What to wear with the kids at the weekend

||- Begin Content -||

I get asked surprisingly often what I wear with my children at the weekend - when there’s a chance I’ll be running round a park, on my knees in a playground tunnel, or simply within range of a ketchup spill. 

There seems to be a presumption that, because many of the clothes we cover are expensive, they must be delicate too, and therefore not up to this kind of activity. 

Not so. Most of the really casual clothing we cover looks better with wearing, washing and general abusing. You can normally machine wash it and the more you do the more it will fade, fray and acquire personality. 

Today’s post is a brief rundown on the kinds of things I mean, with examples from new and old outfits. If any of it doesn’t suit your situation, or doesn’t seem tough enough for particular weekend activities, let me know. 

The starting material here is, of course, denim. Everyone wears jeans, and anyone that admires the beauty of jeans will know they’re better the more they are worn and worn. 

Indeed, a guy working in a denim store would probably be envious of the amount of time you spend on your knees changing a nappy, or crawling around the floor looking for Playmobile. That’s great wear - something he can’t replicate just standing around a shop. 

I’m not suggesting you should be thinking about fade optimisation - quite the opposite. Buy some great denim, wear it all the time, and forget about it. Perhaps know the basics of how to wash it, but don’t worry if you need to do so fairly often - the fades and frays will still come. And that applies to other denim too - jackets, chores, shirts. 

The other default materials are similarly tough cottons - canvas, Ventile, vintage sateen. 

When I wrote about my canvas chore jacket (above), I mentioned that many of these materials could be worn both top and bottom: the canvas could equally be used for tough chinos or for carpenter’s pants; denim could be jeans or a jacket; military sateen could be fatigues or an M65. 

Most readers won’t want to double up on any of those, but it’s good to bear in mind they can be swapped - the chore with jeans shown above could easily be the other way round, like chinos and a heavy denim shirt. 

The jacket I’ve shown at the top of this piece, and above, is an eighties RAF pilot's jacket in Ventile, but it’s the same olive drab as a pair of fatigues or a jungle jacket; we’re playing with the same colours. 

The nice thing about Ventile, of course, is that it’s cotton, so although basically waterproof it ages in the same way as many of these other materials. My Nigel Cabourn parka, below, is the same. 

Underneath these three colours of cotton go T-shirts, or a shirts like oxfords and chambrays. All tougher, heavier versions that look better with age in the same way. 

A robust oxford shirt like a PS one gets better and softer as you wash it, and so does a chambray work shirt, as highlighted in the recent style piece about Alessandro Squarzi (above). 

That article was actually a good example of the difference these kinds of materials make. His combinations could well have been trite, even cheap, were it not for the quality of the jeans, shirts etc and the way they had been worn in, fading and acquiring just as much character as a pair of bespoke calf-leather shoes. 

Then of course we have sweatshirts, which we covered recently here. Wool is great for knitwear of course - and in fact easier for little spills and spot cleaning - but overall cotton is easier to wash and wash.

One area wool can be useful in this kind of wardrobe is with outerwear or overshirts, like the type pictured above (from this article).

It might seem strange to think about this collection in terms of materials, but it makes sense again with wool, in that the best pieces will be made of tough, even coarse wool that can stand a lot of abuse.

Leather is the same, like my Chapal flight jacket and horsehide jacket (below). Both tough, both better with age. And it goes for waxed cotton like a Barbour or Wax Walker

So we’ve got canvas, sateen or denim tops/bottoms; T-shirts and oxfords or chambrays; sweatshirts; wool overshirts; and leather, Ventile or waxed outerwear.

What else? Shoes are usually boots in leathers that age well - cordovan, a pull-up leather - or canvas shoes like tennis shoes, plimsolls, trainers. 

There’s probably a significant point here about types of wear. 

When you buy good vintage, you usually appreciate fad and fraying, but want to avoid stains. It’s the same with looking after these weekend clothes: you can treat them badly in many ways, but it’s good to have some knowledge of dealing with stains and spills, so they last long enough to age in other ways. 

