We may earn money or products from the companies mentioned in this post.
Maybe you weren’t the recipient of a trust fund—but that doesn’t mean you can’t dress like you were, anyway. With these blazers, trousers, button-ups and more, you can look like you stepped right off the campus of your fancy prep school thanks to these classic, academic-inspired designs.
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Thaddeus Men’s Barney Quilted Barn Jacket$275.0$81.0 -
Paul & Shark Men’s Button Down Dress Plaid Shirt$285.0$115.0 -
Paul & Shark Men’s Long Sleeve Striped Polo$395.0$159.0 -
Thaddeus Men’s Barney Quilted Barn Jacket$275.0$81.0 -
Paul & Shark Men’s Long Sleeve Striped Polo$395.0$159.0 -
Corneliani Men’s Hybrid Puffer$1938.0$464.0 -
J. McLaughlin Men’s Solid Milton High V-Neck Sweater$345.0$108.0 -
Thaddeus Men’s Frank Long Sleeve Cutaway Collar Plaid Shirt$195.0$57.0 -
Brunello Cucinelli Men’s Slim Fit Dotted Sport Shirt$525.0$229.0 -
Alex Cannon Men’s Long Sleeve Button Down Plaid Shirt$115.0$23.0 -
Alex Cannon Men’s Long Sleeve Button Down Plaid Shirt$115.0$23.0 -
Corneliani Men’s Id Sportcoat with Removable Bib$1598.0$431.0 -
J. McLaughlin Men’s Plaid Clinton Spread Collar Trim Fit Shirt$155.0$37.0 -
Alex Cannon Men’s Long Sleeve Spread Collar Dobby Windowpane Shirt$115.0$23.0 -
Thaddeus Men’s Montgomery Long Sleeve 4 Pocket Zip Front Jacket$285.0$83.0 -
Haspel Men’s Daytona Long Sleeve Shirt$225.0$61.0 -
J. McLaughlin Men’s Solid Milton High V-Neck Sweater$345.0$87.0 -
Paul & Shark Men’s Button Down Check Dress Shirt$320.0$129.0 -
Thaddeus Men’s Park Long Sleeve Cutaway Collar Plaid Shirt with Pocket$175.0$50.0 -
Thaddeus Men’s Park Long Sleeve Cutaway Collar Plaid Shirt with Pocket$195.0$57.0 -
Alex Cannon Men’s Rugby Stripe Crew Neck Sweater$150.0$46.0 -
J. McLaughlin Men’s Preston Stand Collar Down Vest$215.0$47.0 -
Belstaff Men’s Roadmaster Belted Waxed Cotton Jacket$950.0$701.0 -
Alex Cannon Men’s Long Sleeve Button Down Check Shirt$115.0$23.0 -
Alex Cannon Men’s Long Sleeve Button Down Plaid Shirt$115.0$23.0 -
Paul & Shark Men’s Moleskin Pants$350.0$139.0 -
J. McLaughlin Men’s Plaid West End Button Down Trim Fit Shirt$155.0$37.0 -
Thaddeus Men’s Park Long Sleeve Cutaway Collar Plaid Shirt with Pocket$175.0$50.0 -
Haspel Men’s Clark Knit Polo$395.0$107.0 -
Haspel Men’s Clark Knit Polo$395.0$107.0 -
Haspel Men’s Bernard Trouser$295.0$80.0 -
J. McLaughlin Men’s Solid Milton High V-Neck Sweater$345.0$87.0 -
Thaddeus Men’s Park Long Sleeve Cutaway Collar Plaid Shirt with Pocket$175.0$55.0 -
J. McLaughlin Men’s Plaid West End Button Down Trim Fit Shirt$155.0$37.0 -
