Dress For Success
We all have certain styles we like and ways of dressing for the things we do everyday.
I like to dress professionally for work. I work with people who prefer a casual look, so I am used to being the most dressed up person in the building. But I am ok with that because I would feel uncomfortable being casual at work.
Yes, it is possible to be uncomfortable in comfy clothes.
Where we are going makes a big difference in how we dress.
This past weekend I had two events to attend. One was an afternoon get-together at a friend’s house and the other was my Going Away party.
The get-together was something my friend does every year, around her birthday, that is just to celebrate her. It’s about bringing together all the people in her community and spending time together.
I knew that it was going to be at her house, and that it was going to be casual. I knew the food would be vegan, gluten-free health food and that the other guests would be super laid back. They’d fit my definition of under-dressed.
So I didn’t shower.
Yes, that’s right. I went to a party dirty.
I brushed my teeth and put on deodorant. My hair went up into a pony tail and I put on a pair of comfy pants and one of my brother’s old school shirts. It took me less than 10 minutes to get ready. I was a total scrub, but I knew it didn’t matter. In my rule book, if I’m not going to get all the way dressed up, then I don’t need to shower.
On of my besties calls it my “Dirt-A**” look. I’m ok with that.
I felt totally comfortable at the get together. I was not the most casual person there, and I didn’t stick out at all. Nobody knew that I hadn’t showered. And even if they had, they wouldn’t have cared.
When I left my friend’s house I went home to get ready for my party. That meant showering, doing my hair and make-up, and spending time picking out the perfect outfit. I wanted something that said Summer Fun, but with a touch of Miami style. I wanted to find the perfect balance between backyard bar-b-que and cocktail party. Because that’s exactly what it was.
I figured that anyone who knows me knows what kind of party I would have. Fancy drinks in martini glasses and bite sized, bacon-wrapped h’orderves.
Most of my friends came dressed for the occasion, inĀ dresses, skirts, and cute summer capris.
Then my friend who had the afternoon get-together showed up, wearing the same jeans and t-shirt she had on earlier. I hadn’t thought to warn her because I figured people should wear what they want to wear. And I assumed they knew what I’d be wearing.
But I was wrong.
When I talked to my friend about it later, she told me that she hadn’t thought much about where she was going and what kind of party it was. She said she was usually so comfortable in her skin, that she thought she’d feel comfortable no matter where she was.
But she was wrong, too.
She felt uncomfortable, out of place, and under-dressed.
And that totally changed the way she behaved. She went from being the confident, out-going, fun girl I know, to being the wall flower in the corner.
It was so strange to see what someone was wearing completely change their personality. It made me realize that we don’t dress to impress other people, we dress for ourselves. When we know where we are going we can dress in a way that will make us feel not just comfortable, but confident. Then we can let our true selves shine through.
Not everyone owns a cocktail dress, or wants to. I know that. But if we plan to dress for an occasion in a way that will make us feel good about ourselves, we canĀ go in confident from the start.
Does the way you dress for different occasions change the way you feel? How do dress to feel most confident? Do you change your look depending on where you are going?






Absolutely right, Emma. dress in a way that will make you feel confident about yourself. I get called a princess a lot because I like to dress up just a pinch more than what is expected. I feel better about myself that way.
Great post.
A princess, I love it! One of my brothers calls me a princess all the time, but not because of how I dress.
A pinch more than what is expected is a good measure. That sounds about like what I do. It just feels good to be dressed well in most circumstances, I think.
I find that how I dress makes a big difference in my overall confidence. I can go to a theatre rehearsal in yoga pants and a t-shirt (and no shower), because that it normal–it is what everyone else is in. I can wear the same to a holiday meal at my in-laws, because they usually stay in PJs for holidays. ON the other hand, my family dresses a bit more for holidays–dressy jeans or khakis and a nice shirt. Nothing too dressy, just something nice.
