Looking to step up from Jack Wills? These 17 brands share the aesthetic but bring elevated materials, construction and a higher price tier — ranked by overall similarity.
American preppy staples label, from chinos and oxford shirts to cashmere knits, revived under creative director Olympia Gayot.
Why it's similar. J. Crew's preppy and classic style aligns very closely with Jack Wills. Both offer relaxed and tailored silhouettes, have a neutral palette, and utilize similar materials. J. Crew's position in the mid-range market is one notable difference, though similar in cultural positioning.
Founder-run Baton Rouge label making Southern-lifestyle basics — duck-logo graphic tees, polos, oxfords and quarter-zips — for men, women and kids.
Why it's similar. Southern Marsh shares a preppy and classic style with a relaxed silhouette and neutral palette, similar to Jack Wills. They both focus on comfort and casual wear, appealing to a youthful audience.
Greenville, South Carolina coastal-preppy label known for its Skipjack polo, owned by Oxford Industries since 2016.
Why it's similar. Southern Tide mirrors Jack Wills’ style with its preppy, classic approach. The use of neutral palettes and cotton/jersey basics, along with a similar cultural vibe, make them very comparable.
American retailer founded in 1892, selling casual contemporary apparel — denim, trousers and YPB activewear — and parent of Hollister and Gilly Hicks.
Why it's similar. Both brands embody a preppy and casual aesthetic that appeals to young audiences.
New York DTC label behind the viral Nap Dress, selling smocked "grand millennial" dresses, sleepwear, kidswear and home linens.
Why it's similar. Hill House's style and silhouette align with Jack Wills. Their focus on classic, preppy clothing with a neutral palette provides strong similarities.
American-founded, Stockholm-based preppy sportswear label known for oxford button-downs, rugby shirts, chinos and knitwear, owned by Swiss group Maus Frères.
Why it's similar. GANT's classic preppy designs resonate well with the aesthetic of Jack Wills.
American menswear label built on button-down shirts cut with shorter hems to be worn untucked, now spanning knits, chinos and womenswear.
Why it's similar. Untuckit shares the preppy style and neutral palette of Jack Wills. Their focus on relaxed silhouettes and casual wear closely align both brands.
Grayers is an American men's smart-casual label built on 1950s British grey-flannel style, making shirts, knitwear and soft blazers.
Why it's similar. Grayers offers a heritage style with modern twists, similar to Jack Wills. Shared materials and silhouettes are notable overlaps.
The core preppy sportswear line of Ralph Lauren Corporation, known for pony-logo mesh polo shirts, oxford button-downs and Ivy League–rooted staples.
Why it's similar. Both brands focus on preppy styles and tailored designs that cater to a youthful demographic.
Preppy American sportswear label founded by designer Tommy Hilfiger in 1985, owned by PVH Corp and spanning mainline and Tommy Jeans.
Atlanta-founded menswear label and shop offering soft-tailored suits, shirting and chinos in a traditional American-Italian style.
French sportswear house behind the crocodile-logo L.12.12 polo, blending tennis heritage with contemporary streetwear collections.
Calvin Klein's childrenswear line: minimalist, logo-driven denim, tees, outerwear and underwear, largely produced under license and owned by PVH Corp.
British heritage outerwear label founded in 1894, best known for waxed cotton and quilted country jackets.
British lifestyle retailer known for print-led, embroidered casualwear and homeware, owned by TFG London since October 2024.
British countryside-inspired label known for printed dresses, waxed jackets and floral wellingtons, now majority-owned by Next plc.
Gap Inc.'s premium label, reworking its 1970s safari and travel heritage into tailoring, leather outerwear and elevated basics.
J. Crew, Southern Marsh, Southern Tide lead our ranking. Looking to step up from Jack Wills? These 17 brands share the aesthetic but bring elevated materials, construction and a higher price tier — ranked by overall similarity.