How to dress for the joy you want
Author’s Note: This post was originally published on June 17, 2022. It has been updated and republished.
This might be hard to believe, but if you looked in my closet ten years ago, you would’ve found mostly grey and black.
It was a phase of my life when I was trying to be taken seriously. I wanted my bosses to see me as a “serious” designer. I wanted my clients to listen to my recommendations, not just those of my male coworkers. I wanted to get promoted. And so I pared my wardrobe back to black jeans and grey cardigans and an LBD for every occasion, to feel like I looked the part.
Dressing this way was simple. I didn’t have much to decide each morning, and pretty much everything in my closet went with everything else. But it wasn’t very much fun. And over time I started to notice that it affected how I felt. Seeing myself constantly against a monochrome background, I noticed I smiled less at myself in the mirror. It wasn’t terrible. If I hadn’t been paying attention, I might’ve missed it entirely. But on the rare occasions when I would try on a bold patterned dress in a store, or throw on a hot pink scarf, my face seemed to brighten, and I began to wonder if I was missing out on something.
How to Dress for the Joy You Want
I started to try to bring the joy back into my wardrobe, gravitating toward the kinds of clothes I was drawn to even as a child: vibrant colors, lush patterns, sparkly accents, and flouncy skirts that seemed just right for twirling. But it was harder than I realized.
Liberating myself from black and grey felt freeing, but also confusing. What colors did I like wearing? What kind of top should I wear with a bold print circle skirt? Was a red handbag a fun statement, or would it just feel like a circus with all the other colors in my wardrobe? Could I dress joyfully without wearing a ton of color? Was it silly to buy investment pieces in vibrant colors, or should I stick to neutrals? And where could I find fun, well-made clothes I actually liked?
These practical considerations aside, there were all sorts of other questions that came up. Did it matter whether a color was flattering on me or not? Should I care whether an outfit looked professional in the conventional sense of the word? How much attention did I want to attract to myself, and what distinguished good attention from bad attention?
Of course, clothes aren’t just things we put on our bodies to keep them dry and warm.
They’re also statements, and our choices reflect deep cultural biases. For example, we often equate dark, dull clothes with seriousness and maturity (think: a lawyer’s suit), and vibrant, whimsical ones with childish frivolity (e.g. your kiddo’s mismatched tutu-and-t-shirt ensemble). These effects aren’t just on others. They also influence the wearer. For example, in a study done at Northwestern University, psychologists found that when people were given a white lab coat to wear, they exhibited greater attention and focus. But when they were told it was a painter’s coat instead of a doctor’s coat, the effects went away.
What others believe about our clothes matters, and so does what we believe about our clothes.
So while I could easily say, “Just wear what you want!” it’s not quite that simple. Wanting to dress joyfully sits alongside other needs: to be seen and acknowledged in your workplace, to feel put together and adult, to feel confident in your body.
I’ve spent a lot of time navigating these tensions over the past decade, and I find I get a lot of questions about dressing joyfully. Still, I’ve put off writing this post more times than I can count. I think it’s because I feel like I’m just about the last person to go around giving fashion advice. I’m not the most stylish or on-trend dresser I know. I don’t have that knack for finding the belt or handbag that makes an outfit look perfectly pulled together. Seriously — I don’t even have a full-length mirror in my house at the moment!
But I do love clothes. And I have thought deeply about dressing for joy. So what follows are some things I’ve learned about how to create a joyful wardrobe. Recognize that if you’re starting from all-neutrals closet like I was, it will take time to find your joyful style and build the wardrobe that works for you. But the process can be fun, if you let it be!
Add bold accessories
This is my simplest starting point. It’s also a cost-effective way to start bringing color and joy into your closet. Accessories are great because you can wear them often and experiment with matching them to different colors within your wardrobe. This is especially helpful if you don’t know what kinds of colors you like to wear.
For example, when I was just starting to add color to my wardrobe, I found an inexpensive linen scarf I loved and bought it in four colors: red, coral, light pink, and yellow. Now I had a pop of color I could throw on over a white tee and jeans, a black dress, or a grey cardigan. I wore those scarves all summer, and still have all of them in rotation.
Sunglasses, jewelry, and shoes are all great accessories to play with. One of my favorite items in my closet is a pair of yellow shoes. Yellow seems like it would be a hard color to wear, but actually, if you have a pair of yellow shoes, even a simple jeans + sweater outfit looks lively and fun. If you take care of them, they’ll last years, and be a reliable pop of joy you can turn to when you feel like keeping your outfit simple.
Pick a signature color and build from there
When you start buying colorful clothes after a period of wearing only greys, the array of colors out there can feel bewildering! Buying colors involved a lot of trial and error for me, with expensive and wasteful mistakes along the way. I was drawn to bright yellow and orange tones, because they’re traditionally associated with joy, but I quickly noticed that they tend to wash me out.