A few years ago, when leaving my in-laws house for a holiday dinner and heading right to my parents’ house, I decided that I was just going dressed in my comfy yoga pants. I figured it was only my family, I would be fine. I was wrong. No one said anything about what I was wearing, but I felt out of place. My grandparents and aunts and uncles were all dressed nicely, and I felt like bum. Now, I wear the dressier clothing for both–I would rather be over dressed than under.
I find this carries over into my writing life. I am normally OK in whatever I plan to wear to the gym (which I use as a reward for hitting my writing goal). But, if I am having a day were I am feeling self-conscious or unmotivated, I find that putting on a nicer outfit and a touch of makeup really helps me to feel better about myself, which helps me to reach my goal.
I think you are right, knowing what level of dress is expected helps make me feel comfortable, too. I like the idea of dressing up for writing sometimes. Maybe I’ll get some fancy pajamas or sweats to wear when writing. Great idea!
So well said Emma.
I’ve been there and done that. Under dressed or over dressed and felt totally out of place, uncomfortable and weird. During those times, wall flower would be putting it lightly. Now, if in doubt, I ask around to see what kind of dress code would be appropriate.
Depending on the event, I will either go a pinch cautious or a pinch caution to the wind. LOL! Like a wedding or something for a friend, I don’t mind being a bit splashy but something for work, I always edge on the side of demure!!
Great post!
That makes total sense. I try to be professional at work, too. Not because it’s what’s expected, but because it’s what makes me feel comfortable. I love the idea of going a pinch caution to the wind! I’d love to see that look.
And that is why I wear ugly costco men’s flannel pj bottoms when I write. No creativity stifled with that outfit!
That sounds comfy! I usually write in pajamas. But, I do have some nice ones.
You’re spot on about this subject, Emma. I’ve solved my dilemma by just hitting a happy medium most of the time. When I walk out of the house, what I wear would work in every situation except formal…and thank goodness I rarely have to worry about that.
That is great place to be. I don’t know that I could do that, but it is something to think about. Yeah, formal doesn’t happen often, ok pretty much never, for me. Sometimes I wish life could be like tv, with a fancy ball every now and then.
I feel the same about make up because I wear it for myself. I love the way it feels and makes me feel about myself! I always strive to be the most dressed person in the room. I like to look put together! I love the picture of us Emma!
Yeah, I consider make-up to be professional. I don’t feel right when I don’t wear it to work. On the weekend afternoons, I don’t mind being without make-up. Luckily I am comfortable without it, but it definitely makes me feel more dressed up.
And, I must say, just having met you, Jesse, that you looked maaavalous!
The funny thing for me is that all the bbq’s I’ve been to in the past were out-doors, with bugs trying to eat me, and ripped open bags of corn chips, and a lot of food I couldn’t eat, etc. I had no idea that a bbq could be something more– and this cocktail party (with drool-worthy kebabs) was so much more FUN than my old concept of “bbq.” I’m glad I was there to celebrate you! And sad I missed my one chance to wear that sexy silk tank top I own! =)
I think I do both…dress in what makes me feel most comfortable, but also what fits into the “scene”. I normally wear either jeans and a t shirt (cute one, of course) or a skirt and top to work. One day this past week, I had a vision that I might run into someone from another “life”. So, I chose to wear a skirt. Wouldn’t you know it! I ran into someone from this other life and was so glad I was dressed for success. She knows the work that I do requires me to dress down, but I just felt more confident.
That being said, I always love an opportunity to dress up…and dress up around friends who love me no matter how I look.
Jeans and a t-shirt can be done cute. I think of Eva Mendez in Hitch. That is how I like to do jeans and a tee. But, I agree that dressing up is fun. Sometimes I even put on fancy jewlery just to sit at my computer and write. It just makes me feel good!
Brooke: I know there will be many more opportunities for you to wear that sexy, silk tank top. Maybe we can do drinks in the Pearl and you can wear it then. Fun!
Yeah, in my rule book a bar-b-que is just a cocktail party with good food. Every get together is an occasion worthy of martinis. I’m sure there will be so many more chances to wear that sexy top. If you decide that something is worth dressing up for, then it will be. I think you should try it, and take note about how you feel and how you behave. It might give you more confidence than you would have even imagined.