My Style Evolution: 2000 – 2015

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.


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:

My Style: 2000-2005

My Style: 2000-2005


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.

My Style: 2006-2007

My Style: 2006-2007


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:

My Style: 2008-2009

My Style: 2008-2009


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:

My Style: 2010-2011

My Style: 2010-2011


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:

My Style: 2012-2013

My Style: 2012-2013

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:

My Style: 2014

My Style: 2014

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:

My Style: 2015

My Style: 2015

My Style: 2015

My Style: 2015

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?

16 thoughts on “My Style Evolution: 2000 – 2015

  1. In your favourite outfits of the year – I really love the blue and yellow dress on you (second column, second picture)!
    You can clearly see how your style has evolved over the years !

    • Thanks, Sabrina! I really like that dress, too, and would like to find another one or two in a similar silhouette next year.

  2. I love the outfit ‘black jeans, striped chiffon top, I would wear that in a heartbeat! I also think the cobalt blue outfits look amazing. My style has evolved from corporate wear to Paris fashion editor wannabe! I wear skinny jeans, leather or suede leggings with tunic top & fur topper in winter & silk kaftan in summer. I usually wear black, camel & brown, but this winter I have introduced lots of wine & raspberry which works well with the neutrals. I get lots of compliments when wearing these colours. I previously wore black/camel exclusively in winter & white/beige in summer. My previous wardrobe choices were driven by my golden retrievers who were always messing my clothes but now I have a very elegant kitty I can wear these glorious pieces. Misty likes to be pristine so there is no fear of grubby paw prints! Thank you for all you hard work this year Debbie. With the all the inspiring content & therapy I really appreciate your blog.

    • Thanks, Sharon. I don’t know why it took me so long to wear that top… And yes, cobalt blue is definitely a major favorite of mine. It sounds like you are very dialed in on your preferred style. What you described sounds very nice. I love those wine and raspberry colors, too, and they are in plentiful supply this year. I have a couple of pristine kitties, too, and don’t really have to worry too much what I wear around them (but I do have to use a sticky roller after they have been on my lap). I’m glad you really like my blog and I appreciate your thanking me for my hard work!

  3. Thanks for sharing your photos. It confirms what I’ve learned that when a person dresses in thirds, they look pulled together and pleasing to the eye.

  4. Your current style feels very you. It is simple, and clean, with a focus on color and interesting print or details, and less on accessories.

    I too fell into the What Not to Wear trap. Almost every woman on this show ended up looking exactly like every other woman. Slim, tailored, pencil skirts, side-leg pants, perfectly tailored blazers, and handbags in random “pop” colors. I ended up with a closet full of those things. They never felt like me, so I shopped haphazardly, looking for trendy items or things I thought I wanted to make me feel more complete. Some days, I looked and felt like a banker, other days I was a trend-salad that made no sense.

    A few years ago, my job transitioned to business casual. I live in the south and southern business casual definitely does not involve blazers. I was really lost as I tried to figure out what to wear in the new environment. I ended up with a closet of more than 600 items. I realized it was insane and started purging. A foot injury immediately slashed many shoes. But, it really wasn’t until 2014 that I decided to come up with some style words to hone in my shopping. By mid-2014, I was trying to pare down my wardrobe and make good buying decisions. I’m not perfect, but I am much better. I have only purged one 2015 purchase, although, I have 3 that are on the fence to be decided this spring.

    • I appreciate your kind words about my current style, Barb. I think you encapsulated it pretty well with what you said. I knew I wasn’t the only one who fell into the “What Not to Wear” trap! I had quite a few of the items you mentioned, too. I like the term “trend salad” – been there, done that! It sounds like you have done an amazing job on both paring down your wardrobe and honing a style that works for you and your life. Congrats on only purging one 2015 purchase! Even if you also end up letting go of those 3 on the fence items, you will still be doing a lot better than most. You should be proud of yourself for how far you’ve come!

