Are You Wearing Shorts This Summer?

Are you wearing shorts this summer? I don’t mean when you’re pottering around in your garden, lolling on the deck with a book, or going for your daily walk. I mean in the city, window shopping downtown, or meeting a (fully vaccinated) friend for a patio lunch. You know, when you’re out in public. Where other people might see you. When you step back out into public view this summer, will it be in a pair of shorts?

Lately, I’ve been reading Elizabeth Cline’s book The Conscious Closet. It’s a fabulous book. I’m really enjoying it. Did you know that we wear less than fifty percent of what is hanging in our closets? Way less than fifty percent, actually. But that’s a discussion for another post. I plan to do a vlog and then a couple of follow up posts based on my reading of Cline’s book. But for the moment, I am focusing on shorts. I want to see if my city shorts can become part of the percentage of my closet that I actually wear. Should I wear them for one more season? Or should I consign them to the donate pile? I’m waffling.

In a  black pair of Bermuda shorts, black Everlane cashmere sweater, and cream sandals surrounded by flowers on our deck.
Too much leg?

This is not a post seeking advice about whether I’m too old to wear shorts. I wrote that post in 2019. I asked myself that question. And decided to wear the shorts. This is not a post about whether my legs are too skinny and my knees too knobby to look good in shorts. Or if these particular shorts would look better with this or that piece which I don’t own. I don’t want to go shopping to be able to wear my shorts. A summery dress would possibly be more appropriate. And cooler. But this is not that post either.

Nope. This post is about me trying to cobble together a couple or three outfits that I can reach for, which include my black Theory shorts. Outfits that I’d actually wear downtown, or out for lunch, or wherever I may be able to go in the next month or two.

So. To that end. Yesterday, I donned my black Theory tailored Bermuda shorts. I’ve been fond of this style of shorts for years and years. I like tailored shorts. But they have to be fairly slim in cut, quite long in the leg, and quite high in the rise. Mine are cut like men’s trousers, with a zipper and belt loops and pockets. They are in great shape despite their age, and they still fit me. But usually when I could be reaching for these shorts, I instead pull on my Rag and Bone black cropped Simone pants, or my black cotton cargo pants.

First, I tried my shorts with a new black tank that I recently ordered from Everlane. Last summer I purchased a red tank top from Everlane and loved it. I like the high-neck, cut-away style. The soft cotton is quite thick, not sheer, and the shirt is fitted but not clingy. And the price is right. Everlane have a special (3 tees for $63 CAD) so I ordered three new tanks, black, white, and navy and white striped. Since my summer jackets are black, tan, white, and navy, these tops will go with everything I own. And provide a nice change from my short-sleeve tees.

I really like the tank top with the shorts. Instead of going black and white for this outfit, I wore my brown belt, brown flat sandals, gold jewellery, and my tan linen Max Mara jacket. This outfit pleased me a lot. The jacket is old, but the long, slightly menswear inspired cut makes the shorts look current. I felt comfortable, and pulled together, especially with the addition of the belt. I tried my small black Mackage cross-body bag with this, but preferred my “peanut” coloured straw Eric Javits tote.

Next I tried the white tank with the shorts, white sneakers, and my white Theory jacket. That looked fine too. Bit too stark, though. Besides, I have lots of other outfits to wear with my white jacket. My white sneakers, white tank, with a black H&M hoodie over the tank looked good. This outfit would be great for car journeys. Like down to New Brunswick in August. Hopefully. Fingers crossed.

The last outfit I tried was really simple, and possibly my favourite. The black shorts with my black Everlane cashmere crew-neck sweater. The sweater is just loose enough and just fitted enough to look casual and at the same time polished. I added silver earrings and necklaces and a black and silver cuff. And I slipped on my Michael Kors cream sandals (similar). These have a small block-heel, and can dress up a really casual outfit just that tiniest bit. Or enough for me, anyway. I’d wear this out to a patio dinner. Perhaps with the black tank underneath so I could take off the sweater if I chose. I’d carry my black and cream Kate Spade bag.

