I noticed this past week when we were in Quebec that I was in need of some therapy. Some clothes therapy. A little dreaming of outfits I could wear if I were going somewhere. Anywhere. I think this necessity arose because I was either in my comfy sweats or my ski gear for seven full days while we were away. And the week before that, we skied twice, and I cleaned one day, blogged one day, and packed on another day. The only day that week when I was not in sweats or ski gear was the day I left the house to pick up stuff for our trip. And that was the day after our big snowstorm. Thus I was swaddled to the eyeballs in hat and scarf, and wearing jeans and my heavy winter boots.

So, while we were away, I began to dream of outfits. I’m serious. I awoke one morning after a dream in which I was back teaching, and found I was thinking, “What should I wear to work this week?” And so as Hubby got up, switched on the kettle, and made tea, I lay snuggled in bed pretending to still be asleep, and happily planning a week’s worth of work outfits. Weird, eh?

planning outfits like this one (Uniqlo jacket, Theory sweater, H&M skirt, Brown's boots) in a little clothes therapy.
H&M skirt, Brown’s boots, Theory sweater, Uniqlo jacket

I’ve long believed in the power of clothes therapy to help me through times of stress or pain. I wrote about that idea in this post back in 2018 when I was laid up much of the summer with a bad case of shingles. I’d been in pain and unable to stand the feel of real clothes on my skin for weeks. And so I consoled myself by dreaming of outfits I would wear when I was able to wear clothes again. The idea of equating clothes with therapy came from Haley Nahman who was, at the time, writing for the now defunct blog Man Repeller. You can read Haley’s original post here.

Haley’s idea was that certain clothes made her feel better. Like her best self. So she called them “therapy clothes.” My idea was that just the thought of favourite clothes, not even the wearing of them, but merely the planning of outfits, can be therapy. Thus “clothes therapy.”

“But wait a minute,” I can hear you saying. “You were on vacation, having a lovely relaxing week in the Laurentians. You weren’t in pain or under stress.” I know. Weird, eh? Not to mention the fact that I haven’t worked as a teacher since January 31, 2013. Tuesday will be the ninth anniversary of my first day of retirement. So why the heck was I planning work outfits?

Vince sweater, H&M faux leather pleated skirt, Stuart Weitzman boots
Vince sweater, Stuart Weitzman boots.

Well, let me explain.

I started scaling down my wardrobe before I retired. For two years before my actual last teaching semester, the only clothes I purchased new were clothes I could wear in my newly retired life. And when I did retire, I did a strict edit of my closet and gave away to young teacher friends anything I knew I’d not be able to wear again. Especially those pieces that were good, and which I felt deserved a new life with someone else.

I kept dressy jackets and sweaters I would wear with jeans. Skirts I could wear with tee shirts and flat sandals. And “just in case” pieces I was unsure about. But I talked about all that years ago in a post called “Sunday Style.” Let’s just say that many pieces no longer lived in my closet if they could not be repurposed in my new more casual, Sunday style, life.

But the other morning while I lay in bed in our condo in the Laurentians, I began to wonder whether or not I have edited my wardrobe too much. Whether or not I have culled into oblivion the possibility of outfit variety. I didn’t really think I had. But lying there several hours drive away from home, and unable to look into my closet, I was unsure. So I began to play a game in my head. I pretended that, for whatever reason, I had to go back to work on Monday. What would I wear? Would I have sufficient clothes to create suitable outfits to see me through a week in the classroom without repeating an outfit.

As I said above, I lay there in bed happily thinking through my closet, and deciding what I would wear to work. If I had to go to work. I’d feel great, I thought, wearing my faux leather skirt with boots and a sweater. I could swap out the high boots for ankle boots and change up the sweater for a different outfit. See the first two photos above.

Same with my black Theory leggings, below. I could wear them with ankle boots, my burgundy cashmere turtleneck, down vest and my old Alfred Sung blazer. I might leave off the vest with this outfit. And on another day, I could wear the leggings with the same sweater, my vest, and my high boots.

Of course I’d feel great standing in front of my classes in my knee-length sweater dress from Aritzia, with black tights and ankle boots.

Aritzia turtleneck dress, Cole Haan ankle boots
Aritzia dress, Cole Haan boots

I’d also feel comfortable in my burgundy boot-cut jeans from NYDJ, a long-sleeve matching tee, and a hoodie and scarf. On casual Friday I’d wear my jeans, a white tee, a blazer, and my green hoodie around my neck. I could haul out the old Max Mara black blazer to wear with my black leggings, boots and a cream turtleneck. Actually this outfit would work with almost any sweater under the jacket.