A quick note here: I tend to avoid using the word “flattering” when talking about clothes because I’ve come to see it as a term that reinforces ugly prejudices in dressing. Flattering suggests that what’s most important about clothing is how it makes us look to other people, based on some arbitrary standard of what is physically appealing. Except the standard isn’t arbitrary: it’s fatphobic, patriarchal, and white supremacist.
My standard for what good looks like in clothing is whether it makes you feel good.
I personally avoid certain cuts and colors, but am very careful to interrogate whether I’m avoiding them because I’ve internalized some notion of how my body “should” look (e.g. whether they make me look wider rather than slimmer), or whether the clothes are making me feel less buoyant, confident, and alive. So I avoid most yellows and oranges not because they’re unflattering, but because they make me look tired, which doesn’t reflect joy to me.
But when I wear red, I look in the mirror and I feel like the most upbeat, confident version of myself. So I started prioritizing red when I would look for new clothes. This made coordinating outfits a lot easier — I know dark denim looks great with red, so it became easy to shop and pack around my red clothes. When you’re ready, you can build your color palette out, but your signature color can always be a comforting go-to when you want to feel your best.
An easy formula: multicolor pattern + bright solids
When I was preparing for the book tour for Joyful, I decided to bring in a stylist to help me figure out some new looks. I never thought of myself as the type to hire a stylist, but Charlotte Coleman made it fun and taught me a lot. If you have an occasion you’re dressing for or just want a boost as you get started, I highly recommend finding someone to work with in this way. Make sure the person is the right fit for you — you want someone who will get you out of your comfort zone but won’t force you into styles that don’t feel like you.
One of my greatest takeaways from Charlotte is that multicolor is basically a neutral. Ok, that sounds insane, so let me clarify: multicolor patterned pieces seem hard to match, but actually, they’re easier to work with because you can pair them with any color in the pattern and they will work!
For my book tour, we found this incredible digitally printed splatter skirt. It was a splurge that I had trouble justifying until Charlotte pointed out that I could wear it with red, blue, green, yellow, and black. She ordered me basic, affordable sweaters from J. Crew in an array of hues and I wore this skirt at nearly every stop on the tour. I ended up buying more rainbow skirts and have used this strategy to make a wide range of different outfits.
Swap in colorful neutrals
Ok, this tip took me awhile to figure out, but it completely changed my wardrobe. One of the things that is challenging about color is that it often dulls when paired with black, grey, or beige. (I’m not saying there aren’t times when those pairings work, but in general, standard neutrals aren’t all that joyful.) But colors can act as neutrals too. For example, let’s say you decided to swap black for navy and grey for chambray. You still have some grounding neutrals to pair with your brighter hues, but the neutrals highlight the colors, rather than dampening them.
Here are some of my favorite “colorful neutral” swaps:
- Black > navy blue
- Beige > blush or peach
- Camel > gold or mustard
- Ecru > pale pink
- Gray > chambray or silver
- Brown > burnt orange
This works especially well with accessories. I changed out camel colored flats for gold loafers and it’s one of the things that I keep in my wardrobe at all times (I even bought an extra pair in case they wear out). Gold shoes go with literally everything in my closet, and they’re both more sophisticated and more fun than beige.
Choose a swap to make and see how just this small thing can brighten your wardrobe. (This trick works in your space too. Try a blush sofa instead of a beige one, or a chambray rug instead of a gray one for an easy way to energize a room.)
Filter your searches
I picked up this tip from Carrie Colbert, whose colorful closet puts even mine to shame. When I asked her how she finds such vibrant clothes, she clued me in to the “filter” feature on most online shopping sites. Instead of scrolling through endless pages of clothes, she opens up the filters in a category and scrolls to the color preferences. Most retailers have an option for “multicolor” or “rainbow.” You can also choose your signature color or colors you know you like. I also always eliminate beige, gray, and black from my searches.
This cuts through the clutter and helps you zoom in on colorful options more quickly.
Joyful doesn’t always mean colorful
I’ve talked a lot in this post about color, because that is probably the most obvious way to add joy to your wardrobe. But it’s certainly not the only one. You can look at all the aesthetics of joy through the lens of clothing. A few examples that have been particularly significant as I’ve developed my style:
Freedom: I want clothes that let me move! So I skip skintight pencil skirts and weird sleeves. I wear a lot of flowing dresses and twirly skirts. And while I don’t mind a cinched waist, I always make sure my pants have some stretch or flare. If I can’t easily do a happy dance in it, it’s not free enough for me.
Harmony: I love patterns, and especially stripes. The simplicity of repeating stripes is a grounding motif that feels basic, yet also joyful.
