In my thirties I didn't think much about what I wore. I was married with young kids, and I wasn't trying to impress anyone. When I did need to look good, I trusted my wife's judgment. She rarely put me in anything I didn't like, and I wanted to make her happy.
Then, after a 20-year relationship and a 17-year marriage, I was on my own and in my early fifties. I was dating again, starting a new business, and realising I didn't really know what looked good on me, or why.
I'm not a fashion expert, so I've included what professional stylists say too. But most of this is what I learned figuring it out again at this age: what I stopped wearing, the one piece that changed everything, and what I actually wear now.
Mistake 1: dressing in company swag
For years I wore a lot of company T-shirts and hoodies to work. Partly I wanted to look like a team player. Mostly I didn't want to think about what to wear.
It's easy to pull on a branded tee, and that's the problem: it looks unintentional. People know I'm a team player because of the work I do and the relationships I have, not because we're wearing the same uniform. I still wear a company hoodie once in a while, but I'd rather look like me than like everyone else in the building.
Mistake 2: dressing for easy, not on purpose
In my thirties I lived in cargo shorts and T-shirts. Not because they looked good, but because they were easy and I didn't care.
The shorts weren't really the problem. Mr Porter's guide to wearing shorts now recommends modern cargo shorts as an everyday staple. The problem was that nothing about the outfit was a choice. Whatever was on top of the pile went on. