I’m participating in a trend, this week, my friends. The baggy pants trend. As I said in my May vlog, “Styling a Maybe Jacket,” I have finally found a pair of wide-leg dress pants that I like. And which, I think, do not look terrible on me.

Usually wide-leg, baggy pants do me NO favours. Just ask my friend Liz. She will concur. Over the many years of our acquaintance, in her job as personal shopper at Holt Renfrew and more recently at Nordstrom, poor Liz has seen me try on more pairs of pants that you’ve had hot dinners, as they say.

I am short-waisted, with a flat bum, and a wide waist, and an abdominal region that I would rather hide than feature. Usually wide-leg, trousers make me look heavier than I am, emphasizing my large waist and short body. And they cover up my best feature, my long legs. Women with small waists look fabulous in them. Me. Not so much.

Still, each time they come back in style, I always start my shopping with high hopes and positive feelings about baggy pants. And these hopes usually plummet once I try on said pants. Then I go back to slim, narrow pants which suit me better.

This spring I found myself really, really wanting to find a pair of wide-leg dress pants. I wanted to change up things in my closet. To get away from slim, cropped pants like my Rag and Bone Simone pants. To find trousers that would update my wardrobe, and offer a respite from skinny jeans and narrow pants. Don’t get me wrong, I don’t want to abandon my Rag and Bone pants; I still love them. I just want the option of a different silhouette when I’m getting dressed.

Leaning against the house in black tee, black sweater around my shoulders, and black hoop earrings.
I’m channeling Katherine Hepburn today.

I was spurred on by the fact that the old Theory black dress pants I hauled out during my closet switch-over, and which I doubted would fit me, didn’t even come close. Let’s just say that button and buttonhole were never going to meet again. So I consigned them to the donate pile and started my on-line search. I looked in a lot of places. And I was on one site after another for days, looking at styles and size charts, reading reviews. Then I’d check my measurements, look at my Pinterest inspiration board for ideas, then click back to the shopping sites. Finally I ordered the “Effortless Pant” from Aritzia in a size 12. At least one size up from what I have always worn. As I said in my vlog, I figured that if age (i.e. sixty-five) is just a number, size is just a number too.

When the pants came, I loved the colour. I tried them on, and they fit around the waist; they are even a bit loose, which I think is not a bad thing. However, they don’t fit me like they fit the model on the website. My pants are clearly bigger on me. “Maybe I should have ordered the 10?” I thought. So I tried pinning the fabric to see what they would look like if they were taken in at the hips, in the back etc. But each time I did that, they looked like every other time I’ve ever tried on dress pants and decided against them. They fit in the hips and rear end, but were too tight around my middle. So I tried styling them just as they are. With the exception of pinning up the hem because they are really long.

Standing on the deck, flower pots in the background, wearing tan Aritzia pants, striped Theory tee, white crochet sweater and Eric Javits straw tote.
Look #1

I tried the pants first with my gold and cream striped Theory tee shirt, tucked in, with a brown belt, and my brown flat sandals. Then I added my Theory crochet sweater around my shoulders and my Eric Javits straw tote. I like this outfit, okay. But something’s a bit off. Maybe a lovely chestnut sweater tied around my neck would be better. But I don’t own such a thing. And in looking at this photo again, I think the bright white cotton tank top I’ve just ordered from Everlane might look better with this combo rather than the striped Theory tee shirt. I think that a snug tee shirt would look better with the more voluminous trousers. And the bright white better with the cream sweater.

Sitting on my deck wearing tan Aritzia pants, white Theory blazer, white Vince tee, and white Stan Smith sneakers.
Look #2

Then I tried my Vince sleeveless, muscle tee (similar) with my Theory white blazer (similar) and my vintage ivory cuff. I half-tucked the tee shirt because it looks best if it’s a bit slouchy, and I left off the belt. The loose tee works here with the casual jacket and the sleeves pushed up. But not with the sandals. My white Stan Smith sneakers (similar) are much better. They balance out the more slouchy tee and jacket on top. I love this look. I love the crisp white with the tan pants. Like vanilla and butterscotch ripple ice cream. Even my hair looks vanilla with a few butterscotch strands. Ha.