I love my old Doeks (below) because they have been scrubbed fairly regularly, so they still look pretty clean even though they’re fraying and splitting. 

How about Summer? Pretty much the same goes, just in fewer clothes, shorter clothes, or lighter clothes: hard-wearing shorts in the same materials as the workwear chinos, a lighter-weight chambray, a jungle jacket rather than an M65. 

There’s a lot of rich material here for future articles actually, as different pursuits all have their own particular garments and ways of dealing with their associated rigours. Fishing, hiking, hunting (particularly safari), being a photographer anywhere on location, all have their own ways of dealing with the requisite use, and their own styles in doing so. 

Perhaps making a den in the woods with your boys should be just thought of in the same way. 

Notify of

Inline Feedbacks
View all comments
Guy T

Hello Simon

I think that the olive jacket is an RAF pilots jacket. Although groundcrew I managed to acquire one while serving. I didn’t fully appreciate it then and don’t know what I did with it but I do appreciate ventile now..


Hey Simon,

Is that a Rocky Mountain Featherbed vest I see in the second photo from the bottom? I have been looking at purchasing one over the past few days, but haven’t seen a colorway like that one.

Do you mind if I ask where you got that one from?


Hi Simon,

Thanks for the response. Did you take your regular size or go one size larger?

Will make a trip down to my local Real Mccoys tomorrow, but looking at the size chart was wondering if it might be worth going up a size for the shoulder width?

Peter Hall

Great article ,Simon ,pulling together lots of recent threads into a coherent personal style. I wear so much of this type of clothing.

our RAF jacket is a Mk 3 cold weather jacket(designed to be worn over a flying suit) and was originally issued to aircrew of all three services.

Jim Bainbridge

The sartorial perk of parenting is definitely great looking cottons. The thing that annoys me is when my sons (2-4) tread on my shoes and leave imprints that last the rest of the day. In all other respects, I find tough suede is the perfect material for shoes here – but I may change that view when they start wanting to play football!


A very nice article for stuff almost everyone uses and the post corona period will bring out many workwear-streetwear styles. Which brands would you suggest to look for mid blue Jeans except from vintage Levis and levis lot 0 ?

Leo O-W

Is that jacket a MK4 model? Great one.

Leo O-W

Thx Simon! Mind if I ask the size of yours? I’ve been keen to buy one and know we’re about the same size but cannot make out what the weird military sizing (1, 2, 3 etc) translates to.

Peter Hall


Don’t forget that the template for these was 1960s body sizes. I think the largest size issued was a size 8 (110 cm chest) which equates to a size 44. People were just shorter and skinnier then.

They were also designed to be worn with high waisted trousers and are cut short. They are also not particularly waterproof.


Great article and I think with the following statement you really nailed the challenge of casual wear.
“different pursuits all have their own particular garments and ways of dealing with their associated rigours. Fishing, hiking, hunting (particularly safari), being a photographer anywhere on location, all have their own ways of dealing with the requisite use, and their own styles in doing so”.

It really is a challenge not to have a separate wardrobe for each hobby or outdoor activity to ensure you “fit in” for want of a better phrase

Eric Twardzik

As a father-to-be in two months and counting this is much appreciated. No battle plan survives contact with the enemy, but I’ve thought that the Ivy staples of my everyday wardrobe (khakis/jeans with oxfords, Shetlands, chukka boots and a Barbour in fall/winter, short-sleeved oxfords with chino shorts and loafers in summer) will be up to the task. Ivy’s existing status as “dad clothes” may be one of its chief charms.

Adam N

Just the job for us grandparents too! I have a pair of Moonstar all-weather boots which are perfect for weekends on duty all the playground or anywhere wet or muddy.


In the garden, it’s jeans/t shirt/sweater/anorak/trainers/boots depending on the weather.
All indestructible.
I’d rather not overthink simple things like what I should wear when I’m playing with my children, as the object of the exercise is to entertain/educate them.


