Experiments in Outfit Planning

I planned beforehand what to wear this week. This is what happened.

I planned and wore outfits this week.

I am really bad at planning things. No, this is not true. I actually plan a lot. I am really bad at planning outfits. Here’s why:

1. I consider myself a spontaneous dresser. How could I possibly know what I’ll feel like wearing tomorrow or the day after, or the one after that?

2. My body is going through a lot these days. One day I’ll fit into something, the next, I don’t. I can’t plan which clothes fit me on a given day.

3. The weather in Helsinki is very fickle and it makes planning outfits challenging, even if you keep an eye on the forecast.

Because Rachel of Hey Mrs Solomon has had such amazing success with planning her outfits, I decided to give it a go. (Rachel does an outfit planning session on her Instagram every Sunday night. It’s a hoot!)

I wanted to try planning outfits for a couple of reasons:

1. I don’t get much wear out of most of my clothes. I’m hoping that planning outfits beforehand encourages me to wear some of my less frequently worn clothes.

2. I still run into occasional panic dressing, i.e. mornings when I literally have two minutes to get out of the house and I’m standing in my tiny walk-in-closet in my underwear. I hate it.

3. Rachel and many others say that playing with your existing wardrobe helps you fight the urge to keep buying new stuff. I want to test this, because even after I’ve deleted all shopping apps from my phone, I still think about shopping quite often.

I set my sights for planning my outfits on Sunday, April 7th. My work week runs from Tuesday to Saturday, with Friday being my WFH. I don’t bother planning an outfit for Monday because I’m just going to go for a long walk and get groceries. 

Sunday – The Planning Session

I’m looking at the weather forecast for the coming week. We had heavy snowfall last Friday and despite warmer temperatures in the forecast, there’s still snow on the ground in the suburbs where I live. How quickly will the snow melt? This feels like a major complication. I might have to wear snow boots if the snow sticks around longer, and there are few things I hate more this time of year than having to wear snow boots. I’m not off to a great start here. I decide to plan at least two outfits that I can wear with snow boots or lighter spring boots, and I’ll just figure out as I’m getting dressed in the morning which shoes I get to wear. There’s only one day in this week’s forecast without a chance of precipitation and that’s Tuesday, but knowing the fickleness of the weather in Helsinki, that might all change overnight. The weather is giving me a real headache already.

I’m staring into my closet and I don’t feel a spark. I don’t know what I’m doing. I scroll through my Pinterest for a while, but nothing jumps at me. I know that Rachel has weekly prompts for her outfit planning, but my mind is blanking and I can’t think of any of hers right now. Because of the time difference between the US and Finland, I won’t know her prompt for the coming week before Monday morning.

There’s a fun tulle petticoat piece that I bought at the thrift store a week ago and I’ve been toying with the idea of wearing it on top of a pair of trousers. It’s a start! I try the tulle with a pair of wide leg Dries Van Noten jeans and it’s just not working, not at all. My husband suggests that maybe it would work better with a skirt. He’s right, and I quickly find a black vintage midi-length silk skirt that works. What to wear on top becomes a real challenge because the tulle creates a proportion I’m not familiar with. I try various different top and blazer combinations and about half an hour later I finally have something that I’m pleased with: a black fitted Dries jacket from the 1990s and a sheer black silk turtleneck underneath. Tall black lace-up boots go well with this. The outfit is quite quirky but I’m feeling it. I’m wondering if I’m actually going to wear it. 

It occurs to me that every outfit can’t be adventurous like the first one or this will take all day. I have a long, flowy 1990s Comme des Garcons jacket that I’ve been wanting to wear, but it’s understated, black, and quite simple, so I manage to style it fairly quickly with a long sleeve t-shirt, a Pleats Please fringe skirt, and weather permitting, a pair of houndstooth derbies. It’s another black and white outfit. I’m painfully aware of a lot of people saying right now that black shouldn’t be worn with white because it’s either “too obvious” or it gives butler / penguin vibes, but I really like to wear black and white, so I’m going for it. 

