Dress for the Day; Dress for the Life

dress for the day; dress for the life

I’ve been enjoying following Dear Abby Leigh’s new cause, Dress for the Day. It’s about fashion, but it’s not really about fashion. It’s about intention and cheerfulness and purpose and buoyancy. Here’s the motto:

Dress for the Day you want
dress for the day you want to have…not the one that’s trying to have you

Abby’s quick to point out that she’s not a fashion blogger—and neither am I! But that doesn’t mean we can’t still think clothes are important. Whether I want to or not, I can’t help but send myself powerful messages by the clothes—and hair, and makeup, and shoes-I choose for myself each day.

A few years ago, I realized that I send other people messages with my clothes, too. But maybe not in the way you would think.

I’ve always believed in dressing for the occasion, but I never stopped to think about the more nuanced vibes I gave off with my apparel choices. I’m not sure what brought my attention to it–in hindsight, I wonder if it was Ruth Reichl’s Garlic and Sapphires, but I’m just speculating. I may not remember the trigger, but I know this: when I realized people’s perception of me changed when I changed my clothes, I decided to change the way I dress.

Here’s what happened: by nature, I’m a pretty conservative and classic dresser. Give me my sweater set and string of pearls and I’ll be good to go. (Okay, that’s a little hyperbolic … but you get the idea.) The buttoned-up, sophisticated look came easy to me.

But I’m an introvert, and I finally came to the conclusion that the buttoned-up look I gravitated toward didn’t help me have the days—or the life—that I wanted to have. My crisp style of dressing + my reserved personality could too easily come off as standoffish–but I wanted my style of dress to help me exude warmth and friendliness. In other words, I wanted my style of dress to reveal the real me! I didn’t used to think that clothes mattered in this way. Now, I do.

dress for the day; dress for the life
the new normal: tee, jeans, and ruffled, flowy cardigan. More pictures from this overdue family photo shoot coming soon!

And so I made a conscious decision to change. As I began to shop for new clothes, I steered towards a warmer palette and flowy silhouettes. I began to look for drape instead of crispness in my garments. I chose softer jewelry and fun shoes. I shunned anything that screamed “sophisticated,” because that’s just not what I was going for.

I had to work at it. The change was difficult at first (though if I actually shopped more often, I might have adapted more quickly!), but I was happier in my new style. When I changed my clothes, I began to feel more approachable, more friendly, more fun. Warmer. It didn’t hurt to discover that I looked better in flowy garments than I did in crisp lines anyway.

It’s been a few years since I decided to change my style, and now it comes naturally. In fact, when I filled out my style survey for my first Stitch Fix shipment, I described my style as “classic,” but also “approachable,” “soft,” and “friendly.” (More about Stitch Fix soon.) Taking care to project friendliness with my clothes is how I dress for the day–and the week and the year and the life.

For more great reading about dressing for the day, check out Dear Abby Leigh’s Dress for the Day link-up.

Do you dress for the day you want to have? The life you want to have? I hope I’m not the only one 🙂 Tell us how you approach fashion in the comments!

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  1. Ana says:

    Anne, I like this. Why is interest in fashion considered frivolous and “shallow”, when its another expression of creativity? Unless you are spending lots of money you don’t have, there is nothing wrong with liking to dress well. Sometimes I’m embarrassed to admit that I actually LIKE shopping for clothes and accessories for MYSELF. Like any serious career women hates shopping and a true mother only likes to shop for her kids. I find bargains and change outfits around with accessories and simple sewing.
    I have been doing the opposite of you, trying for more “crisp and sophisticated” and less “fun and pretty” to be taken more seriously at work and out-and-about (i’m petite and young-looking, so I get treated like a child). Being put together helps my confidence and can really change the tone of the day, especially when I’m tired and stressed.

    • Anne says:

      I love how you brought up what you do in your own life: same concept but totally different desired outcome! Thanks for sharing, Ana!

  2. Jamie says:

    It is very true that how you dress sends important messages. I’ve been forced to pause more than once and ponder the unintentional compartmentalization I’ve done of my life and personality when I find items perfect for one environment (coffee with one friend) and completely not right for another (coffee with a different friend!). It’s also been highly informative for me to see what other people are drawn to recommend to me in terms of clothing, as it says a lot about what they see in me – or want to see in me.

