Video chat: How to build a wardrobe from scratch

Friday, June 26th 2020
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This is the third in our series of reader-question videos, with the subject this time being wardrobe building. 

Specifically: “I am building up a wardrobe from scratch. What do I buy first, and how much should I spend?”

It’s a popular question of course, and one that the entire section of PS - Wardrobe Building, here - is designed to break down.

Being so big, it’s not something that can be dealt with comprehensively in a 15-minute video. Let alone for every type of office, lifestyle and personality. 

But, there are some good principles. And that’s what Aleks and I try to explain here. 

The need to plan, so you know what level you should be spending at. The sense of buying classic, foundational pieces like a navy blazer (it’s really not too corporate). The way that accessories can stave off your impatience, keeping things fresh for a while. 

I know from the number of consultancy clients who ask about these things, that this will be a popular video. But I also think there’s something there for everyone - no matter how far along they are in that wardrobe-building process.



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

'How do I build up a wardrobe from scratch?'
  1. Plan over three or four years
  2. Planning sets your item budget
  3. Don't worry if you can't afford the top end
  4. Buy a good navy jacket
  5. Classic pieces are a blank canvas
  6. Shoes are particularly satisfying
  7. Narrow down your categories
  8. Accessories can freshen up a wardrobe
  9. Buy things that go from smart to casual
  10. Capsule wardrobes are travel wardrobes
  11. Look at an interesting brown

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

And the clothes worn in the video are:

  • Me: PS Striped Oxford shirt, with knitted silk tie from Tie Your Tie, under Ciro Zizolfi jacket in Holland & Sherry tweed. Plus Yard-O-Led silver pen
  • Aleks: Stevenson Overalls moleskin western jac-shirt (via Clutch Cafe), over John Smedley merino mockneck
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I was hoping for some carpentry tips.


The biggest challenge is definitely to have the patience to do this.


My own personal story on building a wardrobe is

1. Buy better quality RTW and get your RTW altered . It’s not meant to fit you off the rack !

2. Started buying proper shoes .
Good shoes will elevate you and a RTW outfit immediately . Also they last so long that jumping from buying £50 Clarke’s to discounted Cheaney /Church’s is not that big a hit to the pocket.

3. Get MTM shirts. Again spending £130 on MTM shirts , although expensive relative to RTW, is not so over the top . Furthermore, one immediately noticed the better fit and quality of cloth.

4. What I am yet to do …. buy a MTM suit and jackets .

The trouble with the jump to bespoke or MTM suit or jacket is you are expecting someone to jump from playing for example £2/300 a suit to 5x that .
There is no less painful, incremental way to do it .

In the meantime shop the Sales of quality retailers like Trunk Clothiers and buy better quality .


If I could advice to my 20 years old self with limited budget who has to buy a weekly warderobe over the course of 6 months, it would be the following:
– Get your shirts MTM. A nice collar and a good fit makes a big difference. Not that costley either. Look at olga milano or luxire.
– Buy a few suits and sportscoats at suitsupply and figure out what you like. Avoid highstreet and designer brands. Mostly you’ll pay for the name.
– Get MTM Trousers. Again look at luxire. Depending on the fabric they are not that expensive.
– Get 2,3 different shoes from meermin.

Once you have a foundation, move on to Bespoke. It doesn‘t pay to move to the middle ground only to realise that it‘s Bespoke you‘re after.


Hi simon. On that topic – I’m looking to build my sportcoat wadrobe (only one navy hopsack jacket, no suits) and am keen on a brown sportscoat. I came across this:

How useful is it as an odd jacket to wear casually, with jeans or casual chinos?


Hey simon, that was my first thought. Would something like that have enough texture/details to be an odd jacket?



Since it’s the armoury, you could always send them a message asking how they think certain items would go with others, and whether they have recommendations. I’ve found the team there to be knowledgeable and friendly with that sort of thing


Stanford Chiou

A full suit really isn’t as essential as it once was, is it?


Jesse Thorn wrote a great piece a while back about “the sincere suit” for that “funeral/wedding/job interview/christening/wake/big meeting/court appearance coming up next week”


I’m in the process of getting a navy herringbone tweed blazer (maybe a bit darker than the Disguisery jacket) with some casual touches – 3 roll 2 buttons, patch and barchetta front pockets, and a relatively natural shoulder. Most likely it will wind up being my only bespoke jacket, so I’m hoping it will hit the versatility sweet spot and I’ll get lots of use out of it. The last few posts have made me optimistic that I’ve made the right decision.


