I’m posting some more outfit photos today. While this has often been a nerve-wracking thing for me to do, I feel better about it this time for a few reasons. For one, today’s photos are of ensembles I actually like, in contrast to the last few installments (here and here) of unloved looks about which I was seeking advice from Bridgette Raes. Additionally, writing “Who Are You Dressing For?” last week helped me to turn a corner. I now feel more able to dress for myself after processing and sharing my feelings about being overly concerned with others’ opinions.
It’s Okay If You Don’t Like My Outfits
You may or may not like the outfits below, and I’m okay with it either way. What’s important is that I like them and felt good while I was wearing them. Of course, I’m still in the process of evolving my style (read my thoughts on that here), so I shared photos of my favorite looks with Bridgette Raes for her input. Since I hired Bridgette to help me improve my style, I was open to her feedback on how I could enhance both my problematic and favored ensembles. What helped a lot was that she’s not only a professional, she also had a very clear idea of my objectives as a result of the comprehensive questionnaire I completed prior to our first meeting.
I was pleasantly surprised to learn that Bridgette liked many of my favorite outfits “as is.” In fact, she told me that she was very impressed with the looks I was putting together. She saw a night and day difference between my favorite outfits and the less loved ones I had sent to her previously. She said that it was almost as if she was looking at two different people.
As I mentioned in this post, Bridgette basically told me I should stop trying to make old, sub-standard, no longer my style pieces work when I have so many good items in my closet. Today’s post showcases some of those good items, as well as the advice Bridgette gave me for making my best looks even better.
My Signature Style
I selected around twenty favorite outfit photos to send to Bridgette before our second virtual styling session. There were many more skirt and dress ensembles in the mix than pants outfits, mostly because our session occurred in the heart of summer. When the weather is warm, my preference is for wearing skirts and dresses and I’ve happily begun to embrace maxi silhouettes this year. However, I did include some pants and jeans outfits from earlier in the year to review with Bridgette, too, as I wanted our session to be as helpful and informative as possible.
When Bridgette saw the photo of the teal and black striped bandage-style top below, she said that outfit exemplified my style. The top is just the type of modern piece with intelligent details that Bridgette feels expresses my style aesthetic. The same is true of the cobalt and blue top with horizontal and diagonal stripes. She also loved the forest green thermal top with floral details, as it’s a great color for me and matches well with my casual lifestyle. While she thought the black wrap-style top looked chocolate brown (which she thinks would be a good color for me), she thought the shape accentuated my waistline nicely and paired well with my favorite pair of boot-cut jeans.
A few of my favorite pants and jeans outfits from this year.
Bridgette liked how I paired burgundy with grey in the jeans ensemble below and was also a fan of my maxi-dress outfits. She really liked the cobalt blue color for me, as well as the surplice-style black dress and striped moto jacket (one of my best buys this year!).
Another favorite jeans outfit and the maxi silhouette I started embracing this year.
She was also fond of the three knee-length dress outfits I sent her. She liked how I paired the cobalt dress with the black belt and how I highlighted my narrow waist with the navy dress (which actually looked purple on her screen). She favored the necklines on both dresses and loved the leopard print sandals. She was also a fan of my brown-tone leopard print dress paired with the denim blazer and red shoes. These are three of my favorite dresses which were all worn multiple times this past summer.
Three of my favorite knee-length dresses that I wore a lot this past summer.
Improving Upon Already Good Looks
As I mentioned above, Bridgette identified ways to improve some of my favorite looks. She felt the first outfit below was still a little on the “churchy” side as a result of the swishy and less modern skirt. However, she really liked the top half of the ensemble and told me it would look great paired with white pants (which I don’t have – have never found any I like), black jeans (just found some!), or dark denim jeans (have a few pairs). She also suggested pairing the skirt outfit with black sandals instead of silver for a more balanced look. I’m going to re-style this outfit and others and show some of the results in a future post.
Bridgette gave me some suggestions for improving these favorite skirt and pant ensembles.
