How to Wear a Jacket: The Regent Way

A great Regent jacket isn’t just something you wear – it’s a statement. At Regent Tailoring in Salisbury, we believe a jacket should feel as good as it looks. A well-cut jacket sharpens your posture, enhances your silhouette, and adds an effortless sense of confidence.

Here’s our authentic, no-nonsense guide to getting your jacket just right – featuring heritage-inspired tailoring tips from sleeve length to vent placement. At Regent, it is the small details that make all the difference.

Getting the Essentials Right

1.     Aim for the Perfect V – It starts with Shape

The front of your jacket should form a soft, clean V shape when buttoned – structured, but not stiff. This gives you form through the shoulders and chest, while letting the fabric drape naturally.

It should sit comfortably across your chest, not pushed out too much, but also not sat flush against your chest either – you are looking for a balanced point where the lapels roll out naturally.

Shop this look:

Regent Bannister Check Wool Jacket – Crafted in a rich heritage check, this jacket is perfect for all occasions and seasons.
Blue Bengal Stripe Shirt – A crisp, slim-cut essential that peeks just right beneath the cuff.
Fair Isle Knit Jumper – A perfect autumn layer in classic Regent colours. This seasonal staple will be live on the website soon - keep your eyes peeled.

2.  Check the Sleeve Length – Let the Shirt Speak

A simple but often over-looked rule: your shirt cuff should extend 1-2cm below your jacket sleeve. Not only does this add polish, but it also visually elongates the arm. It is best to avoid sleeves that hide the cuff entirely or swallow the wrist. Ideally, the jacket sleeve should meet the top of your thumb.

However, cuff length isn’t universal — it often reflects cultural norms, historical background, and personal style.

One such notable example is Prince Michael of Kent, a British royal and a prominent military figure. His shirts often feature a much longer cuff, shaped by military tradition and the practicalities of marching. In contrast, other members of the British royal family tend to wear a shorter cuff, sitting higher above the wrist – in line with more formal civilian tailoring. In other countries, preferences shift again. For instance, in parts of China, it’s common to see shirt cuffs extend well over the thumb, reflecting a different approach to proportion and silhouette.

Imagine the ‘perfect British gentleman’ strolling down Old Burlington Street in London — the standard is that clean 1–2cm reveal. But ultimately, sleeve length is a matter of personal expression, shaped by the tailoring traditions you admire.

Try it with:  Smart Shirts Collection

3. Jacket Length – Use the Thumb Test

With your arms naturally by your sides, your jacket should end:

• Around the bottom of your thumb
• In line with the V of your trousers
• Roughly half the length of your body from collar to hem

It should feel comfortable and allow you to move freely in a relaxed position. 

4.   What Is a break – And Why It Matters

In tailoring, the break refers to the subtle fold or dip at the front of your jacket when it's buttoned, specifically where the lapel meets the top button. It’s not just a stylistic detail - it’s a sign that the jacket fits and moves properly with your body.

A break reflects the room between the hollow of your back and the front of your body just below the chest.

What does a good break look like?

For a good break, there should be a small, natural pocket of space that allows the jacket to sit cleanly, not cling.

You should be able to stand upright with the jacket buttoned and:

• See a soft fold at the button, not a strain
• Slip your hand comfortably between the lapel and shirt
• Maintain a smooth line from shoulder to waist

Think of the break as breathing room: the jacket should frame your torso, not compress it. It is worth remembering that your body type will determine how best to wear your jacket. If you have a fuller build, it’s best to leave the jacket unbuttoned. A well-cut jacket will still hold its shape and structure even when worn open – giving you comfort without compromise. 

5.   Vents – Mind your Back View!

The vent(s) of a jacket should sit flat when you’re standing naturally upright. If they kick out or strain, the fit isn’t quite right. For broader hips and fuller seats, a double vent helps the jacket drape naturally and avoids bunching.

The way a jacket sits across the shoulders can tell you a lot about fit. In this example, the subtle creasing shows that the person has naturally lower shoulders, something that can gently affect how the vent and back panel fall.

The Most Common Mistakes 

Even the best jackets can look wrong if they’re not worn with care and attention. Here are a few of the most common fit errors:

1.     Too tight: remember your buttons shouldn’t strain

2.     Sleeves too long: If your cuffs are swamping your hands, revisit the thumb rule.

3.     Length too low: If it’s falling well below your seat, it’s probably throwing off your     proportions.

Remember that your jacket is meant to fit your body – not fight it. It should make you feel comfortable and confident. A relaxed look is far better than one that is stiff and forced.

Don’t get caught up trying to do one thing right, only to end up doing four other things wrong.

It is easy to obsess over a single detail – like whether you should be able to do the buttons up – and forget the overall balance. A well-fitting jacket works when you bear in mind the shoulders, break, length, and movement.

And yet, many of us fall into the trap of testing jackets like our parents taught us – hunching forward, stretching our arms, and contorting in the mirror to check for ‘freedom of movement’. However you’re rarely adopting those positions in real life, so they’re not a helpful guide for tailoring. The aim isn’t to pass a flexibility test, and to look for a jacket to ‘grow into’. Instead, the aim is to wear something that makes you look and feel comfortable, composed, and confident when standing, walking, and living your everyday life.

Style Inspiration: Iconic looks, Timeless Cuts

A great jacket isn’t just worn — it’s styled. A great, easy way to add texture, personality, and practicality is through layering – especially now we are in the autumn months. A bold check jacket, striped shirt, and a warm knit builds a look that’s confident without being too formal.

Use our archive of vintage collage imagery to inspire new ways to wear your Regent pieces. You’ll find the Regent Lookbook, filled with original collages and styling inspiration, on the middle floor of our Salisbury shop. Come in, have a browse, and discover ideas to make each piece your own.

Finish the look with: Ties & Neckwear Collection

Why Regent?

Here at Regent, we have decades of authentic British tailoring expertise, and a wide selection of jackets designed with modern comfort and timeless style in mind.

This guide provides a solid foundation, a set of classic principles for how to wear a jacket well. But of course, fashion moves in cycles. Styles shift from sharp, structured silhouettes to looser, more relaxed fits. What feels modern today may feel classic tomorrow.

At Regent, we’re always aware of these changes but we choose to stay rooted in heritage British tailoring - cuts that endure, shapes that flatter, and pieces that outlast trends. Whether you’re after something traditional or more contemporary, our team can tailor your jacket to suit your shape, lifestyle, and personal style.

Our jackets are built to last, made to move, and crafted to help you feel like the best version of yourself.

Browse our online collection of iconic tailoring staples.

Or visit us in Salisbury for a free 30-minute consultation with Jason himself.

Shop the Look

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Curated by: Becky Colyer and Jason Regent