Trial and Error: Styling a short, boxy jacket

Update: J.Crew is currently having 30% off your order and free ship at any price w/ code WISHLIST (ordered this Crewcuts merino wool dress in camel/navy previously). One of my favorite purchases last month was this J.Crew lady jacket in spicy gold (must thank Elle again for her review and sale alert). It’s a solid quality, ladylike piece that I’ve received many compliments on, but boy is the silhouette hard to work with! The shape is short and square, and the fit is slightly roomy on me – but my tailor didn’t think it was wide enough to warrant taking-in.

I tried this jacket with many different types of garments, in hopes of finding a pattern to what works. Some parings look bad and some look okay, but I can’t put my finger on exactly why. Since several readers have asked for ideas on how to work with this shape, I figured I’d share some photos, and hopefully you guys can help decipher the fit code.

1. Below left: Starting off with the easiest and most natural looking pairing – with the matching pencil skirt. I think this works because the same-color, same-width (at the hips, anyways) bottom piece makes a continuous line with the boxy jacket. But how often does one get to wear a matching mustard wool suit, especially without a politician husband in tow?
2. Below right: With a bell-shaped mini skirt. This looks okay to me. Again the similar width connects the two pieces, and even though the skirt color is different – it’s short enough so that there’s enough leg visible (+ heels) for creating a lengthening line.

3. Below left: With legging jeans, no blouse showing. This looks okaaay, but the tight, narrow bottoms plus wide top is starting to border on football linebacker style.

4. Below right: Un-tucking the shirt. In theory, this would be cutting into the long, lean leg line…but I think it makes this ensemble look more flattering. Not sure as to why.

5. Below left: With fitted cropped pants, blouse un-tucked. Looks similar to # 4, maybe a little worse because the leg’s cut off at the ankle.
6. Below right: With fitted cropped pants, no blouse visible. Yee-uck! Ignoring the embarrassing outlines of camel toe…it looks like the more narrow/fitted the bottoms, the more jarring/wide a boxy jacket appears in contrast. If you are naturally top-heavy, then a square, cropped jacket may be even harder to work with.

7. Below: With a variety of pencil skirts. The right (pardon the hip wrinkles) has the least color contrast and looks better out of the 3, but not as flattering as the slightly shorter matching skirt in #1. From the middle photo, I realized not to wear a boxy jacket unbuttoned.

8. Below: Over some sheath and pencil dresses. Very mediocre.

9. Below left: With an A-line, knee-length skirt. I wouldn’t wear these two exact pieces together, but am undecided about the overall look of the two shapes  together.
10. Below right: Wildcard, because these short shorts were lying on the floor. The long leg line with un-tucked blouse is flattering in my eyes, but I would probably never have an occasion where a wool jacket is warranted while legs are so bare.
There’s one or two last pairing types that I didn’t show here, and they happen to be the more flattering (in my opinion). Please tune back in a day or two for an outfit post : )

Readers – Please share any insight on why some of the above may or may not work. How do you /would you suggest styling a short, boxy jacket?
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  1. Elle wrote:

    i almost bought the grey/navy one but i didn't know how to style it. i wish i would have seen this 2 months ago.

    Posted 12.13.12 Reply
  2. Suzie Q wrote:

    In these photos, I think it works the best with the white bell-shaped skirt and the jeggings with the shirt untucked. I think the shirt untucked look works because it provides a lengthening and slimming silhoutte, making the blouse look less boxy. The skirt is a little bit more puffy than the jacket, so it minimized the boxy look there. Can't wait to see what you ended up choosing for your outfit post!

    Suzie Q

    Posted 12.13.12 Reply
  3. Abby wrote:

    Maybe something like this…but it is too short for work.;=1&pid;=233606022

    Posted 12.13.12 Reply
  4. Anonymous wrote:

    Since it looks good w/ shorts, maybe try jacket (scrunch sleeves and unbutton) + shorts + tights + knee high boots? also you can try wearing it with a short tunic (soft color like grey) w/ leggings/tights and boots cause short tunic = long legs 🙂

    Posted 12.13.12 Reply
  5. Mady T. wrote:

    love the jacket, I don't see it with something fit on the bottom… I like especially the second look…


    Posted 12.13.12 Reply
  6. Anonymous wrote:

    Thank you Abby!

    Posted 12.13.12 Reply
  7. S. wrote:

    I think the jacket looks best with its matching pencil skirt. Yes, it does look a little "politician's wife", but it does have a cool retro vibe that you might be able to play up nicely by wearing your hair up and adding a vintage brooch. This may be too conservative a look for your preferences, but it's certainly office appropriate and classic (and given the popularity of 60s shows like Mad Men and Pam Am, relevant.)

