Lessons from My Outfit Journal – Slimmer-Fitting Jeans

I can’t believe it’s been close to two months since I shared the last post in my “Lessons from my Outfit Journal” series (see the two previous installments here and here).   I have been keeping my outfit journal since July 2014 (more on why and how here) and have been learning a great deal about my wardrobe and style preferences since that time.

Style journal

Keeping an outfit journal has really helped me improve my style.

One of the things I’ve learned recently is that I now prefer wearing slimmer styles of jeans over the wider-legged jeans that were my mainstay for years.   In today’s post, I share four looks that feature boyfriend style and straight-legged jeans.   While I’m not a fan of true skinny jeans for comfort reasons (I have varicose veins and a painful nerve condition), I have embraced these two new styles in addition to my boot-cut stand-bys.   I show the outfits from least to most favorite and share my outfit ratings, where I went, my thoughts about each look, and what I would change in the future (if anything).

If you’re at all dissatisfied with your personal style, or if you look in your closet each day and declare that you have “nothing to wear,” I encourage you to keep an outfit journal for at least a month or two.   You’ll be surprised at how much you learn through the process!   What’s more, you’ll very likely become a smarter shopper through better understanding which of your ensembles are “home runs” and which ones fall flat.   I know that’s been the case for me…

This outfit journal post is a bit different than the two previous ones in that I really like all of the looks shown.   I didn’t see much that I wanted to change about any of the outfits below. I guess that’s a good thing, as it means I’m wearing more of what I truly love (my LIWI challenge is working!).

One quick note… I actually liked all of these ensembles better in person than in the photos.   My husband and I are trying to improve the quality and accuracy of the outfit photos, but neither one of us is a photographer.  Plus, this isn’t a flashy style blog.   I’m mostly just documenting my process and hoping that you’re able to learn something from it.   It’s not really about my outfits themselves as much as it’s about the journey and what I’m learning along the way.

Outfit #1 – Teal Cardigan

Teal cardigan outfit

Rating:   9/10

Where I Went:   Massage appointment and errands


  • I really liked this outfit and felt good in it. I like the silhouette of slimmer jeans with longer tops, which is a new look for me.
  • I felt comfortable both physically and emotionally in the outfit and I felt like I looked attractive. I even felt good without the cardigan on and still thought I looked polished.
  • I used to be uncomfortable in slimmer cut pants, but since I’ve lost some weight, I feel better wearing those styles. I’m sure I probably looked fine in them before, but I still have lingering body image issues (from my long battle with eating disorders – I wrote about that in this post) and feel much more comfortable in my body at a lower weight.
  • This was my first time wearing the new cardigan and the first wearing of the tank this year. I felt very happy in both.  It’s hard to tell from the photo, but there are sequins at the bottom of the tank (there is a diagonal section of them).   I like having that little extra bit of “fanciness,” but don’t feel that it’s over the top.
  • The jewelry pieces are all old favorites from over ten years ago, but I still enjoy wearing them. Now that I’ve pared down my jewelry collection and can better see what I have, my best pieces are seeing more wear. There are some definite benefits to having a smaller wardrobe and a smaller jewelry stash.

What I’d Change:

  • Nothing I could think of really. The jeans felt a bit loose, but they were comfortable and the boyfriend style is supposed to be kind of baggy.

Follow-On Notes:    I later decided that I wanted the cardigan to be a bit more fitted, so I took it to my tailor to be taken in on the sides.   I am happier with the fit now.

Outfit #2 – Waffle Top

Turquoise/navy waffle top outfit

Rating:  9/10

Where I Went:   Lunch and shopping with my mom during her visit to San Diego in late February


  • I really loved this outfit and felt like myself in it. I felt comfortable, casual, and stylish and appropriate for the activities of the day.   This is how I want to dress for most of the events in my life.  Not that I always want to wear a waffle top, but I liked that I didn’t feel too dressed up or “churchy.”   I’m ready to let go of the “church vibe” for good, unless of course I’m actually going to church!
  • I felt like I looked slim in the jeans. I really love these jeans after my recent weight loss (not sure how much I lost, but my clothes fit better now).  Before that, I was much more self-conscious about the size of my hips and thighs.
  • I loved all of the pieces I was wearing, including my turquoise accessories. The accessories are pretty subtle, but that is usually my style.   When I wear jewelry that is too large of too much of a “statement,” I feel uncomfortable and often end up taking it off.
  • My hair was the weak link in this look, as it got kind of frizzy in the humidity. I realize, however, that I notice that type of thing far more than others do.

