Everyone wears loafers, but few syle mens loafers quite like an Italian man. And if you’re here, you’re probably looking for that same effortless balance between polished and relaxed.
Great loafer outfits come down to the details. In this guide, we’ll look at how Italian men style loafers by answering the most common questions and sharing outfit ideas you can recreate yourself.
Table of Contents
PS: This post includes affiliate links. If you click and purchase, I may receive a small commission at no extra cost to you. I only recommend products I have or would personally buy.
How To Style Mens Loafers Like An Italian
Firstly, if you’re just starting the process of rehauling your wardrobe to build a more timeless collection of clothes that help you dress better, keep these in mind.
It’s absolutely ok to look at outfit ideas on Pinterest and be inspired so much to want to shop and recreate them, but not everyone feels comfortable taking a deep dive. The simpler approach is to look at these loafer outfits and spot the ones that fit your current style and the clothing pieces you already own, even if in different colors and fabrics.
That makes recreating outfits so much easier because all you might need to buy is a new pair of loafers and maybe another piece to complete the look. Of course, with time, you can swap and elevate your current pieces, and introduce new pieces to recreate even more outfit ideas.
My tip is to take it at your own pace, to use the inspiration in a way that works with your life, your budget and time.
Now, we can look at more practical tips, starting with answering some questions you might have around styling loafers. I will be inserting the outfit ideas to support my answers.
Do Italian men wear loafers all year round?
Yes and no. Italians, especially Milanese and other Italian men who love dressing well, like to build a robust wardrobe with multiple clothing and shoe options. There are definitely certain pieces that can work all year round, like a good pair of oxford shoes, or a classic white button down shirt. Loafers are not necessarily one of those.
Most Italians wear loafers from late Spring to early Fall, so throughout all seasons except for Winter. There might be some exceptions, especially if you move further South, where winters are milder than in Milan.
How do Italian men style loafers?
If we’re talking about the dressiness of an outfit, Italian men like to wear loafers with anything from casual to very smart, including suits.
To be more specific, here are the 10 most popular outfit formulas Italians wear with loafers.
1. Tailored trousers and shirt tucked in (smart)
Shop Black Men Loafers
2. Suits (to dress them slightly down but also add more personality)
3. Spezzato outfits (where they mix tailored trousers and blazers in different colors, fabrics, or prints)
4. With more casual pants and a shirt, think chinos or jeans.
5. With roll necks and a blazer in Fall and mild Winters.
Shop Brown Men’s Loafers
6. With coats and mac coats, but they usually wear a matching sock.
7. With polo neck shirts and long sleeved tops, for a more casual look (the Italian kind of casual).
Shop Men’s Suede Loafers
8. With a shirt worn untucked for warmer, more relaxed days.
9. With linen in the warmer months.
10. With shorts in Summer. You can see many short and loafer outfits here: Shorts Outfits For Men
What style of loafers goes best with Italian outfits?
There are multiple ones but I’d group them in these categories:
- The classic leather loafer (with horsebit or without)
- Suede loafers ranging from more casual to smarter
- Gommino loafer
- Boat shoe loafer
- Venetian loafers (inspired by the Friulane shoes)
- Tod style slip on loafers
- Tassel loafers
You can have multiple styles mixed into one, like a Venetian loafer in suede and with tassels.
How do you know which loafer style to pick for your outfit?
It all really depends on two things: the vibe of the outfit (is it smart, casual, smart casual?) and your personal style (classic timeless, cool modern, a little quirky, etc).
If you don’t know where to start, the best is to look at the type of loafers you’re naturally drawn to. It usually means you like those loafers, and the style of the outfit too. Start there.
Once you’re ready to make your loafers feel even more like you, you can go in stores and try multiple styles on. You don’t have to purchase them in the store, if you don’t want to. This exercise will give you an idea of the type of styles that go best with the outfits you wear. Ideally, take your partner or a friend with you, so you can have a second option, and repeat this multiple times, so you can do it with different outfits and throughout different seasons. Take this as a fun learning experience to refine your personal style even further.
If you want an answer, here are my general recommendations for different types of personal styles:
- Casual: go for the slip on casual loafer for everyday wear
- Timeless classic: go for the classic leather loafer, preferably with no tassels or horsebit
- Somewhere in between: go for the gommino loafer
- Old money style: go for designer suede and leather loafers
- Coastal style: pick the boat shoe loafer for Spring and Summer
- Quirky: try the Venetian loafer in suede and with tassels, even better if in a fun color.
- Modern, Milanese cool man: opt for black chunkier loafers
Should trousers be cropped when wearing loafers?
Yes, if you’re going for a true Italian style. Having said that, nothing stops you from recreating an Italian outfit but skipping the crop. It just means you made that outfit yours. Of course, there might be cases where it might work and others not so much, but you can be the judge.
Should you wear loafers with socks or no socks?
It really depends on many factors, mainly these:
- The season
- The outfit style
- Your personal style
- The type of loafer
Here are some general guidelines based on how most Italian men do it:
1. If it’s chilly (end of Fall, early Spring, or Winter), definitely wear a sock.
2. If your style is a timeless classic, wearing socks might make more sense, but it’s not a hard rule.
3. If you’re leaning towards a dapper Italian man with a touch of modern, try no socks, only when the season allows it. It’s not just about being cold, it’s especially about looking appropriately dressed for the season. This is something very important in Italy.
4. Boat shoes, gommino styles, and slip on loafers look better without socks.
What socks should you wear with your loafers?
You really have two options.
You either match the socks to your loafers, or you don’t.
But in between the two extremes there are many possibilities. Let’s talk about them.
Let’s say your loafers are brown, you can either go matchy matchy, or you can choose a shade that’s slightly lighter or darker, but still goes with the entire outfit. Italian men usually prefer the latter.
If you want to wear a fun sock, it needs to make sense with your outfit’s color palette, unless you’re going for a maximalist style (in case you don’t know, the latter is about mixing and matching bold color and pattern choices).
Here’s how Italians do it:
If their outfit is monochrome or fairly tonal, they will introduce a pop of color with the sock, and the sock will most likely have a classic print, which means multiple subtle colors.
For outfits that have a lot of color going on, they will choose a sock that includes a print and colors, but the sock colors should match the outfit’s palette, bringing harmony without looking too matchy matchy.
More Italian Men Style Guides
There you have it, 21 real Italian men outfits spotted in Milan throughout the seasons. I hope you’ve found all the answers and ideas you were looking for, and a couple looks to recreate.
Don’t forget you can shop for similar loafers through my recommendations. I put a lot of time and care in picking the same quality ones I would order for my husband.
Please like and share this with your community. It’s the best way for you to support my work.
You’re welcome to join my Italian newsletter – Buona Settimana. I send one email every Sunday, chatting about life, fashion, travel and food. Join through one of the boxes on this page.
Find more Italian men style inspiration here (including more loafer outfits:
Fall Outfits For Men You’ll See In Milan
Men’s Jeans Outfits Italians Actually Wear
Man White Tshirt Style: The Milanese Way
Men’s Wedding Guest Outfits (including a few with loafers)
Italian Men’s Haircuts: 12 Looks That Never Go Out Of Style
Italian Outfits For Men That Always Look Good
Men Spring Outfits To Upgrade Your Style
Shorts Outfits For Men: How To Wear Them Like An Italian
Thank you for reading.
A presto,
Alessia
