Lessons from My Outfit Journal – Maxi Dresses

I didn’t think I would post another “Lessons from my Outfit Journal” installment so soon, but here’s another one right away.   I wanted to do a second post this week, but I’ve been going through a lot of physical and emotional challenges as of late and I just didn’t have it in me to write about anything else today.   But these outfit journal posts are relatively easy to write and seem to be popular with readers, so here goes.

Outfit journal entries

What percentage of your outfits do you absolutely love?

A few people mentioned that they like that I’m highlighting themes in these posts, so I will stick to that approach.   Since spring is upon us and it’s getting warmer outside, I decided to take a look at some of my maxi-dress outfits from last summer and fall (we have warm autumns where I live).

As in my last post, I will share the outfits in the order of my preference, from least favorite to most favorite today (which won’t necessarily reflect my original ratings).   I will highlight where I wore the ensemble, how I felt about it, and what I’d change (if anything) in the future, as well as any follow-on thoughts I’ve had since the outfit journal entry was made.

The Single Most Beneficial Activity

Before I delve into the photos and journal entries, I want to say one thing.   I have tried many things to try to improve my wardrobe management and personal style over the past four-plus years.   I started tracking what I wore and what I bought back in 2011, as well as taking outfit photos.   All of those activities were very helpful, but the single most beneficial activity I’ve done thus far has been my outfit journal.   It really makes a big difference to track my thoughts about what I’m wearing, as well as the changes I would like to make to my outfits.   As a result of jotting these things down, I’ve been able to gradually hone my looks and shop for the items that will have the biggest impact on my style moving forward.

I encourage you to try keeping an outfit journal for a month or two to see how it might benefit you.  You can use a physical notebook like I do (I’m still “old school” about some things), or you can keep a digital journal on your computer, tablet, or smartphone.  You can also take advantage of one of the many style apps available for free or a low fee these days (one reader commented that she likes the Day One app).  Choose the format that appeals most to you and that you think you’ll consistently use.   If you do decide to start an outfit journal, I hope it helps you as much as it’s helped me!

Outfit #1 – Striped Maxi

Striped maxi-dress

Rating:   8/10 (would rate it a 6 now based upon look and feel)

Where I Went:   Lunch and errands with my husband (8/24/2014)


  • I hadn’t worn this dress in a while and had since gotten the top part fixed, or so I thought. But it still looked “drapier” on the left side than the right and that bugged me.  I had to keep pulling the front part of the waistband down a bit so it wouldn’t look weird, which I found “fussy” and annoying.
  • The dress was very comfortable, easy, casual, and appropriate for my activities, but was not my favorite maxi due to the fussiness factor.
  • I love being able to wear dresses with flats, which is part of the appeal for me of maxis. I’m happy that I’ve been able to put together some more casual dress and skirt looks as of late.
  • If I needed a topper (it was a very warm day, so I didn’t), I probably would have gone with my black tie-waist cardigan or one of my bright V-neck cardigans.

What I’d Change:

  • I wouldn’t have bought the dress in the first place! It was a sale item that I should have left in the store.  Instead I took it on as another one of my alterations “projects.”   The top part of the dress just didn’t fit me right at all and the alterations I had done to it were ultimately unsuccessful.

Follow-On Notes:    I tried to wear the dress a couple other times after the above occasion, but I always ended up taking it off and putting something else on.   I just didn’t love the way it looked on me, so I finally let it go a few months later.  I only wore it twice – a purchasing fail.

Outfit #2 – Snakeskin Maxi

Snakeskin maxi-dress

Rating:  9/10  (would rate it an 8 today for look, a 7 for feel)

Where I Went:   Lunch and errands with my husband (11/23/2014)


  • I felt stylish, attractive, and comfortable in this dress.
  • However, I was uncomfortable sitting in the car because the dress ties in the back, leaving a bump from the bow. I have another dress with this issue (a knee-length one) and while I like the way both dresses look, this issue is non-trivial, as comfort is really key!
  • Also, because of the gathering in the front, the dress slipped between my legs quite a bit when I was walking, which I found annoying. I wondered if I would need to wear a slip with it, but I really don’t want to have to wear an additional layer on a hot day.
  • I like the look better with the jacket, as I feel it balances the outfit out more. I worry that I look bottom heavy in the dress by itself because it’s more voluminous on the bottom.

What I’d Change:

  • Maybe wear a slip so the dress doesn’t go between my legs as much when I walk.

Follow-On Notes:    I have decided not to buy any more dresses (or tops) with a tie-back.  While this style often looks nice on me, it’s uncomfortable in practice, as I’m often driving or sitting such that the tie digs into my back.   Also, I need to walk about a bit in dresses (or skirts – or anything) before I buy them to make sure they’re comfortable when I’m moving around.   I still like this dress and will wear it, but I now understand its limitations.

