Are You an Outfit Planner?

If I’m being really honest with myself, which, 9 out of 10 times I am (that one other time gets lost on my relationship with a. my crotch, b. pants), it is impossible to declare that I am not an outfit planner. This is a difficult truth to come to terms with as someone who has historically prided herself on insouciance-in-conjunction-with-clothes.

The fact of the matter is, though, I have long notes — really, really long notes — aplenty languishing in my iPhone, sandwiched between what I call “big ideas” and memorable quotes/jokes that I know I will literally want to pull out of my left pocket at some point between now and the end of this digital device’s lifespan.

The meat of those e-sandwiches are the crux of my relationship with clothing and mental clarity. For as long as I can remember I have spent time doing psychic walk-throughs. What will I wear the following day in the event of rain or shine? Or an apocolapyse? Or should I find myself on an airplane unexpectedly, heading toward the Caribbean? Often, I consider the following weeks and months and semesters, too.

My sister-in-law does not have a boyfriend but I know exactly what I will wear to her wedding.

Just this morning, I stared into the black hole of familiarity that has never not stared back at me and scratched my head while I thought to myself not “what will I wear today?” (I figured that out one day last week when stuck in my own head with nothing to do but organize — and you know that’s what this is, right? A futile attempt at control over nothing — I wrote an entire week’s worth of notes of clothes I might want to wear between then and the end of next week — and in case you’re wondering, it’s a beige blazer, navy blue mid length dress, ripped jeans and yellow satin sneakers) but, what will I wear that weekend I’m supposed to go Boston in October?

I can’t even remember why I’m going to Boston in October. It’s worth mentioning that, even in spite of the recurrent outfit planning, significantly more than half the time, I go rogue, forgo my list and wear the exact opposite of what I said I thought I would. I think maybe the planning makes doing that easier. Or at least more fun.

But I guess the question still stands. Are you an outfit planner? If so, what do you think it says about you? Maybe we’d rather just not think about it — that makes evincing the spirit of manufactured effortlessness much more accurate, doesn’t it? If you don’t plan, do you think you’re better than the rest of us are?

Frankly, you probably are but still there’s something to be said about the fact that none of us may know where we’ll be in 2020, but at least we — the planners — will probably know, within a week or two, exactly what we’ll wear.

-Leandra Medine

  • alicake

    I wish I could outfit-plan. My wardrobe is full of amazing but incoherent pieces that require creative styling to work together. But rather than make a concerted effort to tackle that problem, I continue to buy more incoherent pieces and leave myself 5 minutes in the morning to choose an outfit. Improbable styling and frustration ensue.

  • Reem

    One simple reason to plan my outfits- save time. I could literally spend more than an hour trying to decide what to wear in the morning, and that just kind of gets to my head AND gives me cause to be late, hence my insistence to plan outfits beforehand. Though I really like the thought of going rogue!


  • I love an outfit-plan. I even sketched my outfits before one particular spring season when I couldn’t actually wear the clothes (too cold in Chicago), but needed the spring color/fabric fix.

  • thegospelofmarc

    Planning is so much fun! Even for events in the distant future like your graduation dress or your first magazine photoshoot. Get sucked into the black hole of outfit planning here at

  • Serena

    I always outfit plan! But I don’t do it as long – term as you, more like when I go to bed I’ll lay awake and figure out my outfit for the next day (only to wake up and change this outfit completely 90 % of the time but hey, I tried).

    • Lorien

      I call this a “mental pickage”.

  • I never outfit plan but I do outfit imagine. I have fantasy occasions for every life monument, and I often have a fantasy outfit for each day of the week. It has nothing to do with what I’m actually wearing, but sometimes it helps when I hate my outfit. I can just very vividly imagine wearing something else.

    • Leandra Medine

      Outfit imagining is such a nice way to put it


    Sometimes I outfit plan something that seems like a great idea and then i wake up next morning and say: what on earth was i thinking of!?
    So i do plan my outfits but never wear them as planned because they never feel right with my mood.

  • ee_by_cc

    I’m an unabashed outfit planner. So much so that I may actually invent places to go because some ensemble popped in my head, and I can’t shake the NEED to wear it.


    I’m an outfit planner. I am always thinking of what I’ll wear tomorrow and the next day and the next. The first place my mind goes when I get a new invite is what I will wear. I have all my clothes indexed and a bit of a process (that I’ve been using to much success since I devised it at age 13) that assures a fairly thorough rotation while favoring newer items. I could no longer get dressed without it. The only thing left to play with in the mirror is the jewelry.

  • Charlotte Fassler

    I wish I were more of an outfit planner! I will go through occasional phases but for the most part my outfits depend on mood & weather. The planning process is more of an organic one that is at the mercy of the weather forecast (which isn’t always correct….)

