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Harry's Guide to Layering

Explore simple tips and example ‘fits showcasing the sartorial art of layering.

By: Harry Rosen Staff

Those plugged into menswear circles on social media will be all too familiar with the “can’t wait ’til it gets cold so I can really start dressin’” meme — often starring Kermit the Frog — a playful nod to the very real excitement surrounding layering season, every fashion fan’s favourite time(s) of year.


It’s the in-between months where layering really comes into its own. While winter is all about big cozy coats and summer primarily about how few layers you can get away with wearing, spring and fall are when layering is not only practical, but aesthetically pleasing as well.


Of course, there’s an art to it — simply piling on pieces won’t automatically earn you style points. Here’s how to take a look from simple to standout with the power of layering.



Getting Started


The best way to build any outfit is to start with one foundational “hero” piece, then add layers from there.


Begin with lighter, thinner fabrics closest to your body and gradually add thicker, heavier pieces as you layer outward.


With each new layer, consider sizing up — for example, when wearing tailoring, opt for an overcoat that’s one size larger than your suit or sport jacket.


Generally speaking, you want your longest outerwear piece to be your outermost layer — unless it’s a vest, which is designed with shorter hems.


Contrast is Key


Remember: contrast is your friend in respect to both texture and colour. Mixing different fabrics like wool, suede, leather, and denim creates visible and tactile interest, while tonal or complementary colours help build a palette that’s easy on the eye. Try pulling tones from one key piece to guide the rest of your look.


Juxtaposition adds another layer of visual appeal. Tastefully pairing casual pieces with more formal ones — or relaxed silhouettes with sharper, more tailored shapes — helps layered outfits feel modern and dynamic.


Playing with Proportions


Don’t go buttoning down all your hatches; experimenting with closures — whether a front zip or button placket — is an easy way to play with line and silhouette.


Try fastening only the top button of your jacket to create an A-line shape, or use a two-way zipper to adjust proportions on the fly.


Styling certain pieces in unexpected ways is also key to keeping layering interesting. For example, tie a sweater around your shoulders or hips; wear a thin turtleneck below a button-up shirt and sport jacket, or layer a denim jacket between a thermal underpinning and a wool overcoat. Small changes can make a big impact.


The Finishing Touch


Lastly, remember that accessories are layers too. Incorporating a scarf, hat, statement belt, or piece of jewellery helps round out a layered look while adding a touch of personal style.



Layering for a Coffee Run


Dashing out for a mid-day coffee break is a treat in itself — why not take inspiration from those fresh croissants and embrace a life in layers?


The key is to keep it casual: layering that looks effortless but delivers big results.


Start with a simple T-shirt, then layer in a light knit — like a V-neck or mockneck — and finish with a casual jacket or vest, left open to expose your layering game below.


Finish with a scarf for an extra touch of colour and personality, making sure it pulls from tones already present in your look.



Layering for a Gallery Visit/Date


A date or a visit to an art gallery requires similarly smart looks — after all, both activities involve appreciating beauty.


The goal here is something that lives comfortably between relaxed and refined without sacrificing personality.


Start with an elegant knit, then layer a quarter-zip or cardigan overtop before finishing the look off with a smart jacket or sport jacket.


Down below, opt for a pair of dark wash jeans or chinos and some polished leather shoes or boots.



Layering for the Office


Heading into the office calls for a sharp look that commands authority — if only from your workplace fashion police...


Start with a crisp dress shirt and patterned tie. Over that, a suit or sport jacket-trouser separates will form the foundation of the outfit.


For your commute, an overcoat (don’t forget to size up from your regular suit size) will keep the weather at bay, while a scarf and hat add pops of colour, pattern, and texture to the layered look.