When we think of classic preppy style, we may imagine a private school pupil or Ivy League student in the 1960s striding around campus in classy preppy outfits featuring a cable knit vest or khaki slacks. Argyle print, tweed blazers, loafers and all things plaid have been preppy style essentials since the mid-20th century, and the popularity of preppy fashion has only grown with the passage of time.
Preppy style got a trendy boost in the 1990s when characters from teen movies such as Clueless and Cruel Intentions rocked pleated skirts with matching jackets, modest cardigans and polo shirts, giving preppy clothes a contemporary spin. In the late 2000s, feminine preppy style made another comeback in the TV series Gossip Girl. While preppy old money outfits or fashion from the Gossip Girl era might look dated today, preppy style is undoubtedly still going strong as a fashion trend and evolving with the times. Although preppy aesthetics is more commonly associated with fall outfits because of the collegiate image, preppy fashion works just as well for summer and winter outfits.
The key to a polished preppy outfit is wearing clean, crisp and luxe-looking clothes in understated but well-coordinated colors. Whether your style inspiration is Jackie O or Blair Waldorf, a sophisticated and feminine silhouette is a sure way to nail a preppy look. It’s easily achievable with preppy clothing staples like vests, plaid mini skirts, loafers or a good old button-down shirt. Classic elements such as argyle prints, headbands and pearls are also essential to curating cute preppy outfits for your everyday wardrobe.
The knit vest is an evergreen classic that can’t go wrong for dressing preppy. A chunky grandpa vest paired with a button-up shirt, plaid skirt and ballet flats creates a great semi-formal outfit that is versatile enough to be styled in a myriad of ways. To give a modern twist to an otherwise classic preppy look, choose a shirt with exaggerated puff sleeves or add bold accessories, such as an oversized pearl-encrusted headband or a signet ring. If you’re into girly preppy outfits, consider combining a figure-hugging statement cropped sweater vest with a high-waist pleated mini skirt, crew socks and a pair of loafers.
Another foolproof way to master preppy style is incorporating pieces with argyle print into your casual outfits. Often seen on private school uniforms, this print is a preppy fashion staple and a must-have for building an elegant wardrobe. Choose an argyle vest or sweater to instantly give your attire an academia vibe even when paired with simple dark wash jeans and heeled knee-high boots. Add a timeless navy blue blazer and a sleek leather belt to top off the smart look.
A-line skirts and dresses form the base of women’s classic preppy attire. Chic dresses and skirts are must-have items for preppy girls, as they accentuate the figure to create a defined silhouette. Look for subtle details such as ruffles, pleats and tweed fabric to add structure and interest to a feminine preppy outfit. Choose thicker fabrics like knits and tweed for fall and winter fashion, and breathable lightweight fabrics like linen and cotton for summer and spring fashion.
Remember Blair Waldorf and her signature headbands in Gossip Girl? As are all things retro, headbands are making a comeback, and any preppy outfit would benefit from a pearl-encrusted or puff headband. Headbands are also a great way to craft effortlessly put-together looks without having to spend too much time on hair styling.
If you want to instantly give a preppy touch to your look, pearls are your best friend. A sensible and understated pearl necklace or a pair of elegant stud earrings adds timeless chic even to simple outfits composed of just a blazer, a plain top and khaki pants. To go one step bolder, accessorize with large pearls or modern designs. If you want to increase the level of preppiness, choose a matching set of pearl jewelry to channel your inner Jackie O.
Your wardrobe probably already has at least one essential element for a cute preppy look, such as a blazer, a pair of loafers or that headband from back when everyone was obsessing over Gossip Girl. For everything else, YesStyle offers a great selection of clothes and accessories that would complete your perfect preppy outfit.
