Stuff I Think My Brother Should Wear

if only he read my substack

This week I wrote a workwear edition of The Dress Code in collaboration with

Phia

. You can read it on their substack here. My first time as a guest author!

This send may be too long for some email inboxes so I definitely recommend reading in-app or on your desktop.

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I like clothes a lot and so does my brother. We talk about them at length on the rare occasion we get to see each other. It’s one of my favourite common grounds that we share. I look to menswear for my own outfit ideas, both in imagery and actual stores. Thrifting is not complete without a browse through every rack, not just the section marked womenswear. Also I love a shirt so this approach often works out well for me.

But this is meant for my brother. And since he doesn’t seem like the Pinteresting type, and never seems to have much time for flipping through print media¹, I’m going to forward this to him. Of course, if you like anything you see then it’s for you too.

So here you go Jack.

Let’s start with some icons of men’s style to keep on file as trusted references.

[Time ref: 1990s-00s, some still today]

• Harrison Ford - doesn’t matter the era, the outfits hit.

• Anthony Bourdain - the coolest ever + chef bonus points.

• Richard Gere - classy, always looks like himself. I don't know how else to describe it.

• Channing Tatum - from Step Up to his revamp sponsored by The Row, there’s so much to choose from.

• Denzel Washington - a subtle sporty/streetwear reference done right. Underrated!

• JFK Jr - classic & pretty timeless.

• Br*d P*tt - hate to mention him.* Some 1990s looks were good though, but it could’ve also been the girlfriend effect.

• Andy Samberg - you are not as funny as him, but you are funny sometimes. Don’t underestimate a good t-shirt, a grey hoodie, and letting your hair do most of the work.

• Paul Newman [1950s-70s] - in the running lead for epitome of cool.

*[As I’ve noted in my women’s style writings, it is the person who makes the outfit more often than not. Keep in mind that no amount of clothing can forgive being a shitty person. So be kind and dress well pls.]

Paul Newman shot for LIFE magazine by Mark Kauffman, 1967

Note the t-shirt shapes & fit, the denim, simple jewellery choices, leather jackets in different styles. There’s nothing saying you can’t wear your lucky find rare supreme tee, though I’m partial to a vintage stüssy moment myself, and pair it with jeans you’ve had for so long that the labels have faded. High-low dressing is kind of fail proof if you desire looking like you just “threw this on” without questioning if it would actually work. Because your wardrobe is just that cohesive. Despite what the word might suggest, effortlessness does in fact take thought.

It also doesn’t have to include high price tags if you prefer to spend your money outside of the wardrobe. It may need a little extra effort in the research department but there is a thrill in the hunt for an economic staple. And Jack if you’re still reading this, you can always ask me to find you the perfect secondhand piece.

Jeremy Allen White is a solid style suggestion in my opinion. Especially for you Jack. For his denim choices, his great styling courtesy of Jamie Mizrahi and because you both probably smoke the same copious number of cigarettes, all while blissfully aware that it can kill you. I’m not referencing his Shameless days here. More so his pretend chef days where he does not in fact play a bear. And since you also moonlight as a chef this just made sense. He wears a lot of unbranded, simple clothes. You could write down the pieces you notice and have yourself a basis for the ideal wardrobe if you’re a fan of his style.²

E.g.

• pale grey sweatshirt, slight oversized slouch but not longline

• very deep indigo denim jeans that sometimes look black - slight barrel leg but not too obvious

• classic blue denim jeans - baggy straight shape, no unique detailing

• white tee - high round neck, boxy fit, light material, no clingy sleeves (easier said than done to find)

• black version of the white tee

• black belt - leather, tarnished buckle (bronze/silver)

• classic white trainer - think reebok club c, reebok classic workout plus and scuff, stain and dirty to no avail through wear (or other measures if you’re desperate)

• chunky leather boot - good quality, in black or brown, would recommend looking at paraboot

• standard white button-up shirt

• a black dress pant - can have interesting fit/details if you have a preference but tailor to perfection please

• relaxed striped shirt - roll up sleeves, wear over your white tee etc

• blue denim jacket - older the better, wear it in

• black suit jacket - you should have a suit, you never know when it’ll come in handy

• leather bomber jacket - extra points if it has a warm lining and can double as your cold-weather option

• black knit hat - winter!

