How to Dress Like an Italian Gentleman

To dress like a true Italian gentleman, you must prioritise elegance, quality, and effortless charm. To bring sophistication into every outfit, embrace tailored fits, refined fabrics, and subtle yet impactful accessories like cufflinks and bow ties.

Italian style is more than just clothing; it's about wearing each piece confidently and effortlessly, blending tradition with your flair for a timeless yet approachable elegance.

How to Style Like an Italian Gentleman

If you're ready to embrace Italian style, let's explore the distinctive looks of Milan, Florence, and Rome. Each city brings its touch of refined elegance, perfect for inspiring your wardrobe.

Milan

Take a tour of Via Gesù (the shopping street for men in Milan) on a Saturday afternoon, and we promise you will see more well-dressed men than anywhere else in the world. Attentive to detail, obsessed with tailoring, and willing to invest in the finest fabrics, the Italian gent in Milan has an answer to any men's fashion query. 

Made to perfection, superb dressmaking is a religion in the fashion capital of Italy. The most popular clothing brands in the city, such as Canali, Corneliani, Ermenegildo Zegna, and Pal Zileri, are known for their craftsmanship and fabric quality, from tailored suits to the crucial pocket square. They showcase impeccable craftsmanship and guide you in choosing the best materials for dress shirts, setting a high standard for men's fashion worldwide.

If you want to dress elegantly like a Milanese, explore the finest patterns and styles below to complete your outfit. Milan men's fashion has everything. Whether you're looking for tailored suits or sophisticated casual wear, this guide will help you master the Milanese style quickly and confidently.

Milan is both the financial and fashion capital of Italy. This city has an exciting and pleasant mix of fashion, business, and leisure. Many men prefer to dress more daringly, while others prefer a casual look. This is not to say that any elegance or style is reduced in a casual look with the Milan gent.

The Milanese use touches of classic English styles, such as florals and paisleys. Floral bow ties and ties add a tasteful nod to classic English influences while maintaining the Italian penchant for stylish boldness.

The classic Milanese dressing style pays special attention to the sartorial cuts of suits and fabrics. For example, a notch or peak lapel is appropriate if the outfit is for a more casual event. However, if the event is formal, you can opt for a shawl lapel, which exudes elegance given its simplistic cut. Pay special attention to the correct proportions of the lapel cut based on your body and other accessories. Knowing the precise technique of measuring & sizing men's dress shirts is also crucial, as the perfect fit complements the overall look and ensures a refined appearance.    

Florence

When completing your look, most of your time goes into choosing the shirt, jacket, pants, shoes and other accessories. This essential accessory that draws attention is the necktie, which can make or break the entire ensemble depending on its design and fluidity with the rest of the outfit.

The Florence style is neat, elegant and nearly always tailored. It would be best if you were more conventional and formal with colours and fabrics to emulate the Florence style. Dress formally by choosing classic paisley ties, clean-cut suits, and traditional patterns such as herringbone and solid ties. If you're ever in doubt and choosing between suit styles or men's accessories, go for the classic and traditional styles if you wish to emulate the Florence style. If you are still trying to decide what to wear in Florence, approach a more formal look over a casual style, as Italians appreciate.

Italians consider the whole ensemble a single unit instead of individual accessories. Whilst one bold-patterned or striped tie might initially seem misplaced, the piece will speak for itself with a clean-cut suit and a simple white shirt. The stylish Italian gent will not be too impressed by careless dressing or mistakes such as wrinkled shirts and incorrect tailoring. Instead, an appreciation is given to styling carefully considered to match the individual's temperament and make a statement to the Italian flair.

If you wear a suit in Florence, wear a slim tie too. Skip the tracksuit or sports pants for your daily travels and events, as they look informal and misplaced. If you're attending work-related business, pack casual business clothes for your vacation and have casual items when travelling and on vacation.  

Avoid loose-fitted clothes. Opt for fitted clothing that aligns with your aesthetic rather than a "one size fits all" approach. Italians often pair jeans or chinos with a crisp, classy shirt for a refined yet relaxed look. A white shirt, navy or black jacket, and fitted black pants create a versatile style, complemented by the darkest brown shoes, a silk tie, and sunglasses for a laid-back finish at daytime events. Matching cufflinks to your watch or belt buckle add a subtle, cohesive touch to the ensemble.

A light gabardine is often a perfect choice for unexpected weather changes. In the winter, you'll need a warmer coat; in the north, you'll need a hat, scarf, and warm gloves. A down jacket or vest is your best bet if you're travelling to Italy in Winter, but there's no reason why you can't add your flair to each outfit, too. A pair of leather boots combined with your trench coat or down jacket can still be an elegant look to keep your feet and yourself warm during the colder months. Just remember to be comfortable and have functional clothing.

