Baggy pants are still in style, but skinny jeans are making a comeback.Ted Shaffrey/The Associated Press
On Sept. 19, lifestyle editor Juliette Baxter and senior style editor Haley Steinberg answered reader questions about how to stay stylish in the fall season.
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Readers asked about dressing for the office, the go-to pieces for the season, what’s worth splurging on, and whether skinny jeans are really dethroning the baggy look. Here are some highlights.
Personal style tips
Do you have any tips for dressing nicely for the office? I’m so used to working in sweatpants at home.
Haley Steinberg: I would invest in some classic staples like trousers, button-ups and knit sweaters. Depending on your workplace, something more casual like a tailored jean can also be a great addition, since they pair well with almost anything. Once you have a good foundation of core pieces, you can mix and match. Workwear doesn’t need to feel like a uniform. It’s great to have some neutrals that can be paired with a wide range of pieces, but if you like colour in your non-work life, there’s no reason to avoid colour at work. I like to buy pieces that I genuinely love and want to wear outside of work, too.
Who is the most stylish person at your office? The Globe wants to know
Juliette Baxter: Stay within your comfort zone as you transition back to work style. Start with a loose-fitting dress pant. There are plenty of flow-y pants out right now that have a wider leg in a dress pant fabrics in poly-blends, or men can start with a classic khaki pant. Don’t jump into buying a pair of heels or oxfords with a hard sole that need to be broken in. Invest in a nice pair of sneakers that you use just for work, so they look fresh for as long as possible. A suede ankle boot, for men or women, will also give that extra bit of give for comfort. And instead of a tailored blazer, buy a knit blazer that’s will feel more comfortable while looking polished.
Lifestyle editor Juliette Baxter says stay within your comfort zone as you transition back to work style.miniseries/Getty Images
Do you have any tips for an older person that wants to dress age appropriately, but with some pizazz?
Baxter: Why not try liberating your closet from a neutral palette? For example, if you have a basic black pant, buy a similar style that you know flatters your shape in a fall shade such as forest green or rust. Or trade your wool coat in beige or grey for one in red or leopard print, which can be considered neutrals with punch.
And you can always choose plenty of adventure with accessories, whether that’s experimenting with different eyeglass shapes and colours, statement rings or necklaces. Style icon Iris Apfel often stacked bangles and wore bold eyeglasses. Imagine wearing that with you favourite white shirt, jeans and flats.
Does preparing for a new season always involve buying new clothes? What about looking well put-together using what’s already in your closet?
Steinberg: Fashion is cyclical (just look at all of the ’90s references we’re seeing now), so if you’re interested in dressing on-trend, chances are there are pieces you already own that are back in style. Some examples from this season include plaid, argyle and leather jackets. But you can also look well put-together without following trends at all. There are countless classic items, like a tailored trouser or a well-fitting button-up, that will always look stylish.
Baxter: Never feel stressed to spend more money. Instead, take inventory of what you have and spend some time restyling and retooling what’s in your wardrobe. Also, be sustainable and mend what you have with an artisan touch. We recently sent a writer out to try sashiko mending, which has a visual flourish while sewing up holes. Send sweaters to the dry cleaners, polish shoes, fix straps and fasteners. Like a spring clean-up, think of doing a fall-clean up on your wardrobe. And splurge on a couple of items, if looking seasonal is on your mind. Perhaps it’s a bright argyle sweater for this year, or trading in your baggy jeans for a slimmer style.
What is the item to splurge on this season? And what is a must have item for fall, splurge or no splurge?
Baxter: I like to think about this in terms of items that you can get serious wear out of – a splurge is expensive and you want to wear it for more than one season. Think about a wool or cashmere coat that can stand the test of time (anything from Max Mara comes to mind). Or a designer bag for everyday with no big logos – buy one that focuses more on craftsmanship and longevity. And that can come from a high-end brand like Bottega Veneta or a Canadian brand, like Want Les Essentiels.