    • Anne says:

      Jamie, that’s so interesting that you dress differently for different coffee dates with different friends. Now I’m mentally reviewing how I dress for that sort of thing…

      “It’s also been highly informative for me to see what other people are drawn to recommend to me in terms of clothing, as it says a lot about what they see in me – or want to see in me.”

      YES. Great point.

  3. Amy says:

    Oh, I like this take on it. I’m also an introvert and learn toward classic looks. I have often wondered if I mistakenly come off as standoffish as well. Hm, gives me something to consider!

    • Anne says:

      Well, you don’t at all on your blog, but of course there we get to see what you’re thinking and not just what you look like! And if you’re a fellow “introvert who leans toward classic looks” that explains why I wanted to lift your conference wardrobe you shared right off the screen and put it straight into my closet!

  4. Corrie Anne says:

    I love that quote — dress for the day you want to have. 🙂 I have a piano studio in my home, and my students are always commenting that they are surprised how dressed up I am. One asked me if I have a job interview. Haha. (I have a lot of adult students).But it’s just one of my ways of reminding them that although I have a casual, outgoing personality, and they are coming into my home — this is a professional business. Plus I would miss not wearing heels! Thank for sharing!!!

  5. I’ve actually been working on this lately. I’m an ambivert who tends towards conservative, simple, classic stuff… but I noticed that when I add a fun splash of color or something unexpected, it gives me an extra boost of energy and confidence. And in turn, others seem to reciprocate that. When I wear my crisp button-down shirt and classic grey skirt, I may feel “put together,” but I tend to sit in the corner and people watch, instead of interacting with others.

    Even at home – when I wear something nicer than a comfy hoodie & jeans, I tend to be more alert and aware of what needs to be done. Clothes make such a difference in how you face the day – and in what you get out of it!

  6. Suddenly, I know what I need to think when rummaging through my closet and dresser in the morning trying to find something to wear. Lately I’ve been working at what I deem “dressing like a grown up” but maybe I need to dress with intention, too, and keep in mind the message I am sending.

    Today, I am dressing “college student,” and have already been asked three times if I feel okay (when the alma mater hoodie comes out, all bets are off. it’s soft, warm, comfortable, and not unflattering).

    • Anne says:

      You’ve already been asked three times if you feel okay? Yikes! (That reminds me of my own dislike for wearing pajamas when I’m not sleeping: it makes me feel like I’m taking a sick day.)

      I wonder how many of us spend quite a few years trying to “dress like a grown-up.” I know I sure did!

  7. Sarah Beals says:

    LOVE, LOVE THIS. And yes, I have found that we can unintentionally send messages with our clothes. I once had a woman remark about another woman in our church, “Wow, she’s all business isn’t she!” That could not have been farther from the truth about this woman, but she always.wore.a.suit.–which by the way, made her look a little man-nish because of the cut she chose. Anyway, I realized then and there that clothes totally send off messages.
    I love mixing scarfs with casual jeans and sweaters…and I always look for inexpensive jackets at the thrift shop–jean, corduroy, twill, plaid. My ONE weakness. 😉

    • Anne says:

      So interesting about the “all business” comment.

      I think your scarves with jeans and sweaters look sounds lovely, Sarah. Maybe because it’s one of my favorite looks 🙂

  8. I love how you mention Garlic and Sapphires, especially since I just wrote about it.

    And more on topic, this is one of those things that I know I should do and put more effort in and all that. But instead I tend to think it’s too hard and revert to my usual lazy way of dressing. 🙁

  9. Janice S. says:

    This has been my project recently as well! I’m pretty conservative and professional for my office job. But I want to be seen as the artist that I am and emphasize my creative side and have that show in my appearance. So I’ve been slowly changing hair style and color and adapting my wardrobe to show that. It’s a process, because I’m rediscovering myself along the way.

  10. Heather says:


    I started going for a more sophisticated look a few years ago after leaving college and getting married. I wanted to look and be treated like an adult, and it worked. But now reading this I think it’s time to add some fun to my wardrobe to make myself look a bit more warm and approachable. After all, I have a child and house, and no one’s going to mistake me for a college kid now!

