How to Do Oversized

Already Pretty outfit featuring ivory oversized sweater, olive leggings, Frye Harness 12R boots, JW Hulme tote
I remember being in middle school and seeing a scene from “Sleeping with the Enemy” in which a young, coltish Julia Roberts scampers around an empty house in nothing but a giant men’s button-down. And she looked SO SEXY, and I wanted desperately to be her. So I absconded with some of my dad’s old shirts thinking that all it took was … ya know, a giant men’s shirt. I could be coltish and sexy, too! And I was dumbfounded when I looked like an off-duty linebacker in my version.

It wasn’t until much, much later that I realized two things were amiss:

  1. I didn’t wear my giant men’s shirt over a naked bod. I paired my giant men’s shirt with schlumpy jeans. And, as it turns out, very few things look good with schlumpy jeans.
  2. I wasn’t Julia Roberts. I am a lot of things, but coltish ain’t one of them.

At this point in my life, I’m a little more athletic and I’ve gotten rid of every last pair of schlumpy jeans. So – although I am still not-tall, not-slender, and not-coltish – I have a better shot at looking dead sexy in one of HM’s button-downs. But at this point in my life, I’d much rather work some slightly more practical oversized looks. Ya know, ones that can be worn OUTSIDE THE HOUSE.

And I’ve had a couple of inquiries into the mechanics of oversized garments, and tips on how to make them work. So I’ll share what I know!

  • One oversized piece per outfit: If you’re wearing an outsized scarf or cowl, everything else should be relatively fitted. If you’re wearing enormous wideleg pants, make sure your top is tailored. If you’re swimming in a huge sweater, pair it with leggings. Create balance for your oversized garment with slim-fitting ones, or you’ll just look big all over.
  • OK, OK, you can do more than one: If you simply adore super-sized items, you CAN push the envelope and do multiples. But if you are concerned about looking big all over, make sure that your actual body shape is visually represented somehow. If you’re doing a huge cowl and huge pants, wear a tight shirt. A loose tunic and enormous platform boots will look best with skinny jeans or leggings.
  • Let the big item be the centerpiece: I don’t tend to accessorize my outfits when I sport oversized garments. Not heavily. I’ll throw on some simple earrings and maybe a necklace, but that’s about it. I see this type of ensemble as being fairly edgy on its own, and adding tons of additional elements to the mix just gets overwhelming.
  • Explore various styles of oversized garments: I do much better with looooooong oversized tunics and sweaters than I do with boxy ones. Even though a longer line might make me look shorter by cutting off my legs, a boxy cut just makes me look wide. And I’d rather not. But if you’re petite, looking as tall as possible may be your priority and going boxy could be perfect. There are many, many styles of oversized clothing and some of them may look indescribably horrendous on you. So experiment a little, and be patient.
  • Make sure it’s truly oversized, not just big: A shirt that is two sizes too big for you will just look sloppy. Either buy up three to five sizes, or seek out items that are designed to have an oversized look. (A lot of this is down to sleeves – oversized items tend to still retain slimmer sleeves.)
  • Stick to the women’s section: Some ladies can buy men’s clothing from the big & tall section and look amazing, but many of us are better served buying women’s clothing that is meant to fit large and loose. If you’re tall and narrow in the hips, men’s duds may work just fine. If you have any curves, they may fight the tailoring in dude garments.
  • Don’t expect to look slim: These looks are for fun and experimentation, not traditional figure flattery. I look cute in my huge ivory sweater. I do not look slender. And that’s just fine.

In the middle of summer, when the weather is gorgeous and I’ve been biking my butt off for months, I am unlikely to even THINK oversized. But right now, at the tail end of the Midwestern winter? Curling up inside a sweater the size of an armchair – balanced tidily by some chic-yet-comfy cotton leggings – is all I ever want to do on weekends.

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  • Middle Aged Woman

    I spent so many years doing big and baggy to hide the flaws…until I figured out that it made me look worse! I really can't think of one thing that looks good on me oversized.

  • Clare

    Funny you should write this post today, Sal, as I just wore a majorly oversized cardi yesterday…and got some weird comments for it. Your tips are perfect though, especially about keeping the rest of the outfit fitted and slimming, if possible.

