Consider it's a fantastic autumn day, and you're preparing for a casual outing with friends. You aim for that effortless, preppy, polished yet cozy and comfortable look. The preppy aesthetic you're going for calls for a classic, timeless vibe that feels both chic and relaxed. You know precisely what you want: a cute, classic sweatshirt that will pair perfectly with a collared shirt, a pleated skirt, and some loafers. You can picture the look in your mind, but when you open your closet, it's filled with boring sweatshirts that aren't quite what you had in mind.

Does this sound familiar? If so, you’ve come to the right place. Preppy sweatshirts are a wardrobe essential for nailing that classic, preppy look, and this guide will help you find the perfect one for your style to achieve your desired aesthetic. I'll also show you how to style it for any occasion so you can take your time to reach that polished aesthetic.

One way to find the perfect preppy sweatshirt to match your style is by using WhatColors's AI personal color analysis app. This valuable tool will help you narrow down the color palette that complements your unique features so you can pick the perfect sweatshirt for your preppy look.

Table Of Contents

• What Are Preppy Sweatshirts?

• Origins and Characteristics of Preppy Sweatshirts

• What's with the Enduring Appeal of Preppy Sweatshirts?

• 5 Most Popular Designs for Preppy Sweatshirts

• How to Style Your Sweatshirt for a Preppy Look

• 11 Preppy Essentials to Pair With Your Sweatshirts

• 13 Best Preppy Sweatshirt Brands for 2024

• Try AI Personal Color Analysis For Free Today

What Are Preppy Sweatshirts?

Preppy sweatshirts are classic pullovers that reflect the preppy aesthetic. The sweatshirts are comfortable, practical, and stylish, with a nod to an academic lifestyle.  Preppy sweatshirts come in various colors and styles, from traditional crewnecks to half-zip pullovers. They often include fun graphics or patterns and can be layered with almost anything for a casual yet sophisticated look.  

The Evolution of Preppy Sweatshirts  

Preppy sweatshirts have their roots in the American sports culture of the mid-20th century, when college athletics became popular, and images of athletes and their gear were found in magazines and television sets. As pictures of collegiate sports became more accessible, the general public began to emulate college students' style, and sweatshirts were at the top. 

They became a staple in men's and women's wardrobes and were mainly associated with academic life. They were even adopted as official university merchandise. Preppy sweatshirts are still popular, reflecting a vintage style that evokes nostalgia for college life.

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Origins and Characteristics of Preppy Sweatshirts

The Backstory of Preppy Sweatshirts: Classic Style from the Ivy League 

The preppy style has its roots in the early 20th century, drawing from the attire of students attending prestigious private schools and universities. These students were often from affluent backgrounds, and their clothing reflected a lifestyle of leisure, sophistication, and a subtle nod to tradition. Preppy sweatshirts emerged as comfortable and versatile garments that could be worn both casually and in slightly more formal settings, embodying the preppy ethos of blending practicality with style. 

Preppy Sweatshirt Construction: Quality Features and Fabric Choices

A typical preppy sweatshirt is usually made from cotton or cotton blends, ensuring comfort and durability. It often features a crew neck or a quarter-zip design, adding a formality compared to standard hoodies. Colors are generally muted, with a preference for navy, white, pastel shades, and earth tones, although bolder colors and patterns can also be found. Logos or emblems, often representing the brand or an imagined collegiate institution, are typical embellishments that add exclusivity and tradition. 

Style Elements that Define Preppy Sweatshirts

The essential characteristic that makes a sweatshirt ‘preppy’ is its simplicity. Plain styles hark back to the original style iterations from the 1950s and onwards. They are more often than not constructed from soft cotton jerseys and feature a ribbed neck ringer, collar, and hem. 

Additional preppy details such as collar stripes, varsity logos, and vintage badges add to the vibe. Avoid on-trend logo and slogan treatments – the preppy sweatshirt most definitely has a retro heritage appeal rather than an edgy contemporary look. Plenty of brands are faithfully redefining preppy aesthetics for a modern audience, not least streetwear labels such as Aimé Leon Dore and Noah NYC. 

Styling Preppy Sweatshirts: Effortless Versatility

The preppy sweatshirt is timeless, so it’s easy to style within various menswear genres. For example, keep the vibe sporty with sweatpants and minimalist sneakers; layer it over a white tee and jeans, like Steve McQueen, or go full-on Ivy League with chinos, loafers, and a Harrington jacket. The preppy sweatshirt is also perfect at home as part of your loungewear looks.

What's with the Enduring Appeal of Preppy Sweatshirts?

