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Transitional Menswear Essentials

At least in the northern hemisphere, most of the year is spent in “transition” – that is, conditions where the weather vacillates between chilly yet not quite cold and warm enough for short sleeves. You head out the door with a layer ready, save the shorts for summer, and tend to focus your wardrobe on midweight cottons and lightweight wool. Dressing for the weather through these periods means being prepared for the unpredictably mundane – a middle ground where you’ll attempt to get comfortable without looking too bulky and without feeling too hot or too cold. It’s a balancing act that involves juggling a number of capsule essentials:

A Cardigan 

Unless you’re talking about something strictly fine gauge, sweaters bring up visions of chunky, cable-knit winter garments. A cardigan, on the other hand, presents more possibilities. Both menswear and streetwear enthusiasts have started acknowledging that over the past few years. Whether you’re picturing something navy and made of merino or colourful and draped over your frame, its default construction gives you a lightweight jacket that can be buttoned up the front over a T-shirt or polo for extra coverage in a smart-casual context.


Flannel or Overshirt 

Take your pick. Flannels and overshirts perform the same functions: You can wear one as a heavier primary button-front as the days grow cooler and you start to see your breath outdoors, or you can sport it over a T-shirt, where it functions as a lightweight jacket or as a warmth-retaining mid-layer. As both tend to use wool to some degree, the fabric is built to both hold onto body heat and repel moisture from the exterior. 

Sweatshirt or Hoodie 

Both garments feature a similar mid- to heavyweight construction. A woven, often heathered cotton or French terry exterior holds a fleeced interior that feels soft against your skin and traps body heat. What results trims down bulk, is easily layered over a T-shirt, polo, or button-front, and tends to be a grab-and-go option when you’re not entirely worried about style but prioritize comfort during these segments of the year. These days, you can kick it classic – a Champion sweatshirt seems to do the trick while offering retro appeal – while newer versions lean toward luxury or incorporate performance properties.


Crewneck T-Shirt 

Right now, Hulu’s The Bear has been the talk of pop culture due to how it highlights the abuse-bordering intensity of kitchen workspaces. It’s also been declared a “menswear show,” putting it in the same style inspo category as something like Peaky Blinders or, indirectly, Stranger Things. Yet, while these examples helped amplify and bring back the three-piece suit or illuminate the diverse appeal of ‘80s men’s fashions, The Bear might as well be called “Why we’ve all been loving normcore since 2018”: White crewnecks take center stage, indicating that despite its deceptive simplicity, fit is everything, and sometimes, well-designed basics give you the most mileage. 

Polo Shirt 

Long or short sleeved, polo shirts have transformed into the do-it-all garment. They’re office ready in most instances, have that casual cool that’s just right for chinos, and, with a slimmer silhouette, deliver the structure needed to contrast against a lighter-weight, wider-cut jacket or blazer. As you prioritize versatility, look past the hype pieces to finer knits, a more defined fit, and a solid shade to minimal colour-blocking, based on your stylistic preferences.

Ralph Lauren
Ralph Lauren


Cotton or wool, rollnecks essentially add more coverage to what’s basically a finer-knit sweater or long-sleeve T-shirt. At the same time, this addition – covering half of your neck to folding over – ups the elegance factor. No, it’s not a button-front, but it doesn’t have to be. Rather, it’s substantial enough to be worn on its own, thanks to more midweight construction, its structure contrasts sufficiently against softer pieces, like an unlined blazer or even a denim jacket, and, ideally sitting closer to your skin, it highlights your physical form better than, say, a sweater or a T-shirt. 


This feels like an obvious addition – after all, during which season aren’t you wearing chinos? Summer’s most sweltering days might be an exception – but even then, the shorts-averse among us just might reach for linen or a lighter-weight cotton in tan or an off-white shade to keep cool. Although various guides will tell you to have some grey, tan, and blue chinos in your arsenal, these everyday trousers have more possibilities. Transitional weather keeps your summer-friendly styles in rotation, provided you don’t go too lightweight. Depending upon how open you are to experimentation, consider expanding your palette to greens, purples, and burgundy for these seasons.


A Lightweight, Layer-Ready Jacket 

Let’s not beat around the brush: Excluding puffers and wool overcoats, most jackets out there are built for transitional weather. Trench coats offer that extra coverage without weight for rainy days – and also have the spaciousness for a hoodie or bomber underneath. As well, bombers themselves, in addition to blouson and denim jackets, don’t sit right against the skin. Should you want more warmth on a day when the forecast predicts some sun but mostly wind, you can layer your cardigan, flannel, or hoodie right beneath for the precise level, more adaptability, and less bulk. 

A Sport Coat or Blazer 

Among the multiple factors causing many to proclaim “suiting is dead” for the umpteenth time is that for most occasions where cocktail dress is required, you can get away with pairing a sport coat or structured blazer with a pair of chinos and a button-front or even a polo. Granted, it doesn’t work for every occasion: See Chris Pine’s pleated trousers and double-breasted blazer at the Venice Film Festival premiere of Don’t Worry Darling as one example. Still, for weddings, the odd in-person work event, or going someplace where denim makes you look and feel under-dressed, this singular garment or as part of suit separates tends to get more smart- to business-casual mileage than a full suit alone.

Universal Works
Universal Works

Mid-Height Boots 

The snow won’t be on the ground for a few months. Yet, you can feel the chill through your canvas trainers. So, opt for more coverage without the height. Whether you prefer to pull-on-and-go or the closer fit of laces, chukka, Chelsea, and desert boots deliver these factors through leather, suede, or even textile, often with a more substantial outsole underneath.

Ivan Yaskey

Philadelphia’s streetwear scenes and working as a copywriter for a Boston-based menswear brand sparked Ivan's passion for fashion and style more than a decade ago.

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