Seasonal dressing seems like an easy task for the well informed man right? You have coats for winter and t-shirts for summer – but what happens with those months of changing weather? It is occasions like these that you need a kit full of trans-seasonal staples that can be layered and teamed to suit change in temperature.

We have listed the year-round essentials, that will last more than just a season.


For when you can’t decide if you’re hot or cold, enter the unsung hero of menswear – the over shirt. With different cuts to suit, throw this guy with jeans or shorts and layer under literally anything.

Wings and Horns Tropical Cotton Officer Shirt in Heather Ash / $210 USD SHOP NOW
Engineered Garments Dayton Shirt in Black Tropical Wool / $324 USD SHOP NOW


White T-shirt

So this one is kind of a given, but it’s important to get a good quality t-shirt and the right fit, so you’ll be able to wear the trans-seasonal staple every year.

Lot78 White Pocket T-shirt / $90 AUD SHOP NOW


Classic Chino

Another item that most guys have, but often fit terribly and lack quality. Trust us when we say this is definitely an item you should invest in. Aim for slim, unfussy styles which are sharply tailored and end at your ankle.

Eleventy Classic Chinos / $349 AUD SHOP NOW
Dolce & Gabbana Classic Chinos / $645 AUD SHOP NOW

Mid-Wash Denim

Dark denim is one of those pieces that never go out of style and it’s easy to wear all year-round. But sometimes we need to put them to the side and let lighter washes in. A mid-wash will brighten up the rest of your daily look – especially when the weather is getting colder. This is a trans-seasonal item you need now.

Calvin Klein Fred Blue Slim Jean / $90 USD SHOP NOW
Citizens Of Humanity Ludlow Cropped Relaxed Jean / $328 USD SHOP NOW


Unstructured Blazer

An unstructured blazer is a multi-purpose god send for those who love tailoring and for those who don’t. It is the perfect ‘in between’ and can be worn to the workplace or teamed with jeans and baggy shirt for the ‘smart-casual’ look. This is a staple perfect for the cooler ends of the season.

Venroy Unstructured Blazer / $200 AUD SHOP NOW
Lardini Classic Blazer / $1002 AUD SHOP NOW


Denim Jacket

The denim jacket is an essential every guy should own. Multi-purpose and for every day use, this item can be layered underneath an overcoat when it’s still cold outside or thrown over a t-shirt and dark wash jeans for a ’90s night-time vibe. Opt for a classic shape and minimal embellishments for trans-seasonal staple.

Need Denim Jacket in Judd Wash / $195 USD SHOP NOW
Nudie Jeans Billy Shimmering Indigo Jacket / $260 USD SHOP NOW


Harrington Jacket

Continuing on with the outerwear, the Harrington Jacket is one of those items that literally wont become daggy. Surprisingly good at stopping the cold winds and simultaneously making the wearer looking effortlessly cool, think of this one as the refined bomber jacket.

Desa 1972 Harrington Jacket / $957 AUD SHOP NOW
Burberry Harrington Jacket / $2145 AUD SHOP NOW


Chukka Boots

The chukka boot is the perfect middle ground between a structured boot and loafer and is neither too dressy nor formal. Wear them with jeans, chinos and shorts when the weather warms up. Nothing else can really be said about them other than they’re an essential

Tod’s Desert Chukka Boots / $512 AUD SHOP NOW
Church’s Sahara Chukka Boots / $566 AUD SHOP NOW


Leather Penny Loafers

The iconic leather penny loafer is rarely seen to go out of style and has become the ultimate dress shoe, worn for day or night. The style options are endless for this item and a good quality pair will last the rest of your life.

Loveless Classic Loafer / $441 AUD SHOP NOW
Prada Patina Penny Loafer / $870 SHOP NOW


White Sneakers

Last but certainly not least, the classic white sneaker. The only downside to these is the inability by anyone to keep them clean. Unlike it’s other sneaker counterparts the white tennis shoe needs a little extra love. Regardless, wether you opt for the iconic Adidas Stan Smith or look to Reebok or Lacoste, a pair of these will always have a place in your daily kit.

Reebok Club C 85 RT White Sneakers / $109 AUD SHOP NOW
Adidas Stan Smith Forever White Sneakers / $135 AUD SHOP NOW


Cover photo: @its_hideaki Instagram