• baseball cap - summer! + a good precaution because I just know you’re not wearing SPF

• optional but encouraged: very minimal jewellery - think thin short chain, a go-to watch, couple of staple rings but ONLY if you actually like them and will wear them

Think the denim here is stand-out. And the belt off centre paired with the sweatshirt tuck. Interesting minimal choices that make a difference.

Seems like a lot of stuff but is a good place to start building from. If you couldn’t tell I don’t really subscribe to the capsule wardrobe thing. Where it gets really fun is when you find one-off pieces of clothing that feel like you should’ve always owned them. And then adding them into rotation with your usual lineup and messing around with styling etc. That’s the fun of fashion. And exactly why it is not one size fits all in any sense. I’m trying so hard not to repeat what I have already written in Like What You Like. But if you needed proof that I believe in my words here it is. I also think you could apply that list to womenswear if you like it, hardly any adjustments necessary.

These are some extra photo refs. Find my reasons of note in the captions.

note: so simple yet executed so well, really like the detail of the wired earphones, and the hood out of the jacket, brown leather is a great jacket alternative

note: not typically a gilet fan, but I think a fleece version over a baggy white tee creates interesting layers for the eye and makes casual not boring

note: Paul Newman again, so intrigued by this short v neck sweater over a button up, simple and effective

note: canadian tuxedo AND cord/suede? bomber with zip AND button closure?? the layering is so. good. and you know I love a cap

note: this is one of my favourite forms of menswear dressed down but without bordering slovenly, the colour palette is carrying this fit, love the brogues for a smart touch, the neckline layering AND of course the great cap

note: it was clear JFK Jr cared about fashion as is noted about him in many books so maybe that makes a difference, special mention to the hat & scarf, they add a world of personality to an otherwise uniform fit

note: I am not saying you should be rocking a satin 2-piece anytime soon, but being brave and courageous goes a long way in style, no one is doing it like Mr MacLachlan imo

note: no blue denim in sight, a way to do khakis well and lighter colours that are still natural

Special mentions to Kyle MacLachlan, Matthew McConaughey, Ben Affleck, and Austin Butler’s t-shirt collection. I could go on forever. Every time I find a photo for this substack, I spot another man of note. So if you like the menswear-focused content let me know and I can think of other ways to approach it.

see what I mean about his t-shirts?

All black fit is a classic for a reason; the light colour trouser is a nice way to keep a neutral palette lifted; grey hoodie & cap never fails but you don't need to carry a basketball around dw

Also a necessary shoutout to our dad. Jack, when you’re back home, take a look through our photo albums and his archive³ of stuff. There are some outfits in there that are going to suit you simply because the cool is in your genes. Then put it all back where it was, I’m serious!

I know you have some of his very high quality hand-me-downs somewhere, so it could be of interest to re-work them into your own sense of style. Where he probably wore an Evisu jean with a high-neck wool jumper you might consider a boxy white tee with a slight crop and that leather jacket you have that always reminds me of John Cusack, who is another great reference especially if you like a leather jacket. I’m just saying there are always new ways to look at old things. Use your imagination. Consider how you want to feel when you leave the house.

Ultimately, you’re going to wear whatever you want though that doesn’t always mean you should.⁴

From your sister.

Thanks for reading. See you soon.

If you are not my brother and you have suggestions please drop them in the comments. He did not request this fashion advice deep dive but whateverrrrrrrrrr. Comment anyway. I wanna see.

:)

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1. or he just can’t read

2. As I write this I realise you could probably do this for anyone and suddenly this post is completely redundant.

3. I’m kindly calling it an archive because it’s like over 20 years of clothing, most of it still in incredible condition. But it is borderline just too much stuff.

4. IT’S A JOKE and not for you unless you are my brother don’t worry. The rest of you can wear whatever you like xx