I found Aleks’s point about grey particularly interesting, because I’ve recently been thinking a lot about the same thing. I have two (English Structured) bespoke suits, a 13oz navy twill and a dark grey sharkskin in the same weight. I find the grey more versatile in corporate settings because it seems to accommodate more shirt/tie combinations, but the navy is better for everything else.

Now I’m thinking about a third suit, and I feel the default suggestion would be a mid grey flannel. The trouble is that the more I think about it the more I really don’t know how much I’d wear it. It seems like a huge indulgence – both too smart for smart casual and not quite corporate enough for important meetings. Something you’d wear in a gentleman’s club or to church on Sundays.

I only normally need to wear a suit 1-2 times a week – and I can’t help but think cotton in a softer Neapolitan style (like your Caliendo) might actually be more useful, especially as I travel a lot to warmer more casual climates for work. If I was to get another smarter suit: another navy in a lighter weight; an airforce blue worsted; or even a chalkstripe flannel feel more versatile to me.

But then again, so many people whose style I admire go on about the merits of the grey flannel suit – and so I keep second guessing myself. I’d be really interested to hear your thoughts on whether it still has its place on the list of essentials in a modern man’s wardrobe – or whether you think I should go for something else?


Don’t sell the grey flannel suit short. It looks fantastic with a shirt and tie or with an open collar solid, checked, or striped shirt. Don’t forget wearing it with a black,navy, burgundy or brown rollneck which is a very sophisticated look. And you can wear a polo with it in the same colors for a different, but equally sharp look. Grey flannel can look corporate if you want or not. It’s one of the most versatile and beautiful garment a man can own.


Doubtless of interest for the fledgling flaneur but is this really the terrain of ‘PS’ ?


I don’t mean to be elitist but do you really think it’s possible to be ‘ All Things To All Flaneurs’ ?
Doubtless there is a market for the fledgling but PS’s big appeal to me was that it used to be more advanced and differentiated from GQ/Esquire and the like.


Jason, you’re kidding, right? Comparing PS to GQ/Esquire is ridiculous because there is no comparison. What PS offers compared to the GQs of the world is light years ahead.


How do I get the collars of my button downs to stick out like yours? Looks amazing !


Hi Simon,
Thanks for this video with some very interesting points.
If I could suggest one more, not explicitly mentioned, that will no doubt greatly reassure someone starting out…If you stay with the more subdued, not ‘showy’ elements, the vast majority of people you may see in a day won’t even notice what you are wearing (and that is, maybe, the point of true elegance). One might say “I wore this jacket yesterday”, but who will actually notice ? This is the major reason, IMHO, why the base staples should be, as in your video, subdued classic tones and little or no patterns.
I think the most versatile jacket colour is a very subdued (un-saturated) and medium-dark brown, almost grey but warmer – Alexe says ‘taupe’ – I think that’s about right and in a mid-type cloth texture.
Add 1 good pair of jeans, 2 tailored trousers, 3 MTO shirts, 2-3 pairs of shoes and some accessories and as you say in the video you can play around a lot…but almost no-one will notice, and that’s great !


If a navy blazer is still too dressy, then should you go for a dark brown as a first sports jacket? In what material?


I think there’s two points worth highlighting in relation to one another: 1) clothes look better the more you wear them; 2) take time to plan your wardrobe. As someone who is about ¾ through the first year of starting from scratch, my biggest mistake has been trying to put multiple new outfits together all at once.

In fact, I made the mistake of lifting an entire look from P.S. , only to feel like an imposter in it. I think there are multiple reasons for this (many of which are personal.) But I think the most universal reason is that you have to adapt to the clothing, as much as it has to wear and adapt to you. Doing that with a whole outfit is much harder than with a single new oxford that has a stronger and taller collar.

There’s another piece of indispensable advice, which I don’t remember being mentioned in this video, but is mentioned in your ‘how I’d shop on a budget article.’ That is, budget and spend more on shoes. Your exact wording is: “perhaps one or two weeks’ salary. Expect to buy only one or two a year.” It remains some of the best advice on the website for planning a new wardrobe because the advice changes the way you look at consumption. For me, that was a pair of Belgravia Loafers in brown suede on sale. Those shoes in particular made a new pair of trainers, that will only last a year and a half, look a lot less appealing.


Here are my 2 cents.