My longer sweater dress I might save for a day when I wanted to look a bit more smart. Parent-teacher interviews, maybe. A committee meeting at the board-office. Maybe P.D. Day? I still remember back when we used to get dressed up for the board-wide P.D. Day. And the last couple of years I worked I presented with my friend Krista on P.D. Day, and I’d want to look comfortable but smart for that. Not that I’d be attending any of these activities if I were really going back to work this year. Pandemic school being something completely different from what I experienced.

Aritzia midi-sweater-dress, AllSaints bag, Aritzia down coat, Brown's boots
Aritzia dress, Brown’s boots, Aritzia down coat, AllSaints bag

Would I dare wear leather pants to work? I would now, my friends. With a white tee, a long vintage Max Mara jacket and a matching sweater, I’d feel conservative but still edgy. The purple sweater and pants I’d save for a night out with colleagues. I have to confess that these are my old faux-leather pants. But with my new ones, even though the style is slightly different, the idea is the same.

So yeah. I’d definitely have enough clothes to see me through a week, or even two, of “work” without repeating exactly the same outfit. My little mental exercise was wonderful clothes therapy.

Now, back to the reason I was in need of clothes therapy at all. Firstly, I was feeling a bit outfit deprived. I had not worn anything but sweat pants or ski gear for most of two weeks. Although I loved our week away, we usually eat out at least once when we are at Lac Morency. Both of us love the old dining room at the inn there. We get dressed up a bit, and walk through the snow from our condo. The food is always lovely. And we enjoy the chats we have with the waiters about the food and the wine and winter life in the Laurentians. Last time we were there, in the bar while we waited for our table, we had a really interesting conversation with a bunch of mining engineers from around the world who were in Quebec for their annual company meeting.

But this year Covid restrictions prevented that. The restaurant was closed. And as I said, I wore comfy sweats around the condo, and ski gear everywhere else. It’s amazing how even one night of dressing up and going out can make a difference. But when going out is not an option, planning outfits for going out can help.

And part of the reason for the outfit dreaming was to reassure myself that I could still conjure up some outfit variety. Prove to myself that I had not culled my wardrobe too far. And to see if I still had enough clothes for something other than errand running. Like, say, for work. I was kind of relieved to see that despite the much smaller size of my wardrobe these days, there’s still plenty of variety to be had. I don’t own “business-casual” clothing like I used to wear. Those days are long gone. But I’d be happy to wear any of the outfits in this post to a job. If I had a job. Which I don’t.

Which brings me to my last point. The fact that though I have just planned, with the aid of photos from previous posts, a week of work outfits, I don’t actually have to GO to work. That brings me as much pleasure as the idea that I haven’t edited my closet down to boring basics and nothing else. Now that’s what I call beneficial clothes therapy, my friends.

Of course none of these outfits was originally planned with the idea of work in mind. My style has actually changed quite a bit since I retired. At first I wore mostly jeans and jackets, jeans and sweaters, or jeans and tees. In the past couple of years I have begun to add pieces back into my closet that are a bit more, if not exactly dressy, then a bit beyond jeans and a sweater. And perhaps smarter than I thought I’d need in retirement. I think the advent of wearing sneakers and chunky boots with dresses and skirts has inspired me. It’s so easy to make an outfit more casual with this kind of footwear. No more lady-like pumps and delicate ballet flats for me. Not at the moment, anyway. I’m wearing skirts and pant suits with sneakers, and dresses with ankle boots.

And in my current, happily retired, white-haired state, I find I am more comfortable wearing outfits that are more “out there” than I ever did when I was still working. And that thought pleases me no end.

So how about you my friends? Are you outfit dreaming this winter? Maybe you have witnessed a change in your style in the past few years. Do tell us. We’re all ears, you know.

I’ve created a product widget below of some of the pieces I refer to in the post, if you’re interested. Many of the items I wear are old, so I tried to find something as similar as I could.

P.S. The clothing links in this post are affiliate links. If you make a purchase after clicking my link, I will earn a commission which helps to pay for the blog.