Thanks for the gentle suggestion Simon, but I didn’t mention anything about quality, just the type of things I will typically wear when out playing with the kids.


As a parent of a three year old and four month old sons, I not surprisingly wear things that can be washed easily and stand up to abuse: jeans (blue, white or ecru), oxford or denim shirts in any color, shetlands, m65 or barbour jackets, suede slip ons or boots. I don’t care too much about wearing light colors like white jeans, as long as they can be washed easily and not ruined.


I’ve noticed that when I’m wearing my ecru chinos, other people for some reason seem much more concerned about them than I am. My usual response is along the lines of “don’t worry, they will wash!”; having said which, they really don’t seem to attract stains as much as people think. In the end it’s a case of wearing what you like and dealing with the consequences… I’ve even had a bespoke tailor joke that the PS Shetland tweed currently being turned into a jacket “shouldn’t show the dog hair” (I have multiple hounds including a couple of Golden retrievers) – but it’s not really a consideration! I will look after clothes, but at the end of the day they’re clothes… life is too short to baby them!


I’m of the same school of thought Paul. If my white or ecru jeans get dirty I just wash them on 60. Tweed and covert /cavalry are also very handy I find on occasions when I need to be more dressed up with kids, as they are meant to be worn hard and look better for the wear.


Hi Simon,
A very good summary of options and ideas. In my case a weekday with our younger granddaughter. You’re spot on regarding the nice look of ‘worn in’ clothing (I’ve a very old Belstaff which gets a lot of wear), also the sometimes associated memories.
Be good to see an updated summer capsule (casual ) wardrobe for this year at some point. Updated only in the sense of new ideas for existing clothing (as above) not so much new products.
I’m looking for a Tropical Jungle Jacket and recently reread your article on your vintage one which was very useful.
I’m just weighing up Buzz Rickson vs Real McCoys!
Wishing you and your family a Happy Easter.


Ah, kids.

Boat shoes, old chinos/khakis I wouldn’t wear to work anymore (winter) or cargo shorts (summer). Polo in the summer, flannel in the winter, often with a shacket. Crushable felt fedora in the cold, straw fedora in the heat.

Not the height of fashion, but still classier than a lot of stuff I see at the park.

Gotta say, though… that leather jacket is glorious.


Simon – I’ve been meaning to ask you for a while now: whom would you consider to be the “finest” manufacturers of denim jeans globally?


Hi Simon,

Hope you are enjoying the trip – it certainly looks fabulous!

I just wanted to clarify please:

“The quickest mass production possible at every opportunity” and “ so the Japanese specialists……..are all making like that”.

I am assuming that you meant the Japanese specialists are the opposite of “quickest mass production”?

Thanks in advance.



Thanks and no worries.


As a father who chases after an extremely active 18 month old all day this is extremely in my groove. Great recommendations and looks as always Simon. Cheers.


Simply a great piece – thanks Simon

Aaron L

Last night I was wishing you’d write this (always struggle to pack when I’m on a trip with the kids – particularly outside summer).

Guy W

Brilliant, thanks for the article, Simon (I’ve been one of the readers consistently pestering you for this)!

Much of what I wear around the kids in autumn/winter mirrors your advice here, I often wear workwear chinos/jeans with t-shirts, denim shirts and a buffalo plaid jacket or RRL overshirt. When the weather is worse, I bring out the Private White waxed jacket which also has plenty of pockets (something that comes in very handy with kids!). On footwear, I’m glad that someone else washes their canvas sneakers. Also, after seeing the third photo, I’m going to revisit vintage Nike sneakers (I’ve previously struggled to match them to anything but really athletic clothing, but they look great with the sweatshirt and chore jacket).

To lend an opinion on summer clothing, Sydney summers are particularly hot/humid, with some days being too hot for thicker workwear chinos and a chambray shirt. On those days, I find a nice pair of drawstring shorts (which are looser for breathability) and lightweight camp collar shirt to be particularly useful, with a nice pair of leather sandals or espadrilles.

