We all like to think we’re honing in on our “one true style”: the essence of who we are, expressed through our clothes. Our “cover letter to the world,” authentically articulated and intentionally discovered. Many – myself included – also want to look timeless. Yet sometimes I wonder whether my tastes were just shaped by the prevailing winds of the #menswear movement at the time I joined, and if I’ll find myself hopelessly out of date in another five years regardless. A little bit of the 2000s Ivy resurgence, a heavy dose of soft Neapolitan tailoring, trim flat-front trousers, double monks – you can probably date me to a 3-4 year period of time.

The solace I take when this thought crosses my mind is that whether or not what I like is considered “in fashion,” a rooting in a look that is stylish no matter what time period it originated in can always be appreciated. Soft tailoring is one of those deep roots that you can tap into.

It is nearly universal in the sense that every tailoring tradition of the world includes soft tailoring in its history. Neapolitan tailoring has dominated the conversation for several years now, but never forget the British drape cut essentially inspired it, nor that America’s sack cut reigned for decades.

No matter which silhouette you prefer, there is a strong case to be made for soft tailoring in the casual world of today. Here’s why:

1. Soft tailoring is more comfortable

Let’s be real: no form of tailored clothing will be more comfortable than shorts and a T-shirt. But a soft jacket (cut hopefully with a bit of extra room to reach and move around) with a lightweight canvas or even none at all can bridge the gap. Brands on the higher end who do this well include Boglioli, Corneliani, Caruso and Sartoria Formoa. Somewhat below that is Eidos, Ring Jacket, and Canali. In the lower end is LBM 1911 and SuitSupply. Of course, all those brands can be found on eBay or the Styleforum buying and selling forum, which can lead to amazing deals on high-end clothes

2. Soft tailoring is conducive to off-hours leisure

If you like to wear tailoring even when it’s not required (as I do), soft jackets can help in softening your appearance in less formal settings. To be clear, wearing any form of jacket with lapels will make you look “dressed up” to most. But there are some good in-between options out there that connect casual outerwear influences with tailoring influences. Engineered Garments and Private White VC are two good examples that lean more towards the casual end of this spectrum.

3. Soft tailoring pairs naturally with casual fabrics that pair well with other casual wardrobe items

Summer fabrics like linen, cotton, linen blends (and for the adventurous, madras) pair extremely well with open-collar shirts, light jeans, chinos, linen/linen-blend trousers, and suede loafers. Tweeds and heavy fabrics look right at home with Oxford button down shirts, wool ties, suede loafers, and chunky wingtips or boots. Academics wearing well-worn elbow-patched tweed jackets from Brooks Brothers with an OCBD and penny loafers is a clichéd look, but one that’s rooted in history. It will never be out of style, and the comfort afforded by the softly tailored jacket makes sense for a life on campus.

4. Soft tailoring transitions well from dressed up to dressed down

Many times when my wife and I know we’ll be going out with friends at the end of the day, I know if I wear a softly tailored jacket and the right pair of shoes (usually suede), all I’ve got to do is take off my tie and put on a pair of jeans and I’m good. The two main factors at play are the softness of the tailoring as well as the fabric it’s made from. I tend to wear sport coats with odd trousers instead of suits, which makes it easier to simply change pants, but companies such as Eidos and Suit Supply do make suits in fabrics that are easy to break apart.

Ultimately, who you are is conveyed most importantly by your presence, personality, intellect and heart. Clothes can help make a first impression, but past that, it’s all up to you. The benefits of soft tailoring come into play by making you look good, feel great for knowing that part is taken care of, and allowing you to be comfortable. And once your brain is free to stop worrying about that, then your true character can really shine.