How I organise outfits – and get my style inspiration

Wednesday, January 3rd 2024
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I know I spend too much time looking at clothes I want, and not enough at ways to wear the ones I have. 

There are many reasons for this. There’s the familiar retail fix, the fact I wear a range of styles, the fact that I can afford them (and remember vividly the years I couldn’t). And on top of all that, the fact I can justify it because covering menswear is my job. 

But I’m aware of this, and I’ve recently been trying to spend more time with my existing wardrobe - taking style inspiration from books, from Instagram, from friends, and then organising outfits so I can remember them in the future. 

This last bit of organisation is particularly useful when the seasons change. Suddenly it’s hot again; the olive-linen overshirt comes out of the wardrobe; but I can’t quite remember what I really enjoyed wearing it with last summer. 

Instagram is great for inspiration, given the range of people and accounts. It’s not quite as good as Tumblr used to be, in my book, but there’s no shortage of imagery. 

A problem is that once you’ve saved images you like, they’re not easy to download and organise. What I tend to do is dip into my saved images - using it more like a filtered feed - and then organise my outfits that come out of it.

So I’ll find an image I like that relates to clothes I have - perhaps a pale-green gilet worn with a white T-shirt and chinos - and then try it out. I have a gilet in a similar colour from Rocky Mountain but usually wear it with blue jeans. So I’ll try it with the tee and chinos and, if I like the result, snap a selfie and save it in an ‘Outfits’ folder on my phone (above).

Sometimes, I won’t like the result. Sometimes I’ll play around with other options, but it still won’t work. That’s fine, the outfit just doesn’t get saved - the folder is one more filter on the world of inspiration: a set of looks I know works and I can reach for any time I need it.

A few years ago, I then categorised this folder according to formality and to an extent by weather (there is a separate ‘summer’ category; there should be a rainwear one). 

You can see my categories above. Casual jackets has proved to be the most wide-ranging category, and that has been further broken down (second image). 

The first time I did this it took hours. In fact, the first time I did it I categorised everything during time off at Christmas, backed it up on iCloud, and then found it had been deleted when I ran out of space. 

That won’t happen again - the folder is on my laptop, on my back-up hard drive, and on Google Drive. I tend to download a new set of images and categorise them every six months (a season). The only pain is when I realise I really need a new category (the aforementioned rain one) and that requires going through all 1467 images. 

But it’s so worth it. When the weather turned cold a couple of weeks ago I started going into my Overcoats folder and reminding myself of new looks I really liked - my Ciardi coat with black for instance (the taupe is dark and muted enough) or my Chapal leather jacket with the Adret knit (short enough to work with that rather short jacket). 

As I said, I only need this because I have a lot of clothes, but it is satisfying making full use of them - every browse is a reminder of a great piece I have neglected (eg my hand-dyed Mandarin jacket, below) as well as an outfit. 

I also work hard to keep all my inspiration images in one place. 

So often I’ll be in Ralph Lauren and see a great look on a mannequin - that will be snapped on my phone, but then get put in a Google Drive folder. Sometimes I take a screenshot of something on my phone or computer - that goes in the same place. 

Even that annoying thing on Instagram when you like the second image in a post but hitting ‘save’ gives you the first one too: then I take a screenshot of the second image and put it in the folder. 

Pinterest is something I’ve started using a lot more in the past year, simply because I found more inspiration images there. It tends to work more with archive pictures than new ones too, which with classic menswear is an advantage. 

But there’s no easy way to get decent-sized images downloaded as far as I know (if a reader does know, do shout) so this has become my third inspiration folder (Instagram, Pinterest, Drive). 

Organising outfits like this has had so many knock-on benefits. 

It’s helped me identify tendencies in how I dress. An early example was our ‘Cap and cordovan, felt and suede’ article, which came out of me realising I nearly always dressed in one of those two for the rain. 

Another, more comprehensive example was the ‘Three wardrobes’ article about my working week (above). Not only did that help my identify a tendency, but it gave me a starting point any day depending on what I was doing. I don’t always stick to it, but it’s always nice to have a default. 

These are also benefits for the blog of course, and hopefully they’re of use to readers. The other clear benefit for the blog is that we’ll soon have the entire Lookbook page (below) categorised based on similar ideas of formality and weather - which readers have asked for in the past. 

My system will necessarily be more wide-ranging and complicated than anyone else’s. But if you have any suggestions, or methods you’ve found helpful, please do let us all know. 

