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This post is a guide to putting together the perfect preppy outfits that incorporate both classic and modern trends and will hopefully inspire you to create looks that are fun and chic.
What is preppy style?
The easiest way to define or envision the preppy style fashion trend or aesthetic is to picture what a student might wear to a posh university (think of Oxford or an Ivy League like Yale) or even a fancy private school (think along the lines of what the cast of the original Gossip Girl wore on the show).
It is the type of style that incorporates a lot of pieces you would typically associate with academia (think blazers, pleated skirts, cardigans… That kind of thing!) but preppy fashion is not just about embracing the academic aesthetic side of the style. Think about it, since the preppy aesthetic is based off of the old school students that attended posh schools or colleges, it takes elements of that lifestyle as well. For example, you might picture one of those students doing activities, such as polo or golf or tennis, and so a lot of the outfits you put together with the preppy aesthetic in mind would have pieces such as those involved in these activities (for example; riding boots, tennis skirts, sneakers…)
What to Wear to Look Preppy?
Like I mentioned above preppy fashion incorporates lots of elements and pieces that are academic, sporty and old-money. If you want to experiment with the style you’re going to need a lot of good sweaters, pleated skirts, chunky boots, loafers, that sort of thing… It’s an interesting aesthetic but one you can have a lot of fun with!
The Ultimate Guide to Preppy Style (20 Chic and ‘Classy’ Preppy Outfits)
1. pleated skirt, sweater + boots outfit
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A pleated mini skirt is a staple for preppy style, it obviously has that school/academic vibe that makes it the perfect clothing piece to incorporate into a preppy outfit. A pleated mini skirt is the kind of thing you can wear with anything, but it looks especially good paired with oversized sweaters, like the oversized sweater vest in this particular outfit.
2. Oversized Blazer + Knee High Boots Outfit
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Blazers are another big stable of preppy fashion. They’re obviously super reminiscent of like the old academia style. It’s super cool that blazers are now being embraced by more women and it seems like each has put they’re own chic and modern twist to the piece. An oversized blazer cinched with a belt is just *chef’s kiss*, ugh it’s so so good, especially paired with a pair of sheer tights and some knee high boots.
3. Turtleneck sweater + Pleated Plaid Skirt
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When you pair a turtleneck sweater with a pleated plaid skirt you get the kind of preppy aesthetic outfit that you can anywhere. It’s cute, it’s casual and it’s chic.
4. oversized sweater over jeans outfit + Loafers
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Loafers like the ones in this outfit give off that private school aesthetic, if that even makes sense. Tied in with an oversized white collared shirt layered under an oversized sweater, they make for a pretty stylish preppy fit.
{RELATED POST: 29 Dark Academia Fashion Ideas and Trends}
5. sweater, shorts + red boots outfit
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Cricket sweaters (is that what you call them? You know the sweaters with the stripes around the collar and bottom?) have something about them. As soon as you put one on, it’s like you’re suddenly this fun, playful, sophisticated person! They’re so chic! And you can style them up like you would any other sweater, like in this outfit, with a pair of shorts and a lovely pair of red boots.
6. Cardigan and Plaid Pants Outfit
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This outfit is like the perfect casual preppy aesthetic outfit. Honestly plaid pants deserve more love, they’re super stylish if you actually give them a chance and they look good especially when paired with chunky boots like doc martens.
7. Pleated Skirt + Lettered Sweatshirt Outfit
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This is like the fun and playful version of a preppy outfit. This lettered sweatshirt and pleated skirt outfit with sneakers has all the element that we’ve come to know and love about the preppy aesthetic. It’s an outfit that’s not taking itself too seriously, easy to put together and so cute and fun.
8. Polo Shirt and Belted Shorts Outfit
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A polo shirt tucked into a pair of belted shorts together with loafers is such gorgeous combination of pieces that would otherwise be so simple alone.
9. All Black Cropped Sweater and Pants Outfit
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This is preppy but on an elevated level and with a modern twist. I mean a cropped blazer paired with some loose trousers is the definition of chic and modern especially when paired with shoes like the converse sneakers.
10. collared shirt under sweater with plaid skirt and red boots outfit
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Beige goes so well with preppy or academic aesthetics. There is something about the neutral color that just blends so well with this type of aesthetic. There is something to be said about an outfit made up of a beige sweater and plaid mini skirt of the same color. All beige outfits are just so chic.
11. oversized shirt and sweater with shorts and boots
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I think we’ve firmly established that oversized sweaters and sheer tights are kind of a staple for preppy style but we’ve also come to appreciate the fact that there is something so stylish about layering an an oversized shirt under a large sweater with the collar and sleeves peaking through, it’s a combo that’s *chefs kiss* so good.
12. turtleneck sweater, mini skirt + boots outfit
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This outfit, the tight long-sleeved turtleneck top with the mini-skirt and the boots, is the perfect example of how you can do preppy without having to do too much.
{RELATED POST: 25 Stylish Sweater Outfit Ideas}
13. Oversized Shirt Under Sweater + Boots Outfit
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This is another example of the style that is clearly loved by so many people, with the white shirt that peeks over the sweater, but this is another way to style it, with some tight fitting trousers and a pair of knee high boots. It’s casual, it’s stylish and it’s preppy vibes.
14. Striped Sweater + Pleated Skirt Outfit
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Pleated skirts are that versatile piece of clothing that you can never seem to get tired of and can be styled a million different ways. When styled with chunky loafers and socks it definitely adds to the private-school girly preppy aesthetic.
15. White Shirt, Plaid Mini Skirt + Socks and Heels Outfit
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Honestly socks and heels is a combination I never thought would ever work together. But I guess it’s a combo that just needed the right moment to come along. You just have to fun with these trends honestly and this outfit is giving grown up school girl but in the best way possible!
{RELATED POST: 25 Effortlessly Chic Blazer Outfit Ideas for Women}
16. Leather Jacket, Pleated Denim Skirt + Boots Outfit
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Another way to wear a pleated skirt but this time it’s denim, which is a whole deferent vibe, especially when paired with a leather jacket and black knee boots.
17. Vest Top, Black Skirt and Boots Outfit
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This little beige vest, black skirt and boots is an outfit that is so easy to put together but somehow is able to encapsulate the style so well. Just proof that you can take part in a fashion trend or emulate a certain style with only a few good pieces.
18. blazer with bodycon maxi dress + sneakers
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These days you can throw a blazer over almost anything to elevate an outfit, but it does seem to especially work with a bodycon maxi dress and sneakers. It’s combining two things that shouldn’t work but somehow do.
{RELATED POST: 21 Stylish Ways to Slay in Knee High Boots}
19. Cap, Blazer + Pants Outfit
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This outfit is probably the epitome of preppy style because it combines some of the elements we’ve come to love about the style, a blazer, some loose pants but it does so in a way that’s fun and not at all stuffy.
20. Oversized Sweater Vest and Boots Outfit
Loose baggy sweater vest paired with sheer tights and some boots is honestly a match made in heaven, it an outfit that’s the right amount of preppy but free-spirited!
21. V-Neck Sweater and Pleated Skirt
Classy preppy style look with the V-neck sweater vest, the oversized shirt layered under and the little pleated skirt!