On my deck with the tree behind me, wearing tan Aritzia pants, white Theory blazer, white Vince tee, and white Stan Smith sneakers.
I still need to hem these things.

The next look paired my black, short-sleeve Vince tee shirt with my old Helmut Lang collarless blazer, Michael Kors flat black sandals, and my black Mackage cross-body bag (similar). I changed up my gold jewellry for silver: hoop earrings, watch, and my vintage silver chain bracelet. And I added a narrow black belt. You can’t tell in this shot because my hands are in my pockets, but the longer, slim jacket looks really good with the loose pants. This is Hubby’s choice of all the outfits. And would be a good, somewhat dressy, going out to dinner outfit, I think.

On my deck wearing Aritzia baggy pants, Helmut Lang jacket, Vince tee, and Mackage cross-body bag.
Look #3. This is Hubby’s favourite outfit.

Finally, my last outfit consisted of swapping out the Helmut Lang jacket for my black Everlane cashmere sweater, tied around my shoulders. I love this sweater; it’s just the right weight for summer. I traded my earrings for these big black hoops I bought in Paris, and swapped the leather bag for my straw tote. This is my favourite of all the looks. It’s trendy but still classic. Polished but still casual and comfortable. I’d wear this for a patio dinner with a friend and feel fabulous.

On my deck wearing Aritzia baggy pants, Everlane cashmere sweater, Vince tee, and Eric Javits straw tote.
Look #4. This is my favourite.

I know that some of the looks might benefit from a different belt or sandals. Or bag. Or whatever. But I have to work with what I have, people. When my try-on session was done, and all my good clothes were hung up or folded neatly in drawers, and I was back in my shorts on the deck with my book, I was pleased. A morning well spent in my opinion.

So what have I learned from my baggy pants try-on session? Well, that I can find a pair of baggy pants I like if I look hard enough. That all along I should have tried pants with a much higher waist. And maybe gone up a size. I think the really high waist is what allows the pants to skim over my problem area, instead of emphasize it. That I should have listened to Liz years ago when she tried to tell me this. That after looking at so many videos on the YouTube channels of fashionistas whose style I like, my eye has changed. And baggy pants which channel Katherine Hepburn look current and chic to me now. See here if you don’t agree.

And maybe most importantly, I learned that I don’t have to look as slim as I did in my twenties, or even my forties, to look good. The baggy pants make me look a bit portly. But I am a bit portly. And if I don’t want to wear long full tops and skinny jeans for the rest of my life, I’d better get used to it. I look like my mum, and my aunt Gywneth, and my cousins, and like every other Sullivan woman I know. And like my grandfather, I might add. Long legs and short bodies. That’s us.

Everything is a journey. Even fashion, and what we wear, and will or will not wear. And the learning never stops. Learning about ourselves. Learning to love ourselves… as they say in Bridget Jones’ Diary… just as we are. 🙂

On my deck wearing Aritzia baggy pants, Everlane cashmere sweater, Vince tee, and Eric Javits straw tote.
Now… where’s the closest patio?

Now, it’s your turn to wade into the pants issue, people. Not necessarily my pants. But your own. Let’s talk about you. Any looks that you’d love to be able to wear but have always steered away from? How has your own eye changed over the years? Are you wearing things you thought you’d never wear?

P.S. This post contains affiliate links. If you make a purchase after clicking my link I will make a commission.

P.P.S. A word about the affiliate links I use in my posts. I try to find links to the exact piece I am wearing. But many of the pieces I wear in my posts are from seasons past and are not available anymore. So I try to find something comparable, something similar to what I am wearing. And I wanted to let you know that I spend quite a bit of time trying to find pieces that are as close as I can get, and which I’d look at buying myself, if I didn’t already own something similar. That goes for the pieces in the product widgets as well.