It’s amazing how much nicer this outfit looks with the cream sandals instead of black ones. And the structured bag. How simple it is to up the ante just a little bit, but not so much as to look like one is trying too hard to up the ante. If you follow me.

In a  black pair of Bermuda shorts, black Everlane cashmere sweater, and cream sandals surrounded by flowers on our deck.
I like this outfit. Except for the visible bug bites from our camping adventure.

So I think my shorts try-on session worked well. I wasn’t able to use most of the photos I took yesterday because the camera on my phone is acting up. The cloudy day and the shifting light patterns didn’t help. Still the lens worked well enough to show off the bug bites from our camping week, and the bruised knee from an errant tent pole. Sigh. Hubby and I had a serious conversation about the whole camping thing when we were away. Whether all the work of packing, setting up, taking down, and unpacking when we get home is worth the trouble. Not to mention the rain and the bugs. But I’ll talk about that in another post.

We are home now. A profusion of newly bloomed primroses in our flower beds greeted us with a cheery welcome home when we drove in the laneway a couple of days ago. Everything has been unpacked and put away. And the vegetable garden seen to. The potato plants have all been tied up, with help from the non-gardener. Most of the laundry is done. And Hubby just returned from grocery shopping to restock the larder. My mum had her second shot yesterday and called this morning to say how good she feels. So all is well in our little corner of the world.

Plus I have three new tank tops that didn’t cost the earth and which I really like. And a plan to rehabilitate my old Theory shorts.

You know, I just looked in my “little book of lists.” I bought those Theory shorts in 2007. They don’t owe me anything, that’s for sure. And they are safe from the donation pile for one more season anyway. I am no longer waffling. At least about how to wear my shorts in public. But you can be sure that there’s lots of waffling potential in other parts of my life. Otherwise what would I have to write about, my friends?

Now, if you doubt that classic styles keep on keeping on… Theory still sells tailored Bermuda shorts just like mine. You can see the pinstriped version on the Theory website here. And on sale at Nordstrom in the product widget below. I included a few other examples of longer-style shorts that I like as well. The tan Columbia pair with the drawstring waist would be good for travel, I think.

So tell us… where do you stand on the shorts issue? Not my shorts, necessarily, just shorts in general. Are you a city shorts kind of person. Or as far as you’re concerned are they strictly for exercise and lolling? When you venture into public this summer, will you be wearing shorts?


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62 thoughts on “Are You Wearing Shorts This Summer?”

  1. I definitely wear shorts (I’m wearing them right now!) to run errands in town and go to the farmers’ market. But to go into the city (for me, NYC) or out to dinner? Nope. Your outfits look great, but I just don’t see shorts as part of a polished outfit for me.

  2. Nope, just not a “city” shorts person. Maybe I spent too many years camping, golfing, and hiking in shorts to rid myself of the “sporty” vibe? Or maybe it’s my short legs/long torso which makes me wrinkle my nose at the proportions created by a “city” short on my body? Or perhaps it is the memory of my friend’s father wearing a suit jacket and tie with his Bermuda shorts and dark knee-high socks which seared onto my brain when I spend time with her family who lived just outside Hamilton? This prairie girl really had to work hard to not stare…

    But those are my hang ups so, if you are happy with your shorts, then non-waffling about these outfits is exactly the right stance. And I’ll mute my own issues so I can enjoy your pleasure in your rocking your “city” shorts.

  3. I have thrown caution to the wind and am wearing shorts to loll around the house-deck- patio and out amongst the general population. I have also…big gulp….worn sleeveless tops with them. I turn 65 on July 4th and probably have spent the better part of my life hating one or more parts of my body. I’m tired of waging war with myself. I don’t seem to scare small children or animals so I’m throwing caution to the wind this summer and declaring myself free.

  4. I’m 77, live in NYC, and of course I’m wearing shorts this summer. I wear them around the house and out in the neighborhood to run errands, but those are all casual shorts. I also wear dressier, tailored Bermuda shorts with a tank or shirt and a blazer out to a restaurant. My legs are not perfect, but they never were. I think they look more than just OK, and they suit my casual style. I also love long tailored shorts in the winter with opaque tights and boots. I don’t think age has much to do with it as long as you are in reasonably good shape.

