Fashionable Basics (and Popcorn) for Easy Style on Rainy Days

Fashionable Basics (and Popcorn) for Easy Style on Rainy Days

It’s raining outside and I’m in the mood to eat popcorn as I type away on my laptop. Go get a bowl and join me while we talk about a couple easy ways to bring style to your outfit on a rainy day.

Spring = the Season of Rain

It doesn’t matter where you live here in the U.S.A., it rains a lot during the Spring months, especially in April. It should be called rainy season, but maybe we are all in denial of how much it rains.

I disliked rain very much as a girl because I couldn’t go outside and play.

“No rain, no flowers,” my mom would always say matter-of-factly as she looked out the window at the rain.

One day I argued with her. We stood there, her with a baby on her hip and me only 7 or 8 with frizzy curls framing my face. I tried to convince her that we would still have flowers without rain. She was too busy to argue with me so I felt like I won. And then I stood there alone, watching the rain, and I knew I didn’t win.

Now that I’m grown, I like rainy days. I like them when I’m allowed to stay inside, make popcorn, and listen to soft jazz while I write. Thank goodness I don’t have to go anywhere today.

Looking “Stylish” on a Rainy Day

How do you still look “put together” on rainy days? What’s the compromise when you don’t want to go through the trouble of doing your hair or makeup but you want to look cute when you go out?

The other morning I caught Hilary Rushford’s “style minute” on her Instagram Stories. Hilary is a creative stylist and entrepreneur living in New York City.

Unlike me, Hilary looks effortlessly chic as she dashes about on a rainy day in the murky streets and subways of the Big Apple. In this outfit, she looks put together even though she didn’t wear any makeup or do much to her hair. She gave us quick tips on how to look put together with basics that have something special about them.

Hilary’s Stylishly Basic Outfit for a Rainy Day


In these screenshots, Hilary’s top looks like a basic white tee but it’s actually a light sweater with faux zippers on the shoulders. She encouraged buying a basic white top that has a special detail that you might not expect to help you feel more stylish.


Hilary’s black and white patterned cardigan pulls her look together. She chose a simple outer layer that will keep her dry as she dashes from her flat to the subway.


Instead of sweatpants, Hilary is wearing black velour pants with an elastic waist. She’s completely comfortable without feeling slouchy or unprofessional in a pair of sweats.


Hilary’s classic maroon-colored flats also act as a statement piece, adding a punch of color to her look.


Do you love or hate ball caps and trucker hats? I love them. They’re comfortable and fun with that all-American, southern vibe. By choosing an all black, suede ball cap, Hilary didn’t deviate from her classy ensemble and it adds a cool vibe.


Oh, wait. The only thing missing from Hilary’s outfit is a good leather bag. I wanted to reach through my screen and hand her one of ours.

On days when you can’t get creative with your outfit choices, you’ll always look chic when you carry a good leather bag.

Find Your Own Rainy Day Style

So now we all feel inspired to find some stylish basics for our wardrobes, am I right? The good thing is that we don’t even have to leave our couches to find the perfect pieces. If shopping online intimidates you, Regina wrote a helpful post about shopping online with all the helpful tips!

We chose some stylish basics that inspired us.


There are so many comfortable, cute white tops to choose from when you shop online. When choosing a white top that has a little something “extra” in it, look for patterned knits, unique details around the neckline, or trendy features like an off the shoulder top.

If you dig a basic graphic tee as much as I do, check out this shop on Instagram.


Regina chose a simple black and white striped cardigan for her outfit choice and I chose a tie-dyed indigo kimono. Both of these provide a great layering option to keep you cozy and dry.


I’ve been obsessed with these structured jeggings by Grace and Lace. Finding a pant that is structured like a jean with a comfortable, elastic waist is a huge win for some of us! 

For an edgier look, try a cropped pant. Cropped bottoms of all kinds are in style, from skinny to wide-leg cuts.

My Style Hack: I’ve taken my scissors to a couple pairs of bottoms in my closet to crop them with a frayed edge and now everyone asks me where I bought them. #NoShameInMyGame y’all.


Last year my friends turned me on to Tieks flats by Gavrieli.

Regina loves them so much that she only wanted Tieks for her birthday so her husband bought her not one, not two, but 4 pairs! Just ask her how much she absolutely loves these shoes.

I’ve got my eye on this pair of Olive Green Tieks.

A basic style color that I don’t think you can ever go wrong with is Olive Green. Take the classic, olive-green military jacket as an example — it never seems to go out of style.

If green isn’t your color, Tieks has every shade you could want. I visit their website just to play with the color slider. I love their metallic colors.

I’ve recently fallen in love with a brand new line of neutral colored shoes by Poppy Lifestyle.

→ Trucker Hats

Trucker hats have always been a favorite accessory for most southern girls and now the rest of the world has caught on. Our friends over at Be Strong Story have designed these trucker hats that inspire us to BE our best selves.


Can we just talk about how a classic leather bag never goes out of style? I never enjoyed swapping out purses every time my wardrobe changed its color scheme, so having a good leather bag that compliments everything I wear is a must for me.

This classic saddlebag style is one of our most popular crossbody designs. Regina designed this bag for our Spring Collection with a little nod to our simplistic Amish heritage. Carry it comfortably on your shoulder or in your hand with the vintage style brass ring.

Shop the Heritage Saddlebag.

Putting it all together

Shop the Regina Tote 
Shop the Heritage Saddlebag 


Do you love a good rainy day?

❤ Regina’s Rainy Day Favorites

Eating popcorn.
Watching Gilmore Girls or Parent Trap with the kids.
Making soup for dinner.
Burning candles for max coziness.
Reading a new book on my Kindle.
Counting the rain trails on the window.

❤ Meg’s Rainy Day Favorites

Eating popcorn with a tuna sandwich.
Listening to “Banana Pancakes” by Jack Johnson.
Making a rainy day playlist.
Painting in my art journal.
Watching the rain.
Talking to my mom on the phone.

We love hearing from you!

Comment with your favorite rainy day activity or your favorite rainy day style tip!

The post Fashionable Basics (and Popcorn) for Easy Style on Rainy Days appeared first on Urban Southern.

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