One of the things I enjoy most about Permanent Style is the comments from readers. 

It’s like each article is a new thread in a forum, with subject raised and then comments, experiences and questions all following, vastly enriching the article’s value. 

Over half of comments are on old articles – posted more than a year ago – which really shows how much a body of information is being built up. 

However, one disadvantage is that the comments are not very dynamic. The format limits the amount of back-and-forth that’s possible. 

So as a way to counter this, I thought I’d try a series of videos where a friend – Aleks Cvetkovic, founder of the podcast HandCut Radio – picks out some popular reader questions, and then we dig into them for 15 or 20 minutes. 

The result, I think, is a deeper and more dynamic exploration of the topic. 

This is our first one, where we talk about that old chestnut: dressing up in a dress-down office. Of course, few people are in their offices right now, around the world, but the advice applies to any situation where you want to appear a little more put-together, without wearing tailoring.

I hope you enjoy it.



Our main points are captioned during the video. But for those reading this before diving into the film, they are:

‘How can I dress up in a dress-down office?’

1: Upgrade quality, focus on cut

2: Play around with trousers

3: Wear non-corporate colours, like brown

4: Wear an unstructured jacket or overshirt

5: Upgrade your T-shirt or knitwear to a finer version

6: Think about details, like the shirt collar

7: Trousers and shirts can be dressed up or down

8: Dress down anything worn under a jacket 

Other videos we’ve produced recently are (also all on the YouTube channel):

Clothing shown:

  • On me: White Bryceland’s Sawtooth shirt, under bespoke Loro Piana oatmeal-cashmere jacket by Elia Caliendo
  • On Aleks: John Smedley merino mockneck, under double-breasted Offshore Bespoke suit by Edward Sexton, in Holland & Sherry 16oz corduroy
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Very nice discussion, thanks! A few slightly related questions:

1. How do you like the white sawtooth shirt? I’ve the denim one and I’m considering this one as well.

2. Also, saw your IG post with Brycelands chore coat. What do you think of it?

3. Is your live IG video with Ethan going to be available to watch?



Oooh like the concept of short chats! What’s your view on tebas, Simon? They seem like a great halfway house to me.



I have one in a green linen which I love. I find the lapels remind me of a shawl collar on a cardigan.

Ricky Takhar


Great topic, and superb production quality.
To further this point, would be great if you took an item of clothing and showed different looks depending on its formality, say an Oxford shirt at the lower end with jeans or at the upper end with a jacket and tie.

Or a navy polo/ crewneck. Potentially a specific jacket etc. You might have this covered in other posts

Ricky Takhar

Thanks Simon,

Yes I had read those previously and did think that it was mostly covered. I must say I find this articles mostly useful, without being at the level of full bespoke and general high end I find the concepts can be applied to MTM/ mid tier.

The valstarino post was another favourite, and sort of what I was getting at. This could maybe be applied to a piece of knitwear you enjoy or find particularly transcends formal and casual. A lookbook style post if you will

Again it might seem redundant with the posts you mentioned.


When you say “think about the collar” what do you mean? It wasn’t too clear in the video what sort of collar is more suited to casual dress. Have you written a related article to could point me towards?

Many thanks


Have you any advice on face coverings.
Surely all of our sartorial efforts will come to nought if we are obliged to sally forth with one of those surgical jobs disfiguring us ?
Which flaneur would want to admire himself in a shop window swathed in PPE ?
Surely this is a time to relaunch your PS/Begg & Co neckerchief in a new range of colours ?
Or, perhaps Ethan can get us something knocked up with more of a cowboy feel to it ?
In any event we need to move quick because I’m not going out dressed as Doctor Kildare !

Tim Cooper

I very much enjoyed the video discussion! Thank you.

A topic I would like covered (and maybe you have previously) is discovering great, affordable casual trousers. What to look for and where to find them.

Thank you!

R Abbott

Another option for dressing down is to wear a casual tie over a casual shirt. Eg, pair a denim or OCBD shirt with a wool tie, or a chambray or linen shirt with a linen or cotton tie.

Il vecchio

How do you access Ethan interview. Sorry to be so inept.


