Wide-legged pants have been making a reappearance for awhile, and wide-legged jeans especially are making a huge comeback. Like with skinnies, it's a look I suggest everyone try at least once. While I don't plan on filling my closet with epic '70s flares, I will be picking up at least one pair of the funky style for this upcoming autumn. I hope to find a pair that's just slightly high-waisted, which I will pair with a white tank and a warm scarf when the leaves begin to fall. My first concern, though? What shoes to pair with the look...
The number one rule is for your pants to never drag on the ground, but you don't want to be rocking high-waters either. Find a happy medium so that your pant legs fall half an inch to an inch from the floor. This should be just enough to show off your cute peep-toes without anyone wondering if there's a flood a-comin'.

When dressing in a pair of wide-legged pants, keeping the top slim is key to looking neat and put-together. See Rachel Bilson above, using a structured jacket (left) and a top that cinches at the waist (right) to create a flattering line. You can see that the light-colored jeans add bulk to even Bilson's tiny body, so drawing attention to the waist is important so as not to lose your frame in the large amount of clothing. (A darker wash will also instantly slim you down and make the wide leg appear less dramatic.)
Because wide-legged jeans and trousers can be unflattering, it should come as no surprise that I am recommending they be worn mainly (if not only) with a high heel. Some specific style picks:

A peep-toe helps create a long line down the body, and also adds easy sex appeal to an otherwise playful look.
The two looks above are my favorite ways to wear a wide leg. Kate Moss goes with a slightly high-waisted jean and an indie-style sweater. Victoria Beckham goes all out in a high-waisted pant, simple black top and belt, and platform peep-toes that may be from her Spice Girl years. I normally do not condone platform shoes unless you're on a pole, but it works with the seventies throwback of wide-legged jeans. Keep the top half of your look simple, fresh and modern.
Wedges, like platforms, are another look I find it hard to be entirely in support of. Like the former, they remind me of my middle school days. Worn with a giant flare, however, the look is funky and fun. Pull on some wedges with your wide-legged pants and adorn yourself with some big bangles and bigger sunglasses for the remainder of summer.

Whether you choose a boot with a small kitten heel or a full-on stiletto, my favorites are boots with a long or pointed toe that will demand attention even worn with a dramatic mega flare. Boots can be straightforward chic or do it up like Jessica Simpson for a look that's a little bit country. (I actually can't tell if she's wearing boots or just heels at left, but I can so imagine her in that same outfit and full-on cowboy boots.)
The wide-legged pant is a look for the fashion brave, so if you rock it, own it. Don't forget that fashion is fun! Writing about shoes has really made me think about style and reinforced something I already knew - When in doubt, slip your feet into a pair of sexy heels.
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I am petite and found some really flattering wide-legged pants, I had them hemmed and wore the shoes I would normally wear with them to the tailors. The boot with a pointed toe works very well, as I can attest to.
I know this is really beside the point, but I'm so over Rachel Bilson. Victoria and Kate Moss can do no wrong in my eyes. Refusing to smile... coke headed activities... whatever. They're my top two fashion (and weight) icons.
I'm with you on the wedges - normally wedges go only with the polyesther pantsuits my 7th grade home ec teacher wore. But slap on some wide legs and I loooove it.
I love Victoria Beckham's look! I've been reluctant to try out the wide-legged pants, but I think next time I go shopping I might have a look around and maybe try some on.
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