I included the second outfit in the photo above because Bridgette suggested that I try pairing the black and white print top with the black skirt in the coral jacket outfit. She felt that the top might help to modernize the skirt, particularly if I paired it with my turquoise sandals (which are shown in the photo below). I love this idea and look forward to trying it out now that I’ve been reminded of Bridgette’s excellent advice through writing this post!
I have posted the black tank and red striped skirt outfit here before and it was a favorite look of mine during the long, hot summer that only recently drew to a close. Bridgette loved the skirt and thought it would look nice paired with a denim jacket or a chambray shirt. I’ve worn the skirt with my denim blazer (shown above) many times. While I don’t have a chambray shirt, I can see how the skirt would look nice in that type of pairing. Bridgette’s other suggestion was to switch out the silver sandals for black, which I’ve done regularly ever since I purchased comfortable black sandals (shown with black maxi-skirt below) back in July.
The outfit on the above right is one of the few ways I still like to wear the open cardigans that were closet favorites for years. Bridgette liked the clean look of this outfit, but said that I could kick it up a notch by switching out the black peep-toe shoes (which skew a bit dressy) for my new burgundy ballet flats (shown in this post). I can definitely see that working well, but the pants might need to be hemmed slightly since the peep-toes have a low heel.
New Accessorizing Options
Bridgette felt that I could improve upon the first outfit below by switching out the black accessories for one of the other colors in the floral tank top. She really liked the idea of highlighting either the mint green or red tones in the top through my accessories. She could see me wearing a mint bib necklace, red earrings, or a sharp red blazer with that ensemble (but not all together, of course!). She even thought yellow accessories would look nice with the top, but preferably not close to my face, as yellow is not one of my best colors. Another recommendation she had was to pair the floral tank with the black midi skirt in the photo above, which is something I’ve done.
I can make these skirt and dress outfits even better using Bridgette’s recommendations.
The second outfit above has only been worn once so far, but I loved it. So did Bridgette, but she felt it would look more modern with my new caged black sandals (pictured in this post). The black and cream patent sandals I paired with the dress and blazer are dressier and less modern. The strappy black sandals would take the look to the next level and add some of the edgy vibe I’m looking to cultivate.
The shoes were the issue in the coral blazer and zigzag skirt outfit, too. At the time when the photo was taken, I didn’t have a pair of comfortable, non-dressy black sandals, but now I have two! That’s great, as Bridgette thought the look would be more balanced with black shoes to better coordinate with the top, skirt, and my dark hair.
The final outfit photo was taken shortly after I received my blue sandals as an early Christmas present from my mom. I am new to wearing colored shoes and I went a little overboard with matching them to other elements in the ensemble. I thought I was doing a good job in using blue accessories, but it ended up being too “matchy-matchy.” Bridgette made a few recommendations for improving this outfit:
- Pick just one place to echo the blue of the shoes (i.e. either the bracelet or the earrings, which have a turquoise bead at the end).
- Bridgette recommended replacing the turquoise bracelet with a black or silver one instead.
- I could also do only the blue shoes (there is some subtle blue in the dress, too) and wear silver earrings and a black bracelet.
New Ideas to Try
I love having some new outfit ideas to try and really liked the suggestions Bridgette gave me for amping up my favorite looks. I haven’t had a chance to play with all of the options as of yet, but I look forward to doing so very soon. The final post in my Bridgette Raes styling series (unless I hire her again in the future) will show how I implemented Bridgette’s advice. This post will go live sometime within the next month or so.
I hope you’re finding this series both interesting and helpful. I still don’t love posting my outfits on the Internet, but I did feel less trepidation this time since I’m much happier with the looks above (and learning to value my opinion above all others). Also, I know that while not everyone will love what I wear (is this ever true for anyone?), I’m loving more of my outfits as a result of my work with Bridgette (see all of the posts in the series: 1 | 2 | 3 | 4 ) and my daily outfit journal.
