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:

starting point
starting point

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:

building an outfit
building an outfit

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?

30 Comments on Outfit Planning

  1. Great post! Thanks for sharing some of your process! I’m only at the beginning stages of trying to understand my style, and right now that means tracking the outfits I’m wearing and trying to find common themes/colors/silhouettes. I’ve been big into second hand shopping since college and have major closet envy! You’ve got incredible style!

    • Thank you so much, Katie! I think keeping track of the silhouettes/colours/looks that you enjoy wearing the most is a great idea. I often find that outfits will appear differently in my head than real life, and I will sometimes enjoy them more (or less) than I expected.

  2. Thank you! I’ve been looking for posts like this. I’d really like to make a wardrobe management/exploration app. Stuff like this is really helpful for distilling common themes, like picking an outfit from one piece of clothing or being able to schedule outfits.
    I’ve been scouring the internet so it’s exciting to have this just pop up in my blog feed.

  3. Love this post! Wish I could plan that much ahead of time. In Montreal, the weather is so finnicky during this transitional time of summer to fall that I can really only plan one or two days ahead. I might try out your approach for when fall and winter really hit as those seasons are much more predictable. Thanks for the inspiration!

  4. I started a spreadsheet of my clothing several months ago after I found your blog. Thanks for the inspiration! Instead of notes I use google sheets. There is an app for any type of device or you can just use it in a web browser. What I love is that I can use graphing and sorting functions with out transferring the information to another platform and its always on hand. I have been using the sort function constantly to encourage me to maximize my wardrobe by trying to make outfits with things I haven’t worn as often or that currently have a higher cost per wear. Things are listed by type, brand, description, color, size, year acquired, cost, wears, and cost per wear (which is automatically calculated for me). It also gives me live updates of things like average cost per wear and average purchase price. Its super fun and convenient.

    I plan my outfits on the weekend, usually when putting away laundry. I typically focus on some sort of metric from my spreadsheet to pick anchor items and then build around those. I try on the outfits and hang each one on a single hanger, sometimes with planned necklaces. I work in a lab so I don’t get to wear skirts and dresses but still must be business casual to business formal depending on the day. Pants are a bummer but using the spreadsheet has turned dressing into more of a game for me and I am enjoying fashion a lot more again! THANKS!

    • That’s a great tip! I’ve been tempted by apps like Stylebook and such, but the idea of moving over all my information over is a bit daunting now. But I’m definitely tempted … the math would get done for me 😉

      • I tried Stylebook and in theory I like it but transferring all the info into the app was so much more labor intensive than just making a spreadsheet. And photographing EVERY SINGLE THING YOU OWN. I made it to about 30 items then gave up. Getting a good photo of a flat lay was really challenging for me. This would probably be easier for you as you already have a ton of photos!

  5. I usually put together 5 to 6 outfits while doing laundry on Saturday (so I use different pieces each week). I only need 4 outfits for work so the extra is for a dud outfit – don’t try on ahead of time. I almost always start with the top as I have so many and pull pieces that I want to wear with the top to hang altogether on the closet door.

    • I totally used to do that too … but then eventually decided to go with bigger “batches” — more efficiency, right? LOL! I think a week’s worth of outfits is very reasonable for 99% of the population 😉

  6. This was such a fascinating read! Since becoming a mom, I’ve become a big fan of planning outfits in advance so that my weekday mornings are a bit less chaotic. I use an app called Stylebook to help me plan, but I really like your approach of choosing a foundation piece for each day of the week.

    • Planning is the key to being able to manage my day as a working mom, honestly. So, I’m totally with you. It’s not sexy and fun and spontaneous, but sigh … that’s life 😉

      I’ve been on the verge of buying Stylebook a few times, but it seems daunting to start again from scratch when I already have a system in place, and have so many clothes …

  7. What is this wardrobe wizardry?!
    I admit I am much less of a planner – or rather my lead time for planning is much shorter. Either the night before or the morning of while I scrub up I think about the weather and what I feel like wearing (usually a skirt/dress if I wore pants the previous day or vice versa for variety). I have a fairly mix/match wardrobe in a well defined color palette, so I rarely have duds even if I haven’t tried an outfit together before.
    I do like the suggestions on ways of finding new combos -even if I weren’t a blogger I think I’d still enjoy the feeling when I realize that two pieces I’ve never worn together really look great together.
    Thanks for sharing your method!

