Hubby is away canoeing and fishing this week, my friends, and I have been on my own. Much as I love my husband, I do cherish my alone time. So, yep, this week I have been on my own, on the loose, in loose shirts. Ha. Or one loose shirt anyway. I’ve been making a concerted effort to style my Nordstrom Signature oversized blue and white shirt in a few different ways.

Wearing a loose, oversized shirt untucked and hanging loose is quite freeing, you know. It is so very comfortable. It’s so very on trend. And it can look great.

For years and years I was all about a neat, tailored look. But since COVID, since my hair has been white, I don’t feel that a tidy (almost lady-like) look represents who I am anymore. Partly this is because of fashion’s changing silhouette. Partly I have been influenced by my favourite influencers. Women whose loose and casual style I admire, and who seem to wear their clothes so easily, so lightly, if that makes any sense. But this change has also been wrought by who I am now. Not the person I was in 2013 when I retired, or even the same woman I was three or four years ago.

So for the past while I have been endeavouring to update my style and embrace the loose. Last summer when my beloved skinny leather pants wore out, I replaced them with ones that are wider through the hip and leg. I purchased a new pair of baggy trousers from Aritzia last spring. I bought a pair of loose-cut men’s Levis last fall. And this spring an oversized sweater from COS and a quite voluminous striped top also from COS. Not all the looks I have tried are keepers. Because, like with all change, some negotiation has been required, some experimenting, and a lot of trial and error.

My Tomboy pose.

I’ve worn my new striped oversized shirt with my Stan Smith sneakers and white Frame straight-leg jeans a few times so far. You can see that look in this post. But this past week it’s been cool-ish for early June. And rainy off and on. So when I went into the village to run errands the other day, I wore my oversized shirt with Frame straight-leg jeans, my old Stuart Weitzman loafers, and a white Vince tee under my shirt. I threw my big COS sweater around my shoulders. Then just in case it rained again, I rolled up my raincoat and popped it into my big Michael Kors tote bag.

I like this look. The shirt is long, but not too long. Loose, but not overwhelming so. The sweater is long and oversized enough that I can pull it on over the loose shirt if I get cool. I wasn’t sure about the gold tote bag with the blue and white. But I thought this outfit needed a bag with some strong colour. And I wanted somewhere to stuff my coat, and even my sweater if the weather warmed up. I love this old tote bag, and I don’t use it enough.

Frame jeans, COS sweater, Vince tee, SW loafers, and MK tote.

The next look I tried is my favourite. I wore the oversized shirt with the trousers from my Max Mara suit, my white Stan Smith sneakers, and a navy, Vince V-neck sweater around my shoulders. I left the bottom couple of buttons open on the shirt so it didn’t look like a tunic. The sweater around my neck in this outfit will stay around my neck, as an accessory. The light cashmere of the sweater is too light to pull on over the heavier shirt.

With Max Mara trousers, Vince sweater, and Stan Smith sneakers.

I love this outfit. In flapping shirt and flowing pants, I am happily embracing looseness.

I was joined on the deck for my fashion shoot by Cinnamon, our next-door neighbour’s cat. As you can see, he is very friendly. And if pats are not forthcoming forthwith he flops down in front of me and rolls over. Hubby and I are very fond of him.

“Now don’t get anymore hair on my pants, please.”
“Okay, okay, one pat.”

Later, after I had brushed the cat hair off my pants, I changed and headed into town to pick up supplies for my little get-together the next night. When Hubby goes away I always have the “girls from work” over for a barbeque. Despite being driven inside from the deck by threatening rain and mosquitoes the size of small birds, we had a great evening of good food and wine and much hilarity. But that’s a story for another post. Back to loose shirts.

This time around, I’m wearing my Vince tee again, and my new-ish Levis bought last fall. The loose straight-leg of the jeans looks great with sneakers and loose shirts.

Nordstrom shirt, Vince tee, Levis 511 jeans, Stan Smith sneakers.

So here’s the thing about loose shirts. Besides being comfortable, on trend, and easy to style. They can go from casual-slouchy, to casual with smart elements, to quite smart… without much effort.

