Allow me to paint a picture for you, gents. A tailored jacket that moves as naturally as you do, with soft shoulders that hint at structure, without stuffiness. A crisp shirt and slim chinos that cut just above the ankle and finish at the natural line of your waist. Polished, possibly Italian, loafers.
This is casual tailoring done right – confident, versatile and, most importantly, intentional.
The Italians have a word for this (don’t they always): sprezzatura. It means the art of making something difficult look easy, an effortless sort of grace. And that’s really what casual tailoring is all about.
But let’s be honest, pulling off this sort of effortless elegance isn’t as easy as it looks. Lighter fabrics and more relaxed cuts can all too easily look careless, or worse, contrived. Casual tailoring demands balance.
So, gentlemen, let’s explore how to embrace this philosophy when it comes to your own wardrobe.
The essence of casual tailoring
Simply put, casual tailoring is the intersection of two worlds: where the precision and structure of classic tailoring meet the fluidity of casualwear. It’s modern dressing for men who want comfort and versatility, without sacrificing style.
The key principles of casual tailoring are:
- Relaxed silhouettes: Unstructured jackets, soft shoulders and looser cuts that move.
- Texture: Fabrics that achieve the right balance between interest and comfort. Think wool, jerseys, linens and brushed cotton.
- Versatility: These are some of the hardest working clothes in your wardrobe. Every piece should adapt to multiple occasions, from a relaxed brunch to a creative meeting.
The building blocks of casual tailoring
Casual tailoring is a broad area, so to keep things simple, let’s dig into the foundational pieces that will anchor your wardrobe.
1. The unstructured jacket
An unstructured jacket is the cornerstone of casual tailoring. Done well, and you could look as good as Richard Gere in American Gigolo. If it fails to hit the mark, you risk looking like an estate agent at the weekend.
Where traditional jackets rely on padding, canvassing and interfacings to hold their shape, unstructured jackets forgo the layers for a more natural silhouette that sits closer to the body. It carries the hallmarks of formal dressing but allows for more movement.
Look for lightweight fabrics, such as linen, jersey and unlined wool for year-round wear and opt for neutral colours like navy, olive and green for maximum versatility. Impeccable construction still matters; inner seams should be taped, and the cut should drape naturally.
How to style it: Pair a grey unstructured jacket with a fine-knit sweater and slim chinos for a refined yet laid-back look. Alternatively, throw it over a crisp white t-shirt and tailored jeans for an off-duty look. White trainers are timeless, I urge you to throw away anything heavily branded.
2. The Shirt-Jacket
Part shirt, part jacket, the “shacket” has become a menswear staple. Its structured yet relaxed design is perfect for bridging formal and casual outfits.
Choose boxy, generous cuts, with enough room to layer and a length that falls just below the waist. Look for quality fabrics, like soft flannel, Italian twill or wool, and subtle checks or textured weaves for depth without overwhelming the frame. Fine details, like pearl buttons, will take it up a notch.
How to style it: Layer over a chambray shirt and fitted chinos for a smart weekend look, or layered under a tailored overcoat in cooler months.
3. Tailored chinos
Chinos are the unsung heroes of any man’s wardrobe. An excellent alternative to jeans and wool trousers, a good pair of chinos can be worn throughout the year for a wide variety of occasions. Soft and, crucially, comfortable, chinos offer the structure of trousers, with a more relaxed edge.
Look for crisp and dense fabrics, nothing too flimsy. You want a roomy but tailored fit, with a clean design. Steer clear of tight cuts to avoid the stuffed sausage effect. Again, neutral tones offer the most versatility.
How to style it: For a “goes-with-everything” trouser, the variety in cut and style in chinos is quite staggering – deep pleats, flat fronts, rear patch pockets, widened belt loops, flares, and so the list goes on. For a more casual look, choose a classic pair with a flat front. If it’s summertime, roll the legs up a few times and pair with a stylish pair of white trainers. For a more formal look, choose a slim-fitting pair with a slight taper and a pleated front, then pair with a shirt, leather belt and suede loafers or boots.
4. Relaxed knitwear
Knitwear can be an effective bridge between formal and casual, but keep it simple and avoid any patterns that err on the festive side. As a rule of thumb, the more muted the colour, the more versatile the piece.
Cream is a great option – it goes with everything and clashes with nothing. Browns are timeless, too. Choose fine-gauge, lightweight knits for tailored jackets (bulky knits look ridiculous) and always remember, fine cloth matches fine knitwear.
How to style it: A fine-knit roll neck in charcoal or navy works well as a sleek alternative to a shirt. Neutral crewnecks and chinos are the ideal marriage, while a textured cable-knit with tailored trousers works well for a relaxed weekend look with bags of character.
A note on separates
Separates are the cornerstone of casual tailoring, and it would be remiss to discuss them without mentioning, once more, Richard Gere in American Gigolo. In the space of roughly two hours, he inspired a whole generation of slouchy menswear and suits that don’t quite match, waving goodbye to boxy, crisp and buttoned-up.
If you’re new to separates (tailoring items worn independently), they might feel intimidating – but they shouldn’t be.
The key to mastering this side of casual tailoring is to stick to the rules:
- Contrast is key: Pair complementary colours without matching them too closely. Think navy with beige or charcoal with olive.
- Stick to softer fabrics: Avoid anything that looks like it belongs in a formal three-piece suit.
- Mind your textures: Mix textures for visual interest. For instance, pair a herringbone blazer with smooth cotton chinos.
If in doubt, remember, don’t mix vegetables with animals. That is to say, keep your cotton and linens far from your wools and all kinds of cashmere.
Final words
At Ascots & Chapels, we like to think of casual tailoring not just as a dress code, but a philosophy. It’s about mastering the art of looking polished without appearing overdone. It’s about versatility, confidence and having fun with your wardrobe.
Still unsure about how to master the look? Or maybe you’re inspired? Drop into your favourite store and let the experts guide you. Here’s to dressing well, gentlemen.
Author: Gary Sweeney
