elegance. Through Purple Label, Polo, and RRL, he created products at every price point while maintaining the dream. Ralph Lauren made "preppy" a global language.

Founded by Jacobi Press in 1902, J. Press became the official outfitter of the Ivy League, with shops near Yale, Harvard, and Princeton that served as the arbiter of collegiate style for generations. The brand's natural shoulder sack suits, three-roll-two blazers, and repp ties defined what "Ivy" meant during its golden era from the 1950s through the 1970s. J. Press never chased trends or compromised their traditional silhouettes, earning them reverence among purists who view them as the keeper of the flame. While smaller today, the brand maintains its commitment to American manufacturing and traditional construction. For those who know, J. Press represents prep in its purest, most authentic form, the real deal that inspired all the imitators.

Founded in 1818 in New York City, Brooks Brothers is the oldest continuously operating clothing retailer in America and the absolute bedrock of American preppy style. The brand invented the button-down collar shirt in 1896, introduced the seersucker suit to America, and created the iconic #1 repp stripe tie. For over two centuries, Brooks Brothers dressed everyone from Abraham Lincoln to JFK, establishing the visual language of American business and casual elegance. While the brand has faced ownership changes and quality inconsistencies in recent years, its historical significance as the foundation of prep remains unassailable. This is where it all began.