As we close out 2015 and the third year of “Recovering Shopaholic,” I thought it would be fun to reflect on how my personal style has evolved over the past decade plus.   This is a post I’ve been meaning to do for a while after I had seen another blogger do it, but now seems like a good time since I feel I’ve made a lot of positive changes to my style this past year.

This will be a very photo-heavy post with not as much writing as usual.  There is an old saying, “A picture speaks a thousand words.” Well, that is definitely true when it comes to what we wear, but I will also add some commentary throughout to shed some light on what you’re seeing.  Some of my older photos are a bit embarrassing for me to post, but I’m sure many of you aren’t exactly thrilled with your outfits from days gone by.  It’s all part of the journey, right?   It’s important to note that I liked a lot of these outfits while I was wearing them, but there were definitely times when I felt insecure and uncomfortable in my ensembles.   Again, that’s probably something most of us could say.

2000-2005

Let’s start this retrospective about 15 years ago.   While I have been a shopaholic since my teens, I never really tried to be “mainstream” with my style. I always had an eclectic and quirky sense of style and I basically marched to the beat of my own drummer.   When I shopped, I simply chose what I liked and paid little attention to what was “in” at that particular point in time.   I enjoyed wearing Capri pants, funky patterns, turtlenecks, sweaters, and holiday themed clothing.  Just like now, black was the most prevalent color in my closet.  Here are a few examples of the types of outfits I wore back then:

2006-2007

As I inched closer to the big 4-0 in 2006 and discovered the television show “What Not to Wear,” I decided that I needed to start dressing in a more sophisticated manner and tone down the free-spirited style that I had become accustomed to over the years.  So I started buying more tailored pieces such as blazers, fitted pants, A-line skirts, and heels.   What I didn’t pay attention to, however, was that my life didn’t really call for such items, as I was working from home and lived in a casual city (San Diego – where I still live).  I continued to struggle with this issue until very recently, but its genesis goes back to 2006 and the advice I got from Clinton and Stacy on “What Not to Wear.”

Here are some ensembles that are representative of my 2006 and 2007 style.  As you can see, I kept the Capri pants, but also started wearing skirts with my fitted jackets.  That was also the time when I started to adopt the stripes that remain part of my signature style today.

2008-2009

In 2008 and 2009, I started to move away from blazers and highly tailored clothing and brought a bit of whimsy back into my wardrobe.   At the same time, I let go of the Capri pants in favor of full-length pants (boot-cut and wide-leg styles) and midi-length skirts.  I continued to enjoy wearing prints, primarily those in black and white tones, but I also started to wear more brown and other colors.

Here are a few of my looks from 2008 and 2009:

2010-2011

In 2010 and 2011, I started wearing scarves with a lot of my outfits. Those were also the years when I began wearing cardigans, both the mid-length crew-neck version and the new at the time open cardigan style.  I also moved back into wearing tailored jackets and blazers again, primarily with skirts. I also wore a lot of dresses as well as skirts during these two years.

This is when the “church vibe” was born without my actually realizing it (see this post for more on that topic). I was trying to look more polished, probably upon advice of “What Not to Wear” and various style books, but I didn’t realize that I came across as too formal in what I was wearing.   In retrospect and with what I’ve learned in the intervening years, it’s very clear to me that I veered off in the wrong direction, but my intentions were good at the time.   I wanted to look more put together, but I didn’t think enough about the context, i.e. Bridgette Raes’ famous question, “Where are you going in that?”

Below are some examples of how I dressed during 2010 and 2011:

2012-2013

It was in 2012 and 2013 that I adopted the three primary “uniforms” that I wrote about in this post.  I wore a lot of long cardigans with jeans (I still do that now, but the silhouette has changed), knit blazers with midi skirts, and ¾ length coats with trousers and trouser-style jeans.  I don’t hate any of these uniforms today, although I wouldn’t wear most of them “as is” now.  I would definitely “tweak” them in certain ways as you will see in my more recent outfits.

During 2012 and 2013, I was also really into wearing leopard print, but this is something I’ve gotten away from more recently.  I still have the leopard print dress in my closet and a few pairs of shoes, but I now prefer black and white prints much more.

Here’s a look at how I mostly dressed during the years of 2012 and 2013:

2014 – Enter My Outfit Journal and Bridgette

Around the middle of 2014 is when my most recent style evolution started to take place. My outfits early in the year weren’t too different from my 2013 looks, but I did two things in the summer that made a profound difference in term of my style. I started keeping an outfit journal and I had two virtual styling sessions with Bridgette Raes (read about the process starting with this post).  The outfit journal increased my awareness of what I did and didn’t like about what I was wearing (see my update at the two month mark here) and Bridgette gave me some concrete advice to help bridge the gap between my current and desired style.