The Timeless Appeal of Preppy Sweatshirts

Preppy sweatshirts have gained widespread popularity for many reasons. First and foremost, they are associated with a classic style. The preppy aesthetic offers a reliable alternative in an era of fleeting fashion trends. This style suggests a sense of heritage and stability, appealing to those who prefer understated elegance over transient fashion statements. 

Preppy Sweatshirts Are Versatile Wardrobe Workhorses 

Preppy sweatshirts' versatility makes them a valuable addition to any wardrobe. They can easily be dressed up or down, paired with jeans for a casual outing, or layered under a blazer for a more polished look. This adaptability aligns well with modern lifestyle demands, where individuals often seek clothing that can transition smoothly between different social contexts. 

What's Behind the Preppy Sweatshirt Resurgence? 

The resurgence of preppy sweatshirts can be attributed to several cultural and fashion trends. One significant factor is the broader revival of preppy style in general. As fashion cycles through various eras and styles, the preppy look has made a strong comeback, influenced by nostalgia and a renewed appreciation for vintage aesthetics. The focus on sustainability and quality in fashion has also played a role as consumers increasingly seek durable, well-made pieces that transcend seasonal trends. 

Celebrity Influence and Social Media Spark Preppy Sweatshirt Popularity

Social media and celebrity influence have further fueled the popularity of preppy sweatshirts. Celebrities and influencers often showcase these garments in casual, everyday looks, making them aspirational pieces for their followers. The trend has been powerful among younger generations, who appreciate the blend of comfort, style, and a certain retro charm that preppy sweatshirts offer. 

Comfortable Clothing Is the New Normal

Additionally, the shift towards casual and comfortable clothing has made items like sweatshirts a central component of everyday wear. With their blend of comfort and style, preppy sweatshirts are ideally suited to this new fashion landscape.

5 Most Popular Designs for Preppy Sweatshirts

1. All About Preppy Sweatshirts: Graphic Prints

Nothing says "preppy aesthetic" like a sporty sweatshirt. Within the category of preppy sweatshirts, styles with graphic prints are exceptionally trendy.  Regarding the preppy look, vintage, retro, and collegiate designs are stylish. You’ll also see plenty of motivational and inspirational quotes. 

2. Solid Colors: The Classics and Their Pastel Counterparts

Like any classic style, solid colors are essential to the preppy aesthetic. So, of course, sweatshirts in classic colors like navy, white, and greens are popular picks for a preppy look. And don’t forget about their pastel counterparts. Light blue, mint green, and soft pink hues complement the preppy aesthetic. 

3. Embroidered Details Add Sophistication

Another common design element of preppy sweatshirts is embroidered details. For example, contrasting embroidered logos or designs on the chest of a solid-color sweatshirt add a touch of sophistication that aligns with the preppy style. Subtle logos or monograms are also famous for achieving the sophisticated look of preppy sweatshirts. 

4. Oversized Fits for a Relaxed Vibe

Regarding preppy sweatshirts, oversized fits are trendy for achieving a casual, laid-back vibe. These boxy silhouettes are perfect for layering over collared shirts or pairing with shorts, joggers, or skinny jeans for a stylish preppy outfit. 

5. Hooded Styles for Warmth and Comfort

Hooded sweatshirts are also famous for achieving a preppy look. These styles provide warmth and comfort while maintaining a sporty, classic aesthetic. Look for features like drawstrings, pockets, and graphic prints to enhance the preppy appeal.

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How to Style Your Sweatshirt for a Preppy Look

Choosing the Right Preppy Sweatshirt

To nail the preppy look with sweatshirts, pick the right one. Aim for a high-quality cotton or cotton-blend sweatshirt for a polished appearance. Next, look for a tailored, fitted silhouette. Avoid oversized sweatshirts for a more put-together look. Color choices are also essential. Stick to classic preppy colors like navy, burgundy, forest green, heather gray, or crisp white. Finally, pay attention to details. Subtle preppy elements like contrast collars or cuffs or small embroidered icons (e.g., anchors, tennis rackets, or school crests) add to the aesthetic. 

Layering Techniques to Create Dimension and Visual Interest

Sweatshirts are a great layering piece. Use them to build visual interest in your outfit. Start by layering a collared shirt underneath your sweatshirt. Button-downs in classic patterns like stripes or gingham work particularly well. Experiment with different collar styles, too. Spread, point, or button-down collars all achieve a slightly different look. Roll up the sweatshirt sleeves slightly to show shirt cuffs for added flair. You can also layer turtlenecks or mocknecks underneath sweatshirts for a sophisticated twist. 

