Resolve to Love #8: Dress Beautifully

I had hoped to write this ahead of time, as I did with my monthly bicycle post so it could be posted while I was out of town last week, but alas – I couldn’t get it all done! And maybe I’m glad of that – because this lesson is different than the one I had in mind before my trip. This lesson is truly going to be a challenge for me.

As many of you know, though I love fashion, I tend to dress for comfort above all else – and finding a balance between comfy clothing and pretty clothing is often hard for me to strike. I’d prefer to be comfy and able to ride my bike and play with my students and walk around town and get sweaty and dirty and not worry about high heels that make my feet hurt or silk blouses that would be ruined by sweat or fancy dresses that might get caught in my bicycle chain. And yet, when I dress the way I feel like dressing, I often end up regretting it. I go out in public and feel frumpy, fat and/or downright ugly and it robs me of my confidence.

This lesson was never more apparent to me than when I was in Portland last week for an educational seminar. I knew it was going to be long hours, hard work, never-ending commutes and hot days, so I did what I normally do: defaulted to my comfy, but ugly clothing items. I had my classic sage green cargo pants which are super comfy but aren’t very flattering, clunky sneakers, and an array of loose, unspectacular t-shirts. I didn’t bring a single accessory that I’m famous for at work: scarves, necklaces, etc.

Lessons learned in Portland. Copyright: Five Seed

When I arrived at the first class, I was instantly ready to sink back against the wall. Though everyone was dressed pretty casually, they all had lovely outfits on. Cute flats with a pair of jeans, a pretty skirt with sandals, scarves and tank tops, and the like. I couldn’t shake the feeling that I looked fat and ugly, which affected how I interacted with everyone there.

On Friday night, after an entire week of trying to avoid talking to my classmates or drawing any attention to myself due to my embarrassment by how frumpy I looked, I attempted to dress up for the First Friday event on Clinton, where my sister-in-law has a store (Tangible Gifts). Being as my products were going to be featured there, I attempted to dress up as much as possible with a skirt I bought just for the occasion. Yet still, in my not-so-pretty sandals and droopy shirt, I felt fat and frumpy. It was hot, too, which was making me sweaty and thus, even more self-conscious.

When my brother and I were standing outside, trying to get people to enter a giveaway for a free tonka lip balm, I saw a beautiful young woman in a white dress walk by with one of the most self-confident attitudes I had ever seen. I’m pretty sure it was Christa Taylor, a Portland-based fashion/Christian blogger, which absolutely cracked me up – in a big city like Portland, what are the chances that I would cross paths with (and recognize) someone I’d only known from a blog?!

But the point is, Christa is one of those bloggers who writes about the importance of dressing well and projecting a confident, beautiful exterior to the world, both for oneself, and, in her case, as an expression of the standards of her faith. I have to say, I was struck by this sighting (whether it was Christa or not – and I’m pretty sure it was). Just a few feet away from me sat dozens of stunningly beautiful, classic Portland “hipsters.” The difference between them and Christa was palpable. I wouldn’t have taken notice of any of the young women sitting at The Press Club tables next to me – they looked like any other young woman in her twenties – youthful, stylish, super thin, and emitting that oddly paradoxical combination of arrogance and insecurity. Christa, however, was wearing a classically-cut dress and the most exceptional thing about her was her attitude – confident but open without a hint of false bravado or forced style. Her outfit seemed like a reflection of her inner self.

There it was: that darned truth staring me in the face. Maybe it really is important to dress in a way that uplifts us and makes us feel confident. You can’t imagine how much I hate even thinking of this. I want to be able to wear ugly, old, ripped corduroys, t-shirts and sneakers and feel beautiful and confident. But I can’t. I can’t feel pretty when I see “frumpy” looking back at me in the mirror.

So the challenge this month may be easy for many of you, but not so much for me. Even now, I’m sitting here writing this wearing an old t-shirt, fleece shorts and flip-flops. No makeup, no jewelry. And that’s fine – you know I’m all about embracing ourselves without such embellishments. But maybe it’s time to make the effort to spruce myself up, even on the days when I’ll be home working. Maybe it’s time to extend the boundaries of my “taking myself seriously” project to encompass my closet…

So don’t wear your fat pants cuz they’re the only things you feel comfortable in. Don’t limit yourself cuz everything in your wardrobe is waiting for you to lose weight, or because you don’t feel good enough about yourself to dress up a little. Go buy some bigger clothes (and don’t judge yourself about it). Get up and put a little eyeliner or and a nice skirt or pair of pants. Respect and love yourself and dress accordingly.

12 thoughts on “Resolve to Love #8: Dress Beautifully

  1. My, how timely! I’m going back to school soon (scary) and I had only “mom” outfits (you know, t-shirts and mom-jeans) and shopping for myself for nice outfits was great (and I HATE shopping) and i was kind on a high when i got back home… That same night i threw away all the clothes that were ill fitting and that i didn’t wear for a long time and i’ll try to alter my jeans to make them more “young look” fitting! I’m ready for a change! So count me in this challenge!!

