Striped off-the-shoulder shirt dress in Navy and White

Solo Mission

Perhaps it’s me being stubborn on the style front, but I’m still holding out hope for an endless summer over here…


off-the-shoulder-dress-in-navy-and-white-stripesderek-lam-for-intermix-dress remote-places-to-work-around-chicago-city-winery-riverwarlk best places on where-to-drink-wine-outside-in-chicago hallie-wilson-chicago-style-blogger-wearing-an-off-the-shoulder-shirt-dress-in-navy-and-whtie-stripes vineyard vines straw-clutch-and-bouquet-of-flowers-from-whole-foods

In fact, as I type to you, it’s a beautiful, 70-something-degree day in Chicago — and don’t be mad, but I’m just gonna say it: The first day of fall isn’t until September 22.

… So, like, technically, we’ve got a week and some change to go. Can we please hold on the Pumpkin Spice Latte’s for just a little longer, my friends?

(Just kidding… Kinda. To each her own, I suppose.)

derek-lam-for-intermix-navy-and-white-stripe-off-the-shoulder-dress navy-and-white-stripe-off-the-shoulder-shirt-dress

As a bit of a follow-up to Friday’s post (on learning to say no and take time for yourself), these last remaining days of “Summertime Chi” have been all about making the most of the Windy City’s longer(ish) days and warmer nights — whether it’s an outdoor dinner on the grill or a happy hour well-spent with a glass of wine along the Chicago River.

hallie-wilson-chicago-fashion-blogger-wearing-a-derek-lam-for-intermix-exclusive-dress-and-loeffler-randall-wedges cute-off-the-shoulder-summer-dress-in-navy-and-white-stripes straw-clutch-from-vineyard-vines-and-shellac-cream-puff-manicure cute straw-clutch-and-essie-blanc-white-manicure

Do you ever take yourself out for a drink? Or a solo dinner?

I love it — I used to go to the movies by myself way back in the day. (I’d sneak a shitload of snacks in, too. Rebel, rebel!)

City Winery is one of my favorite outdoor destinations downtown to sit with my computer and a glass of wine (as is Cindy’s Rooftop, if you’ve never been). City Winery on the Riverwalk doesn’t have wifi, so I use it as a productive excuse to just sit and write. Or, you know, people-watch.

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I’ve got a shitload of writing to do, so if you need me after work-hours this week, odds are you know where to find me… Although don’t be surprised if I’m wearing workout spandex and not a cute striped dress. Or at the very least, a dress with my go-to everyday sneakers.

(FYI: The exact dress style I’m wearing is sold out, but I found a near-identical pair for you and linked it here. On sale for under $60, too!)

off-the-shoulder-shirt-dress-with-stan-smith-adidas-sneakersbest place tfor happy hour after work city-winery-chicago

*In this post:


Off-the-shoulder dress: Derek Lam for Intermix (sold out, similar version on sale here)
Leather lace-up wedges: Loeffler Randall (in black)
Straw clutch: Vineyeard Vines (sold out)
Sneakers: Adidas Originals Stan Smith’s (size down)

Click to shop:


Foundation: bareMinerals Complexion Rescue in ‘Desert’
Lip color: NARS satin lip pencil in ‘Rikugien
Nail polish: Shellac ‘Cream Puff’ (the best white!)
Mascara: bareMinerals

Click to shop:



Iron & Honey Photography

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