What I’d Change:

  • My hair, but I still don’t know what the heck to do with it! I’m doing better with it than I was last summer, but it’s still not ideal.   I’m sure I will figure it out eventually, though.

Follow-On Notes:    I didn’t write this at the time, but now that I look at this photo and the one above, I realize that the jeans might need to be hemmed slightly, as they are pooling a bit at my ankles.  However, this is kind of a personal preference thing for slim-legged jeans, though, so I’m not sure how I feel about it.   Sometimes the talls are a bit too long for me, but the regular lengths are always too short.   I guess I’m not tall enough for tall sizes.

Outfit #3 – Pink and Black

Pink and black outfit

Rating:   9/10

Where I Went:   All-day conference


  • I really liked the outfit and felt it struck the right note for the occasion. I was also physically comfortable in it, which was important when I was sitting all day long.
  • Like with the first outfit above, I wrote that I liked the longer top with slimmer jeans silhouette.
  • I liked the jewelry, too, and thought the necklace looked much better after the modification I made to it (see this post for before and after photos). Before I altered it, I felt it was “too much” and never wore it.  I’m now enjoying wearing it in its more subtle incarnation.

What I’d Change:

  • I would wear a different bra with the tank or have the tank taken in at the sides. Although it wasn’t really warm enough to take the jacket off that day, I would have been uncomfortable wearing just the tank because my bra was showing.

Follow-On Notes:   I ended up having the straps on the tank shortened a little bit.  Now I can easily wear the tank alone without having to worry about displaying my bra to the world.   I know that showing one’s bra was a “thing” for a while there, but it’s not my thing!

Outfit #4 – Printed Tunic

Rating:   10/10

Printed tunic outfit

Where I Went:  Charity comedy show


  • I loved the outfit. It was a very different look for me in multiple ways, but I was happy with it.   This was the first time I wore the new tunic (that I bought in February) and only the second time I wore the jeans that I purchased a year ago (now I really wonder why I didn’t wear them before!).  I was very happy with both pieces except I wish the sleeves on the tunic were slightly longer.   Story of my life with my “gorilla arms”!
  • I loved the coat. It was a wardrobe “benchwarmer” last year and I’ve only worn it twice this year, but I want to keep it around. It’s too dressy for most of my life occasions, but it comes in handy for those rare occasions when I go out and want to dress up a bit more.
  • I like the tunic with slim pants look and would like to wear this style more often in the future.

What I’d Change:

  • Maybe wear my hair up and back, as it kind of bothered me that evening.

Follow-On Notes:   I re-wore this outfit just yesterday.  I still really liked it, but found the tunic kind of annoying when I was walking around a lot. I’m not used to having my tops be quite so long.   I think I will confine the wearing of the tunic for events when I am more stationary.  I loved it at the comedy event but not so much for shopping with my friend yesterday (more on the shopping in a future post!).


I hope you enjoyed this third installment of my “Lessons from My Outfit Journal” series.   All of the outfits shown above were worn within the past two months and I was happy with each one.  My track record is definitely improving and I’m satisfied with more and more of my outfits as time goes on.   I still have a few “duds” in the mix here and there (perhaps that will be my next post in this series), but they are fewer and farther between these days.