    I have yet to wear the oversized men's shirt that I, too, ogled. I think I would look like a small child in a large nightshirt. Decidedly not sexy.

  • Marlein

    I have 1 oversized sweater. I think your tips are good…buy something that is designed to be oversized is the safest if you're unsure. And deff team with stuff that's fitted or else you just end up looking waaaaay bigger than you are.
    I was a bit unsure about my 1 big sweater because I'm a size UK14 and always aim to look "slimmer"…which is pretty typical I guess for most woman.
    But I stil loooooooove my huge sweater (with huge hearts on it lol) and I get compliments on it quite often so I guess I look pretty nice in it! 🙂

  • La Historiadora de Moda

    I think the key one is not to expect to look slim. For me that's where I always get upset and demoralized by oversized garments, but I'm now realizing that must be much more normal than I thought.

  • Claire

    Fun! I agree, I love the stylish-yet-comfy way a successful outfit like this makes me feel. As you mentioned though, this is not a surefire look and requires some honing and experimentation to make it flattering. Most of these tips hit on the internal guidelines to which I hold for the oversized look… with one notable exception: for me, I can't have a garment more than a couple sizes bigger than me or it's just a mess. I'm a petite shorty as well as an inverted triangle, so my frame just can't carry it off. It's similar to what I finally figured out with large patterns: although I'm drawn to them, I find it's best for me to stick with smaller prints that don't overpower me and I only try to pull off larger prints in a scarf or something. I also like belts a lot but have a VERY hard time making structured/rigid/buckled ones work (fastening something around an upside down triangle tends to slip ever down); however, I find sometimes I can make them work with bigger tops because the extra material gives them something to hold them in place. 😀

  • futurelint

    I've only done the oversized thing once or twice, and I think you nailed it… you've got to keep everything else tailored or you just look schlubby…

    The master of playing with volume and oversized proportions, in my opinion, is Archibald Maximillion on flickr:

    http://www.flickr.com/photos/archibald-maximilion/sets/72157622277952309/

  • Charlotte

    Like MAW, I used to think that I could hide inside my clothes so everything I had was "floaty." As I'm typing this, sitting at my desk in an XXL Ralph Lauren men's plaid flannel (brand new with tags at Goodwill, 29 cents!!) and cotton leggings, I too find this a much more flattering mix. Always big with small, or small with big. Never big with big. I have lots of big cardigans & coat sweaters, so lately, I've been buying leggings.

  • Mikaela

    oversize is all i study in it seems!! it feels so comfy to be studying away in a big, warm, comfy sweater! i love it.

  • jesse.anne.o

    Absolutely agree with keeping the balance of an outfit tailored. I think heels are almost always necessary (for me) if I'm wearing an oversize top. I think in my mind the drapey quality of oversize is supposed to be countered by trim and tailored and any "stumpifying" (perfect word) works against that? I think, as a shorty, I'd be less likely to go boxy, since that's just really could cut me in *half*. I'd rather just do the long and lengthen the legs to make up for it.

    Good post!

  • The Raisin Girl

    I love the oversized sweater look as well. But I have large ta-tas. And hips to match. I guess I'm an hourglass figure…if the hourglass ate only fast food and home cooking Paula Dean style (lots of butter for those who don't ascribe to Paula Dean). And I've found that oversized items just tend to make me look like I'm trying to hide a pregnancy. Generally, the only way I can pull off oversized tops is by belting them at the waist, which feels sort of like defeating the purpose.

  • WendyB

    Oversize tops are no longer for me…I last did them in college.

  • Kelly

    I pretty much stay away and do more figure-skimming outfits. It just doesn't work on my figure – there ARE big parts of me (hello, boobs and butt) and if I do oversized, they're all you see. So your eye decides that my whole body is large because you can't see anything small about it. Something like that.

  • Blume

    I'll echo a few of the other women here in saying that I'm not sure oversized clothing can be made to work on an hourglass figure. The cowls or scarves seem to be the way to go if you must oversize as an hourglass.