Pairing Preppy Sweatshirts with Bottoms

Next, it’s time to choose a bottom to pair with your preppy sweatshirt. Chinos are a classic preppy bottom that works well with sweatshirts. Look for well-fitted chinos in khaki, navy, or pastel shades. You can also opt for tailored Bermuda or chino shorts if it’s warm outside. A-line or pleated skirts in solid colors or plaid patterns work well for a more feminine look. Finally, dark wash, straight-leg jeans can also fit the preppy aesthetic. 

Completing Your Preppy Sweatshirt Look with Accessories

Every outfit is complete with accessories. For preppy outfits, look for items that add to the classic collegiate vibe. Start with belts. Woven fabric or leather belts with nautical or equestrian-themed buckles add to the look. Footwear is also crucial. Opt for penny loafers, driving moccasins, or classic white tennis shoes to complete your outfit. Jewelry should be kept simple. Think pearl stud earrings, charm bracelets, or signet rings. Finally, choose your bag wisely. Go for a canvas tote, leather satchel, or structured handbag. 

Choosing the Right Outerwear for Your Preppy Sweatshirt Outfit

Pick something that fits the preppy style if the weather calls for outerwear. Blazers are a classic choice. A navy blue or tweed blazer will instantly elevate your sweatshirt look. Cardigans also work well. Opt for a cable-knit or fine-gauge cardigan in a complementary color. Finally, light jackets like quilted vests, denim jackets, or lightweight windbreakers can also fit the preppy aesthetic. 

Nail Your Hair and Makeup

Style your hair and choose your makeup wisely to complete your preppy look. For hair, aim for a polished appearance. Long hair can be styled in a sleek low bun, braided headband, or soft curls. Medium hair can be left in beachy waves or a half-up, half-down style with a barrette. Short hair looks cute and neat, and it is combed with a side part. 

To add volume and texture. Accessorize with headbands, hair clips, or silk scarves for added preppy flair. For makeup, focus on a fresh, dewy complexion with minimal foundation. Use soft, neutral eyeshadows and subtle eyeliner for the eyes. Lips can be tinted lip balm or classic pink or red lipstick. Finally, nails should be well-manicured with clear polish or pale pink. 

Seasonal Adaptations for Preppy Sweatshirt Outfits

Like any other outfit, preppy sweatshirt looks can be adapted for different seasons. In the spring and summer, lighten your look with lighter fabrics, pastel colors, and shorter sleeves. Come fall and winter, layer with turtlenecks, add scarves, and choose richer, darker colors. 

Get Your Color Analysis Done With WhatColors’ AI 

WhatColors helps you find what colors to wear based on your skin tone. Finally, get your season based on our skin tone, thanks to our patented color match technology. Get the perfect colors based on your season. Avoid colors that are a definite no. Based on your skin, eye, and hair color, find the ideal nail color with our WhatColors Nail Color Generator. 

Get your color analysis done within 60 seconds with WhatColors’ AI Personal Color Analysis app. Download our app for free today on the App Store or Google Play store.

11 Preppy Essentials to Pair With Your Sweatshirts

1. Button-Down Shirts: The Preppy Sweatshirt's Best Friend

A crisp button-down shirt is an essential piece for a preppy look. Oxford cloth button-downs (OCBDs) are a preppy staple. White, light blue and pink colors are classic and versatile options that pair well with sweaters. The fit should be comfortably fitted, not too tight or baggy. The button-down collar keeps it neat under the sweatshirt, while the cuffs peek out when you roll up the sleeves for an effortlessly polished look. 

2. Chino Pants: The Quintessential Preppy Bottoms

Regarding preppy bottoms, you can’t go wrong with chinos. Chinos are made of durable cotton twill fabric that holds up well over time and is breathable for warm weather. Khaki is the quintessential color, but navy and pastels expand your options. Aim for a tailored look—not too tight, with a slight taper. The length should lightly touch the top of your shoes, and you can pair them with a belt for a polished look. Lighter weights are great for summer, while heavier ones work well in the winter. A small, neat cuff can add a preppy touch.

3. Skirts: The Preppy Classic

While you can pair preppy sweatshirts with any type of skirt, pleated styles have a distinctively preppy vibe. Choose a classic plaid or solid-colored version if you want to nail the look. The best part about skirts is that they can be worn year-round. Style your skirt with a lightweight sweatshirt and no tights in the warmer months. As temperatures cool, transition to a thicker knit and add a pair of socks for extra warmth and coverage.

4. Classic Accessories: Elevate Your Look

Classic accessories are the cherry on top of any preppy outfit. Look for timeless pieces that won’t go out of style, like pearls, leather belts, and structured handbags. These accessories will elevate your look and add to the sophisticated vibe of the preppy aesthetic. 