As with the previous posts in this series, I’m going to distill down a few lessons that I learned from the entries for the outfits shown above.    There aren’t as many as in the last installment, but here are a few things I learned:

  • I need to give alternate styles and silhouettes a try more often, as I’ll never know what I might like unless I take some risks.
  • But when I do try new looks, I should stick with just one new item in a particular style until I’m absolutely sure I will love and wear the new option.
  • I prefer more subtle and minimal accessories over statement pieces.
  • I need to make sure I’m comfortable wearing my tanks alone if I end up taking my jacket or cardigan off. This requires moving around a bit and making sure my bra doesn’t show.
  • Some styles (like tunics) work better for some types of activities and not others. It may take some trial and error to understand the right types of clothes to wear for our various life events.  It’s a good idea to “test drive” new styles for lower impact activities so we’re not stuck wearing something we’re uncomfortable for many hours at a time.
  • I need to come up with a few new cute and stylish ways to wear my hair up so that I can easily change my hairstyle when my hair starts to drive me nuts.

I will probably continue having a theme for all of my outfit journal posts, as things seem to flow better that way.   While I showed only 2015 ensembles today, I still have lots of outfits from last year to share and my lessons from those journal entries were more profound than what I highlighted today.  However, I think that even the smaller lessons can make a big difference in our lives, so I plan to mix up my entries for that reason.

Your Thoughts?

I’m sharing my process and learnings with you in the hope that they might spark some “aha moments” for you, too.   If you have been keeping an outfit journal or using a similar process, I’d love to read your thoughts on how it’s helped you with your wardrobe and style.

  • What have you learned from writing about and/or photographing your looks?
  • What other methods do you have for improving and evolving your personal style?

I know I asked these same questions in the other posts in this series, but new people are always finding the blog and others who didn’t comment at previous times may choose to chime in now.   Regardless of whether you’re new or have commented many times before, I invite you to share your thoughts with me and your fellow readers!    Comments about my outfit journal entries and insights are also welcome (as long as they are respectful, of course).   I always learn so much from what you all share, so feel free to join in the discussion.

35 thoughts on “Lessons from My Outfit Journal – Slimmer-Fitting Jeans

  1. gosh, I think you look fab in every outfit. Those jeans are really working for you. I agree the tunic is a ten out of ten.

  2. Debbie- I love all of these outfits! I think #3 is my favorite, though, as it seems like something I would wear, just with a skinnier jean.

    I recently downloaded the Day One journaling app for my tablet/phone. It’s been a great place to easily upload a photo from my phone and enter notes. I can even tag the outfits, so I’ve been doing that. It’s been great to compile all of my outfits in one spot and can make notes on the go without carrying an extra notebook. The only downside to the app that I’ve found so far is that you can only upload one photo per entry. I’ve gotten around this with creating little collages with close ups of my accessories so I can get a sense of an entire outfit when I go back into the journal. I’ve found it really helpful, moreso than when I was writing in a moleskine, because I can type quicker and therefore can add more details in a shorter amount of time.

    • Thanks, Melissa. I would like to wear skinnier jeans, too, but it hurts me too much to do so. I’m glad I found compromise that works. The Day One app sounds great. I may have to check into that one. So far, I’ve been very “old school” and have been using a notebook. But I can’t pair those entries with the photos that way and that would be ideal. Maybe I will join the 21st century and start using that app soon.

  3. Those jeans look really nice on you! Outfit #3 is my favorite also. The pink color is very flattering on you and I love the jacket and necklace with it.
    I’m noticing that I have fewer duds as well. This year I’ve had 6 outfits that I didn’t like, about 10 that were okay, and the rest I really liked. Quite an improvement from when I regularly wondered what on earth I was thinking!

    • Thanks, Tonya! Maybe I should wear more pink. It is kind of a “fringe color” in my wardrobe, but I do like it. How great that you have fewer “dud” outfits, too. I think the fact that we’re shopping less often and focusing on wearing what we love is helping both of us a great deal. Here’s to fewer and fewer duds moving forward!

      • Debbie we have similar coloring and cool toned pinks make my complection glow , particularly the right coral color brings out the natural flush in my cheeks. It’s hard to find in garments that are not uber trendy though!!!!

