4 Things I’m Taking To Combat the ‘Windy’ City.

Happy Friday, Penny Darlings!

As I’ve mentioned a few times in the last few weeks – on Wednesday – I am heading to Chicago to visit my BFF/MoH Abby! (yes, same names!). I am so excited! I haven’t been to Chicago since I was a kid!

We’re hitting so many exciting places including doing the John Hancock Tower with the Tilt, a murder/true crime bus tour, the Shedd Aquarium, the Second City, and so I’m also excited for our ‘slumber party’ night where we order sushi in, watch LifeTime movies, and just talk through the whole thing!

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!

But, anyway, I’ll get off my wistful horse over here! So, listen, you KNOW ya girl has a HUUUUUGE love of all things twirly. Skirts, dresses, scarves, etc. Here’s another thing. Chicago has a v. famous nickname. It’s the WINDY CITY! And my aesthetic does NOT blend well with a lot of wind. It blows my skirt up, blows my hair into a rat’s nest, gets my hair in my lipstick, dries out my skin, ugh.

So, obviously, when packing, I needed to make some special provisions to keep my skirts twirly, my curls bouncy, and my attitude not grouchy!

Check out my list of things you need to bring to the windy city!

1.) Undersummers, obviously.

This town is literally called the “Windy City” and wind and ya girl’s skirts DO NOT MIX! I’d rather not flash everyone in Chicago with my booty, although, who knows? Chicago may love the booty!

But, with all of the walking, traveling, and wind up my skirt – these are the first thing I packed in my suitcase! I love Undersummers. I’ve written about them a few times before – but for me they were a game changer!

And the absolute best part is that no matter how windy it gets, I pretty much never have any trouble with my UnderSummers poking out the bottom of my skirts! They’re perfect for protecting thighs against chafing and protecting Chicago from DIS BOO-TAY!


See! You can’t even see them! Not even in the wind!

You totally can’t tell that I am rocking some BALLER undershorts in there! I literally packed some of these in my carry on bag because that’s how serious I am about this.


I absolutely SWEAR by UnderSummers (not a bad thing to stock up on for summer!) and I’ve written a few reviews for them before! Check out those reviews here and here! Also, be sure to check out UnderSummer’s website!

And their social media pages always need some loving!

2.) Hairspray…

Ya girl has got CURLS! And tangles! And knots! And there’s nothing that makes that combination into a rat’s nest faster than a big gust of wind! And since I am going to be sightseeing (and taking a GAZILLION photos!) – I need my hair to look perfect!

Or at least, not like a literal sad sack of straw that takes me nineteen hours to untangle!

*Pro-Tip: Use dry shampoo before you got to bed and brush through! I always think it’s easier to shower after I dry shampoo out my hairspray gunk!

**I am not a pro and that is not a pro tip.


3.) A BALLER Pair of Pants

These pants are NEEDED in Chicago. Sometimes, no matter how much you try, you NEED to rely on pants on really windy days. So I needed to make sure I had a great pair!

They’re glam AF, comfy, warm, breathable, easy to dress up and dress down, and they’re definitely pretty easy to match. Shop them here!

So, I obviously packed these with a pair of heels and a crop top for a night out at a dance party! And I paired it with these flats and this jacket to walk around the city!

EA8B2154 (2)

4.) A Good Moisturizer!

When the humidity is low, the temperature is dipping, and there’s heavy wind – it’s easy to irritate dry skin even more! I’ve been having a WAY dry winter. My hands are cracking, my legs can get scaly, and even my wrists are getting scaly! Add in the wind and you’re DONE-ZO!

So, I always stow away a good moisturizer (I use these for during and after the shower!) in my carry-on, but bring the good stuff in my checked luggage!

I love these items from Paisley & Company (literally the best!). If you have sensitive skin or are sensitive to smells – this is the BEST place. Lots of organic and transparently made items! Looooove it!


*This post was sponsored by UnderSummers & some of the items featured were gifted to me, however all thoughts and opinions are my own!*


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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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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