How to Dress Joyously

Dressing can be a chore. If you’re grappling with body image woes, work in a critical or intolerant environment, or are dealing with chronic pain, peering into your closet each morning may prompt more anxiety than elation. But I firmly believe that striving to dress joyously is a worthwhile endeavor. For all of us. Because we’ve all got to wear clothes every day, and the clothes we choose broadcast information about us to the observing world. And because the clothes we choose can be protective or celebratory or expressive or soothing, and what we wear can change the path we take for the day.

Dressing is powerful. And so it should be joyous.

Here are some ways to ensure the dressing process is joyous for YOU:

Work around negativity

Frequently, the biggest, strongest roadblock to joyous dressing is negative feedback from outside sources. It can seem impossible to wear anything but your most unremarkable clothing if you know that anything more daring will be met with unwelcome commentary. But there are ways to both build your courage and deflect nasty remarks. Start by amassing pieces and tools that contribute to your desired or goal look, then wear them in small enough amounts that it feels like your little secret. Then try cultivating allies: Talk to a select few people about why dressing this way is important to you, so that you have some supporters amongst the dissenters. And then give my tried-and-true favorite comeback a whirl: Laugh. When someone makes a rude remark about your outfit, just laugh and say, “Hahaha, I know! Isn’t this WILD?” Own it. Never apologize. Then walk away.

None of these techniques is foolproof, and your unique situation may make them all seem utterly ludicrous. But the point is this: There are ways. You don’t have to surrender a potential source of joy to buzzwreckers or bullies. Formulate a strategy, take a deep breath, and go forth dressed fabulously.

Fake it

The second biggest, strongest roadblock is self-critique. Whether you believe that your body isn’t “good enough” to pull off a certain skirt, or are convinced that you’re not stylish enough to wear a trendy dress, your own fears and apprehensions constitute a very real impediment to dressing with joy. So try faking it. Throw on the skirt before you can get too freaked out about it, and just GO. Pull on that dress and strut through your day like a superstar. It’s been said before, but bears repeating: Confidence is the most powerful beautifier in the universe. Believe in yourself and you can wear anything. And if your belief is wavering, fake it.

Wear sentimental pieces

Gorgeous clothing that has been beautifully designed and expertly manufactured is thrilling to wear. But the most threadbare tee or scuffed-up shoes can prompt more joy than gorgeous designer duds if those well-worn items have sentimental value. Whenever I wear a dress that my mom made for me, or a bracelet that my dad bought for me, or shoes that my husband gave me for Hanukkah, I feel exponentially happier. Every time I glimpse what I’m wearing, I feel loved and cherished. There is no quicker path to joyous dressing than embracing garments that hold emotional meaning.

Embrace color, texture, and shine

Matte black is eternally chic, but bright red, vibrant yellow, rich purple, and electric blue invigorate both wearer and observer. Sequins and studs add interest and excitement to a garment. Lush layers, draped cloth, richly textured fibers make bodies feel sensually fulfilled. Neutrals are cool and classic, but when you’re aiming for joy, go for color, texture, and shine.

Explore figure flattery

Do NOT interpret this mandate to mean “figure out how to make your big bits look smaller” or “buy clothing, shoes, and accessories that make you look tall and thin.” In my opinion, figure flattery is so much broader than most style experts would lead you to believe. Flattering clothing lies flat against your body. Flattering clothing doesn’t pull, pinch, or subdivide. Flattering clothing works with your eyes, hair, and skin tone. Flattering clothing creates a silhouette that pleases your eye. And all of these things have value because when your body is flattered as you wish it to be, you feel like your best self.

Is it always going to be this simple? No. Will following these exact steps lead to a guaranteed lifetime of joyous dressing? Probably not. Will there be days when dressing joyously falls to the bottom of your priorities? For sure. But again, those of us who move about in non-nudist circles must get dressed every single day of our lives. Many daily tasks are extremely difficult to transform into celebratory affairs: I brush my teeth willingly but without emotion, I do the dishes religiously but grudgingly, and there’s not much I can do to infuse these tasks with my own brand of joie de vivre. But dressing? Dressing CAN be joyous. And I choose to make it so.

As can you.

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  • Brilliant picture!

    I definitely agree that wearing bright colours can improve your mood – something I’m working on this year is adding more colour to my wardrobe!

