When I saw Nicole Richie on last August's cover of Nylon Magazine, I was in love with the party girl look of an oversized t-shirt, skinny jeans and major jewelry. Even though this was a year ago, I think the look still really holds up. Although I am also a fan of more scandalous styles, I love how this look brings the sexiness without showing much more than your arms. What's more, it is a look that can truly be embraced & flattering on all body types.The most important factor when choosing a t-shirt is the fabric. 100% cotton (or bamboo to be more environmentally conscious) is the best choice, although many t-shirts are made with polyester as well, which is fine. Stretchier knit material may cling more than you would like. Most cotton tees will feel pretty soft, but you can also use fabric softener, baking soda, or salt water in the wash to soften further, or try breaking down fibers by rubbing the fabric together, stomping on it, etc.
The next big factor is of course style and size. While a fitted t-shirt may look great, this post is about the oversized tee look, so I recommend taking the size you normally wear and adding a size or two to it. I'm normally a Medium in shirts, so I would search for Large and X-Larges.
The cut of the neck is up to you. I am partial to v-necks, but wearing a standard t-shirt with a rounded neck is fine too. The look is intentionally casual and non-chalant cool, so just throw on what you feel like. If you're crafty, you can alter a t-shirt to your liking. I love the t-shirt surgery LJ community and Ohmystars Craft for tutorials.
When it comes to finding a shirt in the first place, you have lots of options. If you're extra crafty or just extra broke, you can pick up cheap plain and graphic tees at Gen X, Dollar Stores, and Walgreens. Of course tees are also sold at malls, department stores, and boutiques. And there's always the staple of running to your boyfriend's closet or the merch booth for your favorite band.
(ASOS and American Apparel sell foolproof oversized tees that require zero modification.)
Shown: Cory Kennedy in a graphic tee. I know that some love, some hate her, but I adore her look. I wish she was my little sister so I could share style tips and raid her closet. I imagine her closet looks like a messy row of bins with maybe a hat rack of jewelry.
My first pick to pair a large t-shirt with is my first pick for bottoms in general - skinny jeans. Skinnies are at the same time easy, chic, comfortable and versatile.
Another choice is leggings. Yep, leggings. For the last three years, srsly, I have thought they were going out of style, yet they seem to be sticking around. Lucky for all us girls who still have brightly colored leggings, tights and warmers tucked in our underwear drawers. A t-shirt, opaque leggings and boots for fall... you really can't beat that look.
If you decide that you want to advance your t-shirt look to a sexier (er, skankier) level, wear it over a mini skirt, pair of cuffed shorts, or even hot pants. This combo with flip-flops is perfect for barbeques, or with some high boots could make you some extra cash.

Here M.I.A.works the oversized t-shirt look. Along with bold neon colors, the hip-hop-inspired large tee is one of her signature styles. Take a cue from M.I.A. and sport tousled, feminine hair around your face to offset the semi-masculine style of the large shirt.
The beauty of this look is its simplicity, but a few girlish touches show your personality and separate the fashionisha from the tomboys. A long necklace gives a layered, playful look. Personally, I would like the look with a huge pair of hoops and some chunky bangles. With baggy clothing, dainty jewelry will be practically invisible, so select pieces that will stand out.
For your feet, heels or boots are ideal for a chic statement, but anything goes. If you opt for trainers, keep them clean and tidy to avoid looking as though you're running errands (Even if you are just getting groceries, there's no reason to look like it!). If flip-flops are your thing, be sure your pedicure is up to date.

Above, Mary Kate Olsen does a slouchy white v-neck with slim-fitting pants and a heel for a look that's sexy, urban and feminine. Statement tees are fun, but it gets boring seeing the same phrase over and over (Hello, "Frankie Says Relax"), so look for a message tee that is especially you (I almost bought a "Parties Well With Others" last week), or bust out some iron-on letters and make your own message.
Whether you choose a tee that is slightly oversized like Mary Kate's or do the hipster look popularized by Cory and M.I.A., the t-shirt is a closet staple that can be played up or down and will never prove to be a waste of money -- worst case scenario, you can always rock it with a pair of panties and take it to bed.
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All long as I don't see Kate Bosworth wearing it, we're good.
this trend is on its way out along with skinny jeans and itty bitty vests...with the flare leg jean coming back for fall a form fitting t-shit is more appropriate.
this look is one that is only flattering to a select few pint size females
I just started rocking the oversized tshirt/skinny jean look about 1-2 months ago and i love it!! you're so comfortable yet stylish yet sexy. It all started because Nylon mag sent me an tshirt for subscribing that was too big for me and I loved the look. Awesome post.
I love the pic of Nicole Richie. She looks so sexy but so undone at the same time. One of the most popular books that the teen girls borrow from the library is called Generation T : 108 ways to transform a T-shirt by Megan Nicolay. You might want to check it out for some cool ideas.
I LOVE oversized t-shirts!
I've been waiting for this post :-)
Thanks for the tips, will definitely be taking them into consideration when I decide to wear some large t-shirts I haven't got much wear out of!
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