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Andrew Tait

Interesting approach. I sense I need an extra tag on “things I liked wearing but are too small now but have archived for when that day may return”
Have you any thoughts on those wardrobe apps used for women’s clothing? The functionalities look interesting but I don’t know how applicable to men’s clothing they are
Examples in link


I have tried a bunch of those apps and fell for Stylebook for its focus on the clothes. Most of those apps try to build some sort of social feed into the apps which I was not interested in. Stylebook has one app for women and one for men but the only difference from what I saw was that the interface in the women’s app was in lavendel and the men’s app was black (because of stereotypes?)

So anyway, I was attracted to the idea of documenting what I was wearing the most or the least so that I could use more of my closet, or get rid of those garments that didn’t appeal to me any longer.

It also has this outfit feature, where you can compose outfits from your wardrobe. 

To make it work you obviously have to add and take pictures of every single garment you own (or as I did, downloaded similar items from the web to minimize the hassle of taking clear pictures and removing the background.) That took a while.

Because the Outfit part was folder-based and not tag-based, there was only one way to categorize your outfits, without duplicating the outfits over and over. I went for a casual to smart scale. That setup turned up too limited and I didn’t really use it. Also, it’s hard to get a sense of how something will look based on a small picture on your phone. Navy, black, and charcoal pretty much look the same on the phone, you lose the sense of thickness and texture and the whole thing became too abstract.

All in all, it was fun and interesting to see what I wore for 2–3 months, and led to some insights, but since then I have not used it. Now, I only store outfit ideas I come across in my Notes app, categorized by color. It’s not optimal but I haven’t found any decent tag-based image organizers that could work on my computer or phone yet.


I don’t think I would ever go in such an extensive reflexion on outfits, but I guess it’s worth it if you have so many clothes (as you do).
On another note, related to the last article and on appreciating your old clothes: do you still wear conservative tailoring you had made years ago (if you still fit in of course) as your style as evolved? My first thought goes to the RAF blue flannel suit, and the argument that bespoke is ‘supposed’ to last decades if the correct choices are made (argument to take with caution).

robert gault

A bespoke hat is always a good investment piece!

Daniel P

A very insightful piece. Wine and working around wine is the same. The discovery, the wanting, the buying, the collecting, the discussing. Then maybe some drinking if you can organise the occasion with a friend or 3. Last year I controlled myself to very little buying and as much enjoying as possible and it has been very rewarding. Sometimes you just need to have enough, not more.

Mary Parker

Interesting points Daniel. I don’t see wine and wardrobe as remotely connected. Fine wine is an investment but needs to be kept for many years before its value becomes clear. And it tends to increase in value as it becomes more scarce.
More ordinary wines are not the same, and in any event once you drink them they are gone.
Expensively crafted items of clothing are unlikely to increase significantly in value, and have the ability to be worn more than once.

Daniel P

Hi Mary – Simon’s point below re photography is what I was driving at. In addition, wine (whether fine (subjective) or not) is firstly a drink and then a hobby/interest. The investment part is an extremely small part of the market in terms of volume consumed and dare I say it, missing the point of a drink. And clothes, whether fine (subjective) or not, are firstly clothes and then a hobby/interest. In addition, we drink to feel good (subjective) and we dress to feel good (subjective.) So those are some of the similarities I was alluding too.

Simon Chambers

I think pretty much anything you’re passionate about is the same way. In photography, they talk about GAS (Gear Acquisition Syndrome) as people always want to buy new lenses, bodies, accessories, etc. I also buy more books than I ever have time to read. And I spend a lot of time looking at more clothes that I would love to have. Maybe it’s just me who has the problem… 🙂


If you have got a problem, I have the same one too! I tend to think of it as a hobby.

robert gault

I break it down to; there are two types of people, those with the genetic disposition to collecting and those that do not have it. I have the collectors gene….my wife does not. I have collections of; hats, jackets (leather & tweed), overcoats, shoes, boots, and mountain bikes. My wife has one or two of each (just one bike!) and just shakes her head at my acquisition syndrome(s).


Thank you Simon fot the nice article. Even though i save outfits in a similar way, i still face the problem when i wake up in the morning and i have no idea what to wear. Unless i prepare everyting the previous evening. Do you do that?


First thought is that this would be easier to do by adding searchable tags to photos. However I see that the system I use (Apple) only allows you to tag photos on a Mac not on your iPhone. Something like Evernote would probably work well.


Very interesting … I think I’m going to enjoy January’s PS .

