Did you hear the phrase tailored style and find yourself curious about what it really means? Or maybe you already have a sense of it, but you’re wondering how to actually bring it into your everyday outfits in a way that feels natural and wearable.
Hi there — I’m Alessia, the writer and founder behind Italy with an Italian.
I’ve been meaning to write this post for quite some time. It’s not the trendiest topic, and it’s not something people actively search for. But sometimes the most timeless ideas are the quietest ones — and this is one of them.
Tailored style has always been at the heart of how I dress. And today, I want to show you how you can gently infuse your wardrobe with that simple Italian tailored style that never fails to look effortless and chic.
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Table of Contents
What Is Tailored Style?
Although Italians use the word tailleur too, it’s a French word. It means a woman’s tailor-made suit, but it can also be used to refer to a tailor.
I am not going to go into the discussion of who first came up with the tailored style, but from what I know this is how it likely happened: it has its origins in the oldest civilizations – the Egyptians, the Greeks and the Romans. Then the British, French, Italians, and Spanish all took part in shaping this art into what we know it today.
So what is tailored style?
Is it simply a suit, or any piece that makes up that type of outfit?
While that’s also correct, I believe it’s more complex than that.
To me, tailored style is more than just the description of the pieces that create your outfit. It’s not just a suit, a button up shirt, a pair of tailored pants, or a tailored coat.
Tailored style is the style that those pieces, and the particular combination of tailored clothing you choose, create.
Your outfit could fit that style even if you are only wearing one tailored piece. It’s just going to be on the lower end of the tailored style spectrum. Whereas a suit is on the far end.
With that in mind, you can now embrace the fact that you can dress with tailored style even for everyday life. You don’t need a high-position corporate job to dress tailored, nor do you need to be living an expensive upscale life.
Most importantly, if you love the way that wearing a more tailored outfit makes you feel, you certainly don’t need to wait for a special occasion to dress that way.
Tailored Outfits With Jeans
If you thought that jeans cancel a tailored outfit, that’s wrong. You can in fact wear a tailored outfit that includes a pair of jeans, but there are a few criteria that will determine how tailored that outfit feels.
Level 1: straight leg (aka tight fitting jeans) with a tshirt, a blazer and a pair of trainers. That outfit is the least tailored outfit you could wear. The same holds if you were to replace the blazer with a tailored coat or trench.
Level 2: if you take the outfit in level 1 and swap the jeans for tailored jeans – straight leg, wide fit, slightly cropped, maybe with a flare, that single swap is going to elevate the tailored outfit.
Level 3: if you swap the sneakers for loafers, or heels, or heeled sandals, or mary janes, or pointed flat shoes, the outfit will look even more tailored.
Level 4: swap the tshirt for a button up shirt and your outfit immediately looks dressier.
Level 5: your accessories – the bag, jewellery, and your outerwear can also reduce or increase the overall tailored style of your look. And so do your hair, and makeup.
Footwear Matters When Curating A Tailored Style
The world tailored strictly speaking encompasses clothes. However, think about this: you wouldn’t wear your corporate suit with a pair of sneakers, unless you were trying to go for that cool look outside the office space. That’s because we know that a suit goes with a specific pair of shoes for both men and women. And while there are a few options, sneakers are usually not one of them.
Here are the footwear choices that are going to make your outfit look more tailored, even if that’s the only piece you swap today. These shoe choices are inspired by Italian style.
For women:
- Loafers
- Round toe flats
- Mary jane shoes
- Pointed flats
- Oxford shoes
- Heeled sandals
- Slingback shoes
- Heeled pumps
- Flat boots
- Heeled boots
For men:
- Slip on shoes (Tods style)
- Loafers (even Gommino style)
- Oxfords and other similar leather shoes
- Leather boots
These All Count As Tailored Pieces!
In case you are wondering, these pieces can all be classified as tailored.