Rome

If you are in Rome, you better know how to choose the right clothes and outfits. Rome is one place where you must learn to coordinate your clothes to look neat and stylish. Given your day-to-day activities, the selection will depend on the occasion and the place you go. Dressing well for a casual outing will differ from a meeting that would demand elegant and formal attire. The choice for a night out in Rome is yours — go for a formal, tailored look to be safe no matter what.

Choosing a suitable shirt that will complement the tie is one of the most common confusions and points to ponder when dressing. You can either coordinate the shirt to be white but with touches of colours that appear on the tie throughout the shirt (such as a fine pinstripe shirt that has the same blue that appears on the tie), or you can always safely go for a plain white shirt. If you need more clarification, this is your best bet, as pairing the wrong shirt and tie can create a conflicting array of colours without a clear focal point.

You must also know how to pair a shirt with or without a tie correctly. Some shirts have the brightest, bold patterns and striking colours that work best without a tie. If your shirt is for a formal event and you still need something to dress up your look, opt for a tie that is a solid colour in a darker tone than the rest of the shirt. For example, a dark olive tie will work well with a bold-coloured shirt. It will not draw attention away from the shirt but add a touch of formalness without overpowering it. Also, look at the width of the tie and try to match the width of the tie approximately to the width of the lapel on a suit jacket. It can create a more balanced look subtly.

Classic ties are not the only accessories you can use to complement your look. Bow ties have made a remarkable comeback in the men's fashion scene. Now, there are thousands of patterns, colours, and styles to choose from that can make your outfit look complete and classy. Bow ties are ideal for relaxed occasions, outdoor weddings and other casual events. When combined with blazers, coloured shirts, and a vest, the bow tie stands out from the different garments and provides a subtle touch of difference to the eye. If you pair a vest, a jacket and pants with a self-tie bow tie, you will have gone the extra mile to create an elegant, classy, and stylish look.

For a polished Italian look, finish your suit with cufflinks. Cufflinks are an essential detail that adds a layer of sophistication to any outfit. You might opt for modern cufflinks for a contemporary feel or antique cufflinks for a timeless charm. Either way, these accessories can elevate your look—just choose a style that enhances your outfit without drawing too much attention.

When tailoring your suits, remember that the first of the two buttons should be over the navel. When you have a three-button suit, the middle button should be around the navel area to balance out the look. It can also be above. You should not just wear any dress socks with the suit you wear. Although mostly hidden, your socks will show when you walk or sit, so choose pairs that match your pants and are long enough to cover your leg when seated. For formal events, classic colours are ideal. In contrast, a pop of colour or a fun pattern, like polka dot socks, adds personality to casual settings.

Suppose you want to dress like an authentic Italian. In that case, you must take care of the accessories you choose:

• A pocket square.
• A scarf on your neck that replaces a tie.
• A bag or backpack to carry everything.

These other accessories are vital for your day-to-day activities and should be remembered. Always pair up similar tones and be consistent (e.g., dark brown shoes for a light brown pant and black shoes for a navy or mid-toned blue suit).

We insist on making sure your pants fit with style and purpose. Choose a length and width that complements your look, ensuring a clean, polished line. Avoid baggy pants, which can reduce your balance and make you look shorter. Go for a waistband fit that allows you to skip the belt. Aim for a snug fit around the seat with a comfortable thigh. For length, pants should graze the shoe, with the front slightly higher if you want to show off your socks. 

General Fashion Tips

To dress like an Italian man, focus on timeless essentials, impeccable tailoring, and quality fabrics. Start with a sharp blazer, a crisp dress shirt, and polished leather shoes, and ensure every piece is well-fitted to accentuate your body without feeling tight. 

Italians value versatility, so pair these essentials with seasonal colours — such as earthy tones for autumn and lighter shades for spring — to keep your look adaptable year-round. Incorporate classic pieces like a navy blazer or grey trousers and add subtle pops of colour through accessories like a pocket square or scarf. Finally, keep accessories minimal but high-quality and embody a confident, effortless attitude to complete the Italian-inspired style.

Frequently Asked Questions

How do you style like an Italian?

To style like an Italian, focus on well-fitted basics like tailored blazers, slim pants, polished leather shoes, and classic accessories like scarves or pocket squares that add flair without overdoing it.

How to style Italian men?

Italian men's style is built on classic, high-quality pieces, sharp tailoring, and a mix of timeless colours with occasional bold accents for effortless elegance.

Why are Italian men so well-dressed?

Italian men prioritise quality, fit, and a sense of understated elegance, creating refined looks that blend tradition with a modern edge.

How do you style like a gentleman?

To style like a gentleman, prioritise quality over quantity, choose classic pieces that fit well, and embrace understated, refined accessories for a polished look.