    1. I agree, Cathy. It’s all about what makes you feel good, and comfortable in your own skin. Age has nothing to do with it. Dressy shorts are on trend this year, so go for it.

  5. I have never been a shorts person because I don’t find them comfortable or cool enough when it is really hot and humid in Sydney. I prefer a dress or skirt for home, casual and more dressy occasions.

  6. Wendy from York

    In a word , no . I’m not sure why not as I was always told I had great legs & I loved my mini skirts in the olden days . Even on hot holidays I preferred a wafty skirt . I’m not sure I could define my style but it has never included shorts . I could say we don’t have the weather for them except youngsters here wear the shortest of shorts even when it’s chilly . I don’t see anyone in tailored shorts ever . We called them Bermudas & they don’t seem to have travelled to Yorkshire ?
    I’m glad your mum is sorted . You must be very relieved .
    PS we are away in Wales at the moment where there are hiking shorts around

  7. I wear shorts only at the gym or when walking for exercise, because when it is hot enough to need them, a lightweight skirt is cooler. In my city, I’m seeing a lot of slightly shorter, flared, high-waisted shorts with a tucked-in blouses or tees.

    1. I’ve been seeing shorts on IG and YouTube. Those shorter more flared versions you mention. And I’m hoping to see them on someone in person soon. I haven’t been downtown since last July and I am so looking forward to it.

  8. IF I were to wear shorts in hot weather, they would need to be wide legged and wafty. I remember those slim fitting Bermuda shorts with a belt and tucked-in top being very warm and the opposite of casual.

  9. I have several pairs of shorts and occasionally wear them around home, camping, and to play golf. I’m not adverse to wearing them downtown in our small town to pick up groceries and the mail, but for a trip to the city or dinner out I’d probably choose a pair of capris instead.

  10. While I like the look, it’s never been comfortable for me, even in my younger years. I wear shorts around the house, to the grocery story and other errands, but if I am out, I am more likely to wear pants, possibly cropped, or a skirt or dress.

  11. Nope, shorts are too hot. Even in my garden, casual walks, lolling in my deck I wear a casual dress. Skorts for hiking or bike riding. Could never understand the appeal of shorts since they can be so hot and confining….although I can see the appeal in Canada or upper Midwest or mountains of the U.S.

    1. Tailored shorts can be confining in real heat. I remember Hubby and I bought lightweight, quick-dry pants for our first trip to a hot country.

  12. Thanks to your recommendation, I have also read Elizabeth Cline’s books on sustainable fashion. I have enjoyed and learned from your posts on that topic and I look forward to more of your thoughts on this.
    In spite of my untannable and aged legs, I do just love the feel of BARE LEGS in the summer. We have such a short time to do this here in the Great White North. I’ve decided to make them look the best I can so I can enjoy this feeling. Shorts, dresses, I’m in!

    1. I agree. There is so little time to get the legs out in Canada. I’m looking forward to wearing shorts and skirts with bare legs. Pasty-looking though they may be. Ha.

  13. I wear shorts, but usually I go for capris/cropped pants when I go somewhere. This week I bought 3 pair of skorts on the Amazon Prime Day sale (I know, fast fashion/not sustainable) and my husband hates them. I said that if I hadn’t told him that they had shorts underneath, he’d just think they were skirts. But I like them. They feel a little more dressy than the shorts I have. And admittedly, I only have one pair of shorts I’d wear out in public. I think I need more.

  14. I stopped wearing shorts several years ago. I prefer capri length or cropped. Personally, I feel more dressed when going out & about, than I would in shorts. But, you have lovely slim legs, so go for it!

  15. Not a shorts wearer ever! I’m trying to achieve a year round wardrobe so I always prefer pants. I think I’d feel very naked if my lower legs weren’t covered, although I have been known to wear pants that reveal my ankles! You look great in your shorts however, but I don’t think you’ll persuade me.