Penguin outfits in the making.

I figure that I might want an outfit with some color in the mix, and because my first two outfits revolve around skirts, I pick my Dries Van Noten Pamplona khaki trousers to wear with a bright blue Issey Miyake Cauliflower top. The trousers look great with the brown vintage work boots that I bought earlier this year. I then put together a quick fail safe outfit (something I’ve worn before and liked a lot): Pleats Please bouncy skirt with a baby blue shirt and a weird Watanabe cotton knit sweater. I have several shoe options for this. The weather is going to dictate which ones I’ll wear. 

It’s taken me a staggering hour and a half to put together and try on four outfits. I didn’t think this would be so time-consuming, and I have one more outfit to go. I’m getting tired and hungry so I just grab a pair of Dries blue jeans, a sheer Dries turtleneck and I’ll just throw a navy Yohji Yamamoto shirt on top. I know I’m supposed to try on things I haven’t worn together before, but I don’t have the energy and I’m just going to hope that it works out. 

It hits me later in the evening that maybe I should plan what to wear tomorrow for my walk and grocery run as well, because, well, why not? I put together one more quick, comfortable outdoorsy outfit: army pants, a long sleeve tee and a big Ralph Lauren men’s shirt. Lo and behold: I have six outfits! It’s only at this point that I realize that I’ve put together indoor outfits + shoes to wear. I have not considered coats, jackets, hats, scarves and handbags, not to mention any other accessories. F*ck me. I don’t have it in me to start thinking about outerwear now and I don’t have the type of rack space to store full outfits that include outerwear anyway. I might just have to wing outerwear and accessories like I always do.

Takeaways from the planning session

1. I understand why Rachel always has a weekly theme for her outfit planning. It’s challenging to just put together random outfits one after the other. 

2. I have a lot of clothes I never wear. This isn’t exactly news to me, but it is surprising that even when planning outfits I pretty much reach for the pieces that I always wear anyway. Clearly one of my outfit planning prompts should be “things I never wear”, but I feel like I’m too much of a rookie to attempt that one yet.

3. Outfit planning takes time. Like, a lot of time, for me anyway. The weather (and the outerwear) situation really complicates my process. 

Monday

I slept poorly so I’m really tired but glad that I have picked out my clothes beforehand. The weather forecast got it right: it’s a beautiful, sunny day, 11 degrees Celcius (low 50s Fahrenheit). It looks like the snow is melting rapidly, but because I intend to walk on the nature trails rather than sidewalks, there might be snow on the ground. I decide to take a calculated risk and wear sneakers. If I run into snow, I’ll just take a detour. I wear my navy vintage Anne Klein wool gabardine coat, I pick a fun alpaca beanie because it’s windy and I have sensitive ears, and add a big silk scarf, a pair of leather gloves and a 1970s eel skin handbag. 

Monday’s clothes.

I like the way the outfit feels on. It’s nothing fancy or super special, but I am comfortable and I won’t look completely out of place in the suburbs wearing this. I ask my husband to take a quick photo as we’re heading out, and when I look at the photo later, it doesn’t look as good as I think it should. The snow is gone by the time I go outside and wearing the sneakers turns out to be a good choice. This means that I don’t have to wear snow boots this week! The outfit serves me well and I’m pleased. So far, so good!

Tuesday

My work week is off to a terrible start. I have an insomnia-induced panic attack in the wee hours of the morning followed by a migraine. I’m in no condition to go to work and I stay at home all day in my pyjamas. I feel bad for my potential outfits that don’t get worn today.