If you’re struggling at all with your style, I highly recommend doing at least an hour of virtual styling with Bridgette – learn more here (I did two hours and look how much I got out of it!). Yes, hiring a stylist is an investment, but it can end up paying for itself many times over. I feel far less likely to make buying mistakes now that I’ve honed in more on what does and doesn’t work for me.
If paying for a styling session isn’t feasible for you right now, you may want to try keeping an outfit journal. It’s free, easy, and can really help increase your awareness and improve your style. Just do it for a month and see how it works for you! Another option to explore is Imogen Lamport’s “Evolve Your Style” course, which Mette recently recapped on her blog. It’s still only $5 U.S. (price is increasing soon) and seems to be one of the best deals going. I intend to do “Evolve Your Style” myself very soon after Mette’s glowing endorsement.
“Flashback Friday” – What I Was Writing About a Year Ago
I forgot to do Flashback Friday the past two weeks, but I’d like to get it rolling again. Below are a few “Recovering Shopaholic” posts from last year at this time. I know many of you weren’t around back then, so this is a chance for you to read what I was writing during the earlier days of the blog. For long-time readers, it may be fun for you to revisit content you read the first time around. I always re-read the posts Bridgette Raes includes in her “Throwback Thursday” round-ups (most recent one here) and get even more out of them the second time.
- “Wanting Less and More at the Same Time” – As human beings, we can sometimes be walking contradictions. We often say one thing and act in a completely opposite manner. This is definitely true when it comes to many of us and our clothes. We love getting new clothes, but we often become overwhelmed with having those same clothes. In essence, we want more and less at the same time. This post explores this dichotomy of desires.
- “A Different Kind of Shopping” – Shopping for defined wardrobe needs is an entirely different activity from the type of mindless buying that many shopaholics do. We don’t tend to lose ourselves when shopping for things we need. Mindful shopping isn’t exciting or sexy; rather, it’s utilitarian and functional. However, this different kind of shopping can be incredibly satisfying. With shopping, as in many areas of life, we benefit from placing our long-term satisfaction over short-term enjoyment.
- “My Beefs with the Fashion Industry” – This post was a long time coming and was actually pretty cathartic for me to write. I had (have) a number of complaints about the fashion industry and let loose with all of them in this thought-provoking post. My “beefs” include lack of variety, low quality, poor manufacturing ethics, sizing inconsistency, constant sales, and more. Be sure to read the comments on this post, as readers chimed in with their own fashion industry beefs.
Your Thoughts and Survey Reminder
I hope you liked today’s post and the “blast from the past” links above! Now it’s your turn to chime in. Feel free to share your thoughts on the topics of this post, as well as any of the “Flashback Friday” links above. You’re also welcome to ask any questions you have for me or make suggestions for future blog posts.
A big thank you to all those who have completed my reader survey thus far. At the time of this writing, I have received over 350 responses, but I’d still love to get your input if you haven’t had a chance to take the survey yet. It only requires two to three minutes and is completely anonymous. I will share a summary of the feedback I receive in a future post. If you’d like to include your input, please click here. The deadline is Friday, November 21st. I appreciate your helping me to make this blog even better moving forward!
Recovering Shopaholic 
Gee whizz, your outfits are looking nice! I especially like the top with pants. and the maxidress ensembles. But they are all awesomely flattering 🙂
I appreciate your kind words, Fiona. I’m really enjoying wearing maxidresses. I was a late adopter, but I’m glad I finally jumped on board with that trend!
Congrats for valuing your own opinion above others! I think it is very important to help figuring out how you really feel comfortable (as opposed to wearing things that you think may please others). I know from my own experience that I feel much better in my outfits after applying this principle (if only with the example that I almost completely stopped wearing heels after years of believing that’s what I was supposed to do as a petite woman).
