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9 Cute & Classic Boxy Jackets & How-to Wear Them

There’s something about a short and boxy jacket that will forever remind me of Chanel and Jackie O. The now-classic boxy tweed jacket, a prim and proper look, made famous by the aforementioned brunette beauties, is a great investment piece to keep in your wardrobe, as it always is stylish.

However when you think of boxy jackets, you also may immediately think “unflattering”. In reality, quite the opposite is true -as long as you know what to pair them with and how to style them correctly. For instance, wearing a longer shirt or top layered beneath creates perfect proportion, adding a vertical visual line and directs the eye up and down, then settling somewhere in the center. I’ve rounded up 9 cute and classic boxy jackets to shop as well as style tips on how to incorporate each into your wardrobe and everyday ensembles.

  • 9 Classic Boxy Jackets You CAN Wear! 1 of 10
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    Find 9 cute and classic boxy jackets to shop as well as style tips on how to incorporate each into your wardrobe and everyday ensembles.

  • CHANEL Inspired : Boxy Tweed Jacket 2 of 10
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    Admittedly a bit pricey, this is a great CHANEL inspired boxy tweed jacket, complete with a hint of edgy deconstruction, Lagerfeld's signature touch. The black and white tweed is always classic and the lines created in the front are elongating. But also notice the shoulders in this particular silhouette. With blunt edges and super straight sleeves, that hit a hint above the wrist, this jacket is flattering in more ways than one. Adding flared legs, and a darker, longer top beneath, as shown here, draws all the visual focus up and down and then center, making you appear narrower AND taller.

     

    Alice + Olivia Boxy Tweed Jacket $495 at Nordstrom

    Shop more Boxy Tweed Jackets here

  • The Original Jean Jacket 3 of 10
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    The most common boxy jacket is the original denim "jean jacket" and always tends to look better {aka more flattering} with either ridiculously long sleeves to give a an elongated illusion OR rolled up or pushed up sleeves to draw more focus to the waist. Either way, a classic denim jacket is a great staple to keep in your closet, it always comes back in style.  You can wear it with almost anything and pull it off.

     

    Denim Jacket $29.95 at H&M

    Shop more Denim Jackets here

  • A Little Swingy 4 of 10
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    With a slightly more cropped hem in the front than the back, this swingy boxy jacket draws attention to your waist and makes it appear smaller immediately. This short style lends itself well to dressing up or down, as it can go both ways.  And the light colored woven tweed is a nod to Chanel as well.

     

    Whitney Eve Boxy Jacket $57.17 at Asos

    Shop more Cropped Swing Jackets here

  • Boxy with an Edge 5 of 10
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    This is an edgier take on a boxy silhouette with a hint of tuxedo thrown in {notice the lapels}, making it suitable for more dressed up looks as well as edgy looks for evening. Since it's such a bold color, let it be the focal point of your outfit, though adding a print in a complementary color pattern would work as well.  Pairing it with skinny pants and a longer top draws attention upward toward your face, and creates a lean visual line.

     

    Glamorous A Blazer For Everything $73 at Shopbop

    Shop more Boxy Blazers here

  • Leather Trimmed 6 of 10
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    What's special about this boxy jacket, and what makes it flattering, is the bold leather trim around the neck and center. This attracts the eye to the center of your body as well as adds a linear vertical line giving the appearance of length, height, and narrowness.  Again, notice the longer top hanging about 3inches below the jacket, and how it creates proportion, forcing the eye to begin at the bottom and move its way up to your face.

     

    Joie Jacolyn Jacket $398 at Shopbop

    Shop more Leather Trim Tweed Jackets here

  • Boxed In Retro Fur 7 of 10
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    A boxy fur jacket reminds me of the early '80s like no other, yet it was also very stylish in the 1930's and '40s. While they're a bit bulky, they're ultimately fabulously classic when paired with ladylike looks. Notice the vertical "stripes" on this furry number and how it elongates the visual line.

     

    Faux Fur Jacket $59 at H&M

    Shop more Boxy Faux Furs here

  • The Classic Biker 8 of 10
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    The original classic biker jacket is a boxy shape similar to a denim jacket, but in leather, detailed with zippers, studs, quilting, etc. and often zips up either to the side or down the center of the front. There are so many different version of it now, it's easy to find one that's flattering. Edgier than the denim version, the biker jacket has become such a classic, it's virtually always in style and looks best with jeans, a t-shirt, and boots.

     

    Vintage Leather Biker Jacket $398 at Free People

    Shop more Biker Jackets here

  • From The Orient 9 of 10
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    I love the shape along with mixed Kimono prints of this cute jacket that packs a big punch! It immediately gives your outfit a focal point and is interesting and flattering to boot. Win Win!

     

    Jacket in Mixed Print with Trim Detail $59.89 at Asos

    Shop more Silk Jackets here

  • Go Shorty 10 of 10
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    Technically a "bomber jacket, but if you don't cinch the waist, a shorty boxy jacket it is, and because the sleeves are the same length as the waist, makes it more flattering. The print confuses the eye as well and worn with solids, becomes the focal piece, and subsequently distracts the eye from "trouble areas" you may be less interested in showing off.

     

    Giambattista Valli Leopard Jacket on sale for $591 at Shopbop

    Shop more Leopard Print Crop Jackets here

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