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Styling Tips 

How To Rock Oversized Attire Like A Street Style Star

Comfortable and cool AF.

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What's the quality that sets street style mavens apart from the rest of us mere mortals? You would think it's their abundance of silk Gucci matching sets, their stylish mini-handbags or their mastery of the four-inch stiletto, but it's none of the above (although those things do help). Their magnetism is all about their ability to subvert the ordinary and harness the unexpected — the language of too-cool-for-school, slouchy streetwear, for example. As the style has been popularized in the mainstream in recent years, oversized silhouettes have emerged as a major statement in the industry's lexicon. 

But as we all know, there's a fine line between looking like the next Cara Delevingne... and looking like you're swimming in the clothes your mom promised you'd "grow into". Thankfully, it's not about being a 5'11 supermodel — all you need to rock the oversized look can be encompassed in a few pointers about proportion, balance, cut - and, of course, making sure you have all the right accessories.

Ready to rock oversized like a fashion week regular? We've cracked the code for you below:

Watch Your Proportions


Image: Oliviakijo.com

The difference between a piece that's oversized and a piece that's overpowering is the way it fits your frame. So when looking for a trendy oversized blazer for fall, take into account both the size of the piece and the way it's cut. This is where things can get tricky — how baggy is too baggy? In general, even if the piece is voluminous, make sure it still accentuates the natural line of your frame. 

As for cut, you'll want to make sure that your pieces are hitting in the right places. If you've got an extra-large sweater on your hands, for example, the length shouldn't be equally as overwhelming — unless you're planning on wearing it as a dress, of course. Searching for just the perfect size or cut can be frustrating, but it'll be the difference between looking like you're slaying and looking slightly dowdy.

Mind That Balance


Image: Ivaniasmode.com

We used to think that the only way to balance out an oversized top was to pair it with leggings and ankle boots. Granted, despite being a bit passé, this technique still works — but we've been seeing ensembles styled in much more compelling ways. We love how chic a spacious sweater or blazer looks when paired with a midi skirt and a eye-catching shoe. Put on heels for a look that's more runway-ready, or slip on a bejeweled pair of slides for something that's stylish yet still practical for everyday.

Alternatively, step out in a billowing top and pant for the ultimate street-wise, fashion-forward statement — just make sure the pants fit well at the waist, as bigger should not mean falling-off-your-body. But don't over-do it on the roominess either. If you wrap an extra-long scarf around the entire look, people might start asking if you're feeling under the weather. 

Define the waist


Image: Vogue.es

Whether it be with a belt or an easy half-tuck, accentuating the waist is the key to keeping your figure while rocking an oversized look. If you're daring enough to take your sartorial inspiration directly from the runway, a striking corset belt à la Margiela could bring that much-needed definition to a roomier top. But if not, paying attention to the little details (pants that are well-fitted around the waist, knotting a sweater in front of behind as needed) goes a long way. A belt is useful if you want to play with structure — but if the look you're going for is comfortable and the opposite of TTT, experimenting with tying and tucking will be the best.

Get Your Accessories On Point


Image: Whowhatwear.co.uk

The right sunglasses, bag or even pair of earrings can take your outfit from running-errands-on-the-weekend to a full-blown, street-photographer-stopping lewk. With most commodious ensembles, you'll want to make sure your accessories don't add unnecessary clutter to your stylish silhouette, so go with earrings that are sleek, modern and that fit the aesthetic of your look. Smaller bags accentuate this grandiose style well, so pick up a structured purse or a fabulous mini-bag (another street style favorite). Add a pair of trendy shades — the small-'90s-frames-with-oversized-blazer look is a current favorite of Bella Hadid —, and you've got yourself an outfit worthy of a fashion week It-girl... and still comfortable AF.

Ready for your street style moment? Start by shopping our selection of stylish oversized pieces, from puffer jackets to the perfect statement pant.
1/27
Urban Outfitters BDG Willow Inside-Out Cropped Sweatshirt - $69
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2/27
&Other Stories Hooded Puffer Jacket - $245
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3/27
&Other Stories Fuzzy Mohair & Wool Knit - $95
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4/27
&Other Stories Wool Blend Oversized Coat - $245
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5/27
Zara Quilted Jacket With Hood - $70
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6/27
Zara Short Quilted Jacket With Shimmer - $119
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7/27
Zara Textured Sweatshirt - $119
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8/27
Zara Oversized Denim Jacket - $90
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9/27
Zara Oversized Roll Neck Sweater - $50
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10/27
Elvi Cream Ribbed Eyelet Sweater - $61
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11/27
Elvi Pinstripe Oversized Blazer - $58
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12/27
Elvi Hayley Hasselhoff Collection Ivory Long Coat - $77
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13/27
ASOS Oversized Tweed Scarf - $29
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14/27
ASOS Oversized Coat with Jaquard Print - $143
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15/27
ASOS Long Oversized Pastel Stripe Herringbone Scarf - $29
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16/27
ASOS CURVE Oversized Sweat Dress with Zip Detail - $29
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17/27
ASOS CURVE T-Shirt with Oversized Biker Rock Print in Wash - $20.50
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18/27
ASOS CURVE Oversize T-Shirt Dress with Curved Hem - $35
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19/27
Urban Outfitters BDG Jesse Oversized Cardigan - $69
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20/27
Urban Outfitters Lilly Zip-Up Faux Fur Jacket - $129
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21/27
BDG '80s Denim Trucker Jacket - $79
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22/27
Tory Burch Garrett Pleated Plaid Twill Wide-leg Pants - $400
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23/27
See by Chloe Cropped Wide Leg Trousers - $345
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24/27
Proenza Schouler Metallic Textured-leather Straight-leg Pants - $2,450
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25/27
Eloquii Wide Leg Button Culottes - $90
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26/27
Chloé Leather Culottes - $3,950
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27/27
Rut & Circle Pia Wide Pant - $28.50
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Cover Image: Offwithyourclothesblog.com
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