    Second to that, I think finding the correct proportion is tricky here. The cropped jacket is obviously not inherently elongating. Many of these outfits don't work well because the shapes are conflicting; the jacket is short while your dresses, skirts and pants are tailored and much longer. I think a jacket like this is best suited to a mod-style dress because they share the same shape. Most mod dresses are rather short, unfortunately, but I've found some in the past that were in fact office appropriate. Being petite and smaller busted makes this style work for us in a way that it doesn't always for our taller or bustier counterparts. Looking forward to the next post!

    Posted 12.13.12 Reply
  8. laeclectic wrote:

    I think #4 works because it creates the illusion of long, straight legs – I like it! The pants in #3 make you look curvy (which is funny because "curvy" is not the first word I would think to describe your body type.)

    I actually like pairing of the jacket and pleated skirt in #9. Also, we haven't seen that skirt on you in a while, so it's nice to see you pull old pieces out of the closet for a fresh look! (I've been trying to do this with my own wardrobe lately.)

    Posted 12.13.12 Reply
  9. What about cream or ivory slacks with a straight leg or slightly flared leg?

    Posted 12.13.12 Reply
  10. What about cream or ivory slacks with a straight leg or slightly flared leg?

    Posted 12.13.12 Reply
  11. Anonymous wrote:

    I think it looks best in photo#2. Honestly not a fan of all the pockets on the jacket and it's boxy fit. I'd return it.

    Posted 12.13.12 Reply
  12. Anonymous wrote:

    Because it's such a serious looking staid jacket, it seems like the more "relaxed" the bottom the better it looks? IMO it looks best with the bell-shaped mini skirt, the pants/jeans with the shirt peeking out (it looks a little messy-chic i guess lol), and with the shorts.

    Posted 12.13.12 Reply
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    Posted 12.13.12 Reply
  14. sarahp wrote:

    did you check how wendy styles it? I ordered the same jacket in pink and i shall follow how jcrew website styles it.

    Posted 12.13.12 Reply
  15. I like 1 and 4 the best. I think the issue is the jacket is making your torso look a lot shorter than it is..the untucked shirt with skinny jeans lengthens your torso. With the same colored pencil skirt… since it's the same color, you fool the eye into thinking the jacket is longer than it is. Can't wait to see what the other combinations look like! 🙂

    xo, Yi-chia

    Posted 12.13.12 Reply
  16. i think it looks best with the matching skirt (obviously) and then my 2nd fav would be the jeans with the untucked shirt. the rest isn't as flattering. in my opinion 🙂

    Posted 12.13.12 Reply
  17. Nancy M. Martinez wrote:

    Hi Jean,

    I have found short, boxy jackets to be difficult to style on my sometimes size 0P, and more recently (after having kids) size 2P short-torsoed body. I have usually worn mine over a longer, untucked top or blouse, with the jacket open (as I have larger hips than you to balance an open jacket) and the top belted with a Chanel or Chanel style chain belt. So, addressing your looks, I think the jacket looks great with the matching skirt, of course. And you were right about #4. I think both of these would look great with a navy/cream striped tee sticking out the bottom as well, for a cute nautical/classic look (I LOVE stripes!). This would also work with wide legged navy or denim pants as others suggested. Look #2 is also lovely. The bell shape of that skirt is just right with this–not too wide. A short pleated skirt, as you show in #9 would also work in my opinion in navy, black, or cream. And I love this with the shorts. I'm sure you could make it work for cooler weather in the spring with nude or grey hosiery and grey tweed or denim shorts to show off your lovely legs! Don't know if this helps.

    LOVE the posts! I used to dress a lot like you do when I worked outside the home. You always look so polished! I actually used to over dress and wore skirt suits to school as a student! Now that I am a stay-at-home mom, I dress more like Wendy's most casual looks (I haven't been a viewer of yours long enough to have seen your more casual looks). My tweed jackets only get worn with jeans now! Have a great day!

    Posted 12.13.12 Reply
  18. I am quite a bit taller than you, but I wear a jacket like that with a dark, denim, wide leg trouser. I'm not sure if I've ever seen you wear any, but that is my suggestion.

    hope that helps =]

    Posted 12.13.12 Reply
  19. Anonymous wrote:

    Hi Jean,

    and warm greetings from Elle magazine Finland. I´m writing an article concerning tall and petite women fashion and would like to ask a couple of questions from you. Unfortunately I can´t find your contact information. Could you send me your email address so that I could send the questions to you? Mine is

    Many thanks!