Renewal: I love ruffles, floral patterns, and organic details that take their cues from the plant world. These touches, to me, can bring joy even if I’m not wearing any color.
If you’re feeling lost trying to find joyful clothes, focus on the aesthetics of joy that resonate with you. Zooming in will help you identify the specific elements you’re looking for in your clothes.
Make a brands list
There are so many clothing brands now. I feel like every time I open Instagram there’s some new brand I’ve never heard of offering cute dresses or bold activewear or whimsical PJs. It’s… a lot. But it’s also great because there are a lot of independent and women-owned clothing companies offering different kinds of clothes, and many are forging new ground when it comes to ethical, sustainable, size inclusive, and small batch production. It’s nice to have options! And even better to have alternatives to the fast fashion treadmill that has dominated the marketplace over the last decade or more.
Here’s the catch, though: often I’ll see something I like at a time when I’m not really shopping for anything. I don’t want to buy just to buy, so I close the tab. Yes, sometimes that brand will follow me around on the internet for awhile, but it eventually goes away. And then I’m looking for a new dress and suddenly I can’t think of anywhere to look!
Do future you a favor and create a new note in your phone right now.
Start a list of clothing brands that are interesting to you. When you see something you like, pop the name in your notes app. When you need to search for something new, this will be a huge relief, and much more likely to get you something you’ll love. (You can also take your list to secondhand sites like Poshmark or ThredUp for a more affordable, sustainable shop.)
Since I always get asked this, here are some of the brands that are on my go-to list right now. I don’t necessarily own clothes from all these brands, but they’re the ones I pull up to search whenever I need something new:
- Pink City Prints
- Loeffler Randall
- Kitty Joseph
- Olivia Rubin
- Frances Valentine
- Mara Hoffman
- Ulla Johnson
- Celia B.
- All Things Mochi
- Alex Mill
- La Ligne
- Clare V.
- J Crew
- Farm Rio
All this said, one thing I’d recommend when you’re starting to diversify your wardrobe is going to a department store. It’s not my favorite shopping experience day-to-day, but it’s a great way to try on a bunch of clothes at once from a range of different designers.
Try visiting a vintage store near you and focusing on a specific era that brings you joy. Maybe it’s 60s psychedelic prints or 70s disco or even 80s neon. And while the colorful, overflowing racks of a thrift store can be energizing for some, there are plenty of options if you prefer to do your shopping with your thumbs. Etsy is a huge clearinghouse for vintage clothing and that search bar makes it simple to filter for the era of your choosing.
Shop Your Closet
Sometimes dressing joyfully isn’t a matter of buying more clothes. It’s about adding pieces that help you get more wear out of the clothing you already have. So make sure that you’re going through your closet often and getting a good feel for your existing wardrobe.
Do you have a patterned top that seems to overwhelm everything you pair it with? Does a sea of dark accessories drown that breezy dress you keep trying on and taking off? Is there something you bought because you loved the color, but never wear because you don’t having anything to wear with it? (If you said yes to that last one, here’s my secret weapon: enter “how to wear [color] [article of clothing]” in Pinterest. So for example, “how to wear green pants” or “how to wear yellow sweater.” You will find dozens of ideas that can help you figure out what items to add to your closet to help you make the most out of each colorful piece.)
At the end of the day, it’s what makes you feel good
There are no rules in joyful dressing. At the end of the day, truly joyful clothes are the ones that make you feel happy when you put them on. As you figure out what this looks like, you can codify filters to help you decide what works and what doesn’t.
For a long time, one of my filters was, “Do I absolutely love this?” If the answer was no, I often would end up Marie-Kondo-ing that item a few months later. But I’ve since found that sometimes it’s handy to have something in my closet that I don’t LOVE but offers a joyful option in a situation I find myself in frequently. For example, I have a striped knit dress that manages to be both very joyful and very professional in the typical sense. I almost returned this dress, but I’m glad I didn’t because I’ve worn it for talks, on TV, and other situations, and it never fails to make me feel confident.
Now I ask myself, “Does this make me feel like my most joyful self?”
Do I light up when I’m wearing it? If so, then there’s a good chance I’ll reach for it when it’s time to get dressed in the morning. If not, then it’s extremely likely I will reach for something else that makes me feel better.
Over time, you’ll find your own rules for joyful dressing. For my part, I’ve learned that white is nearly always a more joyful pairing for colors than black. That patterns are perfect for moms (they hide messes much better than solids!). That dresses are my sweatpants. That beige is unnecessary and rainbow is timeless.
Your rules will be different from mine, and that’s the joy of it. When fashion becomes play, it’s more inspiring and more fun for all of us!
Do you have any tips for dressing joyfully? Please share them in the comments!