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38 thoughts on “In Need of Some Clothes Therapy”

  1. Hi Sue 😊
    I imagine you were quite surprised to realise you had so many classroom / work appropriate outfits in your collection. You look really great in them all! Your knitted dresses are especially versatile ( haven’t said that in a while😆 ) as I’m finding with my own.
    Over the years, I haven’t really made lists of my clothes or outfits other than holiday planning lists or maybe planning an outfit for a special occasion but thanks to you I’m starting to and finding it so helpful!
    The other day I was thinking ahead to a family wedding in Ibiza, later this year. An event which almost “begs” for a completely new wardrobe lol 😉 It’s extra special as we’re really close to the bride and groom and they’ve had to reschedule twice due to Covid.
    Anyway, I decided to look at what I already had that may be Ibiza and wedding appropriate and I was so so surprised and really happy to realise that like you, I had far more than I realised!
    So yay for lists! 🎉 … and you and your blog. 💕 … thank you Sue!
    Rosie xxx

    1. You have some wonderful pieces in your wardrobe, Rosie. I’ll bet you have whatever you need for the wedding. And because it’s been such a long time since any of us have been to an “event” it will all feel like new. 🙂

  2. Your posts are always thought provoking. I particularly enjoyed this one because I’m planning to retire in the next two years. The “Covid interlude” has enabled me to telework 2 days a week from my position In University administration- something I’ve been calling “practice retirement”. I can already see that there needs to be an intentional reckoning regarding my wardrobe going forward! Thanks for jumpstarting my discernment!

    1. I scaled down to only a morning schedule my last semester and my husband called it my practice retirement too. When I finally retired I got rid of anything that was too obviously business wear. Except suits that could be worn with a tee shirt and sneakers.

  3. Really good to know that I am not the only one who chooses to fake sleep in order to maintain a train of thought. When we thought we were going on a week long getaway in February that we planned in October when the outlook was very promising, I hauled out my rolling rack and started the exciting search for what to wear. Now, let it be said, I am not a light packer and have never gone with just a carry on. Well, I started with skirts for outings and evening meals, then what tops would work for what eventuality. Next on to dresses and palazzo pants for a more dressed look, jeans ( white) or shorts for weather changes, well, you get the idea. It was such fun to add or subtract from the rack as the weeks went by and even down to plotting the accessories that would be ” needed”. Then….. well, when the new year rolled around and the news was not looking good for travel, we had to make the decision on what to do. That was taken care of when the travel agent said it would not be happening. My head knew it was the right thing, but my heart was shattered, I had dreamed and planned and now I had to take down the rack and put everything back. Now, I guess I will wait to try again for next fall and keep fingers crossed that travel is once again in my future, and that means more outfit dreaming. I do love to play in my closet.

    1. I am so jealous, Diana. I would love to have a rolling rack. But we have such a small house there’s no where to put it. I’m keeping my fingers crossed that you get to go on your trip next time.

  4. I love your dream dressing. Before Christmas I kept thinking I would really love a new winter dress in a dark green. Kept thinking the world would heal and there would be a Christmas dance to wear before mentioned dress. Well, maybe next year. Now I have a year to look/shop for my dream dress. Until then, keep well all.

  5. I still have closets and drawers with clothing that have not seen the light of day in a year since my retirement. I gave away or donated a large amount of clothing right after and stalled then. I need to revisit that. I have started to put together a week or two of daily outfits and have them hung with accessories on my rail. Depending on mood or activities for the day I have ready made choices and I feel pulled together. Playing in my closet reminds me not to buy anything new…but to use what I have and enjoy it. I loved the initial rush of freedom that retirement brought me in terms of clothing choices. But the novelty is wearing sometimes. I always enjoyed being pulled together. I’ve found that I’m not a jeans or sweat pant girl everyday. Throughly enjoyed the post today! So relatable.

  6. I remember when it was great fun to get ‘ dressed up ‘ . Occasions like parties & meals out meant dresses , often full length with fancy shoes , little evening bags & jewellry . I don’t miss that but I do miss wearing good coats , especially good wool coats . Towns are a sea of puffas & parkas now . Yes I have those & they are very practical but wool coats can be beautiful . So I try ‘ dress down ‘ my nice wool coats . As you say footwear makes such a difference plus a more casual bag helps . Jeans & a chunky polo neck jumper drags it down nicely . Heaven forbid I should look overdressed ! It’s like walking a tightrope at times 🤪

    1. I love a great cloth coat as well. But I’ve not worn any of mine for at least two years. Like you, I don’t miss deciding what to wear to a really fancy dress-up night… not that I attended many of those. But I do miss dressing up a little for a night out.

  7. Margaretanne Clinton

    What do I do ?
    Well , since finding your site , I find the great outfit photos that you put here.
    Go to my closet and pick out similar. ( copy you )
    Then , wait for people to wildly love what I’m wearing. And,they do ! Especially , women my adult daughters age.
    I love your outfit photos. It’s simplified my life.
    Now. I just waiting for the gorgeous white hair. It’s my favorite accessory you have.
    Finally. I send them your blog site as per requested by them.
    Thanks for doing it.

