Fall Office Outfits That Aren't Basic: The Milan Way

If you love the cosy season, you’ve probably already started daydreaming about it, (even if Summer has just begun!). I sure am, especially during this unbearable heatwave we’re having in Europe.

Since you’re here, I’m guessing you’ve moved past daydreaming and into planning mode. This post is part of my Easing Into Fall series. I’ll link the rest at the end, including the early fall outfit post if you want to start there instead.

Today we’re talking mid-fall office outfits, straight from the streets of Milan. If you like practicality and style combined, you’ll love this one.

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.

The Fall Office Outfits Worth Copying This Season

As most of our day is spent at work, it makes sense to start looking at work outfit ideas for fall. It’s actually useful and helps us plan and organize for the season ahead, but it also puts us in fall mode. Is that your excuse too?

The obvious question is what do we wear to work when the weather suddenly shifts from end of summer/early fall to really nippy, but not quite winter mode?

You likely want something that includes a light to medium-thick outer layer that keeps you warm until you get to the office, but still looks really nice when you remove that outer layer. In some cases, you might even decide to keep that layer on.

I have the perfect mix of outfits that deliver on all of that.

Note: these are not basic work outfits; you’ll find plenty of that on Pinterest.

These are real ways to elevate your work dressing this season. And since no other city does fall outfits and work outfits better than Milan, no wonder they are so good!

As we look at them, we’ll also chat about the elements of Italian style we can recognize, and practical tips on how to dress that way without the overwhelm.

Remember this: dressing better doesn’t happen overnight; it slowly builds up as you take one step after another, starting with inspiration and following with lots of practice, trial and error, and most importantly taking the time to look in the mirror and understand what you like and don’t. Enjoy the journey.

Enough chit chatting, let’s see them!

Blazer Office Outfits For Fall

You know Italians love showing a little ankle, a little arm. It adds visual interest, and makes your clothing highlight your body in an elegant way, rather than completely covering it. This first outfit is a great example.

This outfit is basically telling this: I’m not ready to hide my legs. I might do it later in Winter, and why not take the opportunity to wear those beautiful ankle strap flats I own?

The rest is really basic tailoring, and a nice cool toned color palette that doesn’t feel obnoxiously autumnal.

The straight lines, simple layers, make this fairly minimalist but with a bit of color.

This is my kind of outfit, not just for work.

If you like the idea of cropped pants this fall, try cropped wide leg ones. They are sort of tailored culottes. I love how this woman is styling them. The color palette is introducing a second fall color – mustard, but the grey does two things: it adds that office feel and it balances the entire palette.

This next outfit might scream more Spring than fall because of the light grey blue shade and the slingbacks. Yet, it gives us the perfect way to show some ankle while wearing a suit for work in fall. After all, not everyone can wear the standard warm-toned fall colors! What about you? Do you know your color season?

Read this if you don’t: Simplified Color Analysis For Clothes + Steps To Do Yours

Shop similar suit here

Don’t worry, I’m not saying you can’t wear brown. You just need to make sure you’re wearing the right shade.

Speaking of brown, here’s a tone that’s perfect if you’re a Winter season like me. This outfit also showcases how to combine fall colors and pastels, in case that’s your thing.

Did you notice that’s a romper? If you have plenty of tailored Summer playsuits, you can wear them for work under a blazer in October, even November. You might need a layer underneath once it starts to get colder.

In case you haven’t noticed it yet, all the outfits I have showed you so far are blazer outfits. There’s nothing better than wearing a blazer to work from the end of September. Even if your November weather requires a coat, you can always layer a light one over these blazer outfits. The Milanese do it all the time.

The next blazer outfit is taking black and white to a whole new level, by simply introducing a lot of green. It’s a lot because the woman is tall, and trousers take up a lot of visual space in an outfit. It’s the kind of green you would wear in autumn and winter as opposed to a khaki that’s more Summery.

Browse The Italian Blazers Edit

The next two blazer outfits are very similar, even though I spotted them on two different women. What does that tell you? This outfit combo is really loved by Italian women, especially this time of the year, and I can attest to that. If you’ve read my newsletters you’ve seen me share my black outfits with a mocha blazer. I usually pair mine with pants, but I really love how it looks with a midi skirt.

The slit might not be for every workplace but it definitely adds style. Alternatively, you could opt for a classic black pencil skirt with a smaller slit at the back.

Which one would you wear?

I like the both, but my style gravitates towards the first – more minimal.

Here’s the final fall work outfit featuring a blazer. This one is introducing boots, which is definitely a smart move when it starts getting colder but you’re not ready to wear a coat. It brings in both the warmth and a seasonal shift.

Layering the blazer over the shoulder is both practical if you’re just stepping out of the office to take a short break, and maybe an espresso. And it obviously adds a lot of style.

The dress gathered fabric at the centre, near the tummy area, is genius! Not only does it make the outfit more interesting but it also helps hide any bloating. Most importantly, it makes your outfit uniquely yours, even if someone else is pairing a similar blazer with a similar colored dress. Yours feels different because of that design detail and the boots pairing.

This is how you elevate/make your fall office outfits, and any other seasonal work outfit, not boring.

You take classic pieces that anyone would wear for work, and you style it your way, making sure you’re using your best colors, and working with your body shape and height.

For some women it might be contrasting colors, like the pink and brown outfit.
For others, it might involve adding a little sensuality with the cropped pant.
Or you might put a lot of focus on your shoes, like outfit one and the suit I’ve shared.
We’ve mentioned playing with design details and layering (the boots does the layering).

Of course, you don’t have to stick to just one. It all depends on your style, the occasion, and the starting pieces.

Italian-Style Work Outfits With Trench Coats & Longer Jackets

Whether you’re simply shifting from a blazer to a longer light coat option, or want to layer something on your blazer, these outfits are a great starting point.

The first one is a longer blazer, but it could also be a short light coat.

Introducing leather is a smart move for fall, even for the office; this woman combined the leather with a very seasonal color like burgundy, which makes it even more perfect. And we can still see the ankle crop that Italians love so much.

By adding the black coat and shoes, the outfit immediately feels more dressy (almost serious) and office appropriate.

Remember that skirt outfit with the taupe blazer we saw styled two ways? This almost feels like the long coat version, and it’s as gorgeous. It feels considered, tailored, but not too officey.

I found a similar trench coat here

Do you prefer bolder colors? If so, here’s an idea for fall.

This is also bolder in style. It feels masculine, like the woman is not afraid of that. Her femininity comes through her personality. The cinching and the scarf help too. That’s a different way to make an outfit feel yours.

See a similar trench coat here

Or perhaps, your way to make your office outfits less basic could be by adding a little edge with a tailored longer leather jacket like this one..

And if you’re thinking, do I really have to make all this effort for work?

Yes and no. It depends on what you want, how you want to feel, and your style.

Here are two simpler outfits that don’t scream, they’re neither too masculine nor too edgy. But they are still gorgeous, not basic.

If that’s your style, more minimal and classic, lean on it.

Even if they feel more classic, I can still spot a unique element in each. Can you?

Looking For A Brown Trench Coat?

Outfit 1: the suede effect grey trench coat is not your usual beige one. That makes it stand out from a crowd with beige trench coats.

Outfit 2: the taupy greeny brown suede pumps bring much more personality than a simple beige or brown shoe would. But if your style features more loafers, that could have well been a pair of loafers with a higher ankle crop.

Think this way:
You do you is the main message here, but doing you is not copying the same exact outfit you saved. Even if you start there as you try it on, think what can I change to make it feel like completely mine?

Fall Office Outfits That Aren’t Basic: The Milan Way

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