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Photo: Katie Friedman

How do I wear sneakers and a dress without looking too young?

A: Finally, it’s warm enough that a question about dresses can be asked. How joyous! Personally, I love the combination of sneakers and dresses. The pairing helps keep things casual when you may feel overly girly. However, I do understand the worry that the look can feel very young. I try to avoid this by keeping the length of my dresses on the longer side: A midi-dress is the perfect length to wear with sneakers. While a short dress might make you feel a little high school, a longer dress will give you some sophistication points.

Today I’m wearing a vintage dress that I picked up during my trip to Australia, a striped oxford from the now defunct Rugby by Ralph Lauren line (R.I.P), and classic white Vans sneakers. Now, you may remember that I have quite an affinity for Stan Smith kicks, but they’re leather and warmer weather really calls for a canvas shoe. I do like to change it up every now and again.

Related: Ask DaniELLE: How do I go From Corporate to Cool?

To replicate this look, I would suggest avoiding a dress that’s too short or poufy. Keep the silhouette simple and streamlined, yet still feminine. Another trick: Including some masculine touches—like layering a button down shirt—add an element of surprise that takes some of the focus off the fact that you’re wearing sneakers with a dress.

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“What I started to see were these amazing brands coming into my manufacturing facility with tremendous talent, but without the ability to get capital or the expertise they needed to grow,” says McDougall, the chief executive officer and director of Democratique. A new business idea dawned on him: to help made in the USA fashion brands scale up, incubator style, but to also create a parent company that would be an umbrella for these independent brands.