There’s a difference between looking like you tried and looking like you tried too hard, and it’s often fairly hard to tell where exactly that line is, especially when you’re dealing with new trends. The winter racks are filled with wearable, eye-catching silhouettes of the season, and it’s all I can do to keep myself from going broke as I cherry pick all these thrilling new pieces. However, one errant cut, bedazzle, or affectation in the wrong direction, and what was once a compelling new outfit can quickly become crowd-repelling. So as not to leave you hanging, here’s a little primer on how to look fashion victorious instead of a victim.
DO: Try out combos that involve neutrals and big, bold blocks.
Stella McCartney Colorblock Sweater, $830, available at Saks.
DON’T: Be too literal. A Mondrian-shirt will make you look like you just raided the museum gift shop.
Moschino Cheap & Chic Shirt, $677, available at Farfetch.
DO: Keep the brim wide, and the construction on point. You don’t want to skimp on a hat because you’ll wear it for as long as it lasts.
Rag & Bone Floppy Brim Fedora, $150, available at Stylebop.
DON’T: Opt for this fedora style. If you’ve seen it on a bro with a soul patch, just say no.
Windsor Gray Wool Fedora Hat, $12.90, available at Windsor.
DO: Try out roomy, graphic tunics in heavy silks.
Rag & Bone Bombay Top, $290, available at Rag & Bone.
DON’T: Go for the dress-over-pants look just yet. We’re actually kind of into this look at Chanel from the runway, but haven’t figured out a way to try it out IRL without looking costume-y. We’ll keep you posted, though…
Chanel pre-fall 2012, courtesy of Chanel.
DO: Keep the heel skinny, the platform minimal, and the height reasonable. This is your chance to channel your inner Audrey to perfection.
Dolce Vita Rosetta Pump, $129.99, available at Zappos.
DON’T: Go too high. We said Audrey, not Audrina.
Dolce Vita Devon Shoe, $139.90, available at Lori’s.
DO: Choose structured, modern pieces in simple cuts.
J.Crew Pencil Skirt, $120, available at J.Crew.
DON’T: Go too twee, lady-like, or youthful, otherwise you’ll risk looking like a geriatric 6-year-old.
MSGM Cropped Jacket, $728, available at Luisa via Roma.