    • I think that’s perfectly normal. Everyone has got their own routine, and lifestyle needs, and closet — so many variables. I would say my approach is definitely on the far side of “planning to the max” but my life is hectic as is my closet, so I need a way to keep a handle on both.

  8. This is so interesting, it seems like such an astonishing amount of effort just for getting dressed, even if it is a ‘time saver in the long run’! I don’t mean that in a rude way, I just never knew so much planning could go into a regular person’s daily outfits. I always thought all your and other bloggers’ outfits happened with little planning and a lot of natural style. I only plan ahead if there is something ‘special’ going on at work or outside, but I’m usually happy with my other outfits.

    • No, it’s a fair question. I don’t find it a huge effort, but I enjoy thinking about style (hence this blog, haha) so it’s not a chore. I also spend, like, less an a minute coming up with each outfit, and maybe another 2 or 3 minutes trying them on later. However, YMMV (that might still be a lot of time for some people) and that goes for everything I’m saying here.

      I’m a big believer that routinizing (sorry, not a word) your day, and especially mornings, as much as possible helps overall productivity. Some parts of your day can never be planned/routine by their very nature, but others can. It saves your mental energy for the more complex and unforeseen decisions that crop up (e.g. at work). It takes me less than 20 minutes to get ready in the morning; having an outfit planned in advance is a huge component of that. I don’t have to spend any time thinking about what I’m going to wear. Now, there are two ways of approaching that goal. One, you can be one of those people like Barack Obama, who wear the same “uniform” every day — zero thinking involved. On the other hand, if you like variety in your clothing and/or enjoy being creative with your clothing, then outfit planning is the way to go. Admittedly, I’m a very long-term planner by nature; but even planning your outfit the night before can make a big difference.

      As far as other bloggers go, I can’t really tell you how they do it. I think some of the bigger (full time) bloggers take photos specifically for the blog, which by its very nature will involve some sort of selection process. Most of them don’t photograph their everyday, daily outfits so the outfits they do present on the blog are obviously chosen carefully to fit with the image/brand they have. I think the idea that you can look like a magazine ad without any effort is a bit of a myth, unless you’re just wearing the same things over and over. Having a well-chosen wardrobe and a good sense of style help tremendously in terms of making the process as simple as it can get. But anything creative requires some effort/thought — I don’t care what anyone says 😉

      • Adina, I would love to see a post about your morning routine. I know those kind of posts were popular for a while, perhaps you have! But my mornings are a shambles (two kids to get ready as well) and I was just thinking “I need to plan my outfits for the week”. You would die if you saw how few options I was working with haha. I just listed out my work clothes and I have like 3 of each: blazer, pants, skirt, top, dress. That’s it. Yeesh. But somehow i still need help!

        • Funny you should say that … I did draft one of those “Day in the Life of” posts a while back, but ultimately decided to scrap it for various reasons. I don’t have any advice — not that you really asked, anyway — since everyone has a different “groove”, but I will say that the key to my mornings is well-rehearsed routine. On the rare mornings when, for whatever reason, I need to switch things up, I’m a mess. Everything seems to take twice as long, with infinitely worse results.

          In terms of routine, I mean everything is the same. I do the same things in the same order, to the point that I can basically be on auto-pilot from the moment I wake up until I step out of the door. The kids are also creatures of routine, so that helps tremendously. My son has been known to say, “Mom, it’s 6:45, time to do x” My daughter less so, but she’s your typical 3 year old, LOL!

