What nobody tells people who are beginners — and I really wish someone had told this to me —  is that all of us who do creative work, we get into it because we have good taste. But there is this gap. For the first couple years you make stuff, and it’s just not that good. It’s trying to be good, it has potential, but it’s not. But your taste, the thing that got you into the game, is still killer. And your taste is why your work disappoints you. A lot of people never get past this phase. They quit. Most people I know who do interesting, creative work went through years of this. We know our work doesn’t have this special thing that we want it to have. We all go through this. And if you are just starting out or you are still in this phase, you gotta know it’s normal and the most important thing you can do is do a lot of work. Put yourself on a deadline so that every week you will finish one story. It is only by going through a volume of work that you will close that gap, and your work will be as good as your ambitions. And I took longer to figure out how to do this than anyone I’ve ever met. It’s gonna take awhile. It’s normal to take awhile. You’ve just gotta fight your way through.

~ Ira Glass

Ira is, of course, talking primarily about writing, but also about other artistic endeavors. Yet when I first read this quote several months ago, I thought immediately about style. My own style. I thought about how I started out with good taste, and that got me into good clothing, but that it took a long, long time for my actual style to emerge. And it took a long, long time for me to feel like I’d really hit my stride.

Occasionally, I’ll get an e-mail from a reader who has just read through my archive. This blog contains several thousand posts, so I am always honored and humbled to hear that anyone has taken the time to read them all from the beginning. I’m also a little mortified because my views on style and body image have changed substantially since 2007. I know a lot more now, and have refined my philosophy over the years. So some of those old posts? They’re not really me anymore.

And my, oh my, has my style evolved.

2007

When I began this blog, I had no intention of taking daily outfit shots. Photos of me were used in tutorials to illustrate concepts of figure flattery, and that was it. So there are very few images from the early days, but these two perfectly capture my style back then. I am wearing head-to-toe Boden in both shots, and although I didn’t own a closet full of Boden, outfits like these were my staple: Solid top, cute embellished skirt, the end. I’ve mentioned before that I credit Boden with sparking my style obsession. I saw a catalog at a friend’s house six or seven years ago and my head caved in. Something about the clean-but-quirky design aesthetic just slayed me, and I spent many years relying on Boden’s cute pieces to create my style for me. Purchasing darling pieces meant the garments did all the heavy lifting. I didn’t have to think or be creative, I just relied on my taste to carry me. (UPDATED: Please see this comment thread for a bit more on how I feel about Boden/personality pieces.)

Also represented here are my hairstyles: Ponytails were slicked back and severe, but when my hair was worn down it was an all-one-length curly bob. Before the blog, I was parting it in the center. My grandma made some comment about how she wished I parted it on the side, and I sheepishly took her advice.

2008

By the following year, I began playing a bit more with proportions, separates, and interesting combinations. I began gravitating toward some items that would become signature pieces – like the curved-hem bolero – but also hung onto others that I would eventually realize fought my figure – like wide-legged pants.

This outfit also illustrates how I hadn’t yet started to be more intentional and strict in how I wore my black pieces. I’d still do hot pink and black together now, but not quite like this – there’s nothing uniting these pieces.

This self-portrait shows an outfit that’s slightly closer to what I’d wear today, though I’d likely try for a more unified top and bottom. It also proves how far my standards for photography have come. When I got started, I was convinced that all my photos should be taken in front of a an all-white, non-distracting backdrop, a standard that I bent occasionally for in-the-office-restroom-self-portraits.

2009

This outfit is a great example of my personal version of “trying too hard.” I love all those colors, I probably saw them worn in combination in a magazine somewhere, and I cobbled together an ensemble that threw ’em all in the pot. I was trying to explore new options and experiment a bit more, which was absolutely key to learning about myself and my style. But it didn’t always WORK.

Occasionally, I’d let things flow a bit more organically and rely on some of my favorite pieces as focal points. This technique still serves me well. Though I’m glad to be rid of those oyster-colored widelegs.

As 2009 progressed, I began to make some big changes that helped me eventually hit my personal stride. For starters, I got a layered haircut. I have always needed – not wanted, NEEDED – to be able to pull my hair out of my face. My hair is wild and unruly, and it tickles my face all damn day. At night, at the gym, and when I just need a break, it must go up. So I’d shied away from layered styles for fear that I’d never be able to pull back my locks. When I discovered that certain styles could be worn up and down AND provide some much-needed volume for my ‘do, it completely transformed my look.

Here’s the first outfit I pulled from the archive that I would wear, exactly as photographed, on writing this post. I was still fumbling a bit, but I had begun to find combinations that worked for me: Lots of dresses, fitted tops, heels, fun jewelry. I began to see how pieces interacted with each other, and learned the value of unbroken figure lines.