I will say that you have to be careful when you buy loose shirts to get the right length and the right amount of looseness for your frame. You don’t want to drown in your shirt. And in my opinion loose, oversized shirts look best tucked in if you wear them under a jacket. Especially if that jacket is not oversized as well. I have several summer blazers, and the shirt left untucked hangs below the hem of all of them. Not a good look in my opinion. I will have to leave the loose shirt over a tee under a long blazer until I actually own a long enough blazer. Perhaps I’ll try that look in the fall.

Off to pick up wine and cupcakes.

So that’s me for this week folks. I’ve been on the loose in loose shirts for the past few days. Trying to increase my loose, louch quotient, so to speak. Trying to change up what I wear to reflect how I feel at this time in my life. To make sure my outfits say what I want them to say about my white-haired, almost ten years retired, newly turned sixty-six, somewhat bookish but maybe a teensy bit bad-assed identity. Ha.

How about you, my friends? Have you tried the oversized, loose look in shirts? What’s your verdict? It is a look for you or not?

P.S. If you want to shop for the pieces I’m wearing in this post, or for similar items, I’ve included all the links below.

Outfit#1: Frame straight-leg jeans. Nordstrom Signature oversized cotton shirt (on sale.) Here is the link for the shirt on the Canadian Nordstrom site. A used version of my Michael Kors tote here at The Real Real. Similar sweater from COS. Vince tee shirt. My black, patent Stuart Weitzman loafers are from 2014, but here’s a similar, chunkier pair. Outfit#2: Nordstrom Signature oversized shirt. Vince V-neck cashmere sweater. My Max Mara pants are very old, but here is a similar pair in navy. Stan Smith Adidas. My Michael Kors white cross-body bag is old. But here’s a similar DKNY bag at Macy’s that I like.

P.P.S. All 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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39 thoughts on “In Loose Shirts”

  1. You wear that striped loose shirt so well! Your favourite look here is mine as well and I also really like the combo with the gold bag. I must admit to being somewhat envious because any times that I’ve tried to wear a loose shirt myself, I almost always abandon the effort — in deference to my (lack of) height. My short-waistedness doesn’t help, either. It’s just too easy to get swamped. But you really rock this! And I think the looser styling suits your retired (but not retiring!) personality very well! It’s fun to have the space for her Style Personality to switch it up a bit when we’re not dressing for work anymore, isn’t it?!

    1. Totally agree with Frances. And appreciate your helpful descriptions about proportion and creating a look that is clearly styled, but looks like a bookish bad-ass with white hair simply threw it together.
      Another blogger I used to follow seems to have strayed into the territory of t-shirt or sweater and jeans with added expensive accessories, but unlike you, there’s no “thoughtful style” to differentiate the look as a step up from the one I wear out to weed the garden or tidy the garage. Just sayin’.

    2. Thanks, Frances. The other two are outfits I would wear, but the shirt with my navy dress pants is the most current, and a new way for me to wear a loose shirt. Shirt length and wearer height definitely have to be coordinated, don’t they? Not to mention volume. I think shorter women need shirts with less volume to avoid being swallowed by their shirt.

  2. I’m a shirt fan too , the necklines are so flattering . My favourite is your favourite & I agree even though it’s loose , the fit is crucial . An inch or two longer & it would be in tunic territory . I look awful in those . I bought a loose shirt in Scotland about eighteen months ago then thought it was a mistake but couldn’t take it back . It’s grown on me now & looks even better with the bottom buttons left unfastened ( thanks for the idea ) I do wear mine with a jacket but only a longer casual one , sometimes unfastened with a T shirt underneath . When layers go out of fashion people will wonder why we wore all our clothes at once 😁
    PS I love your new accessory 🐈

  3. You are loose in loose shirts in the wilderness! Now that my friend speaks of adventure! I am like Francis above…short in stature and short waisted. I have tried the loose shirt look only to look like a bolt of cloth swallowed me. I was frustrated and hung it back in the closet. I need to give it another go. I have been watching a number of ‘how to tuck/tie your shirt in666 moves’ on instagram and pinterest. I may try to earn a scout badge and take on the task. I do love a loose dress in summer and have been wearing those nonstop. They are cool and one and done in the mornings. You are right…try new things, express who you are through your clothes and give it a shot!

