Windy City Street Style

The Vintage Bazaar, a monthly showcase of timeless fashion and quirky trinkets, is perfect for catching up on the latest street style fashion in Chicago.
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The Vintage Bazaar, a monthly showcase of timeless fashion and quirky trinkets, is perfect for catching up on the latest street style fashion in Chicago. This market is filled with people whom you're always wanting to ask "Where did you get that from?"

Follow some of the most fashionable shoppers as they peruse objects from the past in this uptown attraction.

Chicago Hooked: Vintage Bazaar
(01 of22)
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Nikea keeps it flirty and cool with a heather tank top and flowing cream skirt. She tones down the whole color palette of the outfit but adds a pop of red in her patterned head wrap. My favorite detail of her look is the gold Nixon men's watch which I thought was a vintage piece. This look is perfect for a summer bike ride around the city or just staying at home to finish up those pesky chores.
(02 of22)
Open Image Modal
Nikea keeps it flirty and cool with a heather tank top and flowing cream skirt. She tones down the whole color palette of the outfit but adds a pop of red in her patterned head wrap. My favorite detail of her look is the gold Nixon men's watch which I thought was a vintage piece. This look is perfect for a summer bike ride around the city or just staying at home to finish up those pesky chores.
(03 of22)
Open Image Modal
Nikea keeps it flirty and cool with a heather tank top and flowing cream skirt. She tones down the whole color palette of the outfit but adds a pop of red in her patterned head wrap. My favorite detail of her look is the gold Nixon men's watch which I thought was a vintage piece. This look is perfect for a summer bike ride around the city or just staying at home to finish up those pesky chores.
(04 of22)
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Ally is a musical theatre student in downtown Chicago who can pull off just about any look. Here, she pairs a nautical-themed blouse trimmed in navy stripes with denim cutoffs and caramel-colored cowboy boots. Her accessories include a pewter owl bangle, an indigo headband, and a turquoise ring (a touch of southwest flavor to go with her boots).
(05 of22)
Open Image Modal
Ally is a musical theatre student in downtown Chicago who can pull off just about any look. Here, she pairs a nautical-themed blouse trimmed in navy stripes with denim cutoffs and caramel-colored cowboy boots. Her accessories include a pewter owl bangle, an indigo headband, and a turquoise ring (a touch of southwest flavor to go with her boots).
(06 of22)
Open Image Modal
Ally is a musical theatre student in downtown Chicago who can pull off just about any look. Here, she pairs a nautical-themed blouse trimmed in navy stripes with denim cutoffs and caramel-colored cowboy boots. Her accessories include a pewter owl bangle, an indigo headband, and a turquoise ring (a touch of southwest flavor to go with her boots).
(07 of22)
Open Image Modal
Ally is a musical theatre student in downtown Chicago who can pull off just about any look. Here, she pairs a nautical-themed blouse trimmed in navy stripes with denim cutoffs and caramel-colored cowboy boots. Her accessories include a pewter owl bangle, an indigo headband, and a turquoise ring (a touch of southwest flavor to go with her boots).
(08 of22)
Open Image Modal
Ally is a musical theatre student in downtown Chicago who can pull off just about any look. Here, she pairs a nautical-themed blouse trimmed in navy stripes with denim cutoffs and caramel-colored cowboy boots. Her accessories include a pewter owl bangle, an indigo headband, and a turquoise ring (a touch of southwest flavor to go with her boots).
(09 of22)
Open Image Modal
Ally is a musical theatre student in downtown Chicago who can pull off just about any look. Here, she pairs a nautical-themed blouse trimmed in navy stripes with denim cutoffs and caramel-colored cowboy boots. Her accessories include a pewter owl bangle, an indigo headband, and a turquoise ring (a touch of southwest flavor to go with her boots).
(10 of22)
Open Image Modal
Ally is a musical theatre student in downtown Chicago who can pull off just about any look. Here, she pairs a nautical-themed blouse trimmed in navy stripes with denim cutoffs and caramel-colored cowboy boots. Her accessories include a pewter owl bangle, an indigo headband, and a turquoise ring (a touch of southwest flavor to go with her boots).
(11 of22)
