To help us create an inclusive platform for fashion knowledge, we've asked our resident aesthetic ace Winona Rose to answer our questions—and yours!—about how to look our best, even if the fashion industry has dealt us the worst of hands.
Dear Winona,
I have to admit, I struggled a bit—at first—as to what to ask you. I myself am a devoted thrift shop hound and love clothes. I know strapless dresses are not my look (I become suspiciously akin to a line-backer) and high-waisted pants give me an ultra camel-toe. The point is, I don't feel intimidated or overwhelmed or made-lumpy by Fashion—I dig it like a proper theater kid does.
UNTIL, that is, I have to look "professional." I basically just resort to wearing black or a brutal blazer and commit to feeling uncomfortable and vaguely ugly all day. So, I am asking you, from the bottom of my funky-freshish heart: how do I maintain my sense of style (without looking dumpy and frumpy or like I'm dressing up as a neo-Jackie O) while still looking like I could cut a mean rug at the corporate conference table?
Yours in perplexed perpetuity,
Katie
Dearest Katie,
First off let me say I totally relate to your corporate fashion conundrum. I love expressing myself through my clothes and when I’m unable to do that I have a hard time, like, functioning in society. When I got my first “real” job, I looked at my closet full of vintage dresses, funky thrifted blouses, and sequined mini skirts and had a legit panic attack. Many years of tragic blazers and Old Navy trousers followed before I was able to find the sweet spot between my personal style and “office appropriate.” 
But I have good news for you, gleaned from years of getting it wrong, myself! As long as you don’t work in an uber-conservative office environment where unadorned pantsuits are the norm, the definition of “professional attire” can be surprisingly open-ended. There’s nothing inherently unprofessional about vintage clothing, interesting prints, unique styles, and bold colors. Especially when you live in a creative city and work in a creative field, as you do. Obviously super revealing and/or casual clothing should be saved for the weekend, but that doesn’t mean you’re relegated to all black or that one sad blazer on corporate meeting days. The secret to looking put-together and professional, no matter what you’re actually wearing? Impeccable fit.
Find an awesome tailor if you don’t have one already, and bring them some of the pieces in your closet that you feel are right on the edge of being conference table-appropriate. Say you want these garments to look like they were custom-made just for you. You don’t have to do this with your whole wardrobe of course (because $$$), but get a few pieces altered to fit you flawlessly. The difference between an off-the-rack garment and one that’s been tailored is staggering. And trust me, a classic vintage sheath that fits you like a glove and makes you feel amazing is going to project a much more polished, confident image than a saggy Ann Taylor blazer that makes you feel ugly and frumpy.
That being said, if you want to avoid falling into the “neo Jackie O” trap, pay special mind to your accessories. “Balance” is your mantra here. A vintage dress with vintage accessories is going to read too costumey for the office, as is a bold printed blouse paired with bold jewelry. If you’re letting your creative style shine through in your clothes, choose accessories that are streamlined, simple, and modern. Same with your hair and makeup. If you’re rocking a funky skirt, leave your turquoise eyeliner at home that day. If you’re wearing a vintage suit, skip the victory curls and red lipstick. Creative/vintage/colorful outfits are totally fine for the office; just be sure to surround them with modern elements to convey a more sophisticated image and avoid looking like an extra from Mad Men.
Alternatively, if you’re wearing a simple outfit and want to express more of your personal style, do it with accessories. Even those boring basic black outfits can easily be livened up with a chunky necklace, colorful belt, or your favorite “art teacher at an alternative high school in the ‘70s” shoes.
Now go forth and lean in, and look fabulous while doing it.
Would you like to be featured in Off The Cuff? Please submit a fashion question along with pictures (if you please) to Winona Rose at Ravishly@Ravishly.com.
