3 Ways to Wear: A Classic Slip Dress

classic slip dress

At the end of the Summer, I was scrambling to find the perfect dress that could feel soft and romantic, yet still city chic for a photoshoot E and I decided to do with the amazing Emma Chasteen to celebrate 5 years in Chicago.

Cue this classic slip dress from Target. It was perfect for our sunset with Emma, and I’ve been able to wear as a daytime and date night look since then!

Why get something you can only wear once, or in one way? I can see this dress working for a wedding or weekend brunch (which hopefully can happen more again soon).

I know you can get as much out of a dress like this as I have, especially with the upcoming holiday season. Check out 3 ways to wear a classic slip dress below and how you can recreate this look yourself!

classic slip dress

1) Simple Yet Sophisticated: Wear as is! I loved that this Target find came with a string tie, gives you more options right off the hanger.

        • Pair with: Strappy heels (nude or bold color, depending on the slip dress); statement earrings & delicate jewelry
        • Wear for: Date night, weddings or events (wedding/engagement shower, birthday dinner/party)

Psst…the burgundy colored Prologue dress you see first is the exact same as mine, just a different shade! 

classic slip dress

2) Rocker Tee Casual: Throw on your favorite rocker or graphic tee and you’re set with an elevated everyday look.

    • Tip: Tie the knot off to the side. Then if it feels tight, tug at it to softly loosen. Keep the shirt tucked under so the hem isn’t showing, gently smooth out, and pull down so it sits like a typical top.
    • Pair with: Wedges/sandals/booties, hoop earrings, your favorite bag
    • Wear for: Brunch, shopping, happy hour

Pardon the low quality photo! It gets dark in Chicago at 4 pm now, so lighting for this anniversary look was a #strugglebus.

3) Sweater Chic: No matter the season, the dress is here to stay! Pair your cute sweaters with this dress instead of jeans.

P.S. Check out my Reel that shows this look off better!

    • Tip: Did your dress come with a string or belt like mine? Have a shoe string or ribbon handy? Throw the sweater on; tie your string around it. Pull up your sweater so just a little is now below the string, and fold over the sweater so it bubbles up and covers up. Bam! You’ve created the same illusion.
    • Pair with: Booties, a dark mani, bold earrings
    • Wear for: Date night, intimate dinner with friends, or holiday gathering with the fam

Which is your favorite??

And if you’re new around here, bookmark some of my favorite Chicago posts to have handy when we can be safely out & about again: Rooftop Bars, Holiday Must-Dos, & Long Weekend Guide.


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