Not all links in my posts are affiliate links. For instance, the collective I belong to, which allows me to make a commission if you buy something, does not have a “relationship” with every brand.

Anyhoo. I just wanted to make all that clear. In case it wasn’t. 🙂


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52 thoughts on “Baggy Pants Try-on Session”

  1. Thanks for this. I too am long-legged and short-waisted. YOu give me hope that I could possibly wear wide-legged pants too! BTW, you look chic in these, and NOT portly at all.

  2. May I ask what color are the Aritzia pants? The ones on the website look much more golden brown. Yours look more taupe brown. I love the color of yours. I do wonder if I can wear something like this as I am only 5’5 and have lots of middle to “skim over”!

  3. I have a short waist as well, and at 5’3″ and a bit, I obviously don’t have your long legs to compensate — I do have shapely legs, though, and there’s no question that wide-legged pants can obscure them. BUT despite those drawbacks, I can’t resist the attitude they represent to/for me, whether it’s the very classic Katherine Hepburn vibe (Oh, I SO regret letting go of a pair of cream, fine-wool, pleated pants, Simon Chang, I think, sometime in the early 90s (as IF that button would still meet that buttonhole even if I’d kept them!). Or, more often, a wide linen pant anywhere from gaucho to palazzo to Haute Hippie to French Riviera (oh, I guess that might be the same as Haute Hippie ;-). I don’t think they flatter my figure, but I like to think they let my style and personality shine. And if even that isn’t true, well, they make me smile. That same contented little smile you’re wearing in those last two photos. Your outfit-trying time was well spent. I think you’ve nailed it!

    1. I’m not sure that flattering is what the vibe is this season. Loose, louche, droopy, baggy… not not necessarily flattering. Still, I’d like my pants to fit me on the butt and hips but I don’t see being able to alter them without spoiling the advantages they have now.

  4. I’ve been wearing baggier trousers for a few years now . I’m 5ft 5 & long waisted , which means short legs of course & much as I love the Hepburn tucked in look I can’t do that . This is what I’ve learnt for me . As ever it’s all about the cut & I’m best in elasticated tops ( I know ! ) with not a lot of fabric at the top . Then loose legs that don’t flare at the bottom & even narrow ever so slightly . My first buys were dark but I’ve got braver & don’t mind lighter ones now . My favourites are heavy chino types by Toast & they do nice cords but I have some light summery ones from Gap that I wear a lot too . Often rolling up the cuff . Now the tops . I’m heavier than you & more busty so I don’t tuck in , much as I like the look on others & it’s great on you . I try find tops that stop two or three inches below my waist & flare out slightly . Neatly cut sweatshirts or blouses seem to look best on me but I’ve found a few fine wool jumpers too . Then I’ll wear a longer loose jacket which cuts the horizontal waistline . I like these tops with a pleated skirt too .It’s a slightly different look to yours but feels right for me . Frances describes it well , it’s an attitude thing , your clothes reflecting your personality . Plus I don’t have your long legs & never did look that good in skinnies .
    You look great in your new pants & that colour is very versatile. I have some in a slightly paler taupe colour & like them with leaf green or soft mauve but black , white or navy is excellent . Where I must disagree is to say not portly . Just a different silhouette & the long legs are still there , making us all jealous .

    1. The shorter tops that skim just below the hips like you describe are a great way to wear baggy trousers. One reason I like my new pants is that they don’t flare. They are more or less straight-leg. So at least sandals can be seen.

  5. I think looks 3 and 4 are spot on. Wide pants require little else and definitely no fuss. Being short, always struggled with my wide-trouser love but back in the late 80s I found some I loved, the only trouble was my huge chest so I felt completely out of proportion. Like you, these days I care less and have come to accept my small waist is gone forever as I age (hormones) and you just have to look harder.