  11. Katie says:

    OH NO.

    It never occurred to me that all the classic/conservative/dark color dressing could make me come off as even more standoffish than my shy introvertness already does.

    As a counterpoint, if I’m dressed in something “daring” (daring to me, anyway), a bright color or a different cut or a dramatic accessory, a lot of times I don’t feel more confident–I feel awkward, unsure, like I’m going to be called out for playing dress up or have accidentally committed some unforgiveable fashion faux pas.

    When I dress in something classic, where I know it looks good and isn’t breaking anyone’s rules, I feel more comfortable and am more likely to act confident and thus friendly, but maybe people are interpreting me completely differently. Weird.

    • mariah says:

      I’d recommend adding in earrings in a bright color or a necklace or purse. Start the “daring” in your accessories before putting it into your clothes.

    • Rebecca says:

      I feel exactly that way. I am an introvert and dress classic/conservatively.
      You could try some other colors within your palette that you haven’t worn as much of but should still find comfortable.
      I am a summer but I tend to wear a lot of black and neutrals. Apparently they can make you look almost invisible. Clothes walking around, all buttoned-up and quiet. I recently picked up a few turquoise tops and they bring out my eyes and clear up my face. And no buttons, as a matter of fact. I feel different, I wonder if I am perceived differently.

  12. Elizabeth Kane says:

    Yes! This is a wonderful mantra to have. As soon as I read your post, I went to the closet and found something that put me in a better mood. The day was *definitely* having me.

    Also, I’m going through a similar transformation of wardrobe pieces. It wasn’t until recently when I looked in my closet realizing I was buying what I thought I should be buying. The image I had and the image I wanted to have just weren’t matching up. Guess we have to go through a little bit of trial and error to find out what feels right to us sometimes 🙂

    • Anne says:

      YES to the trial and error. And I can totally relate to this: “The image I had and the image I wanted to have just weren’t matching up.” Here’s to getting closer to a match!

  13. I didn’t really realize that I dressed in a characteristic way until this Halloween.

    One student dressed up as me for Halloween, with a classic dress, hat, and pashmina. She said people mistook her for me all day.

    I dressed up as a 1950’s housewife, complete with swing skirt/petticoat, tight bun, pearls, and bright red lipstick. I sent my mother a family photo. She asked why I hadn’t dressed up.

  14. Jillian Kay says:

    Very interesting. I have so many days within my day it’s hard to know how to dress some times! I’m lucky that I work in a very casual office (think flip flops in the summer), but I also commute on public transportation, walk 5 miles for exercise, and care for my kids all in the same clothes. This time of year it’s easier because I can do the jeans/sweater/boots thing, but in the summer it can be tough.

    This discussion is also making me wonder what my in-laws mean by sending me a sweater set every Christmas. 🙂

  15. Carrie says:

    What’s interesting to me is how my style always changes after I have a baby. Right now little one is 10 weeks old. Normally I prefer a crisp/classic look with tailored lines and a little bit of funky thrown in. But after my babies I always found myself gravitating towards flowy, feminine stuff – lots of skirts and more color and stuff. Which isn’t “me” at other times.

    But it just so happens that those flowy/soft lines look much better on a postpartum body! And also kind of fit the lifestyle better. Softer blousy type shirts work better with breastfeeding, for example.

    Fun stuff!

    • Anne says:

      Carrie, I didn’t change my style like this after breastfeeding, but I definitely should have! I would have been a lot more comfortable, and I know I would have looked better, too. Those are important considerations for postpartum mamas! Wish I would have known better at the time 🙂

  16. Amanda says:

    I have started giving fashion a little more thought lately, primarily because my new work environment has no real rhyme or reason as far as “what goes” – coming from a formal (suits, slacks, pencil skirts) environment, the question of what jeans to wear and whether I’m a) too casual or b) too prissy/formal is a constant thing on my mind. Bah. I don’t really care about clothes (I do like them, I just don’t prioritize them), so it kind of annoys me to think about them too much 🙂

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  18. Arati says:

    I used to feel like I wasn’t expressing my own creativity when I dressed – black, brown, grey… I now wear what I like, as long as I think it looks good on me!

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