Fulfilling a Bucket List Item Tonight!

Happy Friday, Penny Darlings!

I’m writing to you from the great state of Chicago!

It’s officially Friday and I am PUMPED about my trip in the Windy City! We’ve done a true crime bus tour, hit the aquarium, did the TILT at the John Hancock tower!

I can’t wait to share my photos from my trip!

But tonight. Tonight is the night that I will be fulfilling one of my biggest bucket list items.

I am going to Second City.

Yes, THAT Second City!

The amazing comedy club that was the starting stomping grounds of Tina Fey, Amy Poehler, John Candy, Bill Murray, Stephen Colbert, Steve Carell, Martin Short, Cecily Strong, Aidy Bryant, Rose Abdoo (Gypsy from Gilmore Girls!), Rachel Dratch, and HUNDREDS of other of my comedy heroes.

It has seriously been a bucket item list for me.

(My bucket list also includes having a menu item named after me, be on SNL, sledgehammering a wall, ride the London Eye, see the aurora borealis, do a polar plunge, and a TON of other fun stuff! Should I do a post about my bucket list?!)

But tonight, my best friend, Abby, and I are hitting the comedy show and I am PUMPED!

I wanted to share what I was wearing to the show!

Hmm, blah, blah, blah, – check me out on Instagram here! I also started a Twitter account! Find that here! Follow Preston’s brand new fashion Instagram here! I also have a selling Instagram page where I sell some of my old clothes/styles so that I don’t drown in my own wardrobe. I just listed a few new things – so check that out!





I’m rocking this sequin skirt from Society+ (an absolute fave), this kiss lip top is a few seasons old from Torrid, Kate Spade clutch was a STEAL from TJ Maxx, and my red beret is a borrowed gem!



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What do you think?! I only have about 48 hours left here in the windy city! Are there any must-hit spots or must-eat restaurants I should check out?


If you are at all interested in doing a collab or working with me – please feel free to check out my new Contact Me! page!

I definitely want to do more His & Her fashion. Do you guys like seeing Preston more?

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Comment for topics you would like to see me cover! Like to help my self esteem! What do you think so far? More fashion? More lifestyle? Do you like the mix?

Thank you for all that you do. You are truly extraordinary.

Love all you wonderful ladies (and gents!) out there!

How Very,



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