Styling Oversized Shirts

“Those of us who can’t wear cropped or tucked-in shirts would love some suggestions using a long shirt.” Many have asked similar questions, so I’m sharing my collection of long shirts and how I style them, from casual to dressy. They are often described as oversized, big, or boyfriend shirts.

Similar blue and white oversized shirts are here, here, here, here, here, here, and here. I’ve had mine for a couple of years and often reach for it in warmer weather. It gives the coverage of a blazer without the bulk or weight.

Big shirts are also great as swimsuit coverups. They have been in my summer wardrobe for many years, but they can also look great layered over a turtle or mock-neck top. A slim-fitting first layer will always keep the combinations from looking sloppy. Pop up the collar, leave the front open, and turn up the sleeves to make your look intentional.

The white shirt in every length is a staple in many women’s wardrobes. I like them best when they are soft and lightweight. Big shirts in many iterations are herehereherehereherehere and here.

I bought the blue one last year because I adore the color. Similar blue shirts are here, here, and here. An oversized denim shirt is here.

A black cotton oversized shirt is here, here, and here, and a dressier organza version is here.

I hope this post helps you find the best oversized shirt for you. Recent looks are summarized here. Shopping links may allow me to earn a small commission without cost to you.

Style is about getting dressed, not about dressing up.

  1. Susan, Thank you so much for this post! Because I am long-waisted, I struggle to make the cute crop tops look good on me. The long shirt is definitely a good solution for me. Thanks for all of the effort you put into this post! Hope you have a lovely day.

  2. Love these pictures, particularly the blue colour on you Susan. Could you help me? whilst looking in my wardrobe, and saying ‘I have too many clothes, and nothing to wear’. I’m trying to put together a modular wardrobe, and would love your help for spring from top to toe? My favourite colours are blue, brown black.

    1. Use accessories to add interest and texture. You likely have most of what you need already. Try things on in combinations you haven’t tried before. I’m sure you’ll find some that you love.

  3. Love this post – thanks. My question is whether I am short or long-waisted? I don’t really know the difference. I’m built somewhat like you (but heavier at 150 and 5’8”) busty, no waist at all and zero hips or rear end. Longish legs.
    Could you please help us determine what’s what in this term so we can better figure out from your great posts what works for us? Thank you. And please hug Mr. Mickey for me

    1. If you place your hand flat against your body under your breasts and than place the other hand under it (horizontally) your belly button may be hidden by your second hand. If that is the case, you have a high or short waistline. Here’s a helpful website about body proportions and how to determine yours.

  4. Thank you for a fabulous post! I cannot choose a favorite outfit. Love the quote “Style is about getting dressed, not about dressing up.” None of your outfits look contrived or fussy. Class act!

  5. I love all of these combinations, but the black with silver accessories is inspired! I always take way to many clothes with me when I travel, because I think I need different clothes for every occasion. Look what you came up with for a special occasion! All of those items can be worn casually too. I need to think more creatively! Have a special weekend and wear that lovely outfit somewhere with Mr. Mickey.

  6. Thanks for sharing this Susan I’ve got a lovely summer chambray style shirt purchased last year and this year have purchased a white cotton shirt. Great for the warmer weather over vest tops.
    You give me such great Ideas, I appreciate the way your look is simple and not too overdone.
    I will be purchasing a sunhat like yours for the summer which I like very much.
    I have also seen a kimono by Izabel for wearing over a navy maxi t shirt dress and have purchased some lyocell/tencel denim like trousers quite inexpensive but cool for the summer.
    I’m loving some of the jewellery posted and will have a Sort out and add a couple of new pieces.
    Best wishes
    Sue Smith x

  7. Susan, could you provide a link to those gorgeous silver earrings you are wearing in the first picture with the blue striped shirt? You’ve worn them several times but I’ve not seen a link to where we can purchase them if they’re still available. Thank you for all the great ideas you have given all of us. Have a great day.