  2. Gaining self-worth and self-acceptance is one of the hardest things in the world to do. You could wear a set of pearls with your jeans… dress up and still be comfortable. :) Good luck to you on your challenge.

  3. I’m going to have to deeply disagree with you here, at least to how I understood this. We’ve been trained by society that we’re not beautiful in certain types of clothes and to not look at each other as beautiful unless we meet a certain aesthetic – i.e., putting on a little mascara or wearing something ‘nice’ as a way of showing you respect/love yourself. We need to find MORE clothes we are comfortable in and whether that means they are dresses or sweats. Sorry but when people use make up as a way to make themselves beautiful it to me defeats the purpose – makeup makes you look different, not beautiful versus ugly. Today I met with two clients wearing yoga pants, a white tank top and sandals with my hair pulled back into a loose knot – something that would horrify others. I was comfortable in it, that’s what mattered. Clothes and makeup alter the aesthetic but they don’t imply (to me) that someone is more or less beautiful – because it’s not about what the world says you should wear to prove you have self respect, it’s if you’re doing it beCAUSE you don’t have self respect. I was actually talking about the fact that I went to an executive workshop in CA this spring wearing my usual casual work clothes, and that most women were all dressed up. I didn’t feel uncomfortable at all – I actually felt kind of sorry for some of them in their five inch heels because we were just sitting in a windowless room for 4 hours – something I was fully prepared for in my cotton knit. I was at home in my skin and that transcended whatever people thought about what I was wearing.

    • @EcoGrrl: This is EXACTLY my struggle. Literally, you perfectly verbalized how I feel and my resistance to doing this. I WANT to just wear whatever the hell I want to wear and screw what other people think! But…I also get really tired of feeling ugly or frumpy in my comfy clothes. It’s not the fact that they are comfy clothes that make me feel ugly or frumpy – it’s the fact that they don’t fit me well or flatter my shape. In fact, if I were to alter my wardrobe and replace half my pants with yoga pants, I’d probably feel fine in those – cuz yoga pants can be beautiful and flattering, unlike my baggy cargo pants.

      And you know I’m all about wearing no makeup, or at least very little. Yet I find I feel a little more confident when I’m wearing a touch of blush, or a bit of eyeliner. I HATE that I feel that way, but I do.

      So for me, I’m trying to experiment with dressing up just a little more than usual – stretching myself to wear skirts more often (which I love, but usually save for work days for some reason), and to buy shoes that I think are both pretty AND comfy (not JUST comfy), and to put on some of my favorite jewelry.

      I honestly don’t know exactly how I feel about this one – part of me is seriously rebelling. But…again, it’s an experiment and who knows what will happen. Maybe I’ll end up going hard-core-comfy! ;)

      • The conclusion I came up with was this… when I was a teen I wore comfy clothes, but I managed to look nice at the same time. I did my nails, hair, make-up, and I always wore jewelry. I’ve NEVER been one to wear anything uncomfortable, but since having kids (over 18 years ago) I had stopped taking care of myself unless it was a special occasion. Now granted, I only have a few nice and comfortable outfits, maybe enough for 4-5 days in a row before I have to start repeating elements, but dang it, I’m wearing those things only! I can increase my wardrobe with a piece here and there from a thrift store or clearance rack, but this girl is taking good care of herself for ME, not anyone else! Just like I got breast implants for ME. If I look in the mirror and I see what I think is pretty looking back at me, then I smile and I have feel good. I doubt I’d win any fashion contests, I sort of have eclectic taste, but my confidence shines through and there’s no holes in my pants. lol.

  4. Accessories. That’s my motto. As a person who pretty much has to live in yoga clothes to the trick to making myself feel good is pretty ballet pumps, scarves, necklaces and bit earrings. Otherwise it’s just black pants, black vest, black wrap top…which gets kinda tired!

    • @Rachel: Exactly! That’s what I do when I go to work – I wear mostly my regularly, boring clothes, but always with a scarf and some big earrings or something like that. I don’t tend to do that when I’m not work-bound, for some reason, but I’m trying to get back to that and get that feeling of confidence back.

  5. Are we like soul sisters or something????? I just came to the exact same conclusion last week, and I’ve been forcing myself to get dressed in things that make me feel pretty and confident each day! Because I’m often home for days on end, I got in a rut of changing out of my pajamas, and into another set of clean pj’s. Most of my pants have holes and tears, my favorite pair has a HUGE tear down the seat, but I was wearing a pair of denim colored undies so you couldn’t tell. Seriously??? What had my life come to that I was doing this? lol. I realized that I was never wearing the jewelry I make, because I didn’t want to bring any attention to myself because I was so frumpy. I tell you what, it’s so nice to be dressing confidently each day and wearing my own creations, even if I don’t plan on leaving the house!

    • @SoulSister: LOL! Yes, Stepheny, we must be! :) I laughed so hard when I read about your camo-undies and ripped pants! I totally do that kind of thing all the time! But yeah, as businesswomen, that’s another thing. We have to represent our business wherever we go – we don’t know who we’ll meet or when the opportunity to network might arise. I don’t want to miss an opportunity because I’m trying to keep from being noticed due to my frumpy outfit! :)

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