If you need to find jill wheeler, your best bet is to check the beach. If she’s not teaching a standup paddleboard yoga class, she’s either kite boarding or running. But whatever endorphin-charged activity she’s engaged in, one thing is guaranteed: she’ll look adorable while doing it.
Wheeler runs the Naples-based Wellfit Institute, a discovery-based, multidisciplinary group that helps guide people to happier, more fulfilling lives. Before running the institute, she was a surf instructor, a serious rock climber and a guide with Outward Bound. Part adventurista and part fashionista, Wheeler has always been committed to looking good — even when she hasn’t had a shower.
And if you ever catch her out on the town, you’d never guess that mere minutes ago she was wringing saltwater and sand from her hair. We caught up with Wheeler to hear how she goes from beach to black tie and back again, without ever losing her looks.
When did you start getting interested in fashion?
I grew up on a boat and we’d spend part of the year in the islands and part of the year up north. When I was 14, we moved to Connecticut and at the end of the school year, everyone received superlatives. I got best dressed and I remember walking on stage and just laughing. That year my best friend and I had started a little tie-dye company, we tie-dyed these matching outfits — shirts and cutoffs and tube socks — It was the 80s. But I’ve always loved wearing things that were different, wearing things that no one else had.
Where do you think you got that love of wearing unique things from?
I’m a twin, and my parents used to dress us alike, and at some point I think I got sick of that group identity. I wanted to be my own person, so I think I started expressing that in my clothing. I even remember my mom saying to me ‘Jill, why can’t you just wear normal clothes like everyone else?’
What about when you were working as a mountain guide, how did you stay trendy on the trails?
You know it was always important to me to bring a girly affect to my climbing. I think most of the time I was the only girl, and by having this feminine energy I was able to remind everyone that, hey, I’m not just one of the guys. During a lot of the Outward Bound trips we’d be so dirty, but that doesn’t mean you can’t be cute.
So how do you make workout clothes cute?
I’m always looking for things that are a little bit different. Cute tank tops or tube tops — I wear a lot of strapless tops while teaching, which you don’t see all that often. Sometimes it’s as simple as adding a neat headscarf or something unexpected to your look. But you’ll never catch me in a T-shirt. I am just not a t-shirt girl; I’d rather wear a cute tank than a T-shirt.
What about your charity work? You’re on the board of the Naples International Film Festival, what do you wear to galas and fundraisers?
I love dressing up but I don’t shop all that often these days. In fact, I’m okay with wearing a dress I wore a couple of years ago but maybe with different accessories to change it up. I love things that are really unique — I won’t spend money on Luis Vuitton or things like that, but I will spend money on something that’s like a piece of art. Other than that, I tend to love things with natural-looking elements, organic textures and a balance between fitted and flowy.
Where do you go for fashion inspiration and where do you shop?
I have to give a shout out to Lululemon; I’m an ambassador for them and I love its stuff and the company. But otherwise, I’m really a local boutique shopper; I avoid big box stores and national chains. As far as inspiration goes, Pinterest has some really cute looks. I don’t really read fashion magazines but if I come across one and I see something I like, I’ll tear it out. I’m a very visual person, so I’ll take photos of things I like and try and recreate them.
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