  16. Big yes from me on both shorts and sleeveless tops (not necessarily together)! I’m 67 and newly retired, and have, this year, removed both of these items from my “not at my age” list! I recently purchased the darker color of the Columbia shorts you featured, specifically for a trip to some US national parks in September, although I’m wearing now for walking or playing Pickleball. I’ve also purchased 3 pair of tailored, Bermuda length shorts from Talbots. With ‘nicer than T-shirts’ top, I’m comfortable wearing these out and about for day spent with friends (we’re vaccinated and in South Carolina, most social distancing restrictions have been removed). I’d also wear out for a casual dinner with some sort of jacket.

  17. You look lovely,Sue! Completely city approved,here as well!
    I don’t like to wear shorts,last time I’ve wear them in the city was in 1995.,but I like to see them,especially in this elegant version
    I have/had no problem with wearing skirts above the knee(or bikini f.e.-I like to see one piece swimsuit on others ,it could be very elegant and/or practical,but bikini is much easier to wear,for me!)- so,it is sort of personal preference .

  18. You look fabulous in your shorts, especially the last photo. I don’t own any shorts, can’t remember the last time I actually did. I do have a couple of skorts, but I mainly wear cropped pants. Would love to have more summer dresses, but finding them to fit and that I like is a chore. Hope you get to have a patio dinner out soon.

  19. I wear skorts. They are so much more attractive on me than shorts, as I’ve matured. I grew up and still live at the beach it’s a great way to still look good while enjoying an outdoor life. You look wonderful in the shorts you chose, btw. The perfect choice for a more formal summer style.
    So happy summer is here!

  20. My shorts have moved to just below the knee so I guess that could be moved out of the shorts catagory and into the ‘pedal pushers’ area. My mother wore shorts that were much too short well into her 80’s and I just can’t do it myself with dodgy knees. I wear these around home, but still much prefer to wear a skirt any chance I get when going out. I really like the look of the lighter sandals with all the options you have shown us. You do look great with your long legs in the city shorts.

  21. I wear shorts but if I was going into the city for a lunch (patio) or shopping (remember those days?) I would wear a casual dress or cropped pants. I just feel more chic and pulled together if I can wear a dress.

    You look great in those Theory shorts. Adding a jacket or third piece really pulls the outfit together .

    This is a great post by the way. You help me re-think my closet.

  22. I live in Southern California and shorts are huge in the summer. I confess I don’t wear them out for lunch or shopping only because I have age spots that probably bother me more than anyone else who bothered to notice a 71-year-old redhead. Sunbathing in my teens was a big mistake but it was always fun. My dermatologist refuses to shame me by saying you have memory spots. Haha.
    You look fabulous in your Theory shorts.

  23. I’m a shorts girl from way back. Cotton drill ones for camping and tramping and linen ones for around home. I do wear them to local shops but would switch to a dress or 7/8th pants to wear into the city or out for dinner.
    Mind you with an Antarctic blast forecast for this week it will be fleecy trackpants and thick jumpers for me down in NZ.

    1. I so envy you living where you do. So many wonderful things to do and all so much closer than in Canada. I think we drove from the beaches in the north to the glacier down south in a day.

  24. Hi Sue 😊 so pleased to hear that your mum
    is fully vaccinated but best of all that she seems to be managing and happy to be home again! Especially great news, as going into hospital and then being discharged home again in her 90’s and living alone is a massive achievement. ( as I’m sure you’re aware, with all the planning etc needed) What a strong lady she is! I bet the days just can’t pass quickly enough until your visit … I’m imagining you both watching the new Persuasion film together when it’s released!
    Now onto shorts! I can’t say that I’ve ever ever felt particularly good in them … maybe in my late teens 🤔 but in the last few years I’ve started wearing ones similar to yours when we’re travelling as they’re so practical. They can also look smart with the right top, etc. I’ve never actually worn a jacket with mine but I do wear a denim or chambray shirt open sometimes over a white, navy or striped tee ( again white and navy lol)
    You look really great in yours, especially with your cashmere sweater … definitely my favourite outfit here. Whereas I have a tendency to look “dumpy” in mine lol
    My thoughts on capris are the same as yours but I do love a slightly above the ankle trouser. I don’t have any skirts at the moment but I’m definitely wearing dresses more when it’s warm.
    Have a good week Sue…
    Rosie xxx

    1. I love an ankle trouser too. It’s the most chic length, I think. So happy to see you and your “girls” in Bath on IG. What a wonderful weekend you had.