  6. I love your new silhouette – the higher waist really does work for you. All that trial and error was worth it! I think I’m with hubby – I love #3 the best, although all of them work for me.

    This has me intrigued for when I eventually go clothes shopping again. I’m on a bit of a weight loss journey (my daily walks and a very healthy Portuguese diet are working wonders!), and it will be fun to try on a different silhouette when I hit my goal.

  7. I like both combinations,with black and white as well. You are glowing,so happy…

    I have long legs,too and have wear wide trousers long ago,linen wide trousers maybe a couple of years more recently-best styled simple with fitted top. Nowdays it is out of question (fitted tops :))

    My best choices were slim or straight trousers or jeans,but a couple of years ago,I started to wear wide trousers and jeans again-styling is more difficult now, tops couldn’t be neither wide nor very fitted (but fitted enough). Right now I’m wearing wide silk navy pants with half-tuck linen navy t-shirt,f.e.(or with t-shirts or blouses in  other colours: green,white,polka dots)……it would be great with a linen blazer,but….too hot during the day,rain or even showers in the evening almost every day. Complicated,no?

  8. You look great in the “winner” outfit. I think for me I’m still not ready to make the leap to wide-legged pants. I’m sure, knowing myself, that I’ll cozy up to the idea and find some I like just about the time they’re “OUT” in the fashion world. Haha.

  9. I must say I find it difficult to pick a favorite look with these pants, I like all the looks you have chosen. With gorgeous legs like you have, this is a great look for a change of pace. I too have a pretty much non existant bum but a pooch at the front, so find it difficult to get a good fit, which is why I end up feeling so much better in skirts most of the time. I think I will have to go searching for the high waisted style, but will have to try on in person as on line has not worked for me lately at all. I will just give up on that. With stores reopening slowly now I wonder if the change rooms are open? I will give it a few weeks. I am just eager to try a patio experience for now.

    1. The reason on-line worked for me this time is I was only worrying about the waist fitting. Plus I looked for pants that had a somewhat slimmer line, not huge wide bottoms or anything. Then I had the contents of my closet to try with them when they arrived. In store, I’d only have what I’d be wearing. Or whatever tops were on the rack. So there are downsides with both ways, IMO.

    1. I just added a link to the post, Trish. I didn’t originally because my sandals are years old. But I see that Michael Kors is still selling almost the exact same sandal.

  10. Your husband has a good eye, I like his pick the best. I admire your patience in on-line shopping and coming out with a winner. Have a fabulous time when you finally get to wear your new outfit out.

  11. It sounds like we have a very similar body shape, maybe the Irish genes 🙂 I look much better in slim or straight pants. Last year my hubby found me a pair of Papaya coloured heavy cotton high waisted wide leg pants in the charity shop on deep discount. Made in Italy, so the cut is excellent. He bought them for me and they fit just right. I wore them with flat black leather Indian sandals last summer and loved them. Cannot wait to wear them this summer.

  12. You look great in your baggy pants! Baggy pants are my comfort zone. 3 years ago I tried slim pants, convinced that they would look horrible on me. Surprise, they looked right, to my eye. But they have to be ankle length.
    Not related to pants but to hair: yesterday I went swimming, first time in 20 months. When I bought my ticket, masked up, sunglasses on, the cashier asked me if I qualified for the OAP reduction. When I answered not yet, she said “but you have grey hair!”. Well, that taught me that 2021 is not really far from 1950, that I look older than I feel, no surprise here, and that my buzz cut needed some attention. Good lesson and even better swim!

    1. I agree that slim leg pants are more flattering cut at the ankle. Sometimes I have to have mine let down because they hit me too high on my calf and look like pedal-pushers. Ha.
      P.S. I can’t believe the nerve of that attendant.

  13. I love the last three looks, especially.

    I have the OPPOSITE body. Long torso – I told the woman who made my (second) wedding dress that I was freakishly long-waisted, and she measured me and said, in astonishment, “YOU ARE!” – and short legs. Small(ish) waist and wide hips. I tell people I was made for dropping babies in the fields, like the good peasant stock from which I sprung, but joke’s on my ancestors – didn’t have any!

