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

Popcorn on a rainy day while shopping for fashionable basics.

I’m sorry, this post really doesn’t have anything to do with food. 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.

April = the Month of Rain

It doesn’t matter where you live here in the U.S.A., it rains almost all month long. It should be called rainy season, but 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 have to look presentable to go out?

This morning I caught Hilary Rushford’s “style minute” on her Instagram Stories. Hilary is a creative stylist and entrepreneur living in New York City. Today it’s raining a little bit in New York, too.

Unlike me, Hilary is going out today. She looks really cute and 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

Hilary's Rainy Day Outfit

→ TOP

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.

→ CARDIGAN

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.

→ BOTTOMS:

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.

→ COMFORTABLE FLATS

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

→ BALL CAP

Do you love or hate the ball cap trend? I love it. It’s comfortable and fun. It feels so all-American and southern. By choosing an all black, suede ball cap, Hilary didn’t deviate from her classy ensemble and it adds a cool vibe.

→ LEATHER BAG

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.

Shop Online for Your 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. Last week Regina wrote a helpful post about shopping online.

We chose some stylish basics that inspired us.

→ TOP

I was pleasantly surprised to find so many comfortable, cute white tops. 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.

Basic White Tops with Fashionable Flair

Shop first top.
Shop second top.
Shop third top.

→ OUTERWEAR

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

Great options of outerwear layering options.

→ BOTTOMS:

Right now cropped bottoms of all kinds are on trend, from skinny to wide leg cuts. You don’t have to worry about that embarrassing “high waters” pair of jeans at the bottom of your shelves because now you can wear them with sass and pride.

Basic bottoms for easy style.

Shop the cropped sweats.
Shop the velour leggings.

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.

→ COMFORTABLE FLATS

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! Ask her how much she absolutely loves these shoes.

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

Comfortable pair of olive green flats by 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.

→ HELLO, MY NAME IS…

This isn’t as classy as Hilary’s ball cap, but it’s fun. And I like it. Shop this hat.

Add fun to your style with this basic ball cap.

→ LEATHER BAG

Can we just talk about how a classic leather bag never goes out of style? I never enjoyed swapping out purses every time a new trend came around, so having a good leather bag that compliments everything I wear is a must for me.

Heritage Leather Saddlebag by Urban Southern

This classic saddlebag style has been a popular pre-order design from our new Spring Collection. Regina designed this bag 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

Outfit Board with Fashionable Basics for Easy Style on a Rainy Day

1. Garner Blue Kimono
2. Basic Scalloped White Top
3. Cropped Black Sweats
4. Black and White Cardigan
5. Black Velour Leggings
6. “Hello” Ball Cap
7. Heritage Saddlebag
8. Olive Tieks


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!

Leave a Comment