I've been reading and absorbing here for a while now, and with the influence of so many of you who have shared your goals, I'm beginning to find mine. I hope I'm not setting a record for the longest post ever on the forum.

After a long career which required full business dress and
in the final few years, dressy business casual, I am still struggling to figure out what I want out of my retirement wardrobe. At first, I was it felt so freeing to not have to wear office attire everyday. But my early attempts to build a more casual wardrobe weren’t so successful.

1. Personal Preferences. My early purchases were heavily
weighted toward drapey/flowy items that I had often admired on others. I bought a lot of Eileen Fisher (mostly on sale) during this period. Turns out I don’t really care for flowy clothing. I’ve learned through trial and error that I definitely prefer both the look and and especially the feel of tailored pieces. I also am happiest when I stick to a a couple of defined silhouettes. That makes it easier to mix and match tops,
bottoms, shoes, etc.

2. Climate. I also didn’t really purchase enough clothing for my climate. My warm season is hot and long. Clothing that is appropriate for my warm climate, even if it is high quality, is lightweight - and it simply wears out more quickly. Additionally, it has to be laundered every
time it is worn, which also reduces its life. Furthermore, in the hottest months, I sometimes change clothes (or at least tops) simply to feel fresh. Bottom line – I need a large quantity of summer everyday clothing. Even though it is much less fun to shop for than "special pieces".

3. Real Life. Additionally, I have made the common mistake of buying too much “nice “ clothing and not enough “everyday”
pieces. The reality is that many of my days consist of walking and playing with my dog, running errands, household and hobby projects, working out, etc. In other words, other than workout gear, I could spend those days in a pair of hiking shorts and a t-shirt. And honestly that
is kind of the habit I have fallen into. And there is nothing in the world wrong with that EXCEPT…… I kind of enjoy “dressing up”. It makes me happy to be wearing an “outfit” rather than whichever shorts and tee were clean that day. There has to be a way to do that
without being overdressed for my real life.

4. Body changes. Yep, they happen. I never realized how easy I had it when I was clothing a more trim figure. But the days of emphasizing my waistline are over. That’s ok – I just need to adjust my eye and figure out which silhouettes flatter my shape now and going forward.

5. Style? I have no idea what “my style” is. For now I’m going to focus on two silhouettes with the added goal of being age-appropriate (I’m 59), but (hopefully) not frumpy. That is challenge enough for the
time being, I think.

So, my goal for the next few months is to concentrate solely on rounding out my hot weather everyday wardrobe. I could definitely stand to refine my everyday wardrobe for other seasons as well, but I feel I should be concentrating first on the area where the need is largest.

1. Choose at least two silhouettes – leaning towards:

a. Walking shorts and woven or non-clinging knit tops with some structure. I’d also like to introduce some cropped or ankle length pants that work with the same tops, because sometimes I just need a little more protection from the sun and mosquitos. For the same reason, at least some of the tops must have sleeves that can be rolled down to full length.

b. Just above-the-knee dresses – probably mostly woven. Mostly in a loose silhouette that isn’t fitted at the waist. Cool and comfortable are key.

c. Consider a third silhouette of loose tunic over capri length leggings. But I’ve got a lot on my plate, so maybe that is a project for next year.

2. Pay particular attention to proportions – lengths of garments, fit – especially in the waist area, etc.

3. Since it is just too hot for me to be adding a traditional topper as a “third piece”, I need to find other ways to elevate theselooks a bit. Ideas for this include:

a. More options in footwear. Instead of having one pair of summer
sneakers, why not have 3 or 4 in colors that are chosen intentionally to coordinate with the colors that predominate in my wardrobe. (To some that will sound excessive, but I’m not a minimalist. And having more pairs means that they will last longer.)

b. I’m not a fan of wearing much jewelry with truly casual clothing, but I do always wear earrings and a watch, so I could focus on having some choices that go particularly well with different outfits, rather than always wearing plain gold studs and the same watchband.

c. I do tend to prefer simpler clothing pieces, but can’t deny that multi-colored patterns and details like a bit of embroidery
or contrasting trim add some interest to an otherwise simple outfit.

The Game Plan:

1. My goal is to put together a wardrobe of 8 outfits in each of the 2
silhouettes above. That doesn’t mean I need 8 pairs of shorts/pants/shoes. Certainly those items can be used in multiple outfits. Also, some of the individual pieces will transfer to other seasons. So.for example, a black cotton voilesleeveless shirt that is worn with khaki shorts and sandals in summer can be worn with jeans and and closed footwear in the early fall. I would also like to have 2 loose tops and 2 lightweight dresses that can be worn over workout gear (one of
each to go with black workout capris and one of each to go with navy). The tops will probably only be worn over workout wear, but the dresses could most likely be included in the total of 8 pieces.

2. Try on and assess every piece I have from last summer. Discard the things that are worn. Then make a list of what is needed to create
the wardrobe described in (1) above.

3. Once the clothing has been chosen, start wearing it and identifying
footwear, accessories, etc. that add the finishing touch to each outfit. Purchase those items and time, budget and
availability allow.

There. I feel much better getting this all down in writing. This should be do-able, right?

And thanks once more to each of you who has shared an analysis like this in recent months. It really is invaluable to see how other people's thought process works. I hope that maybe someone can find some small inspiration in my progress as well.