Your favourite ensembles are also very consistent in style, even though these are only pictures it does feel like you are more at ease in some of them than some of the previous pictures you may have shared in the past 🙂 Something I’d like to know, maybe a few months from now or so, is whether defining your style with Bridgette had some effect on your shopping habits (for example did it make you buy more at first to fill the new gaps in your wardrobe, or on the contrary did it help make the most of what you own, hence purchase fewer items in results…)
Good for you for not wearing heels just because you’re petite, Kali. It’s taken me a while to tune in more to my own voice, but I’m liking more of what I wear as a result. I haven’t bought many new things since my sessions with Bridgette and I’m trying to use more of what I have with some strategic additions. But time will tell and I will definitely comment on that a bit down the line.
Thank you again for this series on your session with Bridgette! You’re looking great, Debbie. Your outfits are very flattering and there’s a real consistency in the styles and colours. It’s wonderful that you’re feeling more confident about dressing for yourself.
I’m glad you’re enjoying this series, Kayla. Thanks for your kind words about my outfits and my confidence. I feel good to be honing my style and feeling better about what I’m wearing as a result.
Love all these looks on you Debbie! There’s a consistent style/vibe of modern, comfy & edgy. You seem at ease and happy with your choices. That’s a great thing! I really appreciate you sharing all of Bridgette’s advice here with us. It’s been super helpful to me as I tend to veer matchy-matchy. I’m so glad that you’re now listening to yourself, not others, when it comes to your wardrobe.
I’m glad you’re seeing a bit of edge in there, Kim. I DO feel more at ease in what I’m wearing these days. It helps a lot not to be buying new things constantly and focusing more on shopping my closet. As I wrote, I struggle with the matchy-matchy thing, too, so Bridgette’s advice was really helpful. Happy to share!
Thanks for sharing your style session. It has been really interesting to get a glimpse into what happens during one.
Your outfits look lovely and you look very comfortable in them. I know you’ve mentioned preferring dresses to pants in the past, but I think you’ve made really good outfits with both types of bottoms. One observation from this set of outfits is that you seem to prefer pairing more conservative necklines with pants. I’m probably telling you something you know but it really struck me from these current outfits.
You know, Sara, you’re right about the necklines. I hadn’t thought of that before, but it really is true that I like more conservative necklines with pants! Thanks for pointing that out and thanks for your kind words. I’m glad you’ve enjoyed reading about my styling sessions.
As your journey progresses, I hope you can see (as I do!) how much confidence you seem to be gaining! You are practically glowing in these photos of outfits which not only flatter, but are in your true comfort zone. Love what you are doing, especially the blue sandals!!! I think the glow comes from recognizing your strength and dressing to please yourself. Not only are you helping yourself, you are helping others!
I really do feel more confident, Paula, so thanks for noticing. It’s nice to hear that I am glowing 🙂 I ‘m glad that my posts are helping others, as that’s always my intention even though I’m writing so much about myself and my own journey.
I love seeing a lot of your favorite outfits all at once and agree that you look happy and confident in them. One thing I noticed was how great you look in asymmetrical designs be it in the neckline, direction of the stripes on a top or the hemline. The other looks were great too.
Yes, asymmetry is a new love of mine, Juhli. After seeing it so much on Sylvia from 40+ Style, I decided to add some asymmetrical pieces to my wardrobe. I think they add a bit of subtle edge and artistry to my outfits, plus they’re fun to wear!
Flattering, stylish and confident- a thousand miles , nay a million miles from where you started when beginning your journey and but steps from where you want to be.
Looking good Debbie!!
I appreciate your kind words, Abgurl. I do feel that I’ve come a long way and I hope you’re right about my being just steps from where I want to be. One day at a time, but I feel good about my progress and I thank you for noticing.
I think that Bridgette had a good point about trying to make certain things work. When you’re wearing your favorite pieces it doesn’t seem like you have any trouble putting together great outfits. I’ve admired the red skirt outfit before and I like her suggestion to try black shoes with it. Like everyone else said you really look happy and very “you” in these outfits. My very favorite is the blue maxi dress. I love the metallic shoes and jewelry. It all balances perfectly.
