The Guide To Trans-seasonal Dressing

While I’m savvy about dressing for trans-seasonal weather, I’ve nonetheless copped a few side-eye for wearing a jacket on a sunny fall day or chastised for not covering up on a cool evening. Are you hot or cold, boy? Guys scratch their heads, unsure of what’s appropriate sartorial selection but the concept of trans-seasonal layering is something that can be perfected easily.

From layering with a lightweight jacket to wearing a shirt or trousers that come in a heavier but still breathable fabrication, the idea seems fairly straightforward like mens resort wear yet it’s still one that only fashionistas understand enough to navigate. Maybe the issue isn’t so much about putting together an outfit that works with the weather but rather, finding pieces that are aesthetically pleasing enough to wear during transitional seasons.

Thankfully, menswear designers have noticed the shift where guys are paying attention to their style and starting to invest in pieces that are interesting and not just necessarily utilitarian. One such designer who’s managed to merge both is New York-based Childs.


Childs SS17, New York menswear label, mens transseasonal


Designed by Robert Childs, the Spring Summer 2017 collection is inspired by the designer’s childhood life in Florida. Jackets and double shirt layering for spring and summer? All sorts of yes, I say. Working with artist Zoe Barzca on a rip print and floral motif, the clothes are the perfect merging of style and substance and suddenly, the concept of trans-seasonal layering appears a whole lot easier to grasp.

If you’re still confused about how to achieve transitional dressing, here are 3 foolproof tips to get you across the line.

1. Layer with lightweight outerwear

It’s not quite the time of the year to be rocking winter coats so opt for denim jackets, lightweight lined-cotton bombers, or nylon souvenir jackets instead. These pieces are made for weather that can’t make up its mind, are easy to throw onto any existing outfits and needless to say, you’ll also be right on trend.

When it gets slightly warm, drape the jacket on your shoulders or knot it around your waist like a street style fashionista. That way, you’re no longer just dressing for the weather but taking your outfit to the next level.


2. Cover up with closed toe footwear

I love sandals but they do get impractical when the seasons change. Swap open toe footwear with sneakers or dress shoes to keep your feet warm but opt for thin socks or go sockless to keep your look fresh and current.

If you’re feeling adventurous enough, pair socks with sandals or open toe shoes but only if the footwear are so chic that no style gods can punish you for it. It’s not for everyone and there are still debates on wearing socks and sandals together but rules are made to be broken, if you know how to break them.

3. Cosy up with a heavy cotton shirt or thin knitwear

Just like you can layer things up with lightweight jackets, you can also keep things comfortable with a shirt in heavier cotton or a thin sweater on its own. That way, you can save yourself the hassle of packing a jacket when you go out.

For those who want to push the style envelope, a few designers are changing the knitwear game with short sleeve cardigans or statement sweaters. While this sounds like it’s defeating the purpose of staying warm, on the contrary, it’s the perfect solution helping you stay warm and cool at the same time.

Childs SS17, New York menswear label

Street Style Poser
About me

Henry Ng is a writer, photographer, stylist and consultant. Henry found success owning his own menswear label, Orri Henrisson, before moving into digital marketing where his creative and strategy skills are highly sought after. Henry’s passion for menswear and travel saw him launching Street Style Poser. Henry loves all things bright and colourful, karoke, Kristen Wiig, and salted caramel anything!


Seasons of Queer: Summer Lingering
February 29, 2020
January 13, 2020
Seasons of Queer: Spring Fling
November 21, 2019
Seasons of Queer: Winter Cocooning
August 15, 2019
4 Ways To Elevate Your Look
June 08, 2019
Seasons of Queer: Autumn Dreaming
June 05, 2019
Sly Blue
May 02, 2019
March 24, 2019
Let’s Not Fall In Love
December 18, 2018


Reply September 25, 2017

Amazing Post! The outfits looks simply amazing and so stylish. Good Job!

Leave a comment

Your email address will not be published. Required fields are marked *

Time limit is exhausted. Please reload CAPTCHA.