The J.Crew catalog is one of the best sources for accessory inspiration. They make me fall in love with the weirdest things. A few months ago the catalog had these black acetate frames that reminded me of my sixth grade science lab partner but somehow looked so cool with a simple outfit and high heels. It's an 'I'm wearing four inch heels, but secretly low maintenance - just look at my bad taste in eyewear' look that can be achieved with your basic closet essentials and a pair of thick plastic frames.
One of my cheap thrills in life is ordering glasses from Warby Parker's home try on program, wearing a new pair every day for a week with experimental shades of lipstick, and then shipping them back all for a grand total of $0. (It's crazy, they will ship you five frames for free with a postage-paid box to return them when you're done. But beware of the home try on trap: you'll end up falling in love and suddenly your collection of corrective lenses is out of control.)
Based on my studies of the J.Crew catalog, the guidelines for pulling off Waldo spectacles in real life are pretty easy to follow: wear them with an It-Brit hairdo on top of your head, a cool bag and classic pumps, and bright lipstick.
I found these great black high-waisted COH skinny jeans (that are really pretty much glorified leggings) and can't stop wearing them because they are so forgiving of all of the bad habits I picked up this winter. Warby Parker Winston frames in revolver black, suede Corso Como pumps, a navy velvet J.Crew tee, and a calfhair clutch from Madewell.
Thanks to Madison Weller for the photos!