The Lazy Guy’s Guide to Looking Put Together

Finding your everyday uniform — and why there’s nothing wrong with wearing what works

Welcome to the Lazy Guy’s Guide to looking put together.

You can be lazy. It’s okay. It’s a bit of a downbeat word. And I’d just like to say there’s nothing wrong with being lazy.

Maybe we should define what we mean by lazy. I think it’s often… Let’s not think of it as lazy, perhaps, but think of it as wearing what works for you. There’s no harm in finding something you like and sticking to it. Quite recently, I think I’ve been wearing the same variation of clothing, but that’s because I’ve found what I like. I’ve found what works for me. It consists of a cap, Oxford shirt, jeans or chinos, loafers, or boat shoes. And that’s about it for spring–summer. Sounds boring when you say it out loud — but it doesn’t, not when you think into it — because the variations you can have on that.

The Problem With Effort

The problem of effort almost harks back to the blog I wrote the other week about sprezzatura. As soon as you try it, you’ve failed. You’ve put in too much effort. And that’s why I’d argue: put in the effort finding what you like, what fits you, what looks good on you — rather than trying to look like you’ve made an effort. Because that’s the downfall, I think.

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Why My Lazy Formula Works

So let’s go over it again and make it even simpler. The formula is:

• A cap

• An Oxford shirt

• Chinos

• Boat shoes

This is my lazy look. Why does it work? It’s comfortable. It’s practical. It’s classic. And it works just about anywhere. It’s not just all of these — it’s versatile.

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1. The Cap

I’ve got a ton of caps in my collection, but the ones I reach for most are dark navy and dark green. They go with everything — chinos, denim, Oxford shirts, even a blazer if you’re pushing it. There’s something about those tones that just slot in quietly with most other colours. No fuss. No clash.

Now I know caps get a bad rap. People say they look scruffy. Maybe they are. But I like them — and I’m doing me right now. That’s all that matters. It works. Simple as that.

2. The Shirt

One shirt that’s been in heavy rotation lately is a long-sleeve towelling Oxford I had made by Proper Cloth. I based it on one that Miles Davis wore, which tells you everything about where the inspiration came from. It’s a perfect fabric for summer — it sits somewhere between a sweatshirt and a long-sleeve tee. And if, like me, you’re basically an old man at heart who’s always cold, it keeps you warm when there’s a breeze but doesn’t overheat you if it’s humid. The towelling does its job.

Another favourite is a vintage Oxford from Drake’s — a good example of how to keep things interesting without going overboard. It’s subtle but different, and that’s important when you’re dressing simply. It gives you enough texture and character without shouting about it. Throw it on with jeans or chinos, and you’re good to go — to work, to town, wherever.

3. The Chinos

For this look, we’re going with chinos over jeans. I actually think chinos are more versatile. And that’s the whole point when you’re dressing lazy — you want pieces that don’t make you think. You want to know they’ll go with whatever else you’re wearing.

If you’ve no idea how your day’s going to unfold — whether you’re heading to a café, into a meeting, or just killing time — reach for the chinos. I wear the West Point Twill Taper from Jack Donnelly. It’s a traditional Ivy fit with a taper — not skinny enough to look like you’re trying too hard, not wide enough to feel like a fashion statement. It hits the sweet spot: clean, comfortable, and understated. That’s what Ivy’s really about.

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4. The Boat Shoes

Perfect for summer. Comfortable, breathable, and just the right side of put-together. I’d argue Sebago make one of the best pairs going. They’re from the Northeast, and they’ve got that Ivy pedigree: think New England summers, fishing trips, afternoons on the deck.

They’re built to be functional — they dry quickly, they’re durable, and they work sockless just as well as they do with a pair of scrunched-up white socks. Again, we come back to the same word: versatile. That’s what you’re aiming for. Boat shoes give you ease without sacrificing intention. That’s what makes them part of my lazy uniform.

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Conclusion: Lazy Doesn’t Mean Careless

I think the thing to remember is that we shouldn’t be too hard on ourselves. Maybe I’ve been too hard on this title — lazy doesn’t quite feel right. It’s more about finding your everyday uniform. The stuff that works for you. The pieces you reach for without thinking because they always deliver.

These days, I care more about buying less but buying better. Investing in things I genuinely like, things that are going to last, things with a story — whether that’s who made them or how I found them. And most importantly, things I’ll wear again and again.

If you’re struggling to find a look that feels easy and true to you, don’t be afraid to experiment. Find one item you love — something that fits well, makes you feel good, or that someone’s complimented you on — and build from there. That’s your starting point. From there, just add pieces that work with it. Keep it simple.

And if you ever think, “I’m dressing lazy every day,” maybe ask yourself why that feels like a bad thing. If it looks good, if it feels right, if it makes sense — then maybe lazy just means versatile.