John and I had plans to spend Labor Day weekend in Chicago…a 45th-anniversary gift from our sons.  But then “Hurricane Ida” happened, and our south Louisiana family came for an extended stay…including my 91 ½ -year-old mom!  Though our trip was canceled, that isn’t stopping me from sharing the “windy city” travel style!   

Ralph Lauren Chicago

Ralph Lauren Chicago

I hate getting dressed up…said nobody ever.  For dinner at Ralph Lauren’s restaurant RL, I was planning to wear a vibrant floral Christopher John Rogers dress I purchased in late spring at Target.  I’m also loving a stunning floral dress from Farm Rio…perfect for when you feel like getting dressed up.  

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Are you familiar with Weka sneakers?  I’m smitten with their buckle embellished black sneakers.  Don’t you think they pair perfectly with black jeans and a green sweater?  To complement your chic city style, add LL Bean’s classic utility jacket, a Lululemon crossbody pouch ideal for Chicago’s architectural boat tour, and a Susan Shaw bangle to glimmer in the sun.

Chicago Architecture Boat Tour

Of course, you will want to look tourist-fab when walking the Magnificent Mile.  So, I’m styling light brown joggers with a long-sleeved J Crew striped t-shirt and orange vest.  Pair these with white sneakers and a mini crossbody tote.  Finish the look with a reversible polka-dot or animal print bucket cap and orange sunglasses.  And congrats on getting your 10,000 steps in!  

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  I must admit….“hanging out” in Chicago would have been awesome but “hanging out” with my family was priceless!!!  

Holley Williams is a personal stylist specializing in closet inventory, seasonal shopping, and wardrobe consultation.  Be sure to check her Holley Williams Style on Pinterest.  Contact Holley at [email protected].