I have a few questions:

1. Ee: your deerskin vest. I’ve been looking at something similar (from both Rocky Mountain and Real McCoy’s) – what’s the reason you prefer deerskin to nylon and suede?

2. On rainwear, what do you wear when it’s pouring but you’ve just got to get the kids out of the house? My waxed jacket with jeans and LL Bean duck boots works well, but I haven’t found a good summer equivalent (perhaps I need a lightweight ventile jacket).

Peter Hall

Now might be a good time to look at the sale price of the Private White Ventile Mac.

Guy W

Thanks for the recommendation Peter, that looks spot on!


Hi everyone! I actually have a question concerning the PWVC ventile mac. I have one myself and its great, but wearing to the park gets it dirty ever so often. The care label says dry clean, but what is your (Peter & Simon) thoughts on that? I’m thinking its “just” cotton. Shouldn’t it be possible to wash it in the machine or will i actually ruin something? ?

I came to think of it when you wrote about ventile, Simon, and then I saw this thread!

Peter Hall

I sponge my PWVC ventile Harrington with baby wipes-the water based ones(water wipes)..

Matt L

A brilliant guide Simon. On the topic of hard-wearing clothing, and the fact that you’re in Japan, I hope you get a chance to swing by Hinoya in Ueno, Tokyo. It’s a favorite of mine and very much in-line with hard-wearing military and workwear. It also has a few neighbors further down the street offering excellent re-creation flight jackets.


One type of stain that’s difficult to remove is grass. Jeans (or chinos) look better with age and wear but not with faded green patches around your knees.


This article again confirms that my sartorial tastes and habits are very different to yours, many of your commenters and most Dads in my area. I’ve never owned a leather, chore or M65 jackets/militaria. I gave up wearing anything denim, lumberjack shirts and sweatshirts after university. My trainers are reserved for playing sport. T-shirts are only worn by the pool, on the beach or along the promenade.

However, I agree totally that different pursuits all have their own particular garments and ways of dealing with their associated rigours. Several sports (especially sailing, shooting and equestrian) should be added to your list. It can be dangerous to wear the wrong clothing and footwear. It’s even dangerous if you are properly attired by those with you are not. More articles on that subject would be very valuable and educational.


Hi simon would you say cotton unstructered blazers like the drakes games jackets can be useful outerwear with kids? They look like they can take some beating


Our little one spit one my only pair of quality japanese jeans while I was reading this article. Did some spot cleaning and kept on going. I can hereby confirm the spirit of this article 🙂


Thanks for this article. I’ve 3 boys aged 10 and under and my old “smart casual” style is definately more “casual casual” as a result. I haven’t worn my tailored jackets in a long time. I’m mostly in jeans from Hiut and a pair from Jigsaw from just before they stopped doing menswear. I’ve been wearing more and more overshirts and chore jackets too. When I’m out I wear a backpack to carry water bottles, books, snacks and wipes and so need a coat that doesn’t look to backpack. A OCBD shirt is also really versatile. The original utility field jacket from FRAHM has been brilliant as well with being rugged, lots of pockets and looking good with a backpack. I really don’t like to see Dads dressed as big children in shapeless sportswear and hoodies. It’s easy to do but I need some self respect of thinking at least I’ve tried to make an effort!

Eric Walesh

what kind of nike’s are those?


Great article Simon. Casual clothing is much more attractive once it has that patina of a life well-lived. As another blogger I read put it recently, you want clothes to “look like you’ve actually lived an interesting life in them”, not like you’re a store mannequin. A lesson I’ve learned over the years is that when you buy too much stuff too quickly, and a lot of it isn’t worn often, you forgo creating that lived-in look. Another reason to take a deep breath, resist the urge to accrue, and buy fewer and better … or take the short cut of buying second-hand, which is a fun hunt in itself.

Jamie A

Love all of these pieces and outfits. Olive, blue, grey, bit of beige, and the odd splash of something stronger, all in made-to-last quality, is a winning combo. Also, I hope the shorts are back this summer!


