How should I wear a grey boyfriend jacket?

Illustration of a boyfriend jacket and jeans: Style Sketches™ byt The Style ConfessionsI’ve been hearing a lot about the boyfriend jacket fashion trend recently, so I wasn’t surprised when Greetje sent me this question for the Style Sketches™ series:

I am tall, size Large although I appear to be size zero because I have skinny long arms and nice long legs. No hips, no bum and a so-so waist….I have a grey boyfriend jacket which is not my color either. I need bright colours near my face. I have done so many things to make it work. Any ideas? Or should I have left this look to small girls? I saw a much shorter girl in the shop wearing it and it looked great on her. Surprise me. I am 5 ft 7.

Looking Great in a Boyfriend Jacket

Personally, I think Greetje is being too hard on herself. She explored a number of different ways to wear her oversized grey blazer on her blog No Fear of Fashion in a series of articles including My Grey Boyfriend Jacket Problem Part 1Part 2 and Part 3. I especially like her grey jacket paired with bright tops and white skinny jeans, but I do understand why she’s concerned about the large, boxy shape of the blazer. Petite women do look adorable in slightly oversized garments, and the very young can wear a potato sack and look good. I know that as I’ve gotten older I’ve become more cautious in my clothing choices. Regardless, Greetje looks great in her jacket and I think she should continue wearing it with bright-colored t-shirts and skinny jeans.

Yes Greeje! Your grey boyfriend jacket looks wonderful on you! Really it does! But eventually you’ll get bored with wearing it with white skinnies, so here are two other ways you can wear it.

Boyfriend Jacket and Boyfriend Jeans

First, try your boyfriend jacket with loose, rolled up boyfriend jeans, a white blouse and a big, bright statement necklace like in the sketch above. The colorful necklace will brighten up the grey blazer and the jeans will bring a casual flair to the outfit. I drew my outfit with sandals for a cute, summery look. Here are a few pairs of jeans and necklaces from around the web (Disclosure: Affiliate links are embedded in the widgets below. If you click on an image I will receive a small commission. If you can’t see the widget please click here. The link will take you to my site.) 

Give your Boyfriend Jacket a Feminine Twist

To give your boyfriend jacket a more girly look try pairing it with a dress, kind of like this.


I see the jacket worn with a bright white sheath dress and Greetje’s fabulous yellow purse, but the jacket would look great with a slim dress in a bright color or print too. Pink, white and yellow all look great with grey. For some more ideas on pairing a boyfriend jacket with a dress check out this gallery on Chicisimo. Below are some fun printed and solid sheath dresses from the web.

Contact me here if you would like to ask your own fashion question for the Style Sketches™ series. I will draw a fashion illustration like the one’s in this post to answer your question!

What do you think of my style advice for Greetje? Would you wear a boyfriend jacket with boyfriend jeans or a sheath dress? Do you have any other ideas on how to wear the jacket?

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16 Responses to How should I wear a grey boyfriend jacket?

  1. nofearoffashion June 12, 2013 at 11:11 am #

    It cracked me up when I saw my yellow Coach bag in your drawing. You certainly did your homework. And I think you have done a marvellous job.
    Of course a white blouse with a statement necklace (my bright green one from Rome f.i.). Why didn’t I think of that?
    I have several jeans, so no problem trying out your suggestions. I have a 7 for all mankind boyfriend jeans (a bit short, but perhaps that won’t be a problem) and of course skinnies.
    You obviously have been looking around my blog so you know I have a white sheath (very funny word) dress. Never in a million years would I have combined the two. I am going to try it out this weekend.
    Thanks again for these solutions. I should employ you. What would you ask per advice??
    nofearoffashion recently posted..Graduation Fashion Show ArnhemMy Profile

  2. Marla Robinson June 13, 2013 at 3:50 pm #

    I love the advice you gave. Really cute outfits.

    • Heather Fonseca June 14, 2013 at 11:48 am #

      Glad you agree with my ideas Marla!

  3. Alexis Grace June 13, 2013 at 8:21 pm #

    I really like both the options you put together— but especially the first! Definitely a “cool girl” look. I also agree that it looks best with the sleeves pushed up the arms a bit…..
    Alexis Grace recently posted..Making A Stylish InvestmentMy Profile

    • Heather Fonseca June 14, 2013 at 11:48 am #

      It’s keeping the sleeves up that’s hard! I’m glad you like the look Alexis. Makes me wish it was cool enough here to wear a blazer.

      • Arash Mazinani
        June 22, 2013 at 5:12 am #

        I love all your sketches that you’ve been putting up they’re awesome. I’m always a bit funny about pushing up the sleeves on my blazers in case of excessive creasing. But you can get some lovely cotton blazers that are great for this sort of look.
        Arash Mazinani recently posted..Street Style Icons: Sarah GleesonMy Profile

        • Heather Fonseca June 25, 2013 at 8:31 am #

          I think, on women anyway, pushed up sleeves look great. Certainly it looks good on me to have my sleeves pushed up. But they never stay and as you say they crease!

  4. Annette June 14, 2013 at 2:35 pm #

    Heather, your style sketches are amazing.
    I have a dark grey blazer which I never wear because the colour is not flattering. Actually I never thought of wearing it in summer but I should try it with white.

    Lady of Style
    Annette recently posted..DREAMING OF A BURGUNDY HANDBAGMy Profile

    • Heather Fonseca June 16, 2013 at 4:09 pm #

      Thank you so much Annette for your compliment! I was out of town this weekend and now I’m itching to do more sketches. I’m glad you liked the idea of paring a grey jacket with a white dress. I think white is a nice foil for grey, which can get a little somber especially when mixed with black.

  5. Pam
    June 21, 2013 at 2:52 pm #

    I have a gray boyfriend jacket and you just gave me some great ideas! Thanks so much and have a wonderful weekend!
    Pam recently posted..ROCK ON!My Profile

    • Heather Fonseca June 25, 2013 at 8:33 am #

      Thanks Pam! I’m so glad my sketch inspired you.