Juicy Couture sweat sets and low-rise, bedazzled jeans. Chunky belts and baby tees and miniskirts. Early 2000s fashion is all the rage again. Many millennials might cringe at the Y2K aesthetic, but Generation Z is eating it up.
The Associated Press
Is there anything I can learn from Gen Z fashion styles for my own personal style?
Steinberg: Broadly speaking, Gen Z dressing prioritizes individuality, self-expression and comfort as opposed to just following the latest trends. The rest of us could probably benefit from leaning into that attitude a little bit more. Some practical takeaways are not being afraid to experiment with colour, trying out oversized silhouettes and thinking more about sustainability when it comes to our fashion choices.
Baxter: I think the biggest takeaway is to add colour to your wardrobe. It’s very easy to stick to the basics, when you’re juggling work, carpooling and family get-togethers. Fashion, after all, is a means of personal expression and an instant mood booster. Add a bright, preppy-coded argyle sweater into the mix this season or a faux-leather jacket in chili (think burgundy but brighter), or even a sequined tee for the holiday party season.
Brown seems to be back in a big way this year – I haven’t seen it this prevalent since the mid 1990s. What are some good ways to add brown to one’s wardrobe?
Baxter: Think of brown as a neutral, like beige. So where you would wear a beige or camel sweater, substitute with brown instead. Brown really comes to life in corduroy in the men’s and women’s aisles, whether that’s in a jacket, pants or skirt. If you’re up to it, add texture with chocolate satin, leather, or plaids, for a more conservative play on the trend that you can wear to the office.
Any Canadian recommendations? I am not interested in anything the U.S. brands have to offer.
Baxter: We’ve been working hard to feature Canadian brands to shop for. In this recent summer fashion round-up, many of these brands offer items for every season. And our regular shopping columns by freelance writer Truc Nguyen often highlights Canadian brands. Also check out our Buy Canada guide which offers more Canadian brands beyond your wardrobe.
Luxury brands are not affordable for the majority. They’re fun to look at but difficult to attain. Is there an alternative that’s more relatable?
Baxter: Luxury shopping at its core is focused on fabrications and tailoring. So whether you’re buying your wool sweater from a mall brand or high-end Italian brand, it’s about looking at the fabric label and structural integrity. For example, here’s a good primer on buying the perfect sweater at various price points. I’m hesitant to highlight certain brands, because their integrity doesn’t run the spectrum. For example, they may have great sweaters that season, but their outerwear doesn’t make the cut.
What’s hot in fashion
What’s the biggest trend coming out of New York fashion week?
Steinberg: There are several notable trends coming out of the Spring 2026 collections at New York Fashion Week. Some of the big ones are balloon pants (also known as harem pants), cropped jackets and shrugs, tailored leather, and minimalist fashion with a twist. We covered some of these trends in more detail here.
Senior style editor Haley Steinberg says baggy jeans and shorts are officially back in fashion.Illustration by Gotham/GC Images/Getty Images (J
I’ve seen people out and about wearing baggy jean shorts, are they fashionable again?
Steinberg: Short answer: yes! Longer, looser shorts (particularly in denim) are indeed back–one of many ’90s trends revived by Gen Z.
Will the extra-large legged trousers be around next fall?
Steinberg: It looks that way. Looser, wide-legged trousers popped up in the Spring 2026 collections at New York Fashion Week. At Coach, they were low-slung, belted and so long that they trailed the floor. There’s also the balloon pant (or harem pant) trend, seen at Michael Kors, Brandon Maxwell, Altuzarra and several others.
I read a designer in The Globe say that skinny jeans just make sense. So what was the rationale for wide leg jeans the last few seasons? Did they not make sense?
Baxter: Jeans are a hot topic even among our staff. I think a lot of the confusion about the perfect jeans stems from there being so much choice now. Skinny jeans are making a comeback, but I stand by wearing the pant that’s most comfortable and flattering for your body type, whether that’s wide, skinny or in-between. If you’re faithful to your skinny jeans but craving an update, try a slim cut that doesn’t hug the leg so closely and has a wider opening at the ankle.