I don’t know about you, but where I live, we got hit with a full-blown snowstorm this past weekend. I wasn’t planning to talk about winterwear yet, but here we are, so let’s get into how to dress warm and look good doing it.

I’ve also been thinking a lot about holiday party outfits, mostly how much I hate choosing them for myself but love finding them for my clients. Below, I’ll share a holiday outfit formula and a special offer for a mini digital shopping session with me.

And since this edition comes out on Remembrance Day, it feels right to take a quick pause before we dive in. To reflect, be grateful, and thank those who served.

— Jacqueline, JGYL Styling Founder and Head Stylist

Did a stylish friend forward this to you? Subscribe so you don’t miss the next one.

Send To The Group Chat 💬

Choosing clothes that fit your body type is the foundation of a good outfit. The same goes for your winter coat (the puffy kind, not a peacoat). I get it, it gets really cold in Toronto, so it’s tempting to find the warmest, thickest coat and call it a day. But next time you’re shopping, keep a few things in mind beyond warmth: Length: For taller guys, go for a coat that hits somewhere between your hip and mid-calf. For shorter guys, aim for your hip or just above the knee. Fit: You should have about two inches of space between your body and the inside of the coat. In other words, it shouldn’t be tight because you’ll want room for a sweater underneath. Style: Skip the faux fur hoods and avoid too many pockets. I prefer a flat parka, but if you choose a bubble jacket, find one with a flap over the zipper.

If you’ve got room in your closet for a trendy jacket (warm enough for fall, but not for a Toronto winter), the barn jacket trend is up +171% YoY per Google Trends. The barn jacket: originally designed for farmers, has a rugged, preppy style usually made from heavy cotton canvas, lined with flannel, with big front patch pockets for your tools (or your phone). The fit is relaxed and boxy, perfect for layering over a sweater, and it’s known for its signature contrasting collar.

Have you ever bought anything from SSENSE? No, me neither. I only recently found out they’re a Montreal fashion-meets-tech “success story“ that sells luxury fashion, known for its deep catalogue of designer pieces and global reach (apparently the best international shipping in the game). Once valued at $5 billion CAD, earlier this year, the company filed for bankruptcy protection. The website is still operating, but with all the volatility, I’m not sure I’d trust my money there. Better to wait for the fire sale. 

Here’s your foundation for your work holiday party outfit: blazer, shirt or sweater, dress pants, dress shoes. Simple right? Here are two ways to spice it up. 1. Matching Set: Go for a matching suit with a subtle pattern or texture, like this. Trade the plain white shirt for a thin beige or blue sweater, like this. Finish with dark brown dress shoes or loafers, like this. 2. Statement Blazer: Pick a blazer in a standout colour or texture (this is your chance to try velvet if you’ve been curious). Pair it with a plain white dress shirt, black dress pants with a middle pleat, and black dress shoes.

Need some help putting together a holiday outfit? I’m offering a mini version of my digital shop for the next 30 days. Here’s how it works: after learning more about your style preferences and budget through a consultation call and style discovery, I'll put together outfit mood boards that you can use to shop for yourself online. Mood boards will come with shoppable links, and I'll make sure that all items are in stock and available in your size at the time of delivery. $100 for two looks. Book here.

Indulge 🤑

If you’re in the market for a lifetime winter coat, this is the one. Another Montreal brand, Mackage, has been around since 1999, and I see it as Canada Goose’s more posh uncle. Similar in price, but the pieces are more structured and made for style and warmth. You could take it skiing… but you probably wouldn’t want to get it dirty or scratched. I love the structure, the length, the navy colour, and that hood looks so dang warm.

On My Radar 👀

GQ is celebrating its Men of the Year, 2025, this week. You can watch the live stream on November 13 here, or keep an eye on my Instagram, where I’ll post some of the best looks on my Stories. This year features Oscar Isaac (this salmon suit is fire - the unexpected baby blue shirt is what really makes the outfit pop), Clipse, SZA, Seth Rogen, Sydney Sweeney, and Stephen Colbert.

Add To Cart 🛒

This barn jacket is on sale at Eddie Bauer in three great colours.

Until midnight tonight, Banana Republic is having a holiday preview sale. Lots of great items are 40% off.

Also until midnight tonight, striped styles at KOTN are up to 20% off. I know, very specific. I like this jacket and this sweater.

Ask Me Anything 🙋🏻‍♀️

Where do I shop as a tall/short/slim/plus size guy?

I’ve worked with clients of all body types, and during our first consultation call, I almost always get questions about where to find clothes that actually fit, whether it’s long arms, a short torso, long legs, or a thicker midsection. On the bright side, I love that so many people understand fit really is the foundation of a good outfit.

There are definitely brands that focus on specific body types, but for this list, I’m sticking to brands you’ll find at most malls.

RW&Co - Best for average builds. If you’re very tall, short, or broad, the fit can feel off (even if they technically carry your size). Sleeves and shirt lengths often run short.

Club Monaco - Great for slim or shorter men. Their overall sizing runs smaller, and both tops and bottoms are cut tighter.

Rodd & Gunn - A New Zealand brand that’s popped up in malls recently. A store associate once told me it fits New Zealanders best, which might explain why many of my clients struggle with the fit. Try it if you’re tall and have a broader build.

Banana Republic - Pretty standard fit, but runs slightly larger. Not ideal for very slim frames.

Hugo Boss - Offers multiple fits (like slim and athletic). In my experience, the slim fit looks sharp, but the athletic cut can feel bulky. In other words, I go to Hugo Boss for the slim fit.

George Richards - It’s a myth that big-and-tall stores only carry boxy clothes. Not true! George Richards has great, well-made options designed specifically for bigger and taller builds.

Moores - Not just for suits. I like them for their size inclusivity, style variety, and reasonable prices. They carry sizes from XS to XXXL.

And one last thing: don’t skip alterations. Most dry cleaners can do them, and honestly, most people should tailor their clothes. It’s the easiest way to get the perfect fit.

Have a style question you want answered? Reply to this email and I’ll answer it in a future Ask Me Anything.

Know someone who needs style tips? Share this with a friend.

Keep Reading

No posts found