- Blazer
- Button up shirt
- A high quality well fitted knitted top (like a cashmere crew neck or a roll neck)
- Tailored trousers
- Tailored jeans
- Tailored skirt
- Tailored coat or outerwear (trench coat, cropped blazer, mac coat, belted coat)
- Blouse
- Tailored dress
- Tailored vest/waistcoat
- Tailored shorts (longer, bermuda-style)
You are likely thinking but what does a tailored trousers mean? Or when is a pair of trousers considered tailored and when not?
Let me explain it simply.
A pair of leggings or joggers are not tailored. They are either too tight or too slouchy. They also have a very relaxed waistline and other details that add to that appearance.
Instead, a pair of tailored pants first and foremost must fit you well. It’s neither tight nor too loose. It has a structured appearance, falls nicely, is the perfect length for your height and shoes.
That holds for jeans and also skirts. A mini skirt could be part of a tailored outfit, only when worn tastefully, and in the right proportions to your body type and height as well as the rest of the outfit. Whereas an A line midi skirt will likely always contribute to creating a tailored outfit.
For dresses, both the style and the fabric, but also the color or pattern can contribute to whether a dress feels tailored or not.
A suit dress — usually a sheath or shift style — is the most tailored type of dress you could wear. To give it the most formal look you would pair it with the matching suit jacket and a very classic pair of shoes.
But you could equally wear it with a different colored blazer and shoes to achieve an elegant spezzato look. You could also layer it under a trench coat and pair it with feminine slingback shoes for a classic tailored yet feminine style.
Here’s a list of tailored clothing pieces for men:
- High quality knitwear
- Structured polo shirts
- Turleneck knits
- Tailored jeans
- Tailored chinos
- Tailored trousers
- Button up shirts
- Blazers
- Tailored vests/waistcoats
- Trench Coat, Mac Coats, Tailored Coats
- Tailored jackets (even bomber style, if it has the right fabric, color and fits well)
Italian-Style Tailored Outfit Formulas To Know
Before I end this post, I’d like to leave you with a few Italian-style tailored outfit formulas.
Don’t worry though. You have plenty of Italian tailored style outfits examples on my blog. I will make sure to link a few posts for your reference.
Tailored outfit ideas for women:
- Tailored trousers + button up + loafers + over the shoulder sweater (you could also skip the latter or replace it with a scarf)
- A line midi skirt + button up shirt or tailored tshirt/knit + loafers/flats/mary jane/heels
- Tailored jeans + button up + coat/blazer + boots/tailored shoes
- Tailored dress + mary jane shoes/flats
- Tailored shorts + button up shirt + loafers/heeled sandals
I have given you a mix of outfit ideas that includes very classic Italian outfit formulas I always mention, as well as a few others that you might not think about for specific seasons.
You’ll also likely notice that all these outfits stand around the middle of the tailored style spectrum. They are neither too casual nor too formal, which makes them perfect for most people.
Here are the outfit examples in pictures.
Now, let’s do the same for men.
Tailored outfit ideas or men:
- Tailored trousers + loafers + tailored knit or tshirt
- Tailored chinos + loafers or slip on shoes + tailored polo shirt
- Tailored jeans + button up + blazer + loafers/slip on
- Tailored trousers + button up shirt + tailored bomber style jacket + loafers
- Tailored chinos + tailored shirt + tailored knit + tailored shoes of your choice
Here are the images for those tailored outfit formulas.
More Tailored Style Inspiration
Did you enjoy this read?
If so, please give it a heart and share it with a friend who needs the fashion inspiration to elevate her or his wardrobe.
I think you will love these other reads, as they are related to tailored style:
Understand These To Master Italian Style
Italian Style: 20 Clothing Pieces Your Wardrobe Needs
Blazer Outfits For Women
Wide Leg Pants Outfits
Men Jeans Outfits (including tailored style ones)
Timeless Italian Gentleman Outfits
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A presto,
Alessia