I think for myself, this was the most helpful post in the series. I’ve passed along the things that don’t fit me, are the wrong color, or the wrong cut. I believe that everything in my closet now are things that I love and that are flattering on. Sometimes if on outfit looks “off” all it requires is a little tweaking with shoes or jewelry.
The blue maxi dress is a definitely favorite of mine, too, Tonya, as is the red striped skirt. I think that Bridgette is right that I could just wear these favorite items over and over again and not worry about the rest. I haven’t been as brave as you in letting go of a lot at one time, but I’m gradually paring down and allowing myself to embrace a smaller, more cohesive wardrobe.
I’m glad you found this post helpful. It IS amazing how much of a difference a small tweak can make. I’m wearing one of the re-styled outfits today and I like it much better with Bridgette’s suggestions!
I think Bridgette is right about your signature style. Obviously we should not restrict ourselves to just one type of outfit but it’s good to have that awareness as a “home base.” I still think that cobalt blue looks amazing on you!
Thanks, Sarah! Cobalt blue is my absolute favorite color these days. I agree that awareness of “home base” is good, but I will always be open to trying new things. Even the things I don’t like, I’ve at least tried on. But I’m happy to have a firmer grasp of my style after being all over the map for too long (overshopping can do that to you!).
This is a terrific post — and a great segue from the “Who are you dressing for” post.
You look great.
Thanks, Amy! I think I had to write that other post before I was ready to do this one. I do really feel it helped me to turn a corner and I’m in a much better place now.
Love your new signature style, and how well you wear the look. You have also gained the edge that you were hoping to achieve, but instead of it being all about your clothes, now the well balanced edgy look comes from the confidence you bring to the outfits. Thank you Debbie and Bridget, I learned something important from this style session. Now I understand why I’m often not happy wearing my sliver/puter sandals, because the look is not balanced and I need to wear black with the outfits that beg for black, instead of trying to make do with silver.
I appreciate your kind words, Terra. I’m glad you are seeing some edge in my style. I didn’t to go too far with that, but a little bit can go a long way. I used to make do with the wrong color shoes all the time. Now I’m grasping more and more how important shoes really are. I have “fussy” feet, so it can be tough to find what will work well for me, but it’s well worth it.
I must admit I was skeptical about hiring a consultant, but the proof is in the pudding: all these outfits look fantastic. You have more than 20 there, if I counted correctly: that’s almost a month with no repeats. I too would be interested in hearing if having so many flattering choices quells the desire to acquire.
I think some consultants are better than others, for sure. I was hesitant to do the virtual styling at first, but it worked really well and I was already such a big fan of Bridgette’s. I hope that I won’t want to buy as much now that I am becoming happy with my style and what I have. Time will tell, but I will definitely keep you all posted.
Sounds like you got lots of really great advice! I especially love the blue dresses – that color is wonderful on you 🙂
Yes, Bridgette’s advice was excellent. Thanks for the compliment on the blue dresses. Cobalt blue is my favorite color!
Thank you for sharing your favorite outfits! I agree with all the others that I see a very consistent look. I really do like all of the jewel tones on you. The purple dress is my favorite because you can dress that up or down depending on your shoes – and it looks great on you too!
Thank you for re-posting “Wanting Less and More at the Same Time.” This is one of my favorite blog posts ever because it is so true for me. I really do love having a few items that I wear all the time but I also love the thrill of finding and buying something new. So I end up selling (at a loss) or donating too many items.
Navy dress! It looks purple on my screen too!
Colors really can be different on various monitors, Leah. That’s another reason why online shopping can be touch. I’ve received items many times that look much different from what I saw on my screen. Quite maddening, really! I’ve actually had the navy dress for a few years, but have worn it more this year than previously. The shoes really do make a huge difference.
“Wanting Less and More at the Same Time” is one of my favorite posts, too. We are in a similar boat. I still buy too much AND donate/consign too much, but at least I’m moving in the right direction. Buying over 50 items of clothing in a year still seems like far too much, but it’s a heck of a lot better than the 150-200 items I used to buy even two years ago!