  25. i dont have the legs for shorts any more unfortunately although i will wear them to the beach – you on the other hand have great legs for shorts.
    in australia in summer shorts can often feel too hot and a dress is much cooler anyway so i dont miss them

    1. I can imagine that anything too restricting like shorts with a tailored waistband would be too hot for your summers. I’d be wearing light dresses too.

  26. I am currently on the Central California coastline for an all-girls trip with sisters and their daughters (I had sons), and our 94 year old mother who is still sharp as a tack and has a great appetite for good food and shopping (aided by a walker). We are all fully vaccinated and very thankful to have this five day getaway. We have not been together in over two years. Hoping your August visit to your mother works out.
    I am seventy-two, and years ago, adopted a funny mantra from my younger sister about shorts and sleeveless tops. “Let’s just stay tanned! Maybe we won’t look so wobbly!” Mind you, we are NOT sunbathers. Our regular activities such as gardening and walking (even with sunscreen) add color to our medium skin tones. In the Sierras, where we like to fish and hike, I wear sun-protection clothing. A wide-brimmed hat (w/sun-protection qualities) is de rigueur for our outdoor activities.
    I really like all your shorts outfits! To me, they are so dressy and fit into the Southern California vibe where I live. Yes, I do wear casual and dressier Bermuda/walking shorts. I enjoy the outdoor, active look. I may just have to look at the Everlane tanks you mentioned. Thanks for the link!

    1. What a wonderful trip that sounds, Charlene. I wish I could convince my mum to take a trip with me. I’m not a sunbather either. I don’t even like lying on a beach. The only time I’ve been tanned is when Hubby and I used to golf, or from our canoeing or biking adventures. Hope you like the Everlane tanks. I’m enjoying mine. But I will say that the blue and white striped one is more like cream and navy, than bright white.

  27. Wow! A topic that has really drawn a lot of comments! You look great as always, very stylish. I’ve stuck to longer length , Bermuda style shorts for a few years now, but decided to buy some that hit mid-thigh this summer and I like the way thy look. I’m short, and showing more leg actually makes me look a bit taller I think. A reward for all my barre classes and walking. Not the legs I had when I was younger but good enough to go back to shorter shorts. Her gens tanning cream has helped get rid of that pasty white skin that we all sport when winter finally ends. It’s subtle and never streaks.

    1. None of us has the legs we had when we were younger. Good enough is good enough for me too. I totally get the thing about shorter shorts. Bet they look great on you. 🙂

  28. I have never forgotten this: in the train, a young woman getting in wearing tailored bermudas in burgundy with the matching jacket and black low pumps (not pointy toe mind you).
    And she was oh so elegant and chic and different from all the jeans and hoodies wearer, women included.
    It was in the nineties…
    Your bermuda shorts are very elegant, just the right length, width and colour. And you wear them well. Maybe add a … scarf (You know the french and the scarf everywhere…) or a brooch on the lapel of your jacket, nothing too big if you’re not into it.
    Black allows you to use a huge range of colours as a top including bright ones, pale ones…
    I do not wear shorts outside, only at home when it’s very hot. Not even in the beach because it is so difficult to find the right size and fit for my frame. And in no way would I be seen wearing those very short shorts in fraying jeans. Don’t care of my age, it”s a question of personal taste.

  29. The outfits are wonderful. I’ve always admired the dressier short outfit. Living in the southeastern part of the U.S. you wear wear what you can to stay cool. I’ve stopped listening to all the you shouldn’t wear naysayers. I wear what looks best on me. When out and about I don’t wear shorts, never really have. I do wear sleeveless linen dresses and just recently bought a sarongish skirt which looks better than it sounds.

  30. You look great in those shorts and you have dressed them up so smartly. Perfect for wearing out.

    I wear shorts every day in the summer. I wouldn’t opt to wear them for going out to dinner or an evening gathering. I’d go for a dress, skirt or some sort of pant that felt a little dressier (even linen).

    I do prefer the length a little longer now that I am older.

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