    There is something so wonderful about wearing glitter-encrusted shoes to the office, or a soft sequinned jumper to go food shopping, or a poofy skirt with a petticoat to go and get coffee. Overdressing be damned, dressing joyously is the way forward!

  • Amy

    Love this, and love the happy photo at the top of the post!

  • Thanks for this post. It’s not the usual ‘fashion’ piece but that’s what makes it good. There were things in there that I’ve never heard before and will take back to my own little wardrobe.

    Also, red shoes do equal joy!

  • Georgina

    “And because the clothes we choose can be protective or celebratory or expressive or soothing, and what we wear can change the path we take for the day.”

    Wonderful! I really believe in this but sometimes need to be reminded. I’m going to copy this quote into my book of ‘I feel better if…’

    I feel better if…I wear joyful clothing; my clothes fit well and are comfortable; I wear soft fibres; I wear bold colours; I embrace pattern; I manage to express my individuality.

  • Owning it, if you can, is one of the best pieces of advice I can think of. The other day I went to a vintage sale with some friends and one of them bought a purple satin dress hat with a veil. She was so delighted with it she put it on straight away and wore it for the rest of the day. It was a ridiculous hat and it didn’t match the rest of what she was wearing but she looked awesome and the hat made her happy. She was conscious of people staring at her, but decided that she would interpret that as a compliment and took pleasure in it. It’s one of the many reasons why I think she is an excellent person, and I loved her for the way she paraded around our conservative small town, head held high in her old lady hat. It was brilliant.

  • All of your excellent advice goes hand in hand with my current post about smiling and not settling before we leave the house. One of my personal goals is to make sure I smile at the mirror before I leave….if I can’t…maybe its back to the closet… you gave some excellent advice on ways to make sure we leave smiling!!

  • Sage

    Sal, thank you so much for this post. I really needed to read this today. This morning I put on a funky black croppped jacket with puffy sleeves that makes me feel like a futuristic space warrior. I felt powerful and fun inside my house, but the moment I stepped out the door I had began questioning what other people would think about my outfit–especially when standing at the train station next to dozens of people in T shirts and jeans.

    For the rest of the day, I’m going to keep my head high with my shoulders back and OWN IT! My weird little jacket makes me feel happy, and that’s what counts. By the way, I love your jumping picture!

    –Sage

    • Sal

      Hurrah! Rock on, Sage. I bet that jacket looks SMASHING on you.

  • Jen

    I adore this! Just the other day I saw a woman in a lovely floral maxi dress and said to my girlfriend that I wished (with longing) I could pull that off, but my curvy figure prevented me from doing so. Without missing a beat she dismissed my concerns and said “you only live once, why deny yourself the pleasure of awesome clothes?!” She’s so right. I loved “twirly” dresses as a little girl, and wore them with abandon. Didn’t matter that I was going to be on the monkey bars. So why should I not wear a long flowy dress now if I have swingy hips? I am off to the store tomorrow to find one just for me:)

  • Oh, but you CAN wash the dishes joyously as well! I always make an effort to think about the good that I am bringing my family by doing this chore for them. And if you get someone awesome to sit on the counter and talk to you while you wash, it’s even easier. 🙂

  • Love the photo, Sal! It certainly brought some joy to my morning.

    I love the idea of owning it, and dressing in colors, texture and shine to boost mood- it works for me! In fact I’m often seen wearing sequins or bright colors at work because they cheer me up, which in turn tends to cheer the people around me.

    I’ve had my mind on writing a blog entry about dressing professionally and still showing a little personality. This is more your area than mine since I don’t usually write about fashion, yet I feel how we dress is so important to our mood and success in the workplace. Dress can affect how we see ourselves and how others see us.

    Thanks for this post, and for bringing a little joy to my day on many days!

  • Since I make a lot of my clothes, I have a lot more freedom in what I can wear to make me feel joyous. I’m kinda known as the queen of the prints. Fabric with wild print makes me happy! Yesterday I wore a me-made top that has pin-up cowgirls all over it. It’s not that my whole wardrobe consists of novelty prints, but the garments that do are the ones that feel most like me and guess what? They’re also the ones that get me the most compliments, by far.

