Lindsey Weening, director of marketing and sales of eyewear at TOMS, works in a laid back office with a great outdoor area. "I like to wear an outfit that transitions from inside office to outside office." She opts for a button up shirt, Gap jeans, a versatile sweater, and brown booties.
Creative director of Wearable Experiments Billie Whitehouse loves her Gap denim paired with a varsity jumper and long white shirt. "This is my 'sportivo' outfit," she says.
As someone who constantly meets with athletes, sports companies, and technologists, Billie needs an outfit that makes her feel confident and sticks to her style. She opts for Gap's powder grey 1969 sateen high rise jeans.
New York photographer, Brian Morr wears his Gap 1969 Japanese selvedge denim for a day of exploring. "It's almost as if Gap has watched me grow up over the years. I have been shopping with Gap pretty much my whole life. It's more than a store to me," says Brian.
Tips for fall layering: "I usually go for simple but maybe mix up some patterns and throw in some color when you have the chance. Fall fashion shouldn't be dull."
Singapore-based musician Sandra Riley Tang loves her versatile Gap shirtdress. "I can wear it as a simple dress, or get creative by layering a skirt over it. It’s a piece for all occasions."
As a band member of The Sam Willows, Sandra travels often and always plans ahead of time. "I am a visual person so I like to see everything mapped out. If I am traveling to a country that does not converse in English, I always learn a few phrases in advance."
Founder of Brother Vellies, handcrafted shoes from Africa, Aurora James wears her Gap denim for a day at work. "Everyone should own a pair of simple black jeans. This super comfortable pair is the kind you never want to take off."
Originally from Canada, denim plays a huge role in her wardrobe. "I love denim and fall is a great opportunity to try things like layering jeans under a dress. Denim everywhere, please!"
Caitlin Crosby, founder of The Giving Keys, embraces 'athleisure' style in her Gap jogger pants. "This outfit is something I would throw on in the morning for a day of kicking it around the office. Casual is king!"
The Giving Keys not only helps individuals transition out of homelessness, but also creates a 'pay it forward' movement by encouraging people to pass along their jewelry and engraved keys with inspiring words. As a female entrepreneur, Caitlin's personal advice to young women is to embrace their unique characteristics and integrity.
Founder and director of Hello Mr. Ryan Fitzgibbon is sticking to the basics this fall. "At work I am surrounded by style-conscious guys who inspire my outfit choices. My 1969 slim fit Gap jeans are an essential that I can always rely on for my minimal-yet-layered style approach."
Aurora James, Founder and Creative Director of Brother Vellies, pairs her favorite prints with her Gap 1969 girlfriend jeans. "I love mixing prints, and these simple Gap jeans are the perfect neutral to pair with with my colorful outfit. "
Aurora founded Brother Vellies to introduce the world to her favourite traditional African footwear. She hires local artisans in South Africa, Kenya, and Namibia to handcraft shoes and sandals that speak to their ancestral heritages.
Singer-songwriter and philanthropist Caitlin Crosby wears The Giving Keys' new tank with Gap denim. "I feel very edgy with this take on a biker outfit. It matches the vibe of my vintage taxi cab car."
"While on tour for my music I started selling The Giving Keys at my merchandise tables and they really took off. I employ people who are trying to transition out of homelessness to make our jewelry and to engrave old keys with inspiring words."
Lifestyle blogger and GQ Insider Justin Livingston elevates his summer wardrobe with a floral print shirt from Gap and a neutral tie from menswear designer David Hart. He gives his look a casual spin by wearing Converse sneakers.
Hello Mr. founder and director Ryan Fitzgibbon takes time away from his daily routine for fresh perspective and to avoid the hustle of New York City. Here he wears his Gap 1969 slim fit jeans for a stroll around a park in Brooklyn overlooking Manhattan.
He loves light layering on New York's early fall days. "In the fall, one layer is all you need. I like to keep it minimal with a clean neckline."
Singer-songwriter and founder of The Giving Keys Caitlin Crosby wears her favorite Gap denim for a day at the office. Whether spending a day at the office or on tour for her music career, she loves wearing jeans. "I always feel together and myself when wearing denim."
Caitlin started The Giving Keys as a way to employ people transitioning out of homelessness in Los Angeles to make jewelry and engrave old keys with inspiring words. "The best part is, once someone wears our jewelry, they must pass the piece on to someone else who they feel needs the message more than they do. It's amazing to hear about everyone's 'pay it forward' experience."
Sayaka Shibuki is a yoga instructor in Japan. In the summer she goes to Yoyogi Park in Tokyo where she spends time reading books and enjoying picnics. For an afternoon at the park she wears her GapFit tank with printed yoga pants.
Airbnb photographer David Elliott gravitates towards versatile clothing pieces that can blend into many situations. "I steer away from wearing clothing that stand out too much. This Gap chambray shirt is perfect for traveling because it is easy to mix and match."
As a travel photographer, he is on the road often. "This year alone I have already taken 28 flights."
Fashion blogger Natalya of Five Five Fabulous arrived home from traveling to a surprise birthday lunch thrown by her sister. "After a long flight the last thing I wanted was to dress up so I opted for this simple Gap shirtdress."
Hitoshi Shimazaki, designer of outdoor Japanese fashion brand devadurga, enjoys mountain climbing in his free time. At Anea Cafe, his favorite coffee shop in Tokyo, he wears his Gap printed Lived-in shirt and plans his next travel adventure.
French architect Romain Costa is inspired by architectural culture, urban style, and electronic music. He wears a Gap short sleeved shirt and his Kennedy shorts for a weekend spent cycling through the city of Lille.