Spring in Chicago at Cindy's Rooftop

Sun-deprived Shoulders

It’s been a great week here in Chi-city, you guys.

hallie wilson in a rachel zoe top and white jeans outfit

chicago fashion blogger at one of chicago's best rooftop bars cindy's chicago athletic club

At long last, my sun-deprived shoulders are coming up for air and I think it’s safe to say we’re all feeling a liiittle less miserable on our morning commutes.

(Although my morning commute is in spandex and around 5 a.m., so I don’t see much other than a red-colored sun rising over the lakefront… Hard to complain about that, though — once you’re awake.)

rachel zoe off the shoulder ruffle silk top and white joe's jeans spotless denim collection chicago lifestyle blogger corals and cognacs in an orange off the shoulder top cute off the shoulder top and teal earrings hallie wilson shows how to wear white jeans before memorial day with style

Anywho: Thursday. At last!

Spring is here, it seems (sort of), which means it’s time to retire from the dive bar in favor of something a little lighter — quite literally.

how to style your white jeans this spring and summer

There’s nothing quite like rooftop season in Chicago — which is essentially code for rosé all day… Right?

Well, come Friday, at least. We’re close!

cute off the shoulder top and teal earrings

This weekend — and all warm ones to follow — I plan to camp out(doors) anywhere downtown against the city’s chic-looking skyline with a cocktail in-hand. Our warm-weathered months are at a minimum in the Midwest, so we take full advantage.


I’m working on building a list of my go-to summer spots in Chicago, but one of my favorite upscale jaunts is Cindy’s Rooftop (where these photos were taken), which is perched atop the Chicago Athletic Club.

The food and drinks are stellar, but their sun-soaked private patio is what takes the cake — it features an incredible view of quintessential Chicago.

hallie wilson in a rachel zoe top and white jeans outfit vineyard vines natural straw clutch for summer

This sort of occasion, of course, calls for a flowy top that flaunts a festive ruffle trim — in color that’s fun to flirt with. (This exactly style — Rachel Zoe ‘Gaia’ — is sold out in most sizes, but here’s a less expensive, very similar style.)

… And my new favorite earrings. I love them so much.

Admittedly, I used to turn my nose up at clip-on earrings, but hell — these are awesome. (And if you’re wondering — I eyeballed them for seriously two years before purchasing. Well worth the investment to accessorize anything in your wardrobe, in my opinion.) Browse more colors and styles below:

*Click to shop Oscar de la Renta earrings:


oscar de la renta turquoise teal clip on tassle earrings

TGI(A)F, friends. What’s on the agenda this weekend?

chicago fashion blogger at one of chicago's best rooftop bars cindy's chicago athletic club



Off-the-shoulder shirt: Rachel Zoe ‘Gaia’ top via Zappos
White jeans: Joe’s Jeans spotless skinny jeans (my fave!)
Tassel earrings: Oscar de la Renta (in more colors here)
Shoes: Tory Burch (old, similar pair here)
Natural straw clutch: Vineyard Vines (on sale, similar here)
Lipstick: Kylie Cosmetics #22

*Click to shop:


Iron & Honey Photography

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