How to Dress for a First Date with Italian Sartorial Style

You've finally scored a date with that beautiful girl you've been eyeing for weeks. Now comes the hard part - what to wear? If you want to impress her with your sartorial style, there's no better way to do so than with some Italian flair. From dressing up for a classy dinner date, to going for something more casual and relaxed, IsuiT has got you covered. So sit back, relax, and let us show you how to dress like a true gentleman for your next date night!

In this article we'll cover:

  • Formal dinner date outfit ideas
  • Movie night and more casual date outfit ideas
  • Winter date outfits
  • Summer date outfits
  • How to look more attractive as a chubby man, best date outfits

How to dress for a first Summer formal dinner date - Impress with Italian Luxury

If your first date with this girl is a date at a restaurant, then you're going to want to make sure that you're dressed for the occasion. The best way to do this is to follow the basic principles of Classic Menswear.

If you already own an Italian suit then you're not really going to have to buy anything here. Just put on your favorite suit, a white dress shirt, some nice dress shoes, and that's it. You're done. Don't bother with a tie, it's pointless and to be honest, the tieless look makes men look more attractive than if they are wearing a tie.

The truth is - women like sophisticated men. Thus - you are highering your chances of a successful first date if you leverage your look to look more sophisticated and older.

If you do not own a suit already, don't worry, you can pick yourself up a Navy Suit. Personally, I would recommend a nice simple suit from Kired. Kired and IsuiT recently collaborated to make the ultimate suit for the modern man

Kired KIRED Black Wool Ly Pa Elastane Suit Black 000 Kired KIRED Black Wool Ly Pa Elastane Suit Black 001
€600.00 Regular Price €1,200.00
Kired KIRED Blue Virgin Wool Cashmere Ea Suit Blue 000 Kired KIRED Blue Virgin Wool Cashmere Ea Suit Blue 001
€600.00 Regular Price €1,200.00
Kired KIRED Gray Virgin Wool Cashmere Ea Suit Gray 000 Kired KIRED Gray Virgin Wool Cashmere Ea Suit Gray 001
€600.00 Regular Price €1,200.00

These suits are relatively inexpensive compared to some handmade Italian suits. They are also made from wonderful fabrics. The example here is a Navy Blue Virgin Wool Cashmere EA Suit for only €1200 - if you know anything about how much Italian suits cost, you will know that this is an absolutely amazing deal.

This is a perfect suit for a first date in the summertime. This is because it's made from Virgin Wool, which means it's very thin - allowing your body to breathe properly and not get overly sweaty. Not only this, but the trousers are elastic, meaning that if you eat too much (it happens to the best of us) then your belly will have some space to expand into.

Once you've got your suit, just get yourself a nice White Dress shirt, for example from Luigi Borrelli who make some of the finest Italian Dress shirtsCesare Attolini who make incredible dress shirts also, or finally from Kiton who are world-famous for their shirts.

Here is a great example from Luigi Borrelli:


Luigi Borrelli Luigi Borrelli Purple Cotton Shirt Purple 000 Luigi Borrelli Luigi Borrelli Purple Cotton Shirt Purple 001
€141.60 Regular Price €283.20
Luigi Borrelli Luigi Borrelli Purple Cotton Shirt Purple 000 Luigi Borrelli Luigi Borrelli Purple Cotton Shirt Purple 001
€141.60 Regular Price €283.20
Luigi Borrelli Luigi Borrelli Beige Shirt Beige 000 Luigi Borrelli Luigi Borrelli Beige Shirt Beige 001
€131.28 Regular Price €262.55
Luigi Borrelli Luigi Borrelli White Cotton Shirt White 000 Luigi Borrelli Luigi Borrelli White Cotton Shirt White 001
€131.28 Regular Price €262.55
Luigi Borrelli Luigi Borrelli Gray Cotton Shirt Gray 000 Luigi Borrelli Luigi Borrelli Gray Cotton Shirt Gray 001
€131.28 Regular Price €262.55
Luigi Borrelli Luigi Borrelli White Cotton Shirt White 000 Luigi Borrelli Luigi Borrelli White Cotton Shirt White 001
€155.00 Regular Price €310.00
Luigi Borrelli Luigi Borrelli Blue Cotton Shirt Blue 000 Luigi Borrelli Luigi Borrelli Blue Cotton Shirt Blue 001
€155.00 Regular Price €310.00
Luigi Borrelli Luigi Borrelli Multicolor Cotton Shirt Multicolor 000 Luigi Borrelli Luigi Borrelli Multicolor Cotton Shirt Multicolor 001
€155.00 Regular Price €310.00
Luigi Borrelli Luigi Borrelli Blue White Cotton Shirt Blue / White 000 Luigi Borrelli Luigi Borrelli Blue White Cotton Shirt Blue / White 001
€155.00 Regular Price €310.00
Luigi Borrelli Luigi Borrelli Blue White Cotton Shirt Blue / White 000 Luigi Borrelli Luigi Borrelli Blue White Cotton Shirt Blue / White 001
€155.00 Regular Price €310.00
Luigi Borrelli Luigi Borrelli Multicolor Cotton Shirt Multicolor 000 Luigi Borrelli Luigi Borrelli Multicolor Cotton Shirt Multicolor 001
€155.00 Regular Price €310.00
Luigi Borrelli Luigi Borrelli Light Blue White Cotton Shirt Light Blue / White 000 Luigi Borrelli Luigi Borrelli Light Blue White Cotton Shirt Light Blue / White 001
€155.00 Regular Price €310.00

How to dress for a winter first-date - Formal Dinner

If your date is instead during the winter, then you can still buy a similiar suit. We would recommend a Cashmere suit this time, because Cashmere is a much warmer fabric - meaning that you can stay warm in even the coldest of environments.