Loafers: The Preppy Go-To Shoe

When styling your preppy sweatshirt outfit, you can’t go wrong with a classic pair of loafers. Penny loafers are a classic, but tassel or horse-bit styles work, too. They come in leather or suede, with the former being more formal and the latter great for casual looks. Brown is the most versatile color, but black is great for dressier occasions. Aim for a fit that’s snug but not tight, with minimal heel slippage. Loafers can be worn with or without socks and look great with pants and shorts. 

Blazers: A Preppy Layering Stap

For cooler temps, a tailored blazer makes a great addition to any sweatshirt outfit. Navy blue blazers are a timeless choice that pairs well with nearly any color. Look for one with brass buttons for a classic touch. The fit should be tailored but allow movement, and you can find them in various fabrics. Wool blazers are great for year-round wear, while tweed is perfect for fall and winter. For spring and summer, seersucker is a breathable option—layer one over your sweatshirt for a bright casual look that’s appropriate for various occasions. Blazers with patch pockets add a casual touch, and a two-button style is the most common and versatile.

Polo Shirts: The Preppy Undershirt

Polo shirts are another classic preppy piece that can be worn under sweatshirts. Traditional pique cotton is breathable and helps keep you cool on warm days. Look for a fit that’s slightly fitted but not baggy. The collar should be crisp and lay flat. Brands like Ralph Lauren and Lacoste are preppy classics, and the best options are solid colors in pastels or navy. Subtle stripes add variety without being too flashy. The sleeves should hit mid-bicep and can be styled to peek out from under your sweatshirt. 

Classic Watches: Timeless and Functional

A classic watch is another preppy essential that adds sophistication to any outfit. Look for a simple design with a clean face and minimal features. The strap can be leather for formal looks or a metal link for versatile wear. Avoid oversized styles that won’t fit under your shirt cuffs. Silver and gold add a nice touch; you can’t go wrong with brown or black leather. Brands like Timex make budget-friendly options, while Hamilton and Omega create luxury timepieces. 

Tailored Shorts: The Preppy Summer Stap

Shorts are a must for summer; tailored styles will keep your look preppy and polished. Look for a pair with a length just above the knee (7-9 inch inseam) and a fit that’s fitted through the seat and thigh but not baggy. Cotton twill, like chinos, is ideal, and you can’t go wrong with classic colors like khaki and navy. Pastels like light blue or pink are also perfect for warm weather. Style your shorts with a tucked-in polo or a loose sweatshirt for a preppy look. They’re great for casual summer events or family gatherings. 

Structured Handbags: The Finishing Touch

Structured handbags add a preppy touch to any outfit. Look for high-quality materials like leather or canvas in neutral colors for versatility. A tote style is great for casual looks, while a pouch can elevate a more formal outfit. Aim for a size large enough for daily essentials, and choose one with an internal organization to keep your items tidy.

13 Best Preppy Sweatshirt Brands for 2024

1. Aimé Leon Dore: Leading the Charge for Modern Preppiness 

Aimé Leon Dore, founded by Teddy Santis, is making waves in the menswear community and in many ways, leads the charge for modern preppiness. All of their sweatshirts, which come in classic collegiate colors, have a subtle logo treatment, often with a retro feel, and are constructed from a beautifully soft and dense 20oz French terry jersey fabric. 

2. Noah: Classic Crew Necks with a Retro Appeal 

There’s no arguing that Noah’s classic crew necks are classic. Available in a wide assortment of colors and with subtle embroidered logo detailing to the chest, the New York-based brand’s sweatshirts are constructed from 12oz brushed-back fleece, so they have a soft nap that feels great. Understated with a minimalist retro appeal, it’s how all tremendous preppy sweatshirts should be. 

3. Adsum NYC: Stylish Staples Inspired by the Northeastern USA 

Founded in Brooklyn in 2015, Adsum NYC has developed a cult following for its high-quality staples inspired by the cities and countryside of the American Northeast. With a clean, minimalist aesthetic and utilizing seasonal tones, Adsum has created a line of sweatshirts inspired by rugby shirt patterns, which are a must for preppy aficionados. Most of its wares are made in Canada, too, so you can be assured of fabric and build quality. 

4. AMI Paris: More Than Just Preppy Aesthetic 

While not strictly a preppy brand, Alexandre Mattuissi has created a fine line of comfortable sweatshirts perfect for sliding into a preppy-leaning wardrobe. With the subtle but instantly recognizable heart logo in various formats, AMI’s sweatshirts have a fresh minimalism and are available in pretty outrageous colors, too.  

