Here is a question, from reader L., to kick off another (hopefully) interesting discussion:

Do you plan your outfits ahead of time? If so, how do you do it?

The short answer is that I do, and the process involves a bit of science and a bit of art. I use both of those terms loosely, by the way. It goes without saying that my approach won’t work for everyone; if you’ve worked out a great system of your own, share it in the comments – I (and the other readers) would love to hear about it.

Now let’s explore Getting Dressed 101 (Adina-Style), shall we?

Planning Ahead

The truth is that I generally plan my work outfits one month at a time – because I’m list-obsessed and because I find it easier to go through the exercise in “bulk”, so to speak. (Casual outfits are typically spur-of-the-moment.) I love me a nice Excel spreadsheet, but I can’t pull one up easily on my iPad, so I just use the plain-Jane Note app. It’s easy and convenient, and I can do it while lounging in bed, procrastinating and not getting to sleep at a reasonable hour. Ahem.

I start by listing the work days of the upcoming month, grouped by weeks.

If I know that I will have “special” events on specific days (like presentations, client meetings, hearings, etc.), I make a little mark next to the date to remind myself when “scheduling” that day’s outfit that I may need to take into consideration special requirements (e.g. a blazer or suit, a nicer dress, etc.). I don’t plan for weather, other than in a general, seasonal sense – nor would that be possible given that I am usually planning weeks in advance. As I have mentioned before, I am rarely exposed to the elements for any extended amount of time during my work week; I’m outside for maybe 5 minutes in total during my commute, and I rarely go outside when I’m at work. (If I know I’ll have a hearing outside the office on a particular, that’s one of the things I consider when planning that day’s outfit, and in particular the choice of footwear.)

If, for whatever reason – weather, my mood, unforeseen work event – I need to change an outfit that I planned to wear on a particular day, it’s easy peasy. I have a month’s worth of alternate outfits from which to pick.

The Science and the Art

I told you there was some of both involved, didn’t I? OK, not really. What I’m really getting at is that outfit-planning has a formulaic component and a creative component. This didn’t happen intentionally; in fact, I never thought about it in that way until I started preparing this post. But analyzing my “process” ex post facto, it struck me that there were 2 parts to it.

First, the formula.

In an average work week, I know that I will wear jeans (or other “casual” pants) on Friday. I also typically wear dress pants once a week. The remaining three days are divided between skirts and dresses, depending on what most excites me at the moment when I’m planning my monthly “capsule”. So, I start by filling those things in, like so:

The next step is to decide which pants, skirts and dresses I’m going to be wearing. I have a pretty good mental inventory of my clothes, but if I’m having trouble picking options, I can always refer to my wardrobe spreadsheet – conveniently, also on my iPad (it’s actually another “note”). I try to mix things up every month so that all my clothes, and especially my dresses, see regular action – as much as possible given the extensive contents of my closet.

I make a shorthand note to describe the piece I have in mind:

This now serves as the foundational piece for that day’s look, around which the rest of the outfit is built. For me, pants, skirts and dresses are always the first things I decide on, because that’s how I create outfits in my head. For someone else, a foundational piece might be tops instead of pants, for example. The foundational piece does not necessarily have to be the “statement” item that will be the focus of attention; it’s just the piece that connects all the others, if that makes sense.

And here is where the creative part comes in. Take the Monday in the above example. I think to myself: what would look nice with my navy Nanette Lepore dress? Because I’m a blogger, the next question is: have I worn that combination before? If the answer is “yes”, then I usually push myself to think of a different combination, partially because it could serve as potential blog fodder, and partially because wardrobe re-mixing is one of the ways in which I justify my huge closet to myself. But if you are a non-blogger, you can skip this step. In fact, you may wish to stick with tried-and-true combinations most or all of the time.

Personally, I also break the question down into smaller components. First: what topper would look nice with the dress? Now, even if you don’t have a closet as big as mine, ideally you should have more than one answer to that question. An oft-repeated recommendation is that, when buying new clothes, you should ask yourself whether you could make 3 different outfits using the new piece and old items from your closet. If you follow that rule, you should have a bunch of re-mixable clothes at your disposal. Closet “orphans” are a big source of wardrobe angst for people, in my experience, and should be avoided as much as possible.

OK, so we have picked a topper – what next? For a pants or skirt day, the choice of topper will usually determine, or at least narrow down, the choice of top or blouse, since it has to be something that works with both the pants/skirt and the topper. Then, once I’ve got that nailed down, it’s time to turn to shoes. And, voila, a complete outfit!

As I go through the rest of the month, I do typically try to re-use some of the same pieces – hence the sorta-capsule title of my monthly recaps. For example, if I wore a particular skirt in week 1, I’ll also plan to wear it on week 3 or 4. Or if I wear a specific top with jeans in week 2, then I’ll plan to wear it with pants or a skirt in week 4. You get the idea. I rarely re-wear the same dresses in any given month, but only because I have a bazillion of them to rotate.

A word on accessories. For me, the choice and bag and jewelry is often a game-time decision. Again, I usually have multiple options, but these are far quicker and easier decisions to make in the morning than picking the rest of the outfit. Occasionally, if when I’m planning an outfit ahead of time, I have a specific vision that involves wearing a particular bag and/or necklace, for example, then I will jot that down; however, I don’t make a special effort to do so in all cases.

Trial and Error

All of the above exercise is a purely mental one. It takes 15-20 minutes in total, probably because I’ve been doing it for years. But, here’s the key: I don’t try any of these outfits as I’m brain-storming them. Not at that point. But trying them on is important; occasionally, even a seasoned outfit-planning pro (har har!) can come up with a dud.

I like to reserve 10-15 minutes on a Sunday, when the kids are visiting their grandparents and the house is quiet, to prepare the following week’s outfits. Using my handy-dandy cheat sheet, I take all the necessary pieces out of the closet, and group them together. I try on each outfit to see if it works, and then hang it together on a clothes valet in my closet (or the back of my closet door). That way, it’s ready to go come Monday morning. Or Tuesday. And so on.

In the (rare) event that an outfit I planned looks terrible when I try it on, I will either switch in another outfit from later in the month, or (if I have time), try to create a new one on the spot. For that, I just wander into my closet and pick a bunch of random stuff … usually a dress + blazer combo, because it doesn’t get any easier than that.

And that’s it: that is my outfit planning process in a (typically wordy) nutshell. Your turn: do you plan your outfits ahead of time or are you more of a spur-of-the-moment kind of dresser? How do you do it?