    Posted 12.13.12 Reply
  20. Anonymous wrote:

    Hi Jean,

    I was wondering what size you are in the J Crew mustard pencil skirt?

    Also, if you needed to take it in with any alterations?


    Posted 12.13.12 Reply
  21. I think #4 works because it actually un-boxy-fies the boxy jacket giving an illusion that it's longer. Because the pants are beautifully slim and dark already giving your legs great length, a simple light coloured shirt that complements the jacket gives it a slightly less serious look too. I think it also accentuates your hips a little, that's why it's flattering.
    I like the idea of dark shorts plus dark tights suggested by another reader. I think a shorter skirt with dark tights might also work. If the materials for the bottom half are similar in weight to the jacket, that might also help balance the boxiness perhaps?
    Is Nick considering politics anytime? #1 is quite cute 🙂
    Thanks for this trial and error post – it was fun to read and ponder a bit:)

    Posted 12.13.12 Reply
  22. Some of them were not so matching but I think the long trouser was perfect.

    Posted 12.13.12 Reply
  23. I bought this jacket in pink and I HATE it! It is ill fitting. Thanks for styling tips.

    Posted 12.13.12 Reply
  24. Anonymous wrote:

    The "untucked" outfit look better than "tucked" b/c it creates a heaviness that offsets the wideness of the jacket. The boxiness of the jacket makes the top portion of your body seem very heavy so you need some sort of highlight or "band" to offset and balance your figure. That's also why the mustard pencil dress looks good, b/c it's tight enough that the hip is accentuated, but not too tight that you become top-heavy (which is why the skinny/tight pants do NOT look good).

    Why then does the flowy dress of white bell-shaped dress not look right? That's due to the structured or "stiff" aspect of the jacket. The severe lines/cut looks incorrect or out of place with the soft/flowy aspects of the skirts.

    Have you considered a wide-legged jean in a dark blue color? The wideness of the leg should help offset the heaviness of the jacket.

    Posted 12.13.12 Reply
  25. Carol Li wrote:

    There are 3 main problems with this jacket.

    1. The jacket is not the right style for your body shape. As you say in the post it's boxy and the sleeves are neither long or 3/4. You suit fitted jackets which a longer body. To make this jacket work better, I would recommend taking it in at the waist, at the bottom and also slimming the sleeves to help give you some shape.

    2. The jacket was designed to be worn with the matching skirt. The only other pairings it works with would be a black skirt or cream skirt, but this needs to a pencil skirt. It's hard to a pair the jacket with anything else as it's a statement piece and is fighting with other items which you have pair it with.

    3. The cream horizontal piping detail shorten the jacket and your height as well. You would be better with just the top piping detail rather than the additional ones near your waist which is another reason why the jacket looks boxy. The piping itself is too large for your petite frame.

    I hope these tips help.

    Posted 12.13.12 Reply
  26. Carla Krae wrote:

    Skinny bottom makes your waist tiny. If the jacket was longer and boxy it wouldn't work, but it works with exposing your waist-to-hip line. Don't worry so much.

    Posted 12.13.12 Reply
  27. i like it best with the matching skirt (obvi) and then with the cream shorter skirt. and i definitely like it best with the shirts un-tucked with pants. it is such a beautiful jacket that it seems worth it to me if it only went with those two pieces! =)

    xoxo, jenn
    the stylish housewife

    Posted 12.13.12 Reply
  28. kimmie wrote:

    I have a similar boxy cardigan that I'm at a loss for how to style, because I run into the same issues that you did. Can't wait to see what the winning combination is! 🙂

    Posted 12.13.12 Reply
  29. Anonymous wrote:

    I have a boxy jacket like that. I tend to wear it unbuttoned and with either wide leg trousers or cigarette pants with sky high heels. And if I button it, break up the color on top with a scarf. It also works over a sheath dress, but again, you have to unbutton for the colors to work. It's so cute, hope you can make it work!

    Posted 12.13.12 Reply
  30. SW wrote:

    Just to try out: wear them with your olive skinnies or a white or light blue wash, your leather leggings, and a black sheath dress with the jacket unbuttoned. Also, perhaps a white pencil skirt? Maybe even cream, in any material (tweed/lace).

    Good luck! If all else fails, at least you have the full suit and the skirt to mix and match with.

    P.S. – it seems like the jacket is cutting off at the wrong place at your hips?? I'm not too sure!