          It all clicked for me when I attended a seminar last year that talked about ways of improving your mental energy and productivity, and the speaker spent a lot of time talking about the importance of routines. Eliminate non-essential decision-making, no matter how minor — it can make a huge difference! I’m obviously a fan of outfit planning, but even if you don’t take it to the extreme I do, it might be worth trying it on a smaller scale. Someone suggested making a list of outfits that you can just pick from, and I think that’s a great idea. If you don’t want to bother making new lists all the time (as you cycle through the outfits), you can always just go with a “best of” list — jot down all your favourite outfits (whether it’s 10 or 20 or 30), and then pin that list to your closet door for future reference.

  9. Have you tried the Stylebook app? It’s a bit of work on the front end taking pics of all of your clothes but I love it. The primary thing is to plan outfits visually, but it also keeps track of the last time you wore that article of clothing, price per wear, how many items of that color/brand/type you own, etc. I like to look at my top price per wear items to make sure I am wearing them. It’s also easier to see everything you have instead of not seeing things in your closet. I like to “experiment” with things I’m thinking of buying to see how versatile it will be in my wardrobe.

    • I’ve been really, really tempted by it, but I’m loath to take on all the work of cataloguing my wardrobe again when I have a workable system in place already. The Stylebook app does have features that I don’t currently have (and I think I would enjoy), which is what makes it tempting. Gah, I’ll probably give in one of these days …

  10. is there an Android equivalent app to Stylebook that someone can recommend? Stylebook is currently iOs only…

    • They’re pretty terrible but they definitely exist… Which is why I’ve been wanting to write an Android. I haven’t looked in probably about 6 months so it’s possible there’s something better. The biggest issue I have with the ones I looked at was no background removal and I felt like the outfit layouts ended up looking terrible so I didn’t stick with it.

      • Thanks Krista – I thought it was just me. I had looked at a few and was not really impressed and was hoping I was overlooking one… you should definitely write an Android one!

  11. I’m lucky enough to be able to walk to work (for now…) but I still plan outfits in big batches. My method is to write them down in a list without assigned days, and then delete an outfit once I wear it. I generally pick out outfits from the list 3-4 days in advance.

    I guess the only other real difference is that I actively try to wear new items every week for a few weeks in a row to make sure that I actually do like them and not just * think * they’ll work.

    I find outfit planning very relaxing which is why I don’t mind doing it. It also helps me keep tabs on what I’m not wearing…if I don’t want to wear it on paper I probably don’t want to wear it in person.

  12. Wow – I had no idea that you planned ahead so far! I’ve started planning generally on Monday for what I want to wear for the whole week; helps if I want to wear a certain piece for a certain event during the week I know not to wear it ahead of time of I don’t repeat it. (Such as I have specific shoes to wear to walk to a meeting so I save the pants I like best with them.) I try to cycle through a good number of skirts, pants, and dresses so I’m not always in one thing. Sometimes I will have a new piece I want to wear, sometimes I realise I haven’t worn a certain pair of shoes in a while and try and build an outfit around that.

    I do focus on weather more than you – I find the weather really affects my office temperature. Right now it’s chilly in the mornings but hot during the day as the sun comes in and I think the AC’s been turned off for the year, so layering is key. It will be interesting to see what happens when we move floors at the end of the month!

  13. I am impressed and appreciate you sharing your process! That kind of planning appeals to my inner type A! I like that you reveal the thought process behind a quality stylish outcome. It also is a nice alternative to adopting a “uniform” to save time, energy and decision-making in the morning. I myself plan what I’m wearing while I’m brushing my teeth that morning (!) and then adjust once I check the weather app!! It has always been important to me as a blogger to show what I actual wear, fails and all (coming tonight!), rather than “staged” outfits worn only for the sake of a post. Love your thought-provoking, thorough posts.
    xoxoxo nicole

  14. I use the stylebook app. It takes time but once you have taken pictures of all your clothes it is so easy to make collages and save them. i love using it to help me get creative with my clothes.