Wednesday

I’m feeling really bloated in the morning and even though I had planned to wear the tulle outfit, I decide to skip it because it feels too complicated to wear today. I go for the other black and white outfit – elastic waist for the win! I get dressed quickly, and for outerwear I pick the same Anne Klein wool gabardine coat. (In fact I will pick the same coat every day this week. I don’t change my handbag either.) I’m happy with how the clothes look and feel on me. At work I take a mirror selfie of the outfit but the clothes don’t look like much in the picture. I start analyzing what I could have done differently, and not in a creative, fun way. I’m judging myself and my outfit. I wonder whether outfit pictures in general are distorting our sense of self and the connection we have with our clothes. Maybe it’s just me.

Wednesday's clothes.

Thursday

I had another rough night and as I’m getting ready for work I’ve been awake for 24 hours. I’m beyond grateful that I don’t have to think about what to wear. I look very tired so I think I need to wear some color. I pick the outfit that I hadn’t tried on while planning: the sheer Dries turtleneck, Yohji shirt and Dries jeans with a vintage Mulberry belt and vintage work boots. It’s a perfectly okay outfit and I feel comfortable. The whole day is just a blur though.

Thursday’s clothes.

Friday

I finally have a good night’s sleep. The weather is sunny and beautiful (high of 15 degrees Celcius, high 50s Fahrenheit) and it’s my WFH day. I go for a walk with my husband, and I wear the most outdoorsy outfit that’s available: the Dries khaki trousers, Miyake Cauliflower top and brown work boots.

I can’t get over how much I love these boots: the heel counter hugs the back of my foot like beautifully worn-in ice skates would. When we think of comfortable shoes we often think of sneakers, but well crafted leather shoes can actually feel so much better, like second skin.

We swing by a thrift store and I find a woven, black vintage Mulberry belt for 1 euro. It’s the perfect belt that I didn’t know I needed. At home I go through my belts. I have so many belts that don’t make any sense for my style or size anymore, so I cull seven belts out of my existing wardrobe and welcome the Mulberry. I know that rectangle belt buckles are fashionable at the moment but I am a big fan of rounder buckles myself.

On left, thrifted Mulberry belt. On right, Friday's clothes.

Saturday

I’ve thought about the tulle outfit all week, and today I decide to wear it. I’m wondering if I’m excited about it because I’m wearing a new piece (the tulle), or if my enthusiasm is linked to experimentation and creativity. I don’t really play with my clothes the way I used to.

I’m disappointed that no one says anything about my outfit during the work day. I think it’s different and interesting, and I was expecting a comment or two, but apart from a couple of double takes, I get nothing. Later in the day I look at the mirror selfie I took at work, trying to decide if the outfit looked like a costume after all. I’m also wondering why I wanted to be noticed in it so badly. Typically I’m quite comfortable just existing in my clothes, but there are days when I want my clothes to be seen by others.  

Saturday’s clothes.

In the evening I gather together all five outfit pictures I have from the week. I’m somewhat removed from taking outfit pictures regularly these days and I feel self-conscious about the ones I’ve taken. Are these good, or even decent, outfits? What do they say about me? Why is there a discrepancy between how the pictures look and how I felt in the clothes? I go back to my thoughts from Wednesday. Our outfit pictures are staged moments in time rather than us living, breathing and moving within our clothes. They’re not the whole truth.

Final takeaways from outfit planning

1. Outfit planning felt like a lifesaver this week. Getting dressed was so easy and stress-free. The weather didn’t complicate things nearly as much as I thought it would, and neither did my body issues. I had plenty of options to choose from every day of the week.

2. It takes time to wear your clothes. Life takes time. When you choose one outfit, you’re also choosing to not wear anything else that you own. If you keep buying new things, you’re giving yourself less time to wear the clothes that you already love.

3. I haven’t thought about shopping this week, but it might just be because I was tired and had very little brain activity. I didn’t have any major cravings though, and even during the nights when I was awake, I didn’t go browsing online shops like I sometimes do. 

4. I could definitely see outfit planning encouraging me to wear things I don’t get much wear out of. I have a ton of accessories in particular that I never wear. Planning outfits in even greater detail could be a game changer and I am curious.

5. I’m excited to plan next week’s outfits.