This was an excellent discussion and format. The conversation concerning pants and shirt collars was particularly useful.


What brands of t-shirts would you recommend for wearing under a tailored/unstructured jacket?



Simon, I wonder what your views are on tucking in fine knitwear. I can see that tucking in changes the formality of an outfit and so I probably shouldn’t tuck in with denim, but should when wearing fine knitwear with a suit. Any thoughts?

I was prompted by these images from Jigsaw, which show both:


Hey Simon,
Hope you and your family are safe & sound.
Quick one for more casual environments (t-shirt, jeans etc.): what’s your view regarding having shirts made which can be worn un-tucked? (i.e. oxford, Mao collar, denims just worn loosely?)


What if you’ve fallen prey to the dreaded Lockdown Gut?


I have two (quality) linen shirts that I found on sale when I was looking for cheap summer shirts to wear with shorts. They are actually one size too small but the result is that they are quite slim fitting and too short to tuck in (but not THAT short). With the sleeves rolled up they work quite well as casual wear. One has a button-down collar and the other a Mao collar.


I tend to manage the problem of formality by added or removing layers throughout the day. I enjoy traveling to the office fully dressed up but I bring a knit in my bag. For everyday working groups I remove the jacket and tie and put on the knit. Then for formal meetings I put back on the tie and jacket, subject to not being more dressed up than my boss!


Bang on commentary Simon and thanks for the entertaining video.

In today’s climate, do you think it is OK to wear a polo shirt untucked from my chinos, or should I tuck it in? Equally, if I pop a Blazer over the polo, should it then definitely be tucked in?

And what is your view on rolling up the sleeves of a formal shirt in the office?



Aleks did a good job on the video but he should be forbidden from wearing a mockneck on future shoots. It is a sartorial faux pas of gigantesque proportions.
Back to face coverings – I see it as an opportunity.
Personally I will be modelling my bespoke polka dot wispy cashmere Begg & Co neckerchief. The super fine weave my not keep the virus out but I’ll go down looking good.
If Ethan is up for it, he could perhaps do a Bryceland’s / Begg & Co JV that has a Roy Rogers aesthetic to it. Something we can wear with our Saw Tooth denim shirts and workwear.
We have to think positive and look for opportunities.
I don’t think there are going to be too many tailors flying around the globe in the new normal. Our sartorial supply chains will need to be short.
How should us flaneurs prepare ?


Simon I haven’t been able to see any of your instagram livestream videos after it’s been aired, and it’s not there before the 24 hour expiration…


I’m commenting right now just after the Urban Composition live stream.

I saw the last 20 mins of the live stream, but after the talk it’s no longer on anyone’s story or profile page. Maybe it’s an instagram thing and you just have to show up for the live session.


Simon you did not mention shoes! Nice shoes are incredibly satisfactory in a casual environment. Also, no one will notice that that is the case, something that I personally enjoy.


I am a partner in several small businesses. The dress code is what I would call “mow the yard attire” or maybe “golfing dress”. I don’t care! I’m a well dressed man. Ample collars, 9X160 cm ties, Pini Parma, Chritopher Korey “my favorite right now”, Cucinelli, Tom Ford and Articles of Style. I’ve dressed my entire life and growing up in small town Oklahoma I took plenty of shit! My wife even says she loves how I look but it can be exhausting trying to keep up. I don’t care! It’s me and it’s what I love! I guess I’m a modern day hippy!! LOL


Well done sir and my compliments! It takes a real man to go against the tide of sloppiness and poor taste so prevalent in these United States and elsewhere.


Hi Simon,
This is a useful post. Personally, I would have liked to see your inputs based on your understanding of levels of formality. Which ones are you assuming here?
By the way, two US retails have filed for bankrupcy this week: J. Crew and Neiman Marcus. What does that signal to you and PS readers? Isn’t it time to devote an entire post on the stakes and implications involved in this alarming process?


What do you mean by “we” Simon? Isn’t it just you who plans and writes?

Maybe covid-19 will encourage people to buy less, in better quality. These large companies have always been about overproduction.