Alex Cannon Men’s Long Sleeve Spread Collar Dobby Windowpane Shirt$115.0$23.0 -
J. McLaughlin Men’s Stripe Gramercy Spread Collar Regular Fit Shirt$165.0$39.0 -
J. McLaughlin Men’s Solid Milton High V-Neck Sweater$345.0$87.0 -
Alex Cannon Men’s Long Sleeve Button Down Plaid Shirt$115.0$29.0 -
Alex Cannon Men’s Shawl Collar Sweater with Cable Stitch$165.0$50.0 -
Thaddeus Men’s Park Long Sleeve Cutaway Collar Plaid Shirt with Pocket$175.0$55.0 -
Thaddeus Men’s Croton Long Sleeve Crossover V-Neck Sweater$125.0$38.0 -
Alex Cannon Men’s Long Sleeve Button Down Houndstooth Shirt$115.0$29.0 -
Corneliani Men’s Mini Check Sportcoat with Knit Bib$1695.0$492.0 -
J. McLaughlin Men’s Plaid Gramercy Spread Collar Regular Fit Shirt$155.0$37.0 -
Alex Cannon Men’s Long Sleeve Button Down Check Shirt$115.0$23.0 -
Thaddeus Men’s Murphy Long Sleeve Heather Zip Track Jacket$150.0$46.0 -
Corneliani Men’s Reversible Vest$723.0$224.0 -
Alex Cannon Men’s Textured Horizontal Diamond V-Neck Sweater$125.0$34.0 -
Thaddeus Men’s Montgomery Long Sleeve 4 Pocket Zip Front Jacket$285.0$83.0 -
Alex Cannon Men’s Multi Stripe Crew Neck Sweater$125.0$34.0 -
Thaddeus Men’s Croton Long Sleeve Crossover V-Neck Sweater$125.0$38.0 -
Thaddeus Men’s Fitzpatrick Long Sleeve Stretch French Terry 1/4 Zip$125.0$38.0 -
Alex Cannon Men’s Aaron Cable Stitch 1/4 Zip$130.0$37.0 -
Moncler Men’s Crew Neck Sweater$570.0$342.0 -
Haspel Men’s Clayton Knit Shirt$150.0$44.0 -
Alex Cannon Men’s Long Sleeve Spread Collar Check Shirt$115.0$23.0 -
Thaddeus Men’s Vestry Long Sleeve Ribbed V-Neck Sweater$150.0$49.0 -
Alex Cannon Men’s Textured Horizontal Diamond V-Neck Sweater$125.0$34.0 -
Thaddeus Men’s Vestry Long Sleeve Ribbed V-Neck Sweater$150.0$48.0 -
J. McLaughlin Men’s Chatham Light Quilted Jacket$345.0$83.0 -
J. McLaughlin Men’s Solid Wilson Cardigan$235.0$54.0 -
Thaddeus Men’s Fitzpatrick Long Sleeve Stretch French Terry 1/4 Zip$125.0$38.0 -
Alex Cannon Men’s Full Zip Ribbed Cardigan With Faux Suede Shoulder Accents$165.0$50.0 -
J. McLaughlin Men’s Jacquard Downhill Fleur-De-Lis Sweater$230.0$50.0 -
Haspel Men’s Davis Long Sleeve Henley$135.0$47.0 -
Corneliani Men’s Rain Coat with Removable Bib$820.0$280.0 -
Brunello Cucinelli Men’s Corduroy Pant$625.0$269.0 -
Alex Cannon Men’s Long Sleeve Spread Collar Check Shirt$115.0$23.0 -
J. McLaughlin Men’s Stripe West End Button Down Trim Fit Shirt$145.0$37.0 -
Brunello Cucinelli Men’s Trouser$599.0$259.0 -
Paul & Shark Men’s Button Down Check Dress Shirt$320.0$129.0 -
Corneliani Men’s Mixed Media Jacket$870.0$252.0 -
Thaddeus Men’s Vestry Long Sleeve Ribbed V-Neck Sweater$150.0$46.0 -