1. When starting out your wardrobe it is important to remember that your tastes will change dramatically over the next few years before they begin to stabilize. What you think is really appealing now will likely be quite different than what you find appealing a couples years from now. I think this is a very good reason to start out with the classics. The classics are the things that have withstood the test of time. Additionally, whatever your tastes eventually look like, everyone you will still find the classics useful, even if they might seem boring at first. No one ever regrets buying a good navy blazer, good blue or white or university stripe oxford cloth button-downs, a good herringbone tweed in a muted color, good grey-flannels, etc.

2. Buy these classics from a smaller store that is known for their good taste, e.g. the Armoury, not a big store (even if they are very high-end). If you buy from a store like this, where they think through their product lineup very carefully, you are much less likely to make a purchase that you will regret down the line.

3. Try on shoes in person first so you learn what works well for you. Most people aren’t used to nice shoes and how they fit. They fit very differently than cheaper shoes. A similar point could be made for clothes, but I found clothing fit much easier to figure out than shoe fit.

4. Realize that you won’t have a wardrobe you are happy with for a while unless you have a lot of money to throw around. Accordingly, it is important to come to peace with the fact that you will find many of your clothes beneath your own aesthetic standards for quite some time. Realize that no one else really cares. No one cared when you dressed poorly and they won’t care now. When you start building your wardrobe it is very easy to scrutinize everything you wear and everything everyone else wears and come to think that everyone is doing the same (i.e. that everyone is paying close attention to what you wear). This is not the case. No one is paying close attention to what you are wearing.


What a great comment. I felt number 1 so much, in particular about formality. In my opinion, the quality of cloth, construction and fit in bespoke allows you to go one step lower on the formality scale but still fit into the situation. For example, going for separates, adding a knit tie, more textured fabrics or earthier colours. Before I wore mostly blue and grey, but now I prefer warmer colours on the brown, beige and green spectra.


“Realize that no one else really cares. No one cared when you dressed poorly and they won’t care now. ”
This is right on the money IMHO. We do it for ourselves, mostly. At the same time, if you do take just a small bit of care it’s quite surprising the quarters from which compliments arrive on your door. And this is part of the enjoyment. I was once complimented for what I was wearing by an attendant in a petrol/gas station. People, regardless of social position or background, have a greater aesthetic awareness than they think.


which jacket was this? Now I’m curious!

Peter K

To Aleks’ list of good secondary colours for jackets I would add olive. I have an Etro sport coat in a muted olive shepherd’s check. Not a greenish olive but one that leans more to light brown.

It goes well with light grey flannels, mid grey trousers, jeans and charcoal trousers. It’s the most versatile jacket I own.


Simon/Aleks – again a lovely video. Thank you.

It seems that a casual (maybe Neapolitan) blazer/jacket is THE key item in any modern wardrobe. Maybe the first item you really commit to. So do you have recommendations at the various price points from the lower priced RTW, MTM, lower bespoke to more expensive bespoke choices? I appreciate this is perhaps not straightforward. Does that differ if you are lucky enough to actually visit Naples as I will be in August (UK rules permitting) and April 2021?

Vipul Patel

Simon … I am a big fan of your and meet you in NYC last year.

Beautiful video and highlighting the essential things and emphasizing ….its journey of self expression over time, and to enjoy the things you own and wear it.


Thanks for the tips Simon! Although I must admit, I was a distracted by your Zizolfi jacket.
Its interesting how the Attolini school doesn’t look Neapolitan at all by modern standards.


v useful, thanks Simon. If you were commissioning that first navy jacket tomorrow from an MTM or bespoke maker, and you lived in London, and wanted something that would work in all but the warmest months, what fabric might you go for?

R Abbott

Based on the number of questions you’ve been getting re navy wool selection, maybe you should add as a fourth option to your Escorial offering…

R Abbott

Although the focus of your shop has been filling gaps in the market, there’s also a lot of value in curation by someone you trust; that’s something many people are willing to pay for. Very few products are genuinely unique, but finding them amidst a sea of options is a different story.


What’s Whitcomb & Shaftesbury’s house style like For jackets? Can they do construction that is soft enough for jeans yet also fine for flannels?


They’ve got several examples on their Instagram

Gilbert Weems

IMG_3014. IMG_3013.jpg

Hi Simon, love your site. I was looking at some old Norman Rockwell photos and I could not believe how dapperly he dressed. He reminds me of your style which I try to emulate. Any thoughts.


