Successfully combining high and low is the most rewarding dressing experience I can have.
I love vintage Levi 501s. I think I own as many as 10 pairs, all with different distressing and wear. They're so freaking AMERICAN! I've found most of mine in thrift stores and on Ebay, but if that kind of treasure hunting isn't your thing, you can find some amazing relics in Urban Outfitter's Urban Renewal section.
My favorite way to wear them is with crisply tailored jackets, pretty blouses, and super feminine heels. Elevating old denim with tailored clothing is something that becomes necessary as one gets older. Although I adore the youthful waifs flaunting their under-butt-cleavage in vintage denim cutoffs - it's not so pretty on a gal my age. By keeping the silhouette grown-up, but swapping a boring pant for beat-up denim, I can satisfy the waif and the lady inside.
Jacket: Ann Taylor (Similar Here) Shirt: Zara Blouse with Pleats at Front Jeans: Vintage Levis 501 (Similar Here) Shoes: Schutz Gilberta Suede Pump Bag: J Crew Biennial Satchel Necklaces: J Crew (Embellished with teal ribbon by me) Frames: Thrifted (For $1 !!!!)