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Poppy is my youngest street style find to date! At 3 years old, her fashion choices are already cutting-edge. Plus check out her pose as a teapot to mimic the bright pattern on her cap-sleeved dress. Poppy is a natural-born fashionista. She adds more fun to the look with her purple plastic sandals fit for a Disney princess. The Spongebob Squarepants band-aid is the icing on this fantastically age-appropriate ensemble.
(12 of22)
Open Image Modal
Poppy is my youngest street style find to date! At 3 years old, her fashion choices are already cutting-edge. Plus check out her pose as a teapot to mimic the bright pattern on her cap-sleeved dress. Poppy is a natural-born fashionista. She adds more fun to the look with her purple plastic sandals fit for a Disney princess. The Spongebob Squarepants band-aid is the icing on this fantastically age-appropriate ensemble.
(13 of22)
Open Image Modal
Poppy is my youngest street style find to date! At 3 years old, her fashion choices are already cutting-edge. Plus check out her pose as a teapot to mimic the bright pattern on her cap-sleeved dress. Poppy is a natural-born fashionista. She adds more fun to the look with her purple plastic sandals fit for a Disney princess. The Spongebob Squarepants band-aid is the icing on this fantastically age-appropriate ensemble.
(14 of22)
Open Image Modal
Poppy is my youngest street style find to date! At 3 years old, her fashion choices are already cutting-edge. Plus check out her pose as a teapot to mimic the bright pattern on her cap-sleeved dress. Poppy is a natural-born fashionista. She adds more fun to the look with her purple plastic sandals fit for a Disney princess. The Spongebob Squarepants band-aid is the icing on this fantastically age-appropriate ensemble.
(15 of22)
Open Image Modal
Nikki is perfectly at home in The Vintage Bazaar as she wears a 50's sundress in citrus fruit colors with bobby socks and Mary Janes. With a fanny pack from the 80s (she wanted to take it off, but I insisted she keep it on!), white bolero vest, and collection of bangles, Nikki introduces other decades into her outfit. Fashion is playful and that's exactly what Nikki exudes.
(16 of22)
Open Image Modal
Nikki is perfectly at home in The Vintage Bazaar as she wears a 50's sundress in citrus fruit colors with bobby socks and Mary Janes. With a fanny pack from the 80s (she wanted to take it off, but I insisted she keep it on!), white bolero vest, and collection of bangles, Nikki introduces other decades into her outfit. Fashion is playful and that's exactly what Nikki exudes.
(17 of22)
Open Image Modal
Nikki is perfectly at home in The Vintage Bazaar as she wears a 50's sundress in citrus fruit colors with bobby socks and Mary Janes. With a fanny pack from the 80s (she wanted to take it off, but I insisted she keep it on!), white bolero vest, and collection of bangles, Nikki introduces other decades into her outfit. Fashion is playful and that's exactly what Nikki exudes.
(18 of22)
Open Image Modal
Nikki is perfectly at home in The Vintage Bazaar as she wears a 50's sundress in citrus fruit colors with bobby socks and Mary Janes. With a fanny pack from the 80s (she wanted to take it off, but I insisted she keep it on!), white bolero vest, and collection of bangles, Nikki introduces other decades into her outfit. Fashion is playful and that's exactly what Nikki exudes.
(19 of22)
Open Image Modal
This gentleman is timeless in a tri-toned plaid shirt paired with a vintage bow tie and oxfords. The leather accessories from the belt to the bag and the shoes give his whole look a rugged and modern twist. Grant says that this is his everyday look - refined but quirky, and I'm a fan.
(20 of22)
Open Image Modal
This gentleman is timeless in a tri-toned plaid shirt paired with a vintage bow tie and oxfords. The leather accessories from the belt to the bag and the shoes give his whole look a rugged and modern twist. Grant says that this is his everyday look - refined but quirky, and I'm a fan.
(21 of22)
Open Image Modal
This gentleman is timeless in a tri-toned plaid shirt paired with a vintage bow tie and oxfords. The leather accessories from the belt to the bag and the shoes give his whole look a rugged and modern twist. Grant says that this is his everyday look - refined but quirky, and I'm a fan.
(22 of22)
Open Image Modal
This gentleman is timeless in a tri-toned plaid shirt paired with a vintage bow tie and oxfords. The leather accessories from the belt to the bag and the shoes give his whole look a rugged and modern twist. Grant says that this is his everyday look - refined but quirky, and I'm a fan.

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