Is it practical to make a navy suit such that the jacket can be used on its own? Maybe if soft shoulder and brown horn buttons (rather than navy buttons)?

JJ Katz

Great video. We should bear in mind that this sort of advice is ALSO useful to someone who already has a reasonably full wardrobe but wants to upgrade it in quality (say, from good RTW/MTM to bespoke) insofar as they should probably follow a similar progression of commissions.


I have two practical questions: (1) do bespoke tailors allow you to supply your own cloth or do they insist on using their own selection? Eg, if you really wanted a jacket made out of a particular fabric that you had acquired, would most tailors be willing to accommodate that?(2) most tailors quote a “starting at” price, and although I assume that most of that price is for labor, at least a fraction of it covers materials. But if you supply your own cloth, does that affect price at all? Thanks!


Hi Simon and Aleks,
I don’t know why “black oxfords” didn’t pop up in your conversation. I mean at least within the context of having to mention the navy blazer and the grey trousers. Personally, I find that you’re erring too much on the casual side.
By doing so, unwittingly, you’re putting the black oxfords in a more dangerous territory as you inadvertently tie its fate with the suit’s.
An outfit that would start with a navy blazer paired with grey trours as core items could bear up a pair of black oxfords. The shirt and the tie making the difference relatively to contexts.
I hope we’re not going to rely on the Japanese to save this smart outfit!


Thanks for this thoughtful reply. You’re right.


Thanks for the great video once again Simon. On Aleks’ note about a grey flannel suit looking far too period, I have to disagree, but perhaps not for the reasons others might. During my university studies I worked part-time at a couple of high-end RTW tailoring brands (not in the UK or US) for several years, which was a great insight into how tailoring is perceived beyond the menswear community. I’d also be of similar age to Aleks, so this was not very long ago either. One winter we had a charcoal flannel suit, but the fact it was flannel or even different to any of the worsted wool suits was barely, if ever, noticed by customers. A comment about it being “wintry” or “textured” was the most that was ever said. To them it was just another charcoal suit. Moreover, most of the customers I dealt with were people who wore tailoring every day and had all their careers, many coming from major law and accounting firms. The fact that many of even the most basic details of tailoring is not known or noticed by those outside the “bubble” is something I find that is often overlooked and perhaps very liberating to realise when many of us get too pernickety about the minutiae.


I’m looking to get a navy DB blazer and I am debating whether to have the buttons brass colored, gold plated, or brown horn. Any thoughts on the pros and cons of each, and which would you recommend? On the one hand, metal buttons are showy, but on the other hand, I already own a traditional navy SB blazer with brown horn buttons.

Also, what weave would you recommend? I’m leaning toward a heavy hopsack but would that look too casual for a DB? Thanks!


If only there were an easy way to swap out the buttons…


How well does that work, as a practical matte thanks for the reference – that looks like an interesting solution. Are the buttons secure or do you have to worry about them popping out? And does your solution change the appearance of the buttons from the outside? Would someone 5 or 6 feet out think that the buttons look different or funny? Thanks!

Stanford Chiou


How versatile did that travel blazer end up being? Travel blazers typically lean casual, and your Gieves & Hawkes was so structured and formally cut by comparison.

R Abbott

What makes a travel blazer a travel blazer? Is it the bellows pockets? Or is there some other feature in terms of cut, internal pockets, etc.?

How did you end up liking those pockets? Wet they actually useful for travel? What about from an aesthetic point of view? So the pockets make the blazer to casual looking for a nice dinner?

I’ve flirted with getting a travel blazer but my sense is that the hopsack blazer I already own is more practical. Dressy enough for a nice dinner but wrinkle resistant and breathable enough to travel well.

I guess on the flip side, the casual look maybe more suitable for sightseeing?

Johnny Cyclist

Suggestion and this is gonna sound commercial and uncouth, but have you thought about listing on the video or comment box what your’e actually wearing? Yes, it might distract at the beginning but, hey, I like to know what I’m looking at. Great video by the way and hardly any use of the word ‘like’! 🙂


I’m always excited about your posts an videos.. but I think that your high end items are not helping the average guy the luxury of looking excellent because of your price points…gotta bring it back to us so we can be in the mix and afford the items…rich guys wow
SBOH…Seattle Wa


I personally have found a lot of value in this site as an average guy. As a carpenter, a churchman, and a lover of classic menswear, I find that I learn a lot about fit, fabric, color, and principles of dress that are applicable to how I dress on the jobsite, at mass, at a family dinner party, or on the weekend. I certainly cannot afford anything bespoke, and I’m not pursuing the kind of life which will allow me to. That being said, I have found that this community helps me to be better dressed, and to be exposed to a wider variety of clothes than I otherwise would be, as well as helping me think about how to approach building a wardrobe that I can afford, which often means being on the look out for quality used clothes, and being proficient with a needle and thread. Except for espadrilles, which I had never heard of until the recent article. I can definitely afford those, and am wearing a brand new pair!