  4. I love loose, yet crisp, shirts!
    Alas, I too am height challenged, but I do have longer legs, which helps.
    Now to the all-important question in my mind this morning: what is the best length for a loose shirt? And secondly, is the length measured from the hem of the shirt or from the length of the cut-in of the shirt-tail?
    A bit of help on this, if you can, would bring some pretty cool loose shirts back out of my closet.
    PS. We live in Florida, so all this is probably going to have to be deferred until fall for me, but I love it so much I’m anxious to plan ahead!

    1. I think the current loose shirts should fall about mid to upper-thigh. But that depends on the length of your legs. But you say your legs are long, so you should be okay. Those of us with short upper bodies and long legs can wear loose shirts really well in my opinion. I assess the length as seen from the front, so the hem of the shirt. I have had shirts hemmed before to make sure they are the right length if I want to wear them untucked.

  5. Your work as an influencer is done. I ordered the same shirt from Nordstrom. Unfortunately, your link took me to the American site, not the Canadian one. Did I do something incorrectly? I would certainly like to give you the small commission through your affiliate link. I love all these looks on you, this style suits you to a tee…or should I say, an oversized shirt!

    1. Cosette, I just added a link to the Nordstrom Canadian site at the bottom of the post. 🙂 I didn’t know the links were only going to the American site.

  6. I hear you about all the style changes after retirement. You look so good in your white and navy shirt
    It was one of my favourite pieces,I still remember my first one striped (tailored) shirt,worn with navy skirts and trousers
    Lately,I wear my oversized shirts mostly open,over t-shirs,sometimes tie-front. Tucked in,even half-tuck,there is a lot of loose material .
    Dottoressa

  7. Timely post Sue! I have a looser shirt on its way to me this week. I have never been huge on shirt collars but found one with a small stand up collar which I think will work for me. My only concern is if I should have sized up.

    I loved seeing how you styled your shirt. It has given me a few ideas so can’t wait to experiment with mine!

    Have a great week!

    1. I had thought I would need to size up, but since the shirt is intended to be an oversized style, I went with a Medium and it is perfect. It fits in the shoulders and sleeves and is still loose in the body. Good luck with your new shirt. 🙂

  8. Sisterhood of the loose shirts! I wore a loose shirt over a tank and capri running tights for a fun walk (local beach highway closed to traffic for a few hours) today. My shirt is a little longer and looser (I think I bought it as a bathing suit cover-up), but it’s a very lightweight handkerchief cotton, which balances out the length. A heavier fabric would have looked too tunic-like, I think. But it does put me in mind of something more like yours, and I *still* haven’t been to the COS store in Lisbon, so that’s in my future.

    1. I didn’t want my shirt to look too much like a tunic either. I still haven’t been to our nearest COS store in Montreal. I’d planned to go with a friend next month on a shopping weekend but that’s been cancelled. (:

  9. I love your message in this post. I am not the same person I was even a year ago. It’s very easy to slip into a routine of overthinking and over accessorizing our personal style. You can style an oversized shirt without looking sloppy. For me, it’s the total picture. No more heavy eye liner or lip liner. A hair style that will move in a breeze. Quite often, I will quickly remove an accessory because it felt distracting rather than attractive.
    You let your personality sparkle through your style choices.

    1. I’ve totally stopped with heavy eyeliner too. And any time I’ve tried to wear more jewellery or accessories I have to take them off.. it’s just not me.

  10. Being bad a#@ and short a#@ and wide a#@ has its challenges! Have to be careful with the volume or I end up in Ina Gartner/ Coastal Grandma territory. I stick with the tunic over leggings look or striped T (3/4 sleeves please) over slim-ish ankle pants. Its long over slim or short over a teeny bit bulkier for my shape! I do wear my Jean jacket over tunics or long shirts and leggings and it rocks. Nevah, nevah do I wear loafers, wing tips etc. with my size 9 foot with a 5’1” body we are talking Charlie Chaplin!! BTW it doesn’t take a lot of $$or € or£ to dress well. A woman in Costco commented on my navy ankle pants and boat neck navy striped T. I led her over to wear Mr.Costco had displayed(haha) the garments. Pink Tartan T in several colours 9.98 (reduced) and the pants were 15.98 can’t remember who made them but excellent quality. I talked her into two T’s and two pants and she talked me into another T and another pair of pants.
    Sue you look swell in your stuff…did you ever think about ditching teaching and going into modelling? ?? I mean ‘legs for days’ there:)
    BTW good on you two for building times of separation into your relationship!! Wished my husband fished or golfed…
    He travelled so much during his working life he thinks it his duty to remain glued to my side.LOL