Of course it’s bad that companies will have to fire thousands of workers, but I think the bankruptcies demonstrate that the quantity/consumerist model will not cut it in these times.

Perhaps it’ll show us an alternative way of buying clothes? Is that outlook too optimistic? What do you think?


Definitely will look out for it. I’m not just referencing people who buy cheap brands but also plenty of menswear guys who buy too much.


The video needs some stills, Simon, showing examples of well cut trousers, over shirts etc. These would clarify what is being discussed and add interest. I presume this was recorded before we were all advised not to breathe over each other?


And as for rolling sleeves – chaps roll them to below the elbow, blokes roll them above.


Can you recommend any blue cotton jackets? I think this is a staple missing from my wardrobe that would add a smartness without feeling overly formal.


Do you mean the hopsack blazer Simon?


Hi Simon, there’s a lot of focus on layering, knitwear and what to wear under jackets etc but in reality many offices are pretty warm and it’s uncomfortable to wear layers. As you recently commented, bold striped shirts are nice under a jacket but not so great on their own. There’s nothing that stands out more than an uncomfortably layered person in a warm office when everyone else is simply wearing a shirt. The advice on trousers and short collars still highly relevant though


Hello Simon, Thanks for the post. Its a good idea since a lot of people who like tailoring struggle with this.

I do have to say, the group of people where I’m in, friends, colleagues ect… They are so casual that anything different from wearing jeans or just looking like you took some effort in going to make you stand out. So, playing with all those details has it limits.

I’m not saying these are not good ideas or tips, they are great and fun to play with if you like clothing. But in my case it doesn’t matter because it’s just extremely casual all the time. Doesn’t matter what kind of shirt color or flannel you are wearing, it’s al super formal in there eyes.. It just one step away from sweatpants… 🙁


Excellent post.

I’d quite like to add another problem on this topic for your thoughts.

Suit Jackets have always been a huge struggle for me to get a good fit. Off the peg is never an option for me due to my shape (larger shoulders, chest and back built from my sporting endeavours). As such, bespoke has always been the only option, and from winter to summer, due to changes in training, my shape can also fluctuate a little.

I don’t need to to be “suited and booted” for my line of work, but more formality in a casual way would suit it very well.

I’ve been considering the waistcoat as an alternative to a jacket but have also been second guessing this and also wondering what my options are in terms of what I can pair it with.

Are you able to possibly share any thoughts red my jacket problem and your expertise/thoughts on the waistcoat question?

Many thanks


It always seems to be the approach of having to follow. Never to lead. The background apparently is ‘I would love to dress up but everyone else around doesn’t so I have to look for ways to blend in’. What if you are senior in a job position where you can afford to go by your own preference? I think the approach might be then to dress up in a way that does not leave the dress downers too obviously far away. So maybe yes to the suit, not in hard worsteds but in more playful, comfortable or countryfied variants, like woolen PoWs or windowpanes.
Since I am not in a strictly urban environment I have half a mind to go for tweed suits in such patterns.

Tim Horton

Roll neck sweater under a sports coat or suit jacket is an easy and timeless look. Black, navy, cream, dark green, french blue…


Hi Simon,
In a complete capsule wardrobe, you talked about getting natural shoulder jackets. In this video, you talk about wearing unstructured jackets.

I was wondering what the difference is between the different styles of jackets and if you find that someone could wear a natural shoulder jacket.


Hello sir ! Form the bottom of my heart ur the best dressed gentleman I’ve ever seen!

Just got my first bespoke piece yesterday .It’s a Chester coat (3.75inch wide notch lapel ,single breasted,w/ charcoal gray Zegna cashmere fabric). But sadly ,currently most of my jacket are still designers ?like YSL Thom Browne etc.

But the more I dressed toward the classic man style, I felt a little bit ,actually a lot of uncertainties. As a 19 year old most of my friends are still in big Gucci and LV logo T-shirt. So I found my self so hard to blend in to most of my friends and people around me even wearing sport coat and shirt?

I felt like I’m in a EXTREMELY dressed down environment ?
If I can have ur opinion on this ,it will mean the whole world to me???
Have a nice day!

Btw picture below is my normal daily style