My own personal view on clothes / ‘outfits’ is more to do with colour .
Shirts …white, blue, pink(ish)
Trousers…blue, brown, green
Woollens (jumpers etc)…a variety of colours

Playing with this palette means everything goes with everything .

Having said all that it’s so easy to grab the same old things casual things as it’s easier .
To overcome this I’ve now decided to have at least 3 ‘outfits’ that are ‘working outfits’ …ie worn for 2/3 weeks before being washed and then rotated for a different 3 ‘outfits’.
I’ve found this only becomes possible once the realisation dawns that one has so many trousers / shirts etc that have never seen the light of day !

The only things that don’t get enough (or any ) wear is jackets . Given the British weather I can cover the open chest of jackets with sweaters and scarfs but the unpredictable rain means I opt for a bog standard coat .

I think for most men organising their closet leads to better wearing of clothes .

P.S. Simon , you really should do a ‘daily mirror’ like Manish … maybe just for the whole of January .


The pale green gilet looks fantastic. If it was mine, I would try it first with ecru jeans and my grey PS t-shirt. The chinos in the picture are so bright, I don’t think you can just swap them for regular khaki. That’s why ecru would be my first try.

Thomas Gannon

I enjoyed the tiny photo of you wearing one shoe while the other is bare. It’s a great look

Zak Wagner

This is very cool. I don’t have enough clothes for this level of organization. But I do have folders of saved inspiration on Instagram. I broke it down by season but it is a disorganized mess. I like your screenshot idea. Then I could break it down in finer categories.
also, I look forward to the Permanent Style inspiration board.

Bob M

I use a system from the US Navy. Clothes are always Dress, Working, or Utility.
Dress of course, is jacketed: Suit, blazer with trousers, etc. Working is the daily personal uniform. For me, that’s chinos, chukka boots and a Harrington. But I can swap a sweater or another jacket if needed. Utility means jeans, work chinos, sneakers, and an overshirt and t shirt.
I use a color palette to keep everything in a system. So, get up … decide what level of formality, the weather and … go. Having 3-4 variations within each provides a lot of versatility. It also encourages me to wear more kinds of various clothes.
You don’t need an app. You just need an Excel sheet of all of your clothes and what type and it’s pretty easy. Some keep a log of date purchased and use it to replace clothes after some time.

Jasper Smit

I’m going to use this, great.


Hi Simon,
perhaps it’s not a question that is relevant on this site, but have you ever thought of writing about ski clothes? I think it’s pretty hard to find good looking ski clothes (alpine ski clothes). It would be wonderful with your expertise and thoughts how a man +40 years old 2023 could look good. 🙂

I myself struggle to find a good look on the slopes. Either you find very technical outfits from north face, arcteryx and so on or very new rich (in my opinion) Moncler and Fusalp outfits. I have an all black shell pant and jacket at the moment and the ones I found with smallest logos on. Not very satisified to be honest with this outfit but hard to find good ones…


Yes some content on classic golf style is sorely needed!


I guess vintage is the way to go, to look stylish on the slopes. And in the eighties / Nineties, it was already technical enough for a good day of skiing. For anything more adventurous, modern equipment will always be a safest options.


I have the same issue. There seems to be nothing in between Spyder/Descente/North Face and Loro Piana. It would already be great to have a skiing outfit without branding, but even that is very difficult to find.


I have the same struggle so an article on this topic would be much appreciated!!


Lodenwalker uses traditional cloths with modern style. Not sure that’s your taste but might be worth checking.
Other Austrian companies might also be suitable.


HI Stefan,
Nice observation on the two categories of ski gear.
You may want to have a look at Boston based Alps & Meters who I now understand sell in Harrods.
The founder started the company because he was on some European ski jaunt back in the day and was complemented everywhere he went in Europe about some old ski knit he picked up in Sweden.
Inspired by the workmanship he formed Alps & Meters as a nod to a bygone era of European ski attire and lifestyle.
I own four of their jumpers (You may need a VPN to access a larger selection of gear from the US) and an anorak and can attest to their durability. You will also note the overwhelming majority of people reviewing their gear on their website are 40+
They also used to do a podcast, (Designed by Tradition) the first episode provides some back story on them, the final one featured a very interesting American author who went to all the chalets in France and Italy gathering recipies for her cookbook.
Finally, they do organise a ski tour which you may want to dip your toe into.