    1. I have an old friend who likes to say she is from “good peasant stock.” I love that. Me too, actually. Irish potato farmers. Ha.

  14. I love all the looks but think 3 and 4 are the better combinations. The wider leg and higher waist look very slimming.
    I still have a few pairs from their last round of the fashion cycle but suspect the waistlines might be a bit of a problem now. As my four year old grandson proclaimed recently “Granny you have a wobbly tummy”! Out of the mouths of babes… I still love him.

  15. Even when I weighed 103 lb, many years ago, I did not have a small waist. I’ve shrunk over the years from 5’5″ to 5’2″, and am therefore even more short waisted than in the past. My legs are very long, and look even longer than they used to look.
    So what to do? For the past year or so, I’ve been wearing almost exclusively straight leg jeans with a mid rise. Of course, I’ve hardly gone out during this time due to the pandemic, and certainly nowhere dressy. The thing is, I love the way these jeans fit. Believe it or not, I bought 6 pairs.
    I’ve also ordered several pairs of fuller pants with pleats and returned all of them. I’ve never found pants with pleats at the waist that make me look anything but fat in the middle (though I’m not really fat) and even more short waisted than usual. I feel like I’m running out of options for wearing trendy pants. Now I’m going to try some Eileen Fisher cropped pants which are fitted around the waist and hips, and which are straight from there down. EF is noted for cutting clothes for women with less than perfect bodies, so we will see what happens. If that doesn’t work, I will continue to wear my skinny or slim pants.
    After way too much thought, I’ve decided looking good is more important than looking trendy… when all else fails.

    1. Me neither, Cathy. When I was 120lb in my twenties I didn’t have a waist. As long as the pleats lay flat I can handle a pleated pant. Or I used to be able to Ha. You are right about EF. And sometimes it’s just something mysterious (or mysterious to me anyway) in a cut that will work.

  16. Best accessory for these high waisted pants? An excellent bra! For shorties like me the distance from waist to chest is decreased which can give the old man vibe ( you know the old guy who wears suspenders and a belt?) a good bra jacks me up creating a little distance so I don’t look like a fire hydrant. I cannot with a waist band higher than my natural waist. At 5’1” and on the hefty side I’ll give this style a hard no. They look great on the tall and long legged but not for me. I need the long over lean look and I can’t stand all the material flapping around my legs though your pants are more straight up and down and appear to have less fabric. There are fewer and fewer true petite options out there and pants like yours in a regular cut will have a higher rise which would land them under my bust! I love the taupe and black on you, always a classic combination!

    1. Yep. You are correct. Uplifting is very important for us short-waisted women. My new pants are more of a straight leg, so not too bad with respect to flapping material.

  17. The pants look wonderful. All the combinations are great, but I love the black combinations the best. Wider pants, with a slimmer top is so elegant. So, I’ve added these pants to my summer wish list. I love the 1940’s vibe. The dress of that era was simple but sophisticated. Sweater sets are something that have been catching my eye as well. Styled with intention they are quite stunning.

  18. Looking good,esp the last two. YOu’ve nailed the Hepburn look. Enjoyed the article and slide show.Always fun to see how others looked in day of yore! The slacks are a great color and should go into fall as well. Not too sure when you have fall. We do for about 2 days after Christmas, then we get winter. But this year is going to be different.! get rid of those Covid pounds,clean closets, everything ready for a big bang new start with 2023! Hope you have a wonderful summer. How long does yours last?

    1. Our summer starts in June and begins to wane in mid to late September. Then October is beautiful fall, and November cool and rainy fall. Usually. But nothing seems to be usual anymore these days. Now that you mention it, I can see those pants with my black cashmere sweater and my black boots for fall.