    1. Your comment made me laugh, Margaret Anne. Especially “wait for people to wildly love what I’m wearing.” Thanks for the encouragement that others might get something out of my faffing around in my closet. 🙂

  8. Wonderful fun, clothes therapy! I’m doing the same, preparing for an actual (first ever at 67) trip to Hawaii in March (fingers crossed that Omicron cooperates). Determined not to fret about “bingo arms” and spider veins on ghostly limbs, I plan to go boldly forth in tank tops and shorts.

    1. I completely relate to everything you said, especially the outfit dreaming part. I have 10 years to go for retirement as a high school teacher, and I can attest that outfit planning and what I’m going to wear for the week keeps me motivated. I find clothing to be therapeutic and keeps me from falling into a rut.

      1. Gosh, you are a girl after my own heart, Em. I used to do the same. And sometimes the comments from students about my “cool” outfit just made my day. One girl in grade 11, so she’d have been 16 at the time, came up to me and confided in a whisper one day, that she wanted to dress just like me when she grew up. Ha. I loved that. Not that I didn’t love the other parts of teaching, but, like you, sometimes fashion kept me from despairing too much over the state of things.

  9. You would be the most stylish teacher in the school! I so enjoy your thoughts and photos. Thanks for outfit inspiration.

  10. Dreams are free! Love your “work” outfits. I’ve only been retired three years and haven’t purged my wardrobe completely yet just in case…
    I miss dressing smartly as it is Jean’s or trackpants and jumpers in the winter or shorts and tee shirts in the summer. Covid hasn’t helped as we have either been in lockdown or under restrictions so often in the last two years that outings have been few and far between. We actually went to the movies last week and I was so excited it must have been like Cinderella’s reaction to going to the ball!
    Please keep up the clothes therapy to save the sanity of all of us.

  11. I didn’t need a lot of dressy clothes in the last 10 years of my professional like. Apart from a couple of meetings once a month, work consisted of driving to an office where my colleagues were my husband and two other part-time staff members. Serious professional dressing wasn’t required very often and my wardrobe was “casualised” years ago. What I’ve found more difficult in recent years has been putting together outfits for more formal occasions such as weddings, graduations and the like. I became very stressed about 12 months ago working out what I could wear to a summer wedding and the shoes were as much a problem as the dress. But state border closures solved my problem as attendance became impossible.

    1. That’s one of the reasons I bought those two winter dresses last year. I though if I had a semi-dressy occasion, even a funeral to attend, I’d have nothing appropriate. This year, a nice summer dress is on my wish list.

  12. Love these outfits and photos! You would have nailed it if you were called back to work😁
    I haven’t yet really sorted my retirement wardrobe…still holding on to some things ‘just in case’

    1. I have gradually cleared out most of my “just in case” pile. I have a summer work dress that I still held onto. I can’t bear to get rid of it.

  13. Oh yes Mrs B.,you would be very stylish -in or out of your school😉
    Love your outfits,as always!
    I love to think about my combinations and prepare them in advance,especially now ,when possible goings out are so rare,so decissions are even tougher. I have maxi white wool dress,3 years old,worn maybe three times (because of We-Know-What),all of them to the bank or store….
    Dottoressa

  14. I used to dream of outfits as I ran on the treadmill. It was a great way to pass the time in a boring exercise routine. I haven’t run in years and I haven’t done any outfit dreaming in quite a while. It is good therapy.
    I love the turtleneck sweater with the black skirt. It really suits you. The two sweater dresses are lovely.
    Hopefully you will be able to get dressed up and go out to dinner soon!

    1. Turtlenecks have been my thing since I was a teenager. Not sure the getting dressed up and going out thing will happen for a while. I am staving off my longing by dressing up for the blog. Ha.

  15. Joanne in New Hampshire

    Thank you for another wonderful post. I appreciate the amount of work you put into your blog, all for our entertainment!

  16. Funny you should mention it, but dreaming of putting together outfits to wear for an upcoming trip to the UK helped me to get to sleep the other night. Mentally I selected the couple of pair of trousers to take, then I started to consider a selection of tops that would work in combination with both. By the time I started to drift off, I had almost finalized my selection of scarves and other accessories. Almost ready to pack. Just need to decide on shoes. Outfitting as sleep therapy. 🙂

    1. I do that too. Sometimes I just flip through old memories of outfits from when I was a kid. I hoped you remembered what you’d mentally planned when you woke up. 🙂

  17. Some similarities with me. I am quite sick of wearing super casual clothes and also dream of more put together outfits. It is summer here and the whole city is way more casual after covid. I now only work 1 day a week and I am still trying to get my retirement style confirmed.
    I love all your outfits. You are an inspiration for the way you combine items.

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