So until I got to the paragraph with the link to the Lookbook, I was going to suggest you put together a physical Lookbook. My thoughts were that not only would it be helpful, but it could help generalize your organization system (seasons, or amount of sun, or temperature, etc). As someone who is exceptionally organized I find taking a step back and looking at the larger categories always helped me stop stressing about the finer details and provided an odd clarity for the detailed sorting problems I was struggling with.
That said, I think the Lookbook on PS is a better idea than a physical copy (I especially like the links to what is being worn). Perhaps a simple organization system for the Lookbook (or tags with sorting options) would help both readers and you find the organization that you intend?


I have Dymo tape labels on all my drawers; socks, pants, t shirts etc.
That way I always know where everything is.


It’s wonderful to discover our shared approach! In 2024, I’m aiming for a year of decluttering. I’m gearing up to make significant financial decisions that prioritise essentials over ego fulfilment. This shift means redirecting funds toward necessities rather than luxuries – even an extra pair of shoes feels like a luxury if it’s not an immediate necessity, regardless of the brand or level of extravagance.
I’ve embarked on a journey similar to yours last Spring, I started using Google Drive and it’s proven incredibly helpful!
Initially, I had some reservations about how you manage this space.
However, upon deeper reflection on my clothing inventory…I see that it all ties back to sustainability and accommodating diverse lifestyles.
While I might have been initially disappointed, I’ve come to understand that as readers, we aren’t you! Your principles resonate deeply with me, ones I’ve adhered to since high school – the philosophy of buying less but choosing better.
Taking stock of my clothing inventory I’ve realised that thanks to your work I possess a solid foundation of essentials alongside some ‘just in case’ items.
Now, with a decent buffer, I have plenty of combination i can rely on and through some symbols in my excel I know what works well with…despite I’ve shifted towards a more practical and easier to mix style I am sure my excel will be very useful in case I want to sell my clothes, making conscious choices.
I wanted to drop by and express my appreciation for what you do and the wisdom you impart. If I may offer my perspective, although it might not align completely with your editorial vision: let’s reinforce the idea that we, as readers, are not you!
It’s crucial to discern our style based on our unique financial situations, lifestyles, and self-confidence. That’s the crux of it, and making an inventory helps in getting there.
Wishing you and your Team an incredible 2024 ahead!

Seppo Taalasmaa

I’ve done something similar from time to time: I have images of most my pieces of clothing (or of something very similar) which allows me to visualize and come up with new outfit ideas by creating picture collages with a few mouse clicks, without actually having to wear them. I would suggest looking into some kind of photo management software (I use Google Picasa that hasn’t been updated in ages, so there could be something better available now) instead of organizing the pictures into folders in the cloud. With this kind of software you can more efficiently view, edit, tag and organize pictures in folders etc.


you should try to get the pinterest extension, so if you are using your Mac you can easily pin the Instagram ‘second’ photo persei. Another workaround to download a hi res off Insta is to right click image and choose “Inspect” then go to “Source” tab and under that tab you will be able to open just the photo you want and/or drag onto desktop

Peter Hall

I don’t go any further than having all my shirts on seperate hangers, knitwear in the middle ,on shelves , and then trousers on hangers .Sort of a logical ,Left centre,right formation. Underwear,, tees and vests colour coordinated in a drawer. My wife thinks it’s severe OCD, but I genuinely could not function having unstructured choices.

Shoes and outerwear weather dependent.

Initials CG

and now … I am convinced the next step is a personal valet!
Jeeves & Wooster on YouTube – better than porn…

Tommy Mack

Interesting idea. If I’m wearing a combination I particularly like I quite often send a photo to a mate of mine with a similar interest in menswear. I’ve often thought if I have a spare moment I’ll go back and organise those into a sort of personal lookbook. Fellow working dads will sympathize when I say that spare moment just hasn’t happened yet!


Your systems are not working because the results lack colour and imagination. The photos above confirm that you normally wear black, grey, brown, navy, denim, cream and white. There is no sign of red, pink, yellow, green (rather than olive), bright blue or purple.

It’s odd because you love Neapolitan clothing but have obviously rejected “sprezzatura” in favour of your systems. My advice is to free yourself from the tyranny of the internet and group think. Dress according to your own personality and tastes rather than those of others.


If memory serves me correctly, Simon has recently covered a purple real mccoys sweatshirt, a bright red american boy scout sweatshirt and a pink gab jacket.


Any chance you’d be willing to share some of your favorite (maybe top 15) Instagram accounts for style inspo? Or on your side is there just too many to really list?

Rubato and brycelands guys excluded, as they’re probably pretty obvious to regular readers.


Oh wow, I had forgotten about that one!