We would still recommend a Kired Suit, and still navy. Navy is almost always the best choice, because it's such a great color for almost every single occasion you can find yourself in.



This is only the blazer this time, so you will need to pick yourself up a pair of dress pants as well.

Still dont need a tie, ties are slowly dying out (except for overly formal events like a Black Tie event, galas, funerals etc.)

Finally, your dress shoes. Dress shoes work best when they fit the same color scheme as the rest of your outfit. For navy, black dress shoes work very well.

You could go for a classic Derby shoe, or an Oxford. If you want to be a little more stylish, then you could also go for a Chelsea boot.

As you can see, Italian Sartorial Style is the way to go when dressing for a date - whether in summer or winter - IsuiT has you covered.

Movie night, coffee, or more casual first date outfit ideas for men

If you're going somewhere a little bit more laid back, then you can still dress to impress.

For example, let's say you're going to see a movie. In this case, we would recommend a pair of dark jeans - for example from Kiton - and a nice sweater or shirt.

If it's particularly hot during summer, you can wear a polo shirt. Kired has a fantastic collection of Polo Shirts which can be used to match any outfit.


Kired Kired Green Cotton Polo Green 000 Kired Kired Green Cotton Polo Green 001
€87.50 Regular Price €175.00
Kired Kired Pink Cotton Polo Pink 000 Kired Kired Pink Cotton Polo Pink 001
€87.50 Regular Price €175.00
Kired Kired Green Cotton Polo Green 000 Kired Kired Green Cotton Polo Green 001
€87.50 Regular Price €175.00
Kired Kired Brown Cotton Polo Brown 000 Kired Kired Brown Cotton Polo Brown 001
€87.50 Regular Price €175.00
Kired Kired Blue Navy Cotton Polo Blue Navy 000 Kired Kired Blue Navy Cotton Polo Blue Navy 001
€87.50 Regular Price €175.00
Kired Kired Black Cotton Polo Black 000 Kired Kired Black Cotton Polo Black 001
€87.50 Regular Price €175.00
Kired Kired White Cotton Polo White 000 Kired Kired White Cotton Polo White 001
€87.50 Regular Price €175.00

If it's cold outside, then you can also add a jacket or blazer to the outfit. We personally would recommend a denim jacket from Kiton - or a leather Jacket. This allows you to feel confident and stylish incredibly easily - and the quality is absolutely unbeatable.


Kiton Kiton Blue Beige Cotton Ea Leather Denim Suede Coat Blue 000 Kiton Kiton Blue Beige Cotton Ea Leather Denim Suede Coat Blue 001
€3,320.00 Regular Price €6,640.00
Kiton Kiton Blue Brown Cotton Ea Leather Suede Denim Coat Blue / Brown 000 Kiton Kiton Blue Brown Cotton Ea Leather Suede Denim Coat Blue / Brown 001
€3,320.00 Regular Price €6,640.00
Kiton Kiton Denim Cotton Ea Coat Denim 000 Kiton Kiton Denim Cotton Ea Coat Denim 001
€1,967.50 Regular Price €3,935.00
Kiton KITON Light Blue Denim Cotton Coat Light Blue 000 Kiton KITON Light Blue Denim Cotton Coat Light Blue 001
€1,000.00 Regular Price €2,000.00
Kiton KITON Blue Denim Cotton Coat Blue 000 Kiton KITON Blue Denim Cotton Coat Blue 001
€1,000.00 Regular Price €2,000.00

If you want some advice on how to choose a pair of jeans for your outfit, then we have a great article detailing the best Italian denim jean brands.

Best date outfits for a chubby man

If you're a bit on the chubby side, then don't worry - we have some great recommendations for you as well.

A well-tailored suit will be able to fit your measurements and make sure that your clothes fit you perfectly. This is important because ill-fitting clothes are one of the worst ways to look larger than you actually are.

You should also make sure to wear a pair of boots, because they will make you appear taller, and the taller you are, the less it matters if you're a bit on the chubby side.

If you want some more information on how to dress to make yourself look less chubby, then check out our full guide.

Conclusion

As you can see, there are a few different options available to you when it comes to dressing for a date. It all depends on the type of date, and the location. However, we believe that Italian Sartorial Style is always the best way to go - regardless of the situation.

They simply make the best clothes in the world - and the Italian brands we sell are amongst the best of the best.