Outfit #3 – Black Maxi

Black maxi-dress

Rating:   8/10 (I would definitely rate it higher today, at least in terms of looks)

Where I Went:   Lunch and a movie on my birthday (8/8/2014)


  • The dress was very comfortable. I was experiencing abdominal discomfort that day (a frequent occurrence) and the dress didn’t cut or bind me in any way.
  • The front was a bit too low-cut, especially when I sat down. I wrote that the straps needed to be shortened and that I would have rated the outfit higher if I didn’t have to worry that my bra might show or that I would display too much cleavage.
  • I felt stylish and true to myself in this outfit. I also felt like the outfit was flattering to my figure.
  • Originally I was wearing a gun-metal beaded necklace, but I felt too dressed up. I am still struggling with what types of necklaces I like to wear and for what occasions.   I opted to wear medium-sized earrings and a wrap bracelet instead.
  • I only wore the jacket in the movie and following it, not to lunch. I really loved the way the jacket looked and felt and I wrote that I wanted to purchase another 1-2 pieces in a similar style (I have since bought the black moto jacket that is shown in outfit #2 above).
  • I like to be able to wear flat shoes with dresses, as it’s much more comfortable and easy to walk around in (I walked a decent amount that day).

What I’d Change:

  • Take up the straps so I’d have less chance of showing my bra or too much cleavage.

Follow-On Notes:   I did end up having the straps of the dress shortened and the dress is now one of my summer favorites.   I find it very comfortable and appropriate for many of my life occasions, plus it can be easily dressed up or down.  I have since worn the dress with a necklace, but I prefer a medium-sized one, not a full-on statement necklace.  I think that statement necklaces just aren’t “me” because my style is more streamlined and minimalist.

Outfit #4 – Cobalt Maxi

Cobalt maxi-dress

Rating:   9/10  (I’d probably give it a 10 today – I love this outfit!)

Where I Went:  Movies and errands (10/26/2014)


  • I felt comfortable, stylish, and attractive in this outfit. Cobalt is my favorite color (other than black, of course).
  • The dress, jacket, and shoes have all become summer wardrobe favorites. The necklace and watch are favorites of mine, too.
  • I have often struggled with which earrings to wear with a more prominent necklace, especially since I don’t like to look too “flashy.” The earrings in this photo were new at the time and worked well with the necklace in terms of size and style.
  • I wasn’t happy with my hair that day, yet I think it looks fine in the photo. But I do need to have alternate hairstyles to wear on humid days, as we had a very hot summer last year and that may be the case again this year.   I need to have multiple ways to wear my hair so I can easily make a change if necessary.

What I’d Change:

  • I couldn’t think of anything to change about the outfit, but I did write that I wanted to have other hairstyle options. That would definitely be helpful for me and is something I need to figure out before summer rolls around this year.

Follow-On Notes:   This type of outfit is now one of my summer “uniforms.”  It works very well for my casual lifestyle and it feels like me and true to my style. I like that I can be comfortable and stylish at the same time and that I can wear flat shoes with a dress and not look “frumpy.”


I hope you enjoyed this fourth installment of my “Lessons from My Outfit Journal” series.   I believe that I will re-wear outfits 2, 3, and 4 this year and will continue to be happy with those looks. I’m moving more and more toward maxi styles for my skirts and dresses, as the midi length I used to wear a lot is problematic and tends to look “churchy” or dowdy (I wrote about that issue in my first outfit journal post).  While I would love to find a couple of mid-knee length skirts that work well for me, I’m happy to have the maxi style as a go-to look for warmer weather.

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.    Since I was happy with most of these looks, I didn’t think there would be all that many points to share here.  However, there are still a few useful nuggets to report:

  • Don’t buy dresses (or anything, for that matter) that needs a lot of alterations in order to fit well. Only do simple and straight-forward alterations on my clothes.   This is a lesson that has been very difficult for me to learn (read more about that here), but I keep trying to pound it into my head!
  • Make sure to fully consider the types of activities I will be doing in my outfits. While I’m in the fitting room, I need to walk around, sit, and move in ways that I’ll be moving when I wear the item in question.   We don’t just stand still in our clothes, so we need to make sure they will work for our actual lives and activities.
  • Try things on with the proper undergarments and make sure they don’t show up when they’re not supposed to. Get straps shortened (a common alteration for me and very easy to do) before wearing something out and about to minimize discomfort.
  • Find some alternate and easy to do ways to wear my hair for days when it’s hot and humid and/or when my hair frizzes or otherwise annoys me. Life’s too short to not enjoy what we’re doing because of a bad hair day!

Your Thoughts?

I hope you enjoyed this additional “Lessons from my Outfit Journal” post, even though it came immediately after the last installment.   If you have been keep an outfit journal or doing something similar to improve your wardrobe management and personal style, please share your experience in the comments section.  Feedback on my outfit journal entries and insights is also welcome (as long as it’s respectful, of course).

May Be of Interest

If you’ve been reading this blog for a while, you know I’m a big fan of style expert, Bridgette Raes, and that I worked with her last year to help me improve my style (I wrote about my experience – the series starts here).   Well, Bridgette is currently offering a discount on her virtual style services, so you can be helped by her the same way I was.   Check out this post to learn more!

I hope you all have a wonderful weekend.   I’ll be back next week hopefully ready to write coherently on all of my usual topics.  I’m glad I was still able to get a post out today, though, and I hope you enjoy and benefit from it.

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