How to Make Getting Dressed More Fun

A Whimsical Take on Figuring Out What to Wear Every Day.

A confession: the other day, I malfunctioned when trying to get dressed. Sitting, not standing, at the foot of my wardrobe and blankly staring into the distance. We had to leave. We were late. All I had to do was pick an outfit. Well, the one I had picked wasn’t working. It was a new pair of pants, and it turns out they didn’t look right with the top. And then, I don’t know how to explain it, but it was like my brain froze — I could not think of other options. Blank. After many, many iterations of outfits tossed onto my bed, I finally landed on some white pants. Victory. I pulled them out of the drawer, and lo and behold, there was a forgotten little coffee stain on them. Defeat. I lay back on the ground and stared into space once more.

Clothing ourselves is a creative act. Every day, it’s a conscious decision to pair certain colors and textures together that communicate exactly what we want to communicate to others about ourselves. Sometimes, in the busyness of life, this small creative practice becomes more like a chore. Sometimes, in the scrolling of social media, it feels like a never-ending chase to be dressed on trend, a daunting task to somehow be “effortlessly” chic every single day. And sometimes, we just run out of ideas and sit at the foot of our closets, with no inspiration.

Similarly to how I proposed a reframe to eating at home and making birthdays special again, I’d like to propose a fresh look at dressing yourself each day.

I think getting dressed should be way more fun! It should feel like a creative activity, a small painting we make every day, allowing for room to play and explore.

To help make that shift, I came up with five ways to bring the child-like magic back to getting dressed.

Remember when plastic princess heels and Spiderman masks were the makings of a great outfit? You can get that creative spark back. I tried to think of straightforward, practical, and doable ideas that don’t require an overhaul or tons of spending — and I hope these ideas spark a little fun back into your mornings when choosing an outfit!

Long Sleeve Collared Ruffle-Front Blouse | Linen Polka Dot Pants | Square Toe Mary Janes

1. Introduce color into your wardrobe!

If you know me, it is not unexpected that my first recommendation would be to add more color to anything! Color in my space, on my body, in any area of my life, always sparks joy. I'm naturally drawn to bright colors, and my closet is filled with bubblegum pinks, cobalt blues, and bright reds.

But I understand that the draw to color does not always come naturally. In fact, I think most people are drawn to shades of gray, black, and neutrals in their clothing. If you’ve been feeling a bit uninspired by your outfits, my encouragement would be to try to introduce some color in there and see what happens.

If you're color-averse or color-hesitant, here are some specific ways to ease into a more color-filled wardrobe with fresh hues:

• A solid, bright-colored ballet flat

• Dip into pastels with a button-down

• A bold-colored chunky knit sweater (pair with a neutral pant!)

• A vibrant sock paired with a work loafer

• Choosing a pop-of-color bag instead of a neutral tone

• Even accessories like necklaces or sunglasses can be a low-stakes way to add color

What color will look good on you? Probably your favorite color! Whatever makes you feel happy is going to radiate off of you when you wear it. I would just move toward what you naturally enjoy and start introducing it into your wardrobe. The child-like-ness of simply wearing the color you like the most should spark a little joy back into your routine.

Long Sleeve Collared Ruffle-Front Blouse | Linen Polka Dot Pants | Square Toe Mary Janes

But just in case you need some inspiration for how to make bold colors work together, here are some balanced yet bright color pairings to help guide your outfitting:

(You can draw from the whole palette for a super colorful outfit, or just grab a color or two and pair with neutrals)

Bayley Gingham Vest | Bayley Gingham Mini Skort | Cherry frosting recipe coming soon!

2. Think of Crafting An Outfit Like Making a Meal

I do not have a closet in my apartment; I have a small IKEA wardrobe, which has forced me to be incredibly choosy about what takes up space. Surprisingly, this restriction has been a gift. I’ve slowed down consumption, become more intentional about curation, and discovered new creativity in choosing what to wear.

Every piece I own must work multiple ways, with several pairings, or it doesn’t earn its place.

To spark more fun in your closet, balance your staples with playful variety. You need reliable classics you rotate through, but also a few out-of-the-box pieces to mix things up. A capsule wardrobe doesn’t mean avoiding trends altogether; it means choosing with intention. If a trend genuinely delights you, it can absolutely become a staple. Over time, many of my “trendy” items have become forever pieces.

For example, a Peter Pan collar has been a yes for me since 2012. Matching sets? They’re trending now, but they feel timeless in my wardrobe. When you curate with this mindset, asking, “Can this mix with three things I already own?” your closet stays fresh without ever feeling overwhelming.

So, if you will, think of your wardrobe like a meal. Your staples are the protein — filling, dependable, and the base of every outfit. Your playful pieces? They’re the sides — the unexpected, flavorful additions that make everything more exciting.