    Posted 12.13.12 Reply
  31. Abby wrote:

    Now, I'm thinking this is where the navy or cream lace dress is going to come out. Or the lace skirt. I will have to wait and see.

    Posted 12.13.12 Reply
  32. Abby wrote:

    Hmm…or a navy skirt maybe. Like the mustard…

    No, that might not look good…

    Posted 12.13.12 Reply
  33. Abby wrote:

    Those were from Ann Taylor. They don't have that exact style anymore. Express has some similar ones with cuffs, but they'd probably have to be hemmed.

    Posted 12.13.12 Reply
  34. Mary Ann wrote:

    I think the pictures with the shirt untucked look more flattering because the comparison shots show too much difference between the width of your waist and the width of the hem of the jacket, thus lending to the boxy appearance. With the shirt untucked that line is visually softened. I have trouble, too, with boxy jackets; I feel ya on this one!

    Posted 12.13.12 Reply
  35. Lin wrote:

    I would vote for 1 and 3. I got the same jacket in the same color. Love it! The color is so bright and the shape is really lady like. I wear it with a yellow-grey wool skirt also from JCrew. Got lots of compliments! I haven't tried the 3rd look, but I do think it goes well with dark color pencil pants/jeans.

    Posted 12.13.12 Reply
  36. Krisma wrote:

    Hi! I think the reason why same-colored skirts and an untucked blouse with the jacket works is because it lengthens your overall look and makes it look more balanced whereas just the jacket with a contrasting bottom shortens your torso so it looks kind of awkward.

    Posted 12.13.12 Reply
  37. Olyvia wrote:

    Cant wait to see your best pairings! I just donated one of my boxy cropped wool jacket with similar style because i find myself unable to fit it in my wardrobe. It looked better with my dresses than my pants…. But I usually only wear dresses in the summer, so the wool jacket was too hot for summer , and the cropness was not enough warmth for winter dresses …. Where I prefer to wear longer jackets/coats. So donation pile it went for not being a very functional jacket. Hopefully I don't regret tossing it out if you come with a brilliant way to style this boxy short jacket 🙂

    Posted 12.13.12 Reply
  38. White sheah dress?

    Posted 12.13.12 Reply
  39. v4ever wrote:

    Bootcut or wide-legged in dark denim or other fabrics? Seems like a more relaxed fit might balance better.

    Posted 12.13.12 Reply
  40. Anonymous wrote:

    sorry i have no suggestions but i really want to know the brand and style of those camel colored pants you are wearing!

    Posted 12.12.12 Reply
  41. it's probably the colour that makes it difficult to fit, a neutral tone would have let you get away with the jeans/dress combos. maybe a cream skirt tight at the waist and at least a mid calf/maxi length would create the longline

    Posted 12.12.12 Reply
  42. I'm short and curvy so I'm afraid that this jacket will make me look heavier but since you are thin it looks good on you. I really like it with the legging jeans and shorts with the shirt untucked.

    Posted 12.12.12 Reply
  43. Amy wrote:

    I think #4 works because it elongates your torso, which I think is the central problem with short boxy jackets, especially on short girls like us who don't have a lot of torso to begin with! My favorite combo is #2 though!

    Posted 12.12.12 Reply
  44. Abby wrote:

    OK 🙂

    Posted 12.12.12 Reply
  45. Abby wrote:

    A cream chiffon skirt or a cream skirt with a slim line and shorter length might be nice. But then a shorter skirt wouldn't be work appropriate. I'm just boring. *shrugs:

    Posted 12.12.12 Reply
  46. Stella wrote:

    I just purchased the same jacket! Looking forward to your post. 🙂

    Posted 12.12.12 Reply
  47. No hard feelings here towards the pants : ) They just don't work with a short, boxy jacket with no other layer showing, on me personally.

    Posted 12.12.12 Reply
  48. Abby wrote:

    I'm confused. I'm having the same issue right now.

    You said some pretty negative things about those pants. Do you not like them anymore? Should we get rid of ours?

    Posted 12.12.12 Reply
  49. Anonymous wrote:

    I like 1, 4, and 10. If you have some heavier dress shorts, can you try those with some colored tights and post how that came out?

    Posted 12.12.12 Reply
  50. Anonymous wrote:

    I have the same jacket in the charcoal navy colorway and I paired it with long navy trousers with slightly wider legs, which seem to make the jacket seem less boxy. I am 5'7" though so maybe height helps. I could not seem to pull it off with skirts though, only pants,

    Posted 12.12.12 Reply

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