  19. I’m with Stu, #3 is my favourite look on you Sue. I noticed the ‘Effortless pant’ from Aritzia also comes in a cropped option. The colours are more limited but I would give them a try. For me, this is a pant I would want to go into the store and try on. Hopefully, I can do that soon! Thanks for all the research you did on wide pants Sue.

    1. Good luck with the trying on. One thing that Aritzia does that I have not taken advantage of yet, is they will order a bunch of pieces for you and have them delivered to the store; you go and try them on and buy what you want. I was shopping for my sister one day and a sales assistant suggested that they could do this. I thought it was a great idea. Partly because they rarely have all the styles and sizes in one store.

      1. That is a great feature for Aritzia that I wasn’t aware of Sue. I have found the same thing, not all styles or sizes in their stores. Thanks for passing this along!

  20. No matter what, I really think that baggy trousers, as you call them, are really the embodiment of elegance and chic, a la Katherine Hepburn which I really admire.
    And, most importantly, You do look good with these trousers, really.
    I am short waisted with long legs and I am very petite (under 5 feet, 150 cm) but i never ever liked the slim, short and low waist trousers that we had to bear for so long: for me, this were created by men with pot belly and not by women.
    I hated having to wear some, unable to tuck my shirts properly in and looking, to me, very frumpy because of that.
    So imagine my delight when, 2 years ago I think high waist trousers were, at lng last, back but, most importantly, trousers like those worn by Katherine Hepburn, my style icone. I don’t car if I am petite, I like wearing large legs trousers with tailored waist.
    I like best the last and second look on you, the sneakers do help to make the trousers look more “modern”.
    If you have some and like them, you could even try them with oxfords or even loafers.
    Go go for the “baggy ” trousers, they do suit you.

    1. Low waist trousers or jeans are a no go for me too. I can’t keep them up. I was happy when I started seeing high waisted jeans a couple of years ago.

  21. I’m decidedly in the minority, as I like the first outfit. Love that tone on tone look. Maybe it’s because I really don’t look my best in either white or black. You, however, certainly do, and I agree the black top with the trousers is very chic on you.
    I haven’t tried trousers like these in years. They were once my favorite cut, back when I had a 24″ waist. Waaaaay back. And while I don’t weigh an enormous amount more now, the “redistribution” has certainly been a shock. Thanks to you and others on this journey over the proverbial hill, I’m inspired to try them again!

  22. Love the last two looks. The darker color goes well with the pants, which look great on you. I think that the high waist really suits you.

    I love wide leg pants. Baggy doesn’t work too well for me, because I am a bit heavier and baggy just feels even larger. However, wide legs usually work. I’m tall enough to pull it off.

    Enjoy going out in your new clothes!

  23. Gee Whiz!! You look great in those pants! I love black with taupe, tan, beige. Adding the 3rd piece (jacket or sweater) completes the outfit. Your outfits look so polished!
    I had a similar experience, decades ago, with walking shorts. High waisted, pleated in the front, and worn with a coordinated camp shirt (both in black linen) worked in Southern California for a nice going-out outfit.
    What’s interesting is “where” one defines the waist. Michelle Obama wore many defining belts higher than most, in my opinion, to great success.
    I think your research time really paid off. Thank you for bringing us along!
    P/S I followed your lead on ordering an Everlane cashmere crewneck on sale. (Thank you!) I ordered two different sizes in black to find the best fit. To my surprise, the cashmere was very different for each sweater. One was soft and cushy; the other was labeled cashmere but felt rough and not like cashmere at all. Luckily, the soft, cushy one fit me best. Just an FYI…

    1. Good to know about the Everlane cashmere. I wonder if one was older stock and they changed their product in the meantime. Odd, isn’t it?

  24. Nice looks. Really like the first one with the wide belt. Being tall of average portions, I have always liked and worn wide leg pants, especially in the summer, usually in a striped linen. As my middle has also gotten wider (how did that happen), I find I still can pull off the wider leg as long as I skip ones with pleats which seem to highlight the feature I’m trying so hard to hide!

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