Soooo. Flared jeans are back. High-waisted, 70s flared jeans to be exact. I love the flared look and if you’re not a fan of high-waisted pieces like me, you should be able to find plenty of mid- and low-rise that still fit the bill. Flared jeans can be VERY flattering on all body types. The flare does wonders for your legs and can literally take off 10 pounds. No joke. My boss comments on my weight every time I wear these. Every. Time.
There are a few things to consider when looking for a great pair, namely length and shoe choice. Length is paramount, but the length usually depends on the type of shoe you choose. I highly recommend heels because it gives you more height as a bonus to the cut of the jean. Lengthwise, shoot for jeans that skim the ground. Too short and they will hit your leg at the wrong spot and too long will give a frumpy look on top of making you trip! I love me some dark, polished flares and the darker color tends to be most flattering, but I encourage you to experiment with different washes. 
Outfit:
Leather clutch, thrifted–$5.00!, similar
Tank top, Old Navy, similar
Necklace, Cost Plus World Market (my new fave necklace–$15.00!!)
Jacket, Forever 21, thrifted
Jeans, Paige Denim, Laurel Hills Canyon, thrifted, similar
Shoes, Seychelles, similar (Seychelles is my favorite brand of shoes: high quality, retro sensibility. Look at DSW and Amazon for great finds on sale)
GSW Style Tip: If you can only have one good pair of flared jeans, aim for darker denim with a length that skims the ground. And wear heels! You’ll feel more polished and they can help with the length if you can’t afford a tailor.
Check out Style Files for more inspiration!