  8. Hi Susan!
    You would find a way to look great in a potato sack! Seriously. I love the black evening outfit. The marine blue makes your eyes pop.
    Thanks for the inspiration I always find somewhere in each post. The suggestions for color and fit are always on point.
    I struggle with footwear. I have short wide feet. I’ve read an earlier post you did on footwear; any ideas for an update?
    Thanks again,

    1. My aim is always footwear that is comfortable without looking bulky. Even a flat shoe can look sleek and elegant if that’s what you want. Feet, just like bodies, come in different shapes, and we have to take the time to find what serves us best. Good luck, Georgia! I hope you find a shoe style that serves you well.

  9. i am still confused over proportions. I thought it was long over lean. The idea was 1/3 top and 2/3 legs or 2/3 tops and 1/3 leg but now we see wide leg pants over long tops. HMMMM
    I hope you and Mr. Mickey are feeling strong. Your posts are great.

  10. I love, love you in the white and black trousers that flare out near the bottom. They look so classy on you!

  11. I’m 5’3” and an oversized shirt makes me look lost, as if I had chosen the size wrongly. Sometimes I think an oversized shirt actually makes a woman look bigger unless they’re well-tailored shirts, like your blue and white striped one.
    I’m unable to wear heels which I notice balance your own look out. So the best way for me is to define my waist and choose shirts accordingly.
    The only time I wear an oversized shirt is over swimwear – I choose versions of white linen and navy linen and it works a treat, popping the collar, protection from the sun and just an elegant look in my 70’s on the beach.

  12. Question for you about size. Do you still get your normal medium? Or does the oversized style make you size down? I’m petite, so I’m glad to see these shirts come in petite .

  13. Thank you for taking time to post helpful suggestions on how to put together outfits.
    In this post, are you wearing t-shirts or body suits under the long shirts? My reason for asking is that your t-shirts/bodysuits always have a smooth fit. I prefer bodysuits because they don’t bulge on the sides. They can be constricting & warm in hot, humid weather. If you wear t-shirts, is there a material/brand that you prefer?

    1. I look for a smooth heavier cotton tank to wear under floaty tops and linen jackets when the weather heats up. My current favorite tank is here. I look for smooth fabrics so that whatever I wear over them, moves freely. Sometimes a ribbed knit grabs the fabric and causes it to bunch up.

  14. You have such a beautiful belt collection which you often wear to emphasize your waist and lengthen your legs. I would love to see a blog post on where to purchase good belts and what to look for. Thank you.

    1. Thank you, Grace. I’ve been collecting belts for years, but didn’t wear them so often until the wider leg high waist pants became so fashionable. A belt no more than two inches wide with a very plain design and simple buckle serves me well. I’ll share links to some of my recent favorites. Herehereherehere.

  15. Susan,
    What do you do to keep the collar “popped up “ ?
    I’ve tried starch but soon after wearing I noticed it falls and looks limp.

    1. They don’t always stay put, so if I think about it, I just smooth the collar back up through the day. It’s a bit like wearing scarves, you have to restyle sometimes.

  16. Love your post. Noticed in every picture the shirt is worn over a tucked in shirt with belted pants. Would love to see a post for those of us that cant wear a tucked in shirt with a belt showing. Just how to style looks with shirts that are worn over pants. Love your blog and have been following for years. This is the first time I have ever commented though.

    1. Thank you for your comment, Nancy. Look at the picture of the blue shirt. That tank is not tucked in, but it is shorter, smooth fitting, and made from heavier cotton. The key is not wearing another long, loose, floaty top under the outer layer. I used to wear too-long tanks, sometimes drawing attention to the tummy and making my legs look shorter. The best length might be one that falls below the belly without hugging under it.

  17. Thank you for this post! I recently bought a long shirt at my sister in law’s coaxing and was not exactly sure how to wear it! You have lots of great ideas here.

  18. What a great blog, Susan.
    Your photos speak volumes about proportion and fit when you are styling oversized shirts.

