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:
- 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.
- 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.