Ask HOPE ROBERTSON | Penny Loafers
How do you feel about penny loafers? There’s a really cute pair on page 229 of March’s Lucky magazine. I love the whole men’s/schoolboy look, but what would you pair them with to avoid looking like an elementary-ed teacher?
I feel like penny loafers haven’t been done right since 1995 when Alicia Silverstone rocked them in Clueless and we, the audience thought Cher’s style was the ultimate.
It’s been a while, right?
Thankfully, the definition of ‘penny loafer’ has evolved. Penny loafers from yesteryear have been re-vamped and updated, and today anything from a driving shoe to a high-heeled pump can be considered a type of loafer. My suggestion to you to avoid looking like an el-ed teacher — besides avoiding high-waisted Dockers khakis and old-school florals — is to find a ‘loafer’ you like that suits your personal style.
If you love high heels, I suggest finding a brogues with a thick — but not chunky — heel. I LOVE the chic black and white contrast of Façade’s Betty kiltie pump. Check out the sweet buckle and the kiltie fringe; this shoe is an instant classic that will outlast any menswear/schoolboy trend. They retail for $109.95 at Nordstrom.
As for flat loafers, your options are endless. Calvin Klein’s Monet loafer in red suede is a bright and buckled pair of flats 
that are super-streamlined. Take note of the moc toe and almost-invisible heel. They feature wear almost like a ballet flat. Zappos offers the Monet in four shades of suede for $80.00.
Another option for flats is Michael Kors’s Westside loafer. Fresh for spring in vanilla grained leather, these flats feature a rounded moc toe and contrast stitching. They’re an affordable and quality shoe, retailing for $63.90 at Bluefly.
