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  • Add a classic retro feel to your biking shoes by way of Chukka boots

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    Stylist Advice- How to Style Vintage Menswear Shoes… classic is key

    qDear Sharon: What to wear with these Bridgeport Hush Puppies shoes (pictured below)? I got these shoes a while ago at a Thrift Shop and they were so cute that I couldn’t let them pass me by.

    The problem is, when I brought them home, I didn’t know exactly what to wear them with… and it turns out that they’re actually shoes for men… but they look pretty unisex. Maybe I can pull ’em off?  I just don’t know how.

    I’m open to most types of styles (just nothing too revealing, clownish, or short like a tiny skirt or a crop top). I want to look feminine but a bit modest as well. Any ideas on how I can wear them? Thanks so much! (N. via Fashion Advice)

    >> MORE: How to wear it posts

    Reader pic of her vintage show find

    Reader pic of her vintage show find


    I thought of you the other day when I was walking the poodle in the East Village.  I spotted this girl tying up her bike and thought what a genius way to look cool while peddling around the city.

    Her boots were black rather than your tan, but it’s the same general vibe of a Chukka boot.

    There’s nothing wrong with wearing men’s boots if they fit you. The styling is menswear influenced on its own, like an oxford or motorcycle boot, it’s how you wear them that counts. When it comes to wearing vintage shoes, classic is always key.

    I would follow the styling of our street style snap and pair the boots with rolled skinny pants to show off a little ankle to break the heaviness. As your boots are tan, I’d try a slim chino or khaki jean to for a more pulled together monochrome vibe.

    Top the look off with something more structured, like a tailored coat or blazer and you’re good to go for off-handed, easy style that’s so perfect to wear when biking around the city.

    >>SHOP IT: I pulled a riff on the theme of Chukka boots to click about…

    JUST ASK: Do you need some quick stylist help to amp up your style?  Email us for Fashion Advice.