  • Bubu

    Another great post, Sal! I just picked up two beautiful, hourglass sundresses covered in flowers that I’ve been eyeing and thinking about and hemming and hawing, because they are really much more dressy than necessary for my 3-person office, and over the top for taking care of little boys at home. But I love them! (the kids and the dresses…) – the fit is very 50s and flattering, and the flowers are just pure spring. I actually hung them up in the room the night I bought them so I could wake up first thing and see them again! So I will be way more feminine and dressy than anyone else, but smiling the whole time.

  • I absolutely agree! Also: Hilarious picture 😀

  • I agree with you on the figure flattery. I’m always my own biggest critic, wanting my big bits to look smaller, just like you said. I’m trying very much to embrace my body and non-magazine ideas of “pretty”. Thank you so much for your blog, it’s quickly becoming a favorite!

  • maryeb

    On page 199 of ‘A New Earth’, Eckhart Tolle tells the story of a Zen Master. He is held in high regard by his community until someone tells a lie about him, creating a great scandal and causing him to loose his reputation. Eventually the truth comes out and his good name is restored. Through it all, ridicule or praise, his responds “Is that so?” He doesn’t allow himself to be defined by others comments.
    I try to keep this little story and that short and sweet sentence in mind when dealing with people’s expressed opinions of me.

    Thanks for the additional tips on how to dress fearlessly. Your blog posts are always so encouraging.

    • Sal

      I LOVE that, Mary. Thank you for sharing that story!

  • sometimes dressing joyously has nothing to do with how the clothes LOOK on you, but all to do with how they feel. we get so wrapped up in wearing what fits properly or what gives us the shape we think (or are told) we should have, but sometimes surrendering the look to the FEEL of clothes is just so joyous. maybe the color of that top isnt the greatest for your skin tone or the hem length of that skirt emphasizes your heavier legs — heck, maybe that dress looks like a potato sack on you and is “all wrong.” sometimes, it just FEELS GOOD, and there is so much joy to be had in just that. 🙂

  • You are ROCKING those red shoes!! I will tell you a quick story. I live much of the year, for now, in Doha freaking Qatar. In Doha, you simply cannot wear the clothes that I love wearing because it draws attention from people you don’t want drawn. (trust me on that) Much of the time I am in black high necked blouses and trousers. It wasn’t until a trip to Turkey and Lebanon when I realized I needed an infusion of color and I needed to show my legs.
    I had been in Doha for so long I forgot I could pull off UNBORING clothes and when trying on this really gorgeous blue halter blouse and not thinking I could “own it”, walked out of the dressing room and watched my husband’s tongue drop to the floor. I looked fabulous.
    You know what? My whole demeanor changed too. I remembered to pull my shoulders back and bring my head taller. Later that week we went to a party where I wore a really stunning mini dress (yes, I can still wear them!!) with a fabulous pair of gold python (Dior) shoes and when I walked in I could feel the “super model” in me start to show. Talk about joyous! I felt like a woman again!

  • Sally – I LOVE this photo of you!

  • rb

    Sal, I love this photo. It made me smile today. I am so accustomed to you looking like a glamazon in your photos. Seeing your goofy side makes me feel I know you better!

  • What a gleeful picture to wake up to today! I can’t wait to finish my coffee and get some fun clothes on, yay!

  • I <3 this post! You've made dressing SO much more joyous for me, Sally! 🙂 All the tips when I met with you have been so great! You loved me in a skirt and I haven't ever been a huge fan of my legs. However, I now wear skirts WAY more than ever! Of course I still have days that I feel like, "Oh, I don't like showing my legs." However, I DO fake it until I FEEL it! Case in point? I've got my jean skirt on today and I've been meaning to get out and find myself a NEW full skirt! 🙂 Beautiful post lady! 🙂

  • Wonderful photo! And shoes!

    I so agree about not dressing to look “taller and thinner”. That gets on my last nerve on the TV makeover shows (which I do watch and like): the stylist *always* wants to make the subject look taller and thinner. What if I want to look rounder? Isn’t that OK too??

  • I find that, like other commenters, how I FEEL is critical to how I look in clothes. I have two basic criteria that I use to evaluate outfits when I’m uncertain what to wear:

    1) Does it make me feel like a kid? Most children’s clothes are loose, simple, free and unencumbered. If it has a skirt, can I twirl? If it is a knit dress, can I forego a slip and/or fussy shoes? The more an outfit fits my “inner kid” criteria, the happier I am likely to be in it.