  4. I’ve had that hem problem before too. The regulars aren’t quite long enough and the talls are just a bit too long. Taking them up is usually easier than letting them down. But some styles don’t lend themselves to alteration without changing the way the pants lay. You are wearing boot in all of these pictures which also effect the way pants behave. The teal and pink looks are my favorites, you have a glow with these.
    Have you tried wearing your hair more wavy ? I have learned not to fight the natural inclination of my hair. I do pull out the straightener on that rare occasion I do “dressy”.
    As always, thank you for leading the way.

    • I think I would be able to get those jeans hemmed a bit and have them still look okay. I had to do that with the jeans in the fourth photo and it worked out well. I just didn’t realize the other ones were too long until I saw the photos. Thanks for telling me I had a glow in the teal and pink looks. Nice to know… As for my hair, I’ve tried letting it go wavy, but it looks frizzy. My hairstylist said it’s because I damaged it by flat-ironing too often. But I’ve been “babying” my hair more and gradually cutting off the damaged parts, so hopefully the frizz will tone down over time (that’s what my stylist says will happen and I hope she’s right). I would like to have the option to be lower-maintenance with my hair without cutting it off, especially during the summer.

  5. I really love that tunic on you and the slimmer jeans are great. I have started an outfit journal since you have been having success with yours and it is an eye opener to rate the clothing and write down how an outfit makes you feel. It is easier to weed out the clothes you no longer love. I used to take photos of my outfits, but I have slacked off lately. Photos are great for seeing overall proportions, but, obviously, they can’t show you how you feel about an outfit. You are making such great progress. Congrats!

    • Thanks for your compliments, Lorri. I’m glad I have finally embraced the slimmer jeans. How great that you are doing an outfit journal, too. It really has been the thing that has made the biggest difference for me in terms of improving my wardrobe and personal style. The photos are also quite helpful, but I was doing those before I started the journal. The journal has been the key piece of the puzzle. I hope it helps you as much as it’s helped me!

  6. I forgot to mention a suggestion for your hair. How about trying something simple like a ponytail. Take a look at all the ways celebrities have created pretty ponytails with a bit of height or pretty clips. Super low effort for a good effect.

    • Great idea, Lori. I do wear ponytails sometimes (and my hair is almost always in one at home), but I think I would like it better if I incorporate some pretty clips or a bit of height like you said. I will give it a try.

  7. I highly recommend the clothing journal, too. I used it for 6 months and was able to get rid of lots of “dead weight” because of my journal. Now I just keep a record of favorite outfits so I can repeat them. I also keep notes on items new to my wardrobe. It helps me evaluate how my purchases are working out.

    I have also figured out that how I feel emotionally in an outfit is as important to me as how I look. I appreciated your comment regarding that. Sometimes I emotionally need to wear orange, even though it isn’t my best color. I feel happy looking at it all day. That counts for a lot.

    Thank you for these updates. Looking my own journey along with yours helps me realize how far I have come in the 2 years I have been following your blog. You have helped me tremendously!

    • I really appreciate your telling me that my blog has helped you in your journey, Anne. And thank you for sharing your progress here. I also keep a record of favorite outfits, but I need to re-wear them more often! Yes, the emotional component to an outfit is very important and is often overlooked. It doesn’t matter if everyone else loves what we’re wearing and it looks fabulous. WE have to love it and feel good in it. I think it’s great that you wear orange if it makes you happy. Being happy in what we wear is really what is most important!

  8. Debbie, this was an awesome post! I don’t post often, but I wanted to tell you how great it was to see you branching out, especially since you have been so honest with your feelings about the skinny jean style. Compiling your lessons from one aspect of your wardrobe was very helpful. I think it was much more effective receiving the information this way.

    I haven’t been keeping an outfit journal as detailed as you have, but your points about differences in “outfit feels” after different activities is a good one. It is something that I might consider in the future because it is helpful to know.

    Thank you for taking such time to break everything down and compiling notes. Like Anne mentioned, your detailed journey reminds all of your readers how far each of them have come in their own journeys.