True, at this point I guess what I was suggesting would essentially be a part two of the article, in practice. But yes, excluding brands and people from the “dress like” series, as diligent readers should already of captured them.

Either way, if you think you have enough for an article, it would be a nice one for dry January!

Happy new year Simon


My style heroes Cary Grant, Fred Astaire, Gregory Peck, Steve McQueen, George Hamilton and Charlie Watts all dressed very stylishly without the help or guidance of social media.

Similarly, the internet has not changed my dressing habits over the last 40 years. I just look at the weather forecast, think about what I am doing and where I am going before choose an appropriate outfit.

Btw, I have never used Facebook, Twitter/X, Instagram or Tumblr. I use Opera and DuckDuckGo to avoid being tracked and censored by the Big Tech billionaires.


There’s an app called Stylebook that I use for this. It’s available to download on your phone for free. Once you upload photos of individual clothing to it you can create tags for each individual piece of clothing, create outfits for different levels of formality, weather, whatever. And if you pull out a specific piece of clothing from your closet but don’t know in that moment what to wear it with, but have created seven outfits for it, you can easily see all seven. There’s even a calendar option to log in what you’ve worn and when, so you know how often you are wearing things, and you can even put in the price you paid for an item and it will calculate price per wear.


Totally agree! I’ve been using Stylebook for over three years now, and it’s been incredibly helpful in playing through combinations and compiling looks. It’s great to easily see all the potential outfits for a piece of clothing, especially when you’re unsure what to pair it with.


What brand is the wool/cashmere? Hoodie in the photo on the middle left picture?


Just recently I started doing the same. I take pictures of my outfits every single day, so that I can see, what I‘ve worn the last days and weeks. This is mainly for me to encourage myself to try new things or combinations and see, when I really like an outfit, so I can keep it in mind!
The dry january is a great idea, I will participate in it and I‘m looking forward to read more articles like this one!


Interesting approach and made me thankful I am retired. It’s semi casual, casual or very casual, with weather factored in, for me. Had I still been working, I’d have been tempted to ask one of my analysts to write some algorithms to suggest choices!


One thing i wanted to mention (as i work in tech), is the GenAI tools and how someone can get help when it comes to outfits. For example, one can describe their style preference, enquire inspiration examples from permanentstyle, Drake’s etc. Then copy a list of items they have and ask for outfit suggestions. You might be suprised with the outfit ideas. I use it when i run out of ideas, you just have to ask and try some outfits out. If it works, you save it in a folder. By they way when i say GenAI, i mean ChatGPT etc. It also helps with categorization, season etc. The only caveat is that you have to provide some data about yourself. I hope it helps.


Hi Simon,
I shook my head upon reading this post! Frankly, how can you expect to effectively deal with such a huge wardrobe that a style-conscious parisian woman, even with the help of AI, couldn’t?


Don’t think folder based things works best here, a tagging based system seems better, not sure if it’s available somewhere without writing some yourself but something like Google image but more specific trained (unless generative AI is there already) for style so you can go something as specific as “black bomber inspiration” within your images only, “chalk brown stripe suit with xyz shoe” etc


Derek in the Die, Workwear podcast was talking about this recently. People discuss fancy software systems, AI organizing tools… Obviously pinterest exists, but I’m with you, there’s nothing quite like saving things to old-school folders with descriptive titles. Dropbox. I do like Instagram, but it’s not a long-term solution, I just want to save things to the filesystems that have worked for decades (and with the cloud sync tools that back up and manage my files).


I use Instagram and Pinterest in tandem, as well as the files app on my iPad for some stuff as well.
I have one folder on instagram called “to purchase?” where stuff that looks interesting end up, I also have one called “For Pinterest”.
Every now and again, I go in to that folder and start uploading to pinterest. It’s not ideal, sometimes you get weird resolutions, if there are more than one picture in a post, you might have to do a bit of workaround. But in general I find it works fairly well.
On Pinterest I have main boards with sub boards, i.e. Inspiration – Spring/Summer, Fall/Winter, as well as dedicated boards for people who’s style I really like and come back to.
The main issue with Pinterest is the endless scrolling unless you use a million sub boards, but I’ve yet to find a better solution.

On the files app, I save pictures from lookbooks and stuff online that I want to come back to, stuff in fuller resolution etc.

PS. On saving pictures from Pinterest, if you open any pin, click the three dots, you can download the picture there. Seems to save it in the same resolution it’s displayed, although I’ve not tested that theory. but a nice way to download pictures nontheless.