  • xo, Alexi

    these are actually very great tips. i often find myself wishing i could pull off the baggy look, especially because androgynous fashions now, and i always end up looking more manly than i want. i'll definitely give these tips a go!
    http://steampunkdolls.blogspot.com

  • The Waves

    I wear oversized clothes every once in a while – mainly huge sweaters with skinny jeans or leggings – mostly for comfort. I have noticed that wearing heels and putting on make-up while wearing oversized clothes does wonders to the outfit. There is always that danger of the outfit looking sloppy, and I think your tips are just right.

  • CompassRose

    I love oversized clothes, and in my ideal world, I would wear all Complex Geometries and giant tattered black things from Japanese designers. It mostly looks, objectively, terrible on me. The paradoxically geometric look of that specific Japan-minimalist oversizing only really flatters a skinny, angular figure. A larger person – specifically, someone like me, with wide shoulders and a big chest and some boob – mostly looks like an ambulatory pile of laundry.

    And – whatever. I agree with the skinny bottom/oversized top pairing, mostly – at least it shows that I HAVE legs, and they have a shape (although a big tunic with leggings gets perilously close to the favourite uniform of older ladies of a certain size, still seen in my local bingo parlours as a holdover from the 90s.) An oversize tunic with a short, tight skirt also generally works on me.

    Giant Fail: the wide silhouette which drapes at the side with arms down, if the drapes hit the widest part of my hips. I have a fabulous sweater with a zipper in it in this shape, and it just never ever works well. The ubiquitous drape-front sweater is also keenly unflattering on me, for some reason – although I've only managed to force myself to admit it after buying TWO fairly expensive ones. (I'm getting very tired of that silhouette, anyway, and seeing cheaper and cheaper versions of it around. It's about time it went away.)

    Cropped and boxy I actually find fairly pleasing, if I pair it with a flared skirt or trousers – it feels like a fun exaggeration of my actually-boxy shoulders and chest, but still shows my waist.

    Since I am short, just buying big clothes never works. It's got to be designed oversized. Men's clothing also never works; it will pull in weird ways, or simply be so huge that I'm swimming in it and sleeves are dragging round my knees.

  • Sal

    CompassRose: How much do I love you for coining the descriptor "ambulatory pile of laundry"? Well, LOTS. And it sounds like you've done tons of experimenting with oversized looks and found what does and doesn't work for your bod.

  • Sal

    Hourglassy ladies who have chimed in: Are there any oversized pieces that DO work for you? Someone mentioned accessories like scarves and cowls, but I can see those conspiring with your racks for some imbalance action. What about exaggerated wideleg pants with close-fitting tops? Just curious.

  • FashionTheorist

    I haven't chimed in yet, but as a pretty aggressively hourglassy lady, I can say that when I do oversized or volumetric looks, I have to keep the fullness away from my waist. If I wear an oversized tunic or drapey top, it goes straight from full bust to full hips without letting anyone know that there's a (comparatively) tiny waist in there. Add in my broad shoulders, and I might as well be a linebacker.

    I can, however, exaggerate volume at extremities, as long as I keep the area around my waist quite defined. I don't wear trou much at all, so I can't speak to the wide-legged pants, but I do wear big, ruffly floor-length Victorian-style skirts and killer platforms on the regular. I can also play with sleeve volume with great success: I love gigot, bishop, pagoda, and bell sleeves.

    I can also rock huge, cartwheel-sized picture hats, to my delight.

  • GG

    Much as I love oversized sweaters in the depth of winter (what could be more cosy to lounge around in?, I NEVER wear them or boyfriend sweaters. Not because I don't want to, but because I can't. Being just 5 feet tall, I just cannot carry the oversized look. I also shy away from longer tops, because they make my legs look like stumps.

  • lisa

    Very comprehensive advice as always, Sal. I definitely agree with what you said about keeping other elements of your outfit slim and fitted and shopping for women's versions of things instead of browsing the men's section.

    It's so funny that you're publishing this post today because I've always secretly wanted to look dead sexy in a men's shirt too, or at least be able to wear something that looks like a men's dress shirt. Last weekend, I found a shirt dress with a draw string that fit and flattered my body but was loose enough to suggest "oversized." The sleeves are 3/4 length so they show slim wrists and forearms. I wore it with leggings and boots, and it was so amazingly flattering that I didn't want to take it off at the end of the day lol.