Simon, have you tried the shorts version of the Joe McCoy chinos from RMC? https://therealmccoys.com/products/blue-seal-chino-shorts
I recently ordered them because I like the normal chino version so much from them (even if the rise is a bit low, but the cloth is a dream), I thought the shorts would be a hard-wearing kid-friendly alternative to a more elegant pair of shorts like the PS ones.

Sami Wu

Great style looking effortlessly and yet still awesome! I’m wondering if you could share with me your go-to stores in London (vintage stores would be plus) as I’m about to visit London later this month!
Thank you.


My list as a dad of two boys under 7 –
Drakes Oxfords and work shirts
Real McCoy’s t-shirts
Taylor stitch oxford
PS chambray
Real McCoy’s chinos
Blackhorse lane e5 jeans
Merz sweatshirts
Cheaney kudu leather whiskey boots
Cheaney trainers
Pwvc Harrington jackets

All go well together, all can take a beating. Really happy with all these pieces, all bought since I started reading PS (thank you Simon!). Even just wearing the T-shirt, sweatshirt, jeans and trainers combo looks good because of their plain simplicity.



Two possible ideas for future posts related to this topic:

1. A possible update to your post a few years ago on recommend ready to wear chinos. I believe since that post you’ve further explored other brands?

2. In the reader profile of Simon he made a great comment about casual footwear. I love canvas plimsols but it would be great to get some recommendations on trainers with more all day walking comfort / support that still present stylishly for things like travel.


No – I’ll take a look.


Great article Simon. What you consider weekend with the kids wear, for better or worse, is essentially my daily uniform these days. I’m sure you’ll appreciate this is the same case for alot of people. If anything, it gives opportunity to focus on quality, that quiet, casual luxury you’ve been preaching for a long time now.

The RAF pilots jacket is something special, honestly when I first saw it I didn’t even realise it was Ventile, perhaps because I haven’t seen Ventile in actual military green before, despite being a fabric designed for the military. Ventile really does age beautifully, my PWVC navy Harrington is also an example, not so much the really dark navy it was originally, still muted, it’s taking on a fade, particularly along seams etc. like yours above. If it’s time to head out for a walk and it’s pouring down, that’s what I’m reaching for. In fact, that’s why I have my eye on their frobisher coat as a deep winter version. Along with the wax walker (yet to buy) I reckon thats all wet weather walking covered year round. Excuse the tangent, I enjoy a long walk in the rain and like to be prepared.


Simon, do your wear your hard-wearing cotton and military jackets with Oxford Button Downs aswell?
I am looking at US Navy inspirered Deck Jacket in navy at the moment but I‘m unsure if I can just throw it over when wearing the friday polo or a Oxford Button Down… it seems like it could be the „high-low“ dressing, but also be interpreted as mismatching. I would be kindly interested in your thoughts
Thanks as always for your great work here on permanent style!


Thank you very much Simon, I will try and see!


LIke the Nike sneakers. What model are they?

Andreas Hild

Hello Simon
I am very interested in formal men’s clothing including tailored cloth and all. My personal style is based more on a casual expression. But I don’t necessarily mean English or Italian casual… I thinking of a more Scandinavian casual like Hansen garments, or Hannes Roether in Germany… they call it relaxed fit or supercasual or something like that.
I sometimes think that this fit has something of Arnys Forestiere or certain Japanese brands.
YOU don’t actually mention this styles  at all… that’s completely to be respected, but I would actually be interested to know what you think about it… Best regards, Andreas


Hello Simon,

I wanted to inquire about the olive trousers in the bottom picture (the one with the real mccoys vest). Do you remember what brand is was?


‘His combinations could well have been trite, even cheap, were it not for the quality of the jeans, shirts etc and the way they had been worn in, fading and acquiring just as much character as a pair of bespoke calf-leather shoes’
Could you elaborate a bit on this point.
I am currently in that phase where I cannot spend a lot on clothing and therefore most of jeans and chambrays and denim shirts are from the likes of gap, mango and not great quality. Does it then risk looking cheap and if yes then how to avoid that look with such quality materials?