Perhaps I am an outlier in the community, but I love PS for its style inspiration and philosophy, which are things that I think can transcend class, and can definitely benefit average folks.


Here’s a question on a point that has frustrated me. Where is it possible to find advice about the details necessary for conservative looking clothing?

By this I don’t just mean “classic.” Its easy enough to find information about “classic clothing,” the type that can be worn by three or four generations and make it impossible for an observer to tell if the person wearing them bought them or inherited them.

What I mean by “conservative” is not just classic but along the lines of sober, reserved, respectable. I mean the type of clothes that (without looking like a costume of an earlier period) would suggest a man might be a judge (if its a dark suit) or a professor (if its an odd jacket) rather than the type of clothes which (though classic) make a man look like the life of the party or like he should be surrounded by a crowd of flirtatious females.


Thanks for the response. I would be interested in some specific links and I do understand why the stuff showy get more coverage. Someone like me wants information once and then is done for life. Not much money in writing for that.

The real difficulty I found is that I used to just buy whatever was advertised as “classic fit” or “traditional fit” or something similar. Then I gradually realized that a lot of the suits, jackets, ties, etc. advertised that way were not doing what I wanted—and this with perfect fabrics, charcoal and navy suits, neutral color tweed jackets, etc.

I’d be standing there in a “classic fit” charcoal suit and it still looked a bit too much like the type of thing you could picture James Bond wearing both in the oldest and the newest movies, and anything in between (and so “classic” rather than “trendy”). Didn’t look enough like the original actors who played M or Q or like T. S. Eliot.

Recently one jacket I bought (supposedly around the bare minimum of “classic”) looked way off and I could tell it had something to do with the lapel. Finally found out one problem I’d been having. Most “classic fit” lapels are at the thinner end of the “classic” range and so still have a more “fitted” look. Also discovered that something called a gorge should be on the lower end. And apparently even “classic fit” jackets made today tend to have the waist pulled in enough to have as “trim” a look as possible while still making a jacket that can be worn for decades (or could have been made decades ago) without ever looking either new or outdated.


Any additional tips Simon for young people in their 20’s who know they want bespoke, but are slow to afford it?


Great post Simon! Would you recommend a darker navy or more “lighter navy blazer/sports coat for first jacket? I ended up buying a Ring Jacket but find it almost too dark navy for casual use. Probably picking up a lighter one when the


This is a great video and a really important subject for dedicated PS readers. I started a detailed planning process for myself a year ago (part of how I dealt with quarantining.) For me, I decided that coming out of quarantine, I wanted to wear tailored jackets and suits 50% of the time, and more business casual outfits like knitwear or blousons / overshirts the other 50%. Then I did some rough, simple math. Assume there’s five days in a work week and four weeks in every month. That means I needed 120 days worth of “tailored” clothes a year and 120 days of “business casual.” Then break that down further. For instance, if half of my business casual outfits were going to include knitwear, then if I acquired 30 pieces of knitwear, each piece would only be worn roughly twice a year. You can then do similar things for tailored outfits too, determining how many blue / grey / brown pieces you want, how seasonal your collection should be, etc. It may sound a little ridiculous, but listing this out in a simple spreadsheet gave me a ton of clarity around what I wanted to build. And then I worked with a great tailor (in my case, J Mueser) to realize all of it. I showed them my plan and they helped a ton in executing the right fabrics, etc. You can get deep in the weeds, but it’s a lot of fun to think about a wardrobe in a wholistic way.


Hi Tom,
Template sounds great. Would you mind sharing it?
Thanks, Shawn


Hi Simon,
When talking about shirts that are in the middle of the range between smart and casual, I was wondering what you think of the kind of shirts that Sid Mashburn produces in an Oxford cloth or a royal Oxford cloth (Example: versus a button down shirt with or without a pocket.