Thaddeus Men’s Marty Long Sleeve Thermal Mixed Media Crew Neck$110.0$35.0 -
Alex Cannon Men’s Textured Horizontal Diamond V-Neck Sweater$125.0$34.0 -
Alex Cannon Men’s Reversible Herringbone/Solid 1/4 Zip Mock Neck Sweater$130.0$37.0 -
J. McLaughlin Men’s Solid Milton High V-Neck Sweater$345.0$97.0 -
Alex Cannon Men’s Reversible Herringbone/Solid 1/4 Zip Mock Neck Sweater$130.0$37.0 -
James Tattersall Men’s Covent Gingham Shirt$110.0$169.0 -
James Tattersall Men’s Covent Gingham Shirt$110.0$53.0 -
James Tattersall Men’s Covent Gingham Shirt$110.0$154.0 -
Haspel Men’s Jones Colorblocked Sweater$495.0$50.0 -
Haspel Men’s Constance Long Sleeve Shirt$195.0$50.0 -
Haspel Men’s Nicholson Sweater$495.0$145.0 -
Alex Cannon Men’s Shawl Collar Sweater with Cable Stitch$165.0$46.0 -
Alex Cannon Men’s Full Zip Ribbed Cardigan With Faux Suede Shoulder Accents$165.0$26.0 -
Armani Collezioni Men’s V-Neck Sweater$395.0$24.0 -
Thaddeus Men’s Vestry Long Sleeve Ribbed V-Neck Sweater$150.0$55.0 -
Alex Cannon Men’s Long Sleeve Interlock 1/4 Zip Mock Neck Knit$90.0$26.0 -
Alex Cannon Men’s Long Sleeve Interlock 1/4 Zip Mock Neck Knit$90.0$29.0 -
Alex Cannon Men’s Jacquard Fair Isle Crew Neck Sweater$125.0$69.0 -
Thaddeus Men’s Vernon Long Sleeve Interlock V-Neck$95.0$34.0 -
Thaddeus Men’s Vernon Long Sleeve Interlock V-Neck$95.0$33.0 -
Victorinox Men’s Sleaford Crew Neck Sweater$165.0$31.0 -
Alex Cannon Men’s Textured Horizontal Diamond V-Neck Sweater$125.0$51.0 -
Victorinox Men’s Long Sleeve Villamont Sportshirt$165.0$45.0 -
Thaddeus Men’s Marty Long Sleeve Thermal Mixed Media Crew Neck$110.0$39.0 -
J. McLaughlin Men’s Milton V-Neck Sweater$325.0$37.0 -
James Tattersall Men’s Woven Long Sleeve Shirt$125.0$36.0 -
Thaddeus Men’s Marty Long Sleeve Thermal Mixed Media Crew Neck$110.0$35.0 -
Alex Cannon Men’s Reversible Herringbone/Solid 1/4 Zip Mock Neck Sweater$130.0$31.0 -
J. McLaughlin Men’s Solid Jake Slim Fit Pant$225.0$30.0 -
Scott Barber Men’s Long Sleeve T-Shirt$90.0$239.0 -
Alex Cannon Men’s Long Sleeve Interlock 1/4 Zip Mock Neck Knit$90.0$169.0 -
Thaddeus Men’s Ringo Long Sleeve Stretch Slub Crew Neck$85.0$126.0 -
Brunello Cucinelli Men’s Slim Fit Striped Sport Shirt$545.0$79.0 -
Brunello Cucinelli Men’s Striped Sportshirt$560.0$63.0 -
Thaddeus Men’s Eli Knit Blazer$395.0$29.0 -
Scott Barber Men’s Roll Neck Striped Sweater$200.0$25.0 -
Thaddeus Men’s Rick Sleeveless Reversible Zip Vest$185.0$24.0 -
Thaddeus Men’s Vernon Long Sleeve Interlock V-Neck$95.0$ -
Alex Cannon Men’s Reversible Crew Neck Sweater$125.0$ -
Alex Cannon Men’s Long Sleeve Interlock 1/4 Zip Mock Neck Knit$90.0$