  • Charlotte Fassler

    Except when I get a new garment I am more inclined to plan how i will wear it and all the different outfits I will incorporate it into. So I suppose i do plan but only when I have new, exciting pieces entering my closet…

  • Nico

    I am an outfit planner and now I have a 3 month old baby girl and also am an outfit planner for her. It’s getting very complicated to be an outfit planner for 2 jajajajaja

  • Lyric

    I have to plan for work, because I work in retail and whatever I’m wearing needs to fit our aesthetic, and I am getting my costumes planned out for Comiccon (soooo excited), but other then that, I don’t plan much. Just wear what’s clean.

  • Tara Hagan

    Every Sunday afternoon or evening, I lock myself in my room for 30 minutes to an hour to plan what I will wear next week. Big meeting on Tuesday? gotta iron my pink tuxedo shirt. Concert after work on Thursday? gotta find a dress that looks good with flats. Every morning knowing what I am wearing and that it works for what I have planned = at least 10% more confidence every day = more than worth it.

  • I plan my outfits, right down to the lipstick shade using Excel spreadsheets. And i am not ashamed to admit that.

    • Leandra Medine


      • Effie

        ME TOO!!!

  • Kat

    Ohh, I wish I could plan my outfit and stick to it! If I plan it, I always change my mind in the next minute, it is hopeless. If you own a bunch of clothes, you don’t need to plan, if you ask me. On the other hand if you own a small amount of clothes, you always have in your mind what goes with what. 🙂




  • GapToothedGirl

    Definitely I’ m an outfit planner

  • I do outfit plan most week days but sometimes I pick on the fly as well. Either way I end up looking pretty good 😉

  • Dido

    I don’t have a date tonight still i have been thinking all day what i would wear if had one. maybe i should invest the same energy in actually finding a date, but – oh – is not as fun!

  • Alessandra

    My friend just texted me, “What are you wearing Saturday?” Homegirl, it’s Monday and we haven’t even made plans yet.

  • megdobbie

    I’ve always been an outfit planner… trying to get dressed in the morning without a plan has me running around my apartment leaving a massive trail of discarded, tried-on clothes behind me and usually makes me late.
    On Sunday nights I plan out (and set out) five full work outfits but don’t commit a day to them. When I wake up in the morning I choose one of them depending on how I feel. This way — no stress of picking clothes in the morning, but no disappointment of settling for an outfit that is nice but doesn’t jive with how I feel like that day 🙂

  • Mariah

    I’d say I’m an outfit planner part of the time. When I have to pack for a trip, I’ll plan outfits or “outfit ideas” where I’ll have certain colors or shapes that I’ll wear together. Sometimes if I’m beyond bored I’ll plan some outfits. I used to try and plan outfits a week at a time on Sundays, and that ended quickly. Besides, I don’t know what I’m going to feel like, nor what the weather’s going to do (living in Georgia here, the land of unpredictable weather). I feel like it’s so I can streamline my mornings since it takes me 20 minutes to make up my mind, but I like that process of making up my mind.

  • Okay, this is me. Just last week I had planned an outfit for saturday… All summer-ish pastels with a floral short and a kimono. I’ve been wanting to wear it all week. Then when it was saturday I did a 180 degree change and opted for an all black outfit :'(

  • Stephanie

    It’s a mix for me. Outfit planning for new ideas, but once an outfit is vetted as passable it goes in the mental catalog of go-to outfits to throw on when I don’t want to think about it or when what I was planning just looks plain wrong. Lack of any outfit planning leads to me wearing the same 10 outfits on a 2 week rotation. Bo-ring!

  • Daniella

    I’ve planned outfits for a few years now, I find it a lot less stressful. I have a “thoughts for outfits” list on my phone and I don’t think I could be without it. Though like yourself, I sometimes rebel against “The list” and I can’t help but revel in this as sadly I see this as quite the achievement! I’m like yo, check this somewhat effortless shiz out! Ha! I can’t promise that this comment makes sense but I thought I’d at least try as I can definitely relate to this post 🙂

    Take care,
    Daniella x

  • Martin Chavanne

    I do the same thing you do, I plan outfits and then I dont wear them. I feel like I do that because in that exact moment I feel inspired and I want to use up all that inspiration on things, I dont want to waste it, cuz I know that in the event of waking up completely lost It will help me remenber those plans alredy made to remenber also the inspiration (even though it never happens, and I feel more lost than ever) If its winter, Im alredy planning what I want to wear to the beach next summer, and I make list of the things I should get for those outfits, but I do that also with decoration, or what I want to do for my next birthday party and things like that. Maybe its the desire of being in control of who we want to be, but who we alredy are is way stronger. The only outfit that will always be planned and will stay that way, is the one we plan for a wedding, and that’s because Im a guy, and I only need to show up in a tuxedo.

