Planning 10 Outfits for Days Ahead with Trendy Chickadee

Molly styles her favorite Sperry footwear in ten ways, for the days she can hit the town again.

Molly Hogan
May 15, 2020
in Self-Care

Self-care is more important than ever. At Sperry we’re encouraging you to take a little time for yourself every day. We’ve lifestyle and beauty blogger and influencer Molly Hogan, also known as Trendy Chickadee.

“With all of the craziness going on during this quarantine time, it felt so good to sort through my wardrobe and plan outfits for the future when I’m able to get out of the house and explore! For the first time in a while, I felt excitement about the months ahead and started to look forward to days spent on the beach, at the farmers market and gathering with family + friends.

While we may be safer at home for now, I know there will be a day when I can throw on my Sperry shoes and hit the town!”


“This A/O Boat Shoe is, in a word, classic. I love the rich brown leather look, and how this shoe can pull together any outfit! I’m always pulling brown, leather accessories from my wardrobe to compliment these classic boater shoes. Styling them with distressed denim, a felt hat and a Moroccan market bag is my go-to!”


“The metallic color of this Seaport PLUSHWAVE Woven Loafer is so cute and a little bit fancy! While it can totally be styled with jean cutoffs and a casual sweater, I’d also wear these to a daytime wedding or bridal shower. This shoe can easily go from day to night, which is a staple when packing for a long weekend or for days when work turns into happy hour drinks!”


“I might as well order another pair of the Crest CVO Retro Sneakers now, because I’ll be wearing them everyday! This sneaker is the ultimate everyday shoe, for running errands or going to brunch with the girls. It’s super comfortable, but elevated with leather laces and stripe detail. I’d style this with anything from a sweatsuit to a mini dress…and everything in between!

One thing I look for over everything else in a brand is quality. So it’s a no-brainer that I’d be sharing ten looks styled with Sperry shoes today! Sperry is a truly iconic brand that’s been creating handcrafted boater shoes, sandals + more for over eighty years. While you may know them for their classic “boat shoes”, they have so many styles available for women, men and kiddos!

As you can see, a pair of Sperry’s can be worn with just about anything from casual denim to feminine dresses + skirts! I had so much fun playing around with different looks, it was difficult to stop after ten.”

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