    • I’m glad you liked this post, Di, and found it helpful. I agree that these posts are more beneficial when they are more focused like this one was. I’ll do the future ones like this, too. The outfit journal has really been teaching me a lot. I didn’t even realize until recently that a loved outfit in one setting may end up being a so-so outfit in another situation. Where we are and how appropriate what we’re wearing is to the situation is really a key part of the puzzle that shouldn’t be overlooked.

    • Thanks, Maryann. I really like it, too, and it was an impulse buy. You never know… I think we should always be open to the “love factor” with our clothes. It’s good to have a priority list and plan our purchases, but also allow for a little magic to come along.

  9. That’s a great idea about a outfit journal…just like a food journal! I really like when you have pictures (quality, schmality) because then us readers can really relate to the descriptions.
    On a more personal note, you are such a young and beautiful woman, yet your choice of clothing tends to be more muted. That printed tunic has such personality and looks so great on you—I hope you choose more pieces like that in the future! jodie

    • I’m glad you like these types of posts, Jodie, and aren’t too concerned about having superior photo quality. Thanks for calling me young and beautiful. Did you know I am turning 49 in under 4 months? It’s always a joy to be referred to as young! I would like to find more pieces like the tunic, too. I like to wear bold clothing sometimes, especially black and white items. I think there is a place for both bold and muted items in my wardrobe, but I definitely like pieces that have personality.

  10. So excited to see that you decided to try the new cut of jeans – you look so tall and trim in these. I emailed you details about some that I’ve found by Loft and Jones New York that fit me perfectly, and since we seem to be body clones, I hope they’ll work for you, too. To echo other commenters, don’t worry about photo quality. You look absolutely radiant in these outfits, and it’s not about photo quality, it’s about your joy in these outfits shining through. The colors and silhouettes you’re trying are so flattering, and I hope you’re enjoying your new look as much as we are! I really appreciate the combination of these very detailed posts with the photos, and they help me figure out why some of my outfits just don’t work. For example, I have learned I need a blazer that’s at least 24″ to wear it with pants. The shorter ones are now reserved only for wearing with skirts or dresses and it’s made a huge difference. Sally McGraw at Already Pretty did a good post on this that explains it better than I can, but seeing the proportions in your outfit photos helps me adjust mine. I can’t seem to get a journal going (I’m doing one for the research study right now) but LIWI is working very well, especially since my clothes were all out of my closet for the painting ordeal. Now if an outfit earned an “8” or higher, it goes into the closet. If it falls short, I try to tweak it and if all else fails, it goes to the consignment or charity baskets. I think by early summer I will have this down to a science, and then it will be much easier to replicate when it’s time for fall/winter clothes. Hope you will keep these very detailed posts coming – they help so much!

    • Thanks for your kind words, TexasAggieMom, as well as the jeans suggestions. Yes, I am enjoying my new look very much. I’m glad you and others like these types of posts. I’m going to keep the series going for the forseeable future and will try not to go so long between installments next time. You are so right about jacket proportions for skirts vs. pants. I need at least a 24″ jacket for pants, too, or else it looks “off.” I think it’s because we are so tall and have long legs. I remember that post from Already Pretty. I think it’s this one: http://www.alreadypretty.com/2014/11/how-to-fit-a-blazer.html (posting in case others may find it useful).

      I’m glad the outfit journal is helping you. Good for you for weeding items out that don’t work in your outfits. Over time, you will definitely have a more cohesive and workable wardrobe. It’s already making a really big difference for me and I know it will for you, too!

  11. You look absolutely amazing in the yellow/black/white tunic and you should definitely go in that direction! Maybe black jeans or dark indigo instead of the lighter blue too? However, if I had your stature I wouldn’t abandon wider leg pants just wear them with shorter tops. If I had your colouring and stature – I am 5′ nothing with naturally ‘mousy’ hair – I would go way more ‘edgy’! If you don’t want to cut your hair you could try all those updos that I envy so much, but I think you would look even more amazing with a shorter, sharper hairdo, maybe chin length or similar bob? If you have a curl in your hair, have a look at Ines de la Fressage (not sure I’ve spelt that right…) who is an icon here in France and always looks so classy, and has similar colouring to you I think.