  • Cyrena Monique

    My initial answer was no, but then when you say you know what you’re wearing to your sister in law’s wedding – I can relate, and I have to say yes, I am!!! C x

  • By nature, I’m NOT a planner. But I have been late too many meetings from standing before my closet as if it was completely barren with nothing to wear that I’ve tried to force myself into being a planner. I do find the mornings where I have an outfit planned go much smoother. But that’s only one day at a time. I have absolutely no idea what I will wear two days, a week, a wedding, or a year from now. And it kind of stresses me out to think about it haha

  • katie o’meallie

    I (quite seriously) have spreadsheets full of outfits I’ve worn, on what day, and for what event for the past few years. I have outfits planned for events months in the future and instead of doodling I make notes of outfit ideas. I pack for trips a week in advance and have a spreadsheet of packing lists for trips for the rest of the year.
    After all that – like you – I rarely actually wear exactly what I planned

  • Margaret Ely

    my mom has been trying to plan out what she will wear at her own wake, she isn’t even terminal, just kinda old. smart lady

  • Sandra Saimon

    I plan everything, writing to-do lists, wish lists, everything. I guess this is my way of putting some control over life which is essentially chaotic. It comforts me even in the perspective of not making it to the list. I write a big list of what-to-wear twice a year at the beginning of each season. Then I emphasise those looks I’d like to show to my readers. That means these are the options that I consider on days I plan to take photos for the blog. An outfit plan is great for those (like me) who have waaay more clothes of way more styles than you need, when you just want to open your closet and put on whatever, and you know that everything matches anything in your wardrobe. I guess planning is the price for allowing yourself to be different.

  • Louise Jacobs

    Yes Yes and Definately Yes, I am an outfit planner! and Proud of it. My older sister thinks I’m weird for doing it. But I simply do it to save time in morning while getting dressed, so that I can catch some extra Zzzz’s. Its as simple as that 🙂

  • Hannah Thompson

    I tend to plan outfits with items that I don’t even own yet! I get these vivid ideas of what I would like it to look like and what I would wear with it and where I would wear it to and then can never ever find anything like it! If anyone knows where to get a soft leather white t-shirt with raw edging then please alert me!

  • I woke up at 4 this morning for an ass-early flight. I put on some track pants and a baseball tee like any normal person at that hour and was so grossed out by its practicality (sleeping on a plane, you know) that I changed into high-waisted acid-wash jeans with a white button down. I missed my flight, but I am sitting here at Cinnabon looking effortless if I do say so myself.

  • Jelena Keravica

    I love imagining my outfits, planning them, shopping for them, making them, even giving them away. I love everything about clothes and people can call me shallow or materialistic, but I cannot exist in this world if my outfit doesn’t click. I usually have my outfits planned for an entire week and for most special occasions – weddings, job interviews, holidays, graduation day and stuff like that. Then I never seem to find the clothes I imagined in the shops, so I get a mini panic attack and have to choose something else. But still, it feels nice to think about it.

  • marinacasapu

    so, are you coming to Boston in October?:)

  • Where I live it’s quite hard to outfit plan, because the weather changes fast. One day it’s sunny and warm and the next day it’s raining and cold. But sometimes I plan.

  • Lili

    I’m embarrassed to say I keep a clothing calendar to keep track of what I wore and what I will wear – for months in advance. I hate repeating outfits.

  • Ruthy Castillo

    Planning is definitely a better way to go. It is something I struggle with especially, when its time to travel. What would your travel essentials be?

  • Georgia Booth

    I’m heading to New York in September and have already imagined what I will wear for each place I’ll be visiting! It’s making me even more excited!

  • ShanIsRad

    When I was younger, my mom always tried to get me to plan my outfits the night before, and I never did; I finally realized that she had the right idea! I started outfit planning once I began my “real” job last summer (my job before was retail, and I had to wear all-black, not much planning was involve). I finally realized that if I plan the night before, I can save time in the morning, and sleep a little later!

  • I’m an outfit planner maybe 1% of the time.

    The rest of the time, I go with how I’m feeling…or the weather.

    This past winter, I defaulted to jeans, boots, and sweaters. Not the most professional choice, but when you’re walking outside to chip ice off your car in -20 degree temperatures, professionalism goes out the window.

    Now, luckily, it’s warm enough for dresses. So I toss one one with some flats and walk out the door. I look put together, and I didn’t have to do ANY thinking. It’s genius. 🙂

  • Effie

    Every night before I go to sleep I think about what I am going to wear to work the next day. I am going on holidays in a fortnight and I HAVE A SPREADSHEET of what I will be packing and wearing. Need to buy is in italics. I’m that person.

  • Ela

    I’m CERTAINLY an outfit planner! Every night when I’m trying to fall asleep, the best method to successfully do it it to think rethink and rethink about what I’m going to wear next day. Kisses from Poland!

  • cogitate10

    lots of hahah.. im definitely an outfit planner though sometimes i change clothes in an instant.hahah