    1. Ha. Your comment made me chuckle. If I’m shopping on my own I often end up in discussion with another woman who is also shopping on her own. I love doing that. I’m sure Mr.Costco approved. 😉

  11. We could be twins, at least so far as the way we dress is concerned! I love loose shirts. Over the past two or so years, I’ve collected 9 of them. That may sound ridiculous, but I wear them nearly every day in the summer. I’m short (5’2″), short waisted, and have ridiculously long legs. Most shirts are much too long on me, but I finally discovered LL Bean petites. They are just right.
    These shirts can be worn over a tee or not, partly buttoned, always with the sleeves rolled up. I love them with slightly loose jeans and pants, but I really need some more loose pants.
    I’m also thinking about a silk or even satin shirt with a thin cashmere shell or sweater and loose wool pants for fall… if I could ever find all the pieces.
    Thanks for another terrific post!

    1. Petites are a gift to women with short upper bodies, aren’t they? I remember convincing my mum to try a jacket in a petite style. But because she was tall, she never thought to look there. With her short upper body, the jacket was perfect.

    2. Hi Cathy, I’ve discovered petite shirts as well. I’m 5’4 and short waisted. One thing, I will often size up because I have broad shoulders and long arms.

  12. Another loose shirt fan here. I wear them often in the summer as a third piece over a tank or tee, especially going into places with AC on full blast.
    You look great in yours and I really like the pop of colour with the tote. However my favourite look is with the navy trousers and sneakers. Very classy and classic.

  13. Big time loose shirt fan Sue and I have several, both long and short sleeved with a variety of lengths. The longer tunic style, I wear with skinny jeans or cigarette pants and the shorter version, I wear with straight leg jeans, joggers and cargo pants. I find a collared loose shirt adds a bit of a tailored look that is unfussy and never feel the need to add a blazer or cardigan. I love to pop the collar sometimes too. Enjoy your the rest of your “alone” time Sue!

  14. I’m a fan of the loose relaxed style. It’s perfect for the summer heat but keeps you warm in the air conditioning. My favorite is the shirt and the Max Mara trousers.

  15. I like a loose shirt too. They are so comfortable and it is easy to wear them buttoned, open over a tee shirt or tank top. I’m going to try the trick with the bottom buttons left undone.
    I particularly like the yellow tote with your outfit. I’d scrolled down to see it before I read what you said about it. I immediately loved the pop of color. I think that is my favorite of all of your outfits, but you wear that shirt well! You look great in all of those outfits.
    I like wearing a loose shirt for plane trips (not that I’ve been on one of those in a good long time). I wear a tee – long or short under it and then I can take the top shirt off when warm and throw it back on when cold. It works with jeans or leggings (a little longer with leggings) for travel.

  16. Loose shirts are definitely up my street. I cannot bear being restricted by tailored shirts. But I think there can be a fine line between just wearing a loose shirt and going coastal-gran style – for me, a no-no. And double loose can make you look very…odd. I managed to nail it this week when I needed something pale and loose and to stop my legs being bitten by insects. Rolling up the bottoms of my biscuit coloured trousers suddenly made all the difference.

    1. I agree… coastal granny style is a risk. Ha. Btw I’m reading your comment as I scratch bug bites. The mosquitoes are big and bloodthirsty and so numerous this year. 🙁

  17. I just stumbled on your blog today and subscribed. Your styling for the blue and white shirt is very helpful. I have a new AYR blue and white shirt and love it. However, I’ve only worn it this summer tucked into jeans. Your ideas will help me this fall and winter here
    in southwest Florida

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