  19. Nancy, try ironing a crease in the center back of the collar, with starch or sizing. Can’t guarantee it helps any more, maybe my imagination!!! Ha

  20. Thank you for this post. I have bought a few big shirts from J. Crew, but haven’t worn them, because I was not sure how to style them. The first pic is my fav, and a real showstopper! Would you please share a link for those white pants? Are they new? You look great in them!

  21. Thank you so much for the suggestions for styling oversized shirts. So helpful to us with tummies! All suggestions are Right On and I’ll follow them all.

  22. Love your blog! It helps me to look stylish at 75 years old.
    I would like help knowing what necklines to wear with different length necklaces.

    1. Thanks for the suggestion. I’ll work on that, but in the meantime, if the necklace I’m thinking of wearing, won’t hang right because the neckline of my top gets in the way, I look for a different length.

  23. Great tips and photos! I have a few oversized shirts in my closet and I can never find a good way to wear them! Thank you

  24. Continue to enjoy and learn from your blog. You look radiant. Last post included Mr Mickey too… his touch too.
    Someday I would love to see a post about your belts. You seem to have a variety and they add to your style!

  25. I have a blue and white stripe oversize shirt that I think I’ll give a second chance for the look you showed in this fashion lesson. Thanks for sharing.

  26. I love the look with a belt but I don’t wear them as I have a more rectangular shape and carry my weight in my midsection. I feel it draws attention to my belly. I have thin legs. What are your suggestions for my body type, Susan? I would really appreciate your thoughts!

    1. Anything that creates the illusion of a waist suits the rectangle body shape. Fit-and-flare tops and dresses help draw attention to the waist and give a fuller look to the skirt to balance your figure. Look for cinched waist lines but not so that they show the shape of the tummy. If the garment falls away from the tummy after the fullness it is more flattering.

  27. Love these looks on you. Thank you for this post, I’ve been struggling with how to cover my midsection yet look stylish. Can you also tell me where I can purchase the tan flats ? Thank you !

    1. The first layer under the blue shirt is not tucked in. A long, loose first layer under a long, loose shirt will only make you look larger. Experiment with shorter, more fitted first layers. You may be surprised at your results.

  28. Hi Susan!

    I LOVE the black outfit and was wondering about the V-neck black sequin top. Please share the details – if it is sleeveless , are the sequins all black and where you purchased it.

    Thank you –

  29. Love the tan loafers you are wearing in the white shirt and light blue jeans photo. I think you featured them in the past but cannot find in your previous posts. Would you please send the link or any other info on the shoes?
    Thanks so much-

  30. Dear Susan,
    You are the one person I have found that has the same taste in style! I love all the outfits you have put together and enjoy the ease of the links to purchase.
    Thank you for the fun informtation.
    From another – Susan

  31. You’re recently shared wide leg pants worn with heels (spring looks) and flats (a week of looks). Can you share how you manage different pants lengths? Do you buy/ hem different lengths or fold a neat “hem”? If you have pants of various inseams to work with different shoes/looks how do you organize them and how do you decide which pairs are hemmed for flats vs heels? I hope this question makes sense. I’m short legged and depending on style/shoe choice I wear 26-30 inseams. I’d love to read your insights.

    1. Thank you for your question, Anne. I hang my pants and jeans by color and within each color group by length. The longer lengths are for the higher heels, and the middle lengths are for block-heeled short boots and shoes. The shortest jeans are for flats, trainers, and sandals.

      My calves are too thick for most straight-leg styles and all the skinny jeans ever made. (It’s also why you never see me wearing knee-length boots.) For that reason alone, you will most often see me wearing flares or pants with fuller legs. When I say you have to dress the body you have, that’s what I mean. For years, people gave me grief for wearing skinny jeans when, in fact, they were always straight-leg jeans, which look skinny on me.

Leave a Reply

Your email address will not be published.

I share tips and inspiration for using what you already have in contemporary ways. Defining words include effortless, classic, refined, discreet, and elegant. My style is chic, minimal, and timeless with a bit of edge.