Protein examples: a classic white skirt, black trousers, vintage-wash jeans, a pinstripe button-down, a cream knit sweater.
Side examples: a red vest, a slouchy green cardigan, a yellow headband, patterned pants, a pink hat.

Just like a great meal, a great outfit is balanced. Use your fun pieces to enhance your main pieces, and dressing becomes delicious again.

The Kiera Light-Denim Long-Sleeve Blouse | Liora Ruffle Pants | Iced lavender oat milk matcha

3. Add a pop of the unexpected!

Rah! A little razzle dazzle goes a long way. I think what makes certain outfits eye-catching is often when there’s a subtle moment of surprise. A colored pair of glasses. A bag shaped like a fish. A pattern of bold food choices.

If you’re not sure how to begin, try this:

• Add a surprising accessory (ex: an extravagantly beaded purse, bollo tie, or sparkling shoes)

• Layer something a bit offbeat with something classic (ex: a classic tailored pant style, but covered in polka dots)

• Let one element be a conversation-starter (ex: sardine earrings or a jumbo scrunchie)

4. Dressing a Little Better Than the Occasion Warrants

I picked this up from women in my life that I really admire: they often dress nicer than they need to. Not in a fussy way, just a little more polished and thoughtful. Something about how they showed up for life expectantly really inspired me.

And since I want to be like them, I started picking up the habit too. Perhaps this is a response to wearing pajamas daily for all of lockdown, but now, I reach for outfits that make me feel slightly elevated, even on casual days. It could be a crisp shirt, a swishy skirt, or an elevated flat. Not overdressing, just a little polish, and I immediately feel different. It always feels good to have intentionality in what I pick to wear.

Bayley Gingham Vest | Bayley Gingham Mini Skort

Here are a few ways I elevate an outfit when I want a little extra “umph:”

• Tuck, cuff, or roll – Small adjustments (like a French tuck, cuffed sleeves, or rolled hems) make clothes look super intentional.

• Earrings – Simply, I elevate the earrings, and everything feels nicer! Go for a nice hoop.

• Do a quick “third piece” check – Outfit + shoes is a start, but adding a third piece (jacket, cardigan, necklace) often ties things together.

• Pick a signature detail – Red lips, a bold hair clip, signature perfume, a funky chain. Something small that feels “you” and adds consistency.

• Trousers – I found super comfortable and relaxed trousers I wear all the time that look polished but feel like pajama pants, and so I wear them to work constantly.

I’ve gotten so into this practice, I’ve even been trying to slowly elevate my pajama collection too!

5. Try New Things!

As I’ve often said…you are the creative director of your life! You are not confined by trending items or brands. You can construct incredible outfits as a creative act every day, whether you’re leaving the house or not! Just make it fun and playful. Put on a playlist when you’re getting dressed. If you can, wake up with enough time to really relax while you’re putting your pieces together and let it feel like you’re making something creative (you are).

Some playful ideas:

• Make your own punch cards (like the ones I designed with Nuuly!)

• Take photos of every outfit you wear in a month and keep them in a folder to reference on uninspired days (publish a limited-release zine of your incredible outfits and sign it for your friends so they, too, can be inspired)

• Create a “clothing calendar” with some photos of your pieces and light graphic design work. You could make a master plan if you really wanted.

• Assign weekly themes for yourself. No need to even tell anyone. Like dress subtly like characters from a book you love, or a favorite movie.

• Use Pinterest like a sketchbook and create outfit moodboards from what you already own!

Some days I really do feel uninspired, and I think it’s a helpful idea to have a backup plan — a fallback for a morning when there is no capacity to piece it all together. On a good day, put together a few easy outfits that you feel like you in, then photograph them and save them on your phone. If there is ever a day that you have to get up and get dressed, but circumstantially it feels impossible, you already made yourself a kind little backup plan.

I hope this sparked a few new ways to look at your wardrobe with whimsy!

If you need a sustainable way to add some fun into your wardrobe, I have good news! I asked Nuuly if I could offer my Feeling! readers an extra treat, and they generously offered $15 off two billing dates for new Nuuly subscribers! (good for 500 total redemptions, expires 8/14/25).

You can use the code “jennaisfeeling” to redeem! I have used Nuuly many times (especially to get through a season where I had a bunch of formal events) and have always been so impressed with their curations and product.

I am so honored they wanted to work together on a fun design project, and so grateful they made a discount just for you all!

MORE INBOX CANDY:

The Latest Episode of Feeling! TV (my favorite so far):

---

🐚 Read more thoughtfully created articles here

🎱 Subscribe to the new video version of Feeling! Magazine

🍒 Let’s be internet friends, please! @ jennaisfeeling

🪄 Get more inspiration