Slowly but surely, I started to move my style in a direction that felt more congruent with my personality and lifestyle. In the summer of 2014, I began to embrace the maxi silhouette for skirts and dresses, which is a better match for my casual Southern California lifestyle.  I also shifted from knit blazers to moto-style jackets, which have a less dressy feel to them. I didn’t change the style of my pants and jeans outfits much last year because we have late summers where I live and I continued to wear dresses and skirts through Thanksgiving.  However, I did decrease my frequency of wearing open cardigans in favor of long sleeved tops, especially waffle weave styles, and I wore jeans far more often than other types of pants.

Last year was also when I started to really embrace cobalt blue, which is now my favorite color other than black.  I refined my color palette considerably last year such that the main colors in my closet now are black, cobalt, burgundy, turquoise, green, purple, grey, pink, and red. The outfits below show how my style changed in 2014, especially in terms of my warm weather looks:

2015 – My Current Style

I continued to refine my style in 2015 and have kept up with my outfit journal through the entire year. I also took on the “Love It, Wear It” challenge (LIWI) in which my objectives have been to wear what I love and to have the right types of clothing, shoes, and accessories for my life.  No longer was I pushing myself to wear “wardrobe benchwarmers.” Instead, my focus shifted to simply wearing what I felt “called” to wear each day and dressing appropriately for my activities, most of which are very casual in nature.

This year, I shifted toward wearing narrower pant silhouettes, which helped to balance out my open cardigan outfits.  My favorite pant looks included straight-leg jeans with boots.  The top halves of my outfits were similar to what I wore in the past, either fitted long-sleeved tops or long cardigans worn with t-shirts or tank tops of close to the same length.   I also got back into wearing more long necklaces.

I continued to enjoy wearing maxi length skirts and dresses, but my topper of choice shifted away from moto-style jackets and more toward tie-waist cardigans.  I wore midi-length dresses and skirts less often, but the ones I decided to keep either have asymmetrical hems or were shortened to a more flattering knee length.  I also purchased a few new printed knee-length dresses that I enjoyed wearing this past summer.

Almost all of my outfits over the past six months have been rated as “9”s and “10”s.  I truly believe this shift can be attributed to keeping an outfit journal for the past year and a half, investing in some virtual styling help from Bridgette Raes, and taking on my LIWI challenge over the course of 2015.  It also helps that I have dropped some weight and am happier with my figure these days, but I believe I would still rate my outfits highly even if my weight had remained exactly the same.  I have discovered my authentic style and it works well for my body, personality, and lifestyle.

Below are some of my favorite outfits from this year:

Moving Forward

I know that I will continue to evolve my style in the coming year.  I plan to continue with my outfit journal (perhaps not for all outfits but for at least some of them) and I’m going to also place increased focus on my at-home wardrobe.   I spend a lot of time at home and I feel it’s important that I’m happy with what I’m wearing there as well.   For years, I didn’t give much thought at all to what I wore at home – and it showed.  I’ve made some progress in this regard during 2015, but there is still room to grow.

In terms of my “out and about” wardrobe, not much work needs to be done. I see myself making strategic purchases and buying a lot less. I plan to replace wardrobe staples as needed and buy just a few pieces each season to refresh my closet and keep my style fresh and modern.   I think it’s important to continue to have fun with our clothes and our style, but that can be accomplished without spending a lot of money or buying too many items.   I do plan to take on some sort of wardrobe challenge for 2016, but I haven’t decided exactly what I’m going to do yet. I will finalize my plans and announce them on the blog in early January.

Your Thoughts?

I hope you enjoyed this retrospective on my style over the past fifteen years.  I feel that I’ve come a long way over the course of this time.   There have been lots of ups and downs, many wasted dollars, quite a few not so great outfits, and too much shopping overall. But over time, I’ve learned a great deal and have gradually come around to the place I’m at today. I feel happy and comfortable in what I wear now and feel good about how I look.  Style is not a static thing, so I know that I will make changes as 2016 inches along.   I look forward to it!

If you have any questions or comments for me about my style evolution, please share. Also, it would be great to get your thoughts on your own style journey over the years.

• What do you love to wear now versus five, ten, fifteen or more years ago?
• How has your style changed?
• What changes would you like to make in 2016 and beyond?