1. Mary Jane Heels
Regular pumps are great, but Mary Jane heels will give you a preppy, girly vibe that’s necessary when recreating this style aesthetic. As an added bonus, I find them to be much more comfortable than regular heels, since they fit around your ankle so well.
Love height but have tender feet? Go ahead and buy a wedge mary-jane – it’s better to be comfortable and do something unique than stick with a trend that makes your feet ache.
For a polished and sweet ensemble inspired by Miss Pillsbury, try a brightly colored (8) sheath dress with a (13) patterned cardigan. Finish with a matching pair of Mary Jane heels, a (7) pearl necklace, and a structured purse.
Mary Jane heels will also look great with a pair of skinny jeans and a fun party top. Curl your hair with a large-barrel curling iron, and finish with shimmery make-up and a fancy (5) headband.
2. Pearl Jewelry
An absolute staple of any preppy and sophisticated wardrobe is a classic set of pearl jewelry. Real pearls are expensive, but awesome look-alikes can be found almost everywhere. Look for pieces that have a substantial weight to them and aren’t too iridescent in color.
Pearl stud earrings make any outfit — even scrubby jeans and a t-shirt — look polished and intentional.
A pearl brooch pinned to the lapel of a blazer or used to hold a scarf in place will look unexpected and – dare I say – editorial.
A long string of pearls around your neck will look fantastic with any LBD or sheath dress. Very Holly Golightly.
3. Sheath Dresses
A perfect Jackie O-inspired sheath dress will carry your through interviews, nice lunches and dinners, business casual functions, hot dates, and so much more. The key to keeping this piece from looking boring or stuffy is to freshen it up with well-placed accessories.
Sheath dresses are ideal for formal occasions because they’re thick and structured. Pair one with (#6) Mary Jane heels, a (9) long necklace, and an easy updo for a great date night look.
Don’t be afraid of patterned sheath dresses! You can always tone it down with a (3) blazer or a solid-colored (13) cardigan. They will also look mod and fabulous with (2) opaque colored tights!
Look for styles that hit right at or slightly above your knees. They’ll be conservative enough for proper functions, but short enough to play!
4. Statement Necklaces
I’m always amazed at how much a little jewelry can do for an outfit. A statement necklace is perfect for breathing life and glamour into basic tops.
Those J.Crew-inspired bubble necklaces are hotter than ever, and with good reason! Wear one with a (4) thin sweater, a chambray shirt, a (8) sheath dress, an open (3) blazer…the options are endless.
I’ve always loved the look of wearing a long necklace with an infinity scarf or a triangle-shaped patterned scarf. Make sure that they’re two distinctive lengths so that you can see both the necklace and the scarf.
Nautical-inspired chain necklaces are perfectly preppy, and will look great with a (3) blazer, a striped shirt, khaki chinos, and (11) ballet flats.
5. Fantastic Skirts
Whether you prefer A-line, skater, or pencil-style skirts, these babies are essential for crafting a sophisticated Blair Waldorf-inspired wardrobe. Get a mix of solid and patterned styles for maximum versatility.
Pair a skirt with a matching cami and (13) cardigan combo and a pair of ballet flats for an outfit that’s perfect for school.
Blair Waldorf rarely wore a skirt without a pair of (2) opaque tights. To remix this look, wear with a pair of ankle boots and a military jacket.
Never underestimate the proper, feminine look of a (1) girly button-down blouse tucked into a skirt. Finish with knee-high socks, a (5) headband, and (6) Mary Jane heels.
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