  • virago

    1. "So I absconded with some of my dad's old shirts thinking that all it took was … ya know, a giant men's shirt … And I was dumbfounded when I looked like an off-duty linebacker in my version."

    Speak it, sister! Which is why the preppy look of the 1980s (OK, I live in Maine, where prep never fully goes away, but the '80s is when the trend-followers embraced it) made me look like Das Michelin Madchen.

    For me, Breasts + Button-down shirts = Barrel-shaped torso

    2. "What about exaggerated wideleg pants with close-fitting tops?"

    This works for me, esp. w/my beloved black patent leather Dansko Marcelles (I can't wear high heels, but I can do these platforms) or my black low-heeled Italian boots.

    Fashion Theorist has inspired me to search the closet for some long skirts that might work w/the same fitted-top-and-Danskos/boots combo. This blog always gives me so many ideas!

  • Lisa

    Great advice! I always have trouble with oversize garments because I'm short but have wider hips. When I wear things that show off my waist I look curvy, but I always thought oversize garments made me look frumpy. I think I need to do some more experimentation to get it right.

  • Karisa Tells All

    Ooh I don't think I could pull this off like you since I'm sort of shaped like "I'm a little teapot!"

    Btw, I love your blog and you inspired me to post about my personal style. http://karisa-tells-all.blogspot.com/2010/03/coughtoo-many-colorscough.html

    I'd love it if you stopped by!

  • Rosie Unknown

    I love over sized clothing! I used to wear men's shirts quite often, but now I tend towards large sweaters, usually "borrowed" from my mother. I have gotten away with a boxy sweater, but it's pretty short, so you can still see that I get smaller above the hips, and I wore it with a bodycon dress.

  • Amy

    I've got to say, as an hourglass with full thighs and a fairly large bust – oversize doesn't work for me at all. Oversize tops just make my bust and top half look big and my legs look bizarrely small. Wide leg pants (when I have even bothered to try them on – I hate pants) call attention to my thighs and make everything look bigger.

    While I agree that not everyone has to wear figure flattering things all the time and there can be joy in experimentation – I just can't feel good about the way I look if my clothes don't flatter my figure. I wish I had the confidence to not feel that way – but years of bad body image won't allow it quite yet!

  • Eyeliah

    Sometimes I try to do oversize, it usually doesn't go well (lol). Thanks for the tips. 🙂

  • RoseAG

    Movies have costume designers. I'd put money on the notion that even if Julia Roberts was wearing a shirt was off-the-rack, it'd been tailored to look just right on her.

    Which is why if I'm aiming for an over-sized look I'll look for an item in my size that's been designed to appear over-sized!

  • Rad_in_Broolyn

    Oh my, your ancedotes, fahion related or otherwise, always have my heaving in my chair. I love the image of youngster Sal running around in a man's shirt, in an early attempt to sexpot-hood.
    Your tips are right on, and I think it's important to remember that we don't have to dress to flatter always. And than creative uses of volume can make for a creative outfit. Great advice as usual!

  • V

    Long-legged, short-waisted hourglass looks good in a giant maxi skirt and a fitted top.

  • Kate

    I love oversized stuff, makes me feel super sexy. Way more so than skimpy or figure hugging stuff. I guess it's comfort, comfort = confidence for me.

  • FashionAddict

    Great post! I love the oversized sweater look with skinnies or leggings.

  • Anonymous

    I am 5'2" and wear a 36DD bra. I have a rounded tummy and slim shapely legs and ankles and find that I have always drawn much more positive attention from men and women when I wear an oversized T shirt and bike tights. In spite of everything they try to convince all of us on "What Not to Wear", curves in the wrong places are just not pretty to see. Nice soft fabric that skims over curves is much more flattering and easy on the eye. The over-sized clothing they demand the person get rid of on the show is not flattering due to age, wear and unflattering color but loose things in nice fabrics that don't cling would be much better than the snug things they recommend in the makeovers.

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  • New Sweater

    So i got this vintage sweater and the size is either large or X large. I want to know is that good a good size or do i have to send it back cause its too big.
    how the sweater looks:
    https://www.etsy.com/transaction/147220518?ref=fb2_tnx_title