  5. Debbie, this is a fun photo journey of how you have evolved style-wise over the ages. What stands out most of all is your smile, your graceful body, your delight in the moment, along with the fun of clothing. My wardrobe also took a nose dive after I began watching What Not To Wear. Suddenly I found myself dressing for my office job 24/7. Like you I am glad those days are behind me! Love your newfound style on you and that it is all coming together for you in good ways.

    • So you fell prey to the “What Not to Wear” effect, too, Terra? I’m in good company, it seems… I’m glad we are both in a much better place with our style now these days. I appreciate your kind compliments about me. I can always count on you to help brighten my day and my spirits.

  6. Fortunately I disliked the presenters on the US version of What Not To Wear – sounds like I dodged the bullet on that one, although I did go through a heavy Talbots shopping period, but I bought mostly dresses at that time. Having just retired 6 months ago I still have lots of nice things to wear and can probably go for another 5 years without buying much. I wore knit tops or blouses with jeans to work so I am continuing with that look. I have noticed though that unless I have an outing planned, I sometimes spend the day in a sweatshirt, especially now that it’s cold here in Montreal. It was easier in the summer to get motivated to get up and dressed, winter is causing me to want to hibernate in casual clothes. I want to fight against that tendency though, don’t want to get too frumpy. 🙂

    I especially liked your black and white print dress from 2008-2009. The black, white, cobalt and yellow are very striking on you. I am switching from boot leg to straight leg jeans too.

    • It’s good that you dodged the “What Not to Wear” bullet, Tara. It definitely got a lot of people into trouble if they took the advice too literally. I find it easier to “get dressed” in the summer months, too. It can be easy to stay in really casually and comfy clothes when it’s cold out. I have to push myself to make more of an effort for sure.

      I still like some of my earlier looks, too, including the black and white prints. Overall, I am much happier with my current style, but there are still bits and pieces that I appreciate from the older outfits. Sometimes it more a matter of fine-tuning than a total overhaul.

  7. Thank you for such an interesting post. It shows so well how style can evolve over time, and also how difficult it is to pin down exactly what personal style is in a few words. For example, I really both the black chiffon top outfit (those jeans seem to fit really well!) and the blue/yellow dress – but what exactly do they have in common? Possibly that they are simple, with clean lines, and bold colours, but there would be 1001 outfits out there that would match that description that would not look so good!
    I’ve confirmed this year that I really love tailored, modern and simple outfits, but more work is needed to hone this down. Lately I’ve been moving away from brighter colours to more muted ones, and trying to mix textures. Recording outfits I like helps a lot, plus summarising the very favourites at the end of each 3-month season.

    • I’m glad you liked this post, Alice. You raised some very interesting points. Yes, style can be hard to pin down, but having some style descriptors like what you wrote (tailored, modern, simple), can help for sure. Maybe outfits may look quite different but they look like the same person might wear them. That’s what I hope is evident in my more recent looks. I still see elements in a lot of the older looks that I like, but I would feel the need to “tweak” at least one or two things. I agree with you that taking photos or doing an outfit journal can help us to hone things. I love the ideas of summarizing favorites at the end of a 3-month period. I may adopt that practice! I wish you the best with your style evolution!

  8. I am so sad that What Not To Wear did so much damage to people. Honestly we don’t all have to dress the same.

    I love your 2015 favorite outfits. Cobalt definitely looks striking on you. I also like that black/white/yellow geometric top on you. You have the body for it, for sure. That said, I really dig some of your outfits in the 15 year old pics. You look so comfy, free-spirited and happy in those clothes.

    • I think “What Not to Wear” helped people, too, Jane, but some of us took the advice a bit too literally. It got me to look more closely at what I was wearing and how others perceived me, but I agree that we don’t have to all dress the same!

      Thanks for your kind words about both my current outfits and the ones from long ago. I am trying to get back to that free-spirited and happy place with my clothes and my life, as I got far too uptight for a while. Clothes should SUPPORT our lives, not BE our lives. If we’re thinking too much about our clothes once we have them on, it can be a problem.

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