WOW, I am so impressed with this series of working with Bridgette. This post, in particular, feels like you had a breakthrough. I am so happy for you! Thank you for sharing this process with us, in such great detail. I appreciate that while it’s a lot of work and it’s not easy, it is also very rewarding. This whole post screams “confidence”, which I find inspirational. Congratulations Debbie!
Just like Kali’s comment above, I am interested in how your style breakthrough is going to affect your future shopping behaviour. I am also interested in how you are going to live with this style going forward, and how you are going to “evolve” it. What I like the most about you is that your approach to style is dynamic – so I’d like to see what’s to come. And also, a comparative analysis (or just a historical view) of how far you’ve come in terms of style, but instead of focusing on what you style was at a particular point in time and what it is now, a discussion on how and why your style changes, as in what drives the changes and how you translate these into changes in your style (and what impacts they have on your closet and shopping behaviour). I think some of your posts in the past have already touched on a few of these themes (especially in terms of shopping), just would be nice if you can expand those into some form of style implications. Sorry in advance if this is too much to ask, and this is also probably better posted in your previous entry.
As always, love your blog, I read every single post, even when I don’t comment very often.
I’m so thrilled that so many people are commenting on my confidence, Belle! I didn’t really think about that when writing the post, but I guess it is true. I DO feel more confident in myself and about what I’m wearing. I’m glad you’re finding my journey inspiring!
I like your post suggestions and will add them to my list of topics (it’s long and always evolving). I think what you suggested will be of interested to a lot of readers – and interesting for me to write, too.
Seems like a really well-balanced wardrobe you have there – you’ve done well with your selections!
Thanks, Stacey. Yes, my wardrobe is a lot more well-balanced these days. It’s taken me a while to get there, but I’m happy with how it’s coming along!
You look great in all these photos, I’m impressed with both your positive approach and the emerging signature style – huge progress!
Thanks so much, Alice! It makes me happy when people see my progress, and I like that you noticed my positive approach, too.
Debbie, you look fantastic in all these outfits. I particularly like the diagonal stripe tops (I am a stripe-a-holic too!) and the blue dress which looks purple is also one of my favourites. You definitely look happy and are exuding so much confidence. On a separate note, I think it is so important to dress for ourselves (than for anyone else’s approval) and be comfortable in what we are wearing. For instance, not everyone likes my distressed jeans but I love them to bits. Your work with Bridgette has been great and the proof is displayed in the outfits.
Nice to hear from a fellow “stripe-a-holic,” Sharon. I agree with you that it’s most important for us to like what we’re wearing and be comfortable in it. Enjoy your distressed jeans! I don’t think there is ANYTHING that everyone likes, so we fight a losing battle if we try to please everyone else. Of course, I had to learn that the hard way!
That’s a nice looking set of outfits.
I particularly relate to the comment about white pants. Yes, I think think white pants would look nice with the top you mention, but I so understand you when you say, “but I haven’t found any I like on me.” Giving up that vision of something that looks great on other people or laid out on the bed, verses something you just don’t like on your body is one of those breakthroughs that it can take a person a long time and a ridiculous amount of wasted money, to accept. The thrift stores of the world must smile when I start thinking about buying white pants because every pair I’ve ever bought have ended up hardly worn on their racks.
I have never had good luck with chambray shirts. I love denim, I love jeans, but somehow the shirt in a fabric that seems like it’s just made to go with it hasn’t ever been a success for me. For me it’s like the pair of white pants that looks so good in mind, but not in mirror.
I can really relate to what you wrote about the white pants, Ginger. I love them on so many other people, but just never like them on me. I always think they make me look really bottom heavy. That may just be my bad body image talking, but if I’m not happy wearing something, it will just sit in my closet. I contribute enough to thrift and consignment store racks as it is. No need to add to it! I haven’t tried chambray shirts, but I don’t tend to do well with button-down shirts in general. They just never fit me right and the amount of tailoring that would be required never feels worth it to me. Fortunately for us, there are a lot of other great things out there for us to wear!