Italian blogger Giotto Calendoli wears his Gap bedford jogger shorts with a simple grey sweater for a day of relaxing by the water in Milan. He loves early summer days like this one when there is a slight breeze in the air.
Elliot and Natalie Bergman, the brother and sister duo behind band Wild Belle, pair their favorite Gap basics with edgy pieces. "We loved mixing Gap's chambray shirt and relaxed henley with rock 'n' roll accessories and leather pants."
When selecting outfits for their concerts Natalie looks to music legends like Sun Ra, Keith Richards, and Jimmy Hendrix for style inspiration. "When we’re touring we don’t have much room in the van, so I usually have one main blouse and a great pair of leather pants."
Refinery29's Grace Choi carries her Gap leather drawstring bucket bag on a summer stroll. "Colours aren’t the only way to make a statement this summer. Mix prints into your look with accessories, like this snake print bucket bag."
Liz and Louie of band HOLYCHILD love to incorporate relaxed pieces like Gap's sleeveless striped tee and floral pool shorts into their edgy looks. "These are both classic pieces that we wanted to play with for a fun disco-inspired look."
Their vibrant "Brat Pop" music style is reflected in their personal style and the duo is not afraid to go out of their comfort zones. Liz says that her current fashion inspiration is Disco Sport: '70s colours and fabrics with a Sporty Spice sensibility.
Russian TV producer Marusia Karmen pairs her Gap sexy boyfriend denim shorts with a linen shirt and pastel sneakers for a day of biking around the park. She ties Gap's boyfriend shirt at her waist for a lightweight summer layer.
London-based artist Nas Abraham stays cool in the heat of summer in his Gap lightweight t-shirt and seersucker blazer. He adds a bit of contrast to the look with his white wash 1969 straight fit jeans.
Airbnb host and event planner Natasha Lo wears her Gap denim maxi dress for a day at the studio. "Paired with sneakers, this dress is perfect for moving around in and getting things done."
To celebrate Pride this month Natasha hopes to recognize everyone in her life that has taken the stance to shine in their true colours. "I am inspired by them every day, and as an Airbnb host I have the unique opportunity to take their inspiration and share it with those around me."
Refinery29 editor Annie Greenberg wears her Gap tailored heathered shorts while relaxing on a fire escape in New York City. She loves that these shorts are relaxed enough for casual summer afternoons and chic enough for dinner with the parents.
White with navy is her go-to classic colour combo for summer. "I like to mix up the traditional 'nautical' theme by adding cropped jackets and unexpected textures to make the ensemble feel luxe."
Fashion photographer Alex Finch pairs Gap shorts with loafers for an easy and casual look while traveling in Seoul. He enjoys capturing the local surroundings while feeling relaxed in his go-to basics.
Blogger and globetrotter Park & Cube spends a sunny day outside reminiscing about her childhood. "I love spending time on my pennyboard discovering the neighbourhood just like how we used to when we were twelve!"
She wears her Gap shirtdress to feel relaxed and chic at the same time. "A loose, light dress like this one is ideal for dressing up or down. I tied a light jacket around my waist and added my trainers and a small cross-body pouch for snack money!"
Once she's done boarding, she can dress the look up for an evening dinner or event. "I love that this dress comes with a belt that allows you to cinch in the waist for a bit more shape and a more polished look."
Creator of Hello Mr. and self-proclaimed "tennis pro wannabe" Ryan Fitzgibbon lets it all out on the courts in his Gap stripe polo. "Publishing a magazine can put you in some high stress situations, and playing tennis helps me decompress."
His personal style both on and off the court is comfortable, minimal, and smart. "To me, Gap is simply classic, like a reliable friend who is always there for you."
Ryan Fitzgibbon, creator of Hello Mr. magazine keeps his style simple on his days off. "When I don't have work, I love taking it easy around my home in Brooklyn. I love how simple and comfortable this Gap V-neck t-shirt is."
To celebrate Pride in June, Ryan looks forward to rooftop parties with his friends. "There is nothing better than being above the action, listening to music, and feeling accepted by an entire community of supporters. Plus the weather in New York City is perfect in June."
Style blogger Anthony Urbano of Closet Freaks hangs out in New York wearing his favourite Gap basics. "My summer style is very casual and minimal so I stick to comfortable, no-fuss staples."
He layers the Ikat denim worker shirt over his Lived-in print pocket t-shirt for a cool summer look. "I love the prints and coordinating blue hues of these pieces. No matter where I’m going or what I’m doing, wearing shades of blue always puts me in my sartorial comfort zone."
Style blogger Anthony Urbano of Closet Freaks believes that being confident in your own skin applies to your personal style. He loves making adventurous sartorial choices but also appreciates anchoring his wardrobe with timeless classics. "Gap has always been a brand that I rely on for authentic, casual wardrobe staples."
To celebrate Pride this month Anthony will be attending events in NYC including the historical march down Christopher Street. "In New York City there’s an overwhelming sense of support and pride in the air, and that’s what I love the most."
Bethany Cosentino of band Best Coast wears a Gap relaxed stripe tee with a form-fitting skirt for a sophisticated-cool look.
As a performer who is always traveling, Bethany prefers comfortable and casual pieces that she can add her own unique twist to. "I think that my career as a musician has allowed me to be myself in so many ways, including my fashion choices."