    As one comment says, you are such a young and beautiful woman – make the most of it whilst you can! I am in my 60’s now and think “oh why didn’t I make the most of youth and be braver with clothes!” Thank you for all your wise words which have helped me so much after a lifetime of struggling with what to wear and before I retired, way too much buying.

    • I actually just found some great black jeans, Julia, after a long time of searching, so I will be able to implement your suggestion very soon. I agree that the wider pants look better with shorter and more fitted tops. I am trying to gradually push myself into an “edgier” direction with my style, but I tend to change slowly. I love Ines de la Fressange’s style and would love to dress more like her. Maybe I need to create a Pinterest board with some of her inspired looks and/or do a post about emulating her style. Food for thought… You are the second commenter who called me “young and beautiful” and it is much appreciated, especially since I turn 49 in August! But if I still look young, I am very grateful for that and would definitely like to make the most of it. I’m glad you have found my blog helpful and I appreciate your letting me know.

  12. The outfits look great! I have the same issue with pant lengths, but with the boyfriend style I usually just cuff them – that way I can adjust the length slightly for boots vs flats.

    • Thanks, Sheila. I will try the cuffing and see what I think. I don’t really like the rolled above the ankles look for me, but maybe just cuffing to the right length will work. I will try that out before I decide if I want to hem the jeans.

      • But just for a spring/summer experiment is what I meant. Boyfriend jeans, rolled, with ballet flats, can be a fun, new, warm weather option. And after you “try it for a while” if you discover that you really don’t like the way you look and feel, you can always hem in the fall so that you can return to wearing the jeans with boots in the winter.

      • I will definitely give it a try, Terra. It never hurts to try new things and sometimes we end up liking them.

  13. Not to parrot the others, but you look fabulous and I’m so happy you ended up loving those jeans! And of course, the tunic is fab 🙂

    I’ve been moving to a much different silouhette than I originally went with. I wear looser tops and more fitted bottoms now than my old mainstay. I also really love tunic style tops, despite my 5’4″ self. I’m doing up a ‘week of outfits’ journal to post sometime soon because I love yours- the visual part really helps understand vs. Just words! 😉

    • Thanks, Meli! I’m liking the looser top with fitted bottoms silhouette more these days, too, but I will probably still do the opposite silhouette, too. I look forward to your week of outfits post!

  14. Debbie, you look wonderful in all of the photo shots. Most important is that you look like you “feel” wonderful, at home in your body, and in your clothing. I’m guessing that you are having a lot more fun too. Now that you no longer have the pressure of dressing up every single time you leave the house I’m sure you are now having a whole lot more fun dressing up for activities that actually require dressier attire. And you look great with your hair tied back in a simple pony tail. Remember, I saw you in person with your hair pulled back, and you looked stunning and you have great bone structure. I don’t think you need to worry about fussing with pulling your hair back with fancy clips. A simple pony tail is always appropriate, even for special occasions because then all you need to do is wrap a strand of hair around the band.

    Although I don’t keep a specific clothing journal, I do write regularly in a journal, and I’ve begun to write down what I’m wearing, but not how I feel about the outfit. Instead I write about how I feel, or what I’m thinking about, and it provides a lot of insight. I’m more likely to love my clothes when I’m feeling good about myself overall, or when I’m feeling my best health-wise. But when I’m not feeling my best my judgment is cloudy, and on those days nothing feels right. I’ve learned to let it go and move on to doing something that improves my mood such as turning on music, or looking forward to a long walk , or reading a good book, or just relaxing and not doing anything at the end of my long work day.

    • Thanks for your kind words, Terra. It means a lot to me. I am feeling more comfortable in my clothing and my body, but I still feel I have some more growth to do in both areas. I like your journal idea and I totally agree that how we feel physically or emotionally can color our perceptions about what we’re wearing. I also like your suggestions for mood improvement. I need to do more of those things.

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