    2) Does it make me want to sing? Let’s be frank, I have a voice like a sick cow. But when I feel good, I like to jump around the house and lip sync or sing along to music. If I can jump around in clothes — or even better, if they make me feel like jumping around — then it’s all good.

  • Sally,
    I’ve had such a good time reading your blog! It’s really refreshing. After reading it Friday you inspired me to go through my closet and pair up the outfits that make me feel beautiful, not just to grab the easiest thing that will cause the least amount of attention to my least favorite body parts. All weekend I had compliments and it felt great. Today’s post was especially encouraging. Thank you for doing what you do.

  • I’m totally trying to channel that thought. I always think I can’t wear anything but knee length skirts. But yesterday I felt amazing in my midi-length dress and today I’m wearing a mini! I’m trying some immersion therapy to “fake it” til I feel confident in the mini.

    Thanks for these wonderful reminder posts. They always seem to hit me on the right days.

  • I’d also add another angle to your point about combating negativity, and that is that sometimes comments aren’t negative at all, but can still provoke the same response. If you’re taking a risk with something you’re wearing and someone comments on it, it can be really easy to turn even a compliment into criticism in your own head. So dressing joyously also means really hearing the positive feedback.

    Also, your husband gives you shoes for Hanukkah. If that’s not a cause for joy, I don’t know what is.

  • What a great message. So true too. Although i make dishes and laundry joyous by drinking. 🙂

    Seriously though, my mother has significant health issues and cannot wear pants or anything tight around her waist. For nearly a year she wore the same dresses and seemed so depressed about it. Then my SIL and I each bought her a new dress. Then she bought a few. Now she is the sundress queen and always looks like a million bucks. She still feels like shit but you can’t tell at all b/c she’s gorgeous. I sent her your post about body gratitude in the face of illness and I think she could really relate. I believe that dressing in a way that makes her appear happy and healthy has helped her feel more normal and not like a sick person.

  • Beautifully timed post. I was wondering what to wear and this has helped to give me some ideas. Some days, it’s just hard to get dressed.

    For me, the key is inspiration from elsewhere, wherever that might be. It keeps things fresh and gives me the jolt I need.

  • Wonderful post. The two methods I use most often are faking it (until I make it) and using color. Less so on the shine for daytime but definitely at night. And feather earrings. I don’t know, they just make me happy.

  • Sal, this post is absolutely fantastic. I’ve printed it out and hung it in my closet to reread when I’m having trouble getting dressed in the morning during those bad body image days. I love how you linked dressing joyously to a celebratory and expressive experience. You are so correct in stating that confidence and courage are key components in dressing with joy. I will definitely keep those words in mind when deciding what to wear. Thank you for yet another brilliant, thought-provoking, incredibly wise post.

  • That is an awesome photo. Thank you for writing this — I’ve been trying to wear more things that make me truly happy lately.

  • I LOVE the photo! =D Totally was not expecting that; it kind of made my morning (back when I first saw it)…

    I’ve been reading your blog for a the last couple of months, pretty much every day, but I never quite got around to posting…Whoops! Well, here I am, and I really enjoy your writing and hope you post lots more!

  • Annika

    You are hitting the nail on the head again. I am at a point in my life where I want and need to start building a wardrobe with more than the bare necessities. Now I believe I will have to take the joy factor into account before adding any new item. Thanks for a great post.

  • Cathy

    I did the sentimental dressing today. My weight has been higher than I like, I feel heavy, I feel bloated, I’m moody with PMS, I feel stymied by a change of season and what on earth did I wear last summer? Getting dressed has felt like a chore. After a half hour of struggling I put on an okay skirt and a matching summer sweater-t that might be too warm for this poorly air conditioned office on a record setting hot day. I was dressed appropriately for work and I know I look.. okay. But I put on my Nana’s necklace so I’d feel pretty and good about something.

  • Geri

    LOVE this post 🙂

  • Wonderful post Sal – thank you!

    Sarah xxx

  • That’s such a great photo of you! I loved this post — what a great set of tips!

  • I love the picture and the tips. I misread whirl as twirl. So I think I’ll say ‘Isn’t it wild?’ & then twirl because if they’re cool they’ll like that & if not they will think I’m nuts & leave. lol.