Also notice that photos are more interestingly composed and NOT confined to white backdrops. I’m finally letting Husband Mike‘s skill set shine through!

2010

And then, a setback. In my glee at discovering that my style could be funky and fun, I pushed the envelope a bit further than I now believe I should’ve. The above outfit is cute, but also a bit “off.” The brooch could probably stay, but the scarf-as-belt is jarring. Since it’s the object that ties all the other pieces together, it needs to remain in the mix, but would be better around my neck or in my hair.

At this point, I wanted to be Creative with a capital “c.” I was putting lots of pressure on myself to wear cool and unusual ensembles, and that pressure prompted some unwieldy combos.

It was also around this time that I began obsessing over color. In the summer, I’d launch the Summer Black-out, which was a fun and worthy experiment, but also added to the self-generated pressure to be super-duper creative and new and fresh and different and unique. On writing this, I still consider myself to be a champion of color, and still love to experiment with unusual and unexpected pairings – and encourage you all to do the same! But I’ve since eased up on myself about making every outfit burst with brights.

Another example of an outfit I’d wear unchanged! And another example of how my style works best when I have fun, but don’t push too hard. Sure, red and leopard is a bit “expected,” but damn. It works.

This is another outfit that I’d probably still wear, but shows quite well how incredibly LONG my hair got by the end of the summer of 2010. Having pored over photos from that era, I’m pretty convinced that – at least, in this style and with these products – shoulder length is ideal. Longer gets frizzy and bushy.

Here’s a late 2010 outfit that shows how I continued to wear longtime staples – the color red, curved-hem boleros, obi belts – but did so with a little more refinement. I’ve made a lot of progress.

2011

Before I started this blog, I had two completely separate wardrobes: One dressy, one casual. I was fairly formal during the week and pretty disjointedly messy on weekends. I spent YEARS working my fancier duds into weekend wear and attempting to merge the two styles. This is the first year I’ve felt like I have my casual looks nailed. In fact, at a certain point over the winter, I began to PREFER my weekend looks.

Also this year I felt like I could “style” challenging pieces better than ever. This sweater duster could totally swamp my figure and age me 15 years, but paired with the unusual necklace and edgy boots it looks just right. Just right on me, anyway.

Also this winter I discovered blush. I’m amazed by how much more defined my face looks with just a touch of blush on my cheeks.

Looks like a pretty tame ensemble, eh? But with this outfit, a few things clicked into place: I have long joked about being the Mayor of Matchy-Matchytown, and done so a bit sheepishly. But the fact is that I LIKE matched looks. I feel chic and refined and pulled-together when my belt and boots match, and I’m good with that. Also, I don’t need to force my wardrobe staples – like this fabulous shirt dress – to look super trendy, unique, or unusual. They work, I feel great in them, and that’s good enough.

It’s fun to see how much more refined my standby formulas – cardigan, dress, belt, heels, for example – started to look. My eye for fit and garment interaction has truly evolved, and I’m just more comfortable constructing my ensembles. I definitely miss the mark sometimes, but as I ease the pressure on myself to deliver innovative, colorful outfits every single day, I find that what I wear looks better. Looks more natural, more cohesive, more like me. (Since the post you’re currently reading is older, it may interest you to read more recent updates on my style evolution here and here.)

I am in no way ashamed of my 2007 looks, and I did not write this post in an attempt to tear myself down OR pat myself on the back because “I’ve come so far.” The point is to say that style evolves. ALL style evolves. I am quite sure that I’ll be dressing in an entirely different way three or four years from now because my style, like all personal styles, is in a constant state of flux and refinement. And that is a very, very good thing.

In fact, if I hadn’t changed my look at all since 2007, I’d be a bit worried. Occasionally you’ll come across someone who shifts her look so frequently that you can’t get a bead on her personal style, but far more often you’ll come across someone who has stagnated. Tweaking and refining your look helps you to look fresh and current.

If you’re exploring your personal style and you’re in a place now that feels like what Ira Glass is describing – experimental and exploratory, but frustrating because it’s just not “good” in the way you want it to be – don’t give up. What you are doing is an artistic endeavor, a very personal and emotional artistic endeavor, and you WILL get there. If you keep playing and trying and creating and recombining, you’ll find your way. Be patient with yourself, and enjoy the ride.

Although I’d never intended to do daily outfits, I’m glad that you folks eventually demanded them. All the style guides and fashion advice in the world won’t teach me nearly as much about what I should and shouldn’t wear as a daily catalog of my looks. Even just assembling this post opened my eyes to a few things. So thanks, friends. You tell me with humbling frequency how much of an inspiration I am to you. Your feedback, input, and comments have had an incredible impact on my personal style, too. And I’m truly grateful!

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