5. GANT: An Icon of American Preppiness 

Another icon of American preppiness, GANT has stood the test of time thanks to its unwavering dedication to traditional preppy silhouettes. From classic crew necks in myriad tones to zip-throughs, half-zip sweaters, and retro-styled versions with the archive shield logo, you’ll find plenty to indulge your modern Americana tastes.  

6. Ralph Lauren: The Grandfather of Preppy Style 

Ralph Lauren, the grandfather of modern preppiness, has built an entire empire out of collegiate excellence, channeling all classic motifs via his Polo brand. Naturally, the sweatshirt plays a crucial feature in the perennial Polo collections, and you’ll find hundreds of colors to integrate into your sporty preppy fits, from those with the inimitable polo player logo to many derivations of the Polo bear.  

7. Rowing Blazers: The Kings of Modern Retro 

Rowing Blazers are, without a doubt, the kings of modern retro. They use their passion for preppy nostalgia to create a fun, stylish brand from the ground up. Their sweatshirts are hilarious, in the best way, with fun vintage logos, graphics, and slogans. Never one to take itself too seriously, Rowing Blazers is perfect for those looking for a more tongue-in-cheek take on traditional Ivy League style.  

8. Drake’s: Elevated Casualwear with a Preppy Touch 

Formerly of Clifford Street, London, and now pride of place on Savile Row, Drake’s is widely loved and well-recognised for its excellent tailoring and modern preppy casualwear. Its team combines the best of both worlds in a uniquely relaxed way so that the tailoring feels casual and the casualwear feels elevated. You can always count on exquisite fabrics and build quality at Drake’s, and its sweatshirts are a testament to this well-earned reputation made from densely woven loopback jerseys.  

9. J. Crew: A Classic Americana Brand 

What you’ll immediately notice about J.Crew’s sweatshirts is that they feel substantial. That’s because the flag-bearer of modern Americana uses a dense 14oz cotton fleece brushed to create a super-soft internal nap. Available in an array of colors, it’s excellent value at just over $100/£100. Also, check out its Wallace & Barnes line of sweats, modeled after vintage athletic gear and knit in a hefty, soft, brushed-cotton blend.  

10. Oliver Spencer: Eco-Friendly Preppy Sweatshirts 

Oliver Spencer has always cleverly spun preppy silhouettes and motifs into his casually tailored collections, which also lean on traditional workwear silhouettes. Recently, his loungewear and jersey creations have been right on the money, using some unique waffle knit and terry cloth fabrics to significant effect. The British designer is a big advocate of using organic cotton, too, so you’ll find plenty of eco-conscious crew-neck sweatshirts that come without the consumer guilt.  

11. Sunspel: Minimalist Luxury 

James Bond’s favorite label, British icon Sunspel, is masterful at creating modern minimalist menswear. Probably most recognized for its luxury T-shirts and polos, the heritage brand also produces some stunning sweatshirts, namely the classic loopback style with the v-stitch insert, which comes in various colorways. Also, check out the Paul Weller collaboration, which includes loopback sweatshirts inspired by vintage American college varsity tops. 
 

12. Fear of God Essentials: An Elevated Streetwear Aesthetic 

Founded by Jerry Lorenzo in 2013, Los Angeles-based Fear of God made an instant splash on the luxury streetwear scene thanks to a clean, minimalist aesthetic and tight, muted color palette. Its Essentials line is similar to the collection’s signature fleece crew neck. Featuring a tonal velvet flocking logo, its minimalist design and retro athletic feel make it ideal for layering with preppy polos, Oxford button-downs, and chinos.  

13. Thom Browne: Avant-Garde Style with Classic Appeal 

When the avant-garde American designer isn’t creating fantastical runway performances with his seasonal collections, he’s settling down to make some pretty iconic sweats – the instantly recognizable four stripes on the left arm marking out a Browne sweatshirt from a mile away. Crafted beautifully in loopback cotton in Japan and available in various clean colorways, it will easily slide into an elevated preppy look with chinos or joggers.

Try AI Personal Color Analysis For Free Today

WhatColors helps you find what colors to wear based on your skin tone. Finally, get your season based on our skin tone, thanks to our patented color match technology. Get the perfect colors based on your season. Avoid colors that are a definite no. Based on your skin, eye, and hair color, find the ideal nail color with our WhatColors Nail Color Generator. 

Get your color analysis done within 60 seconds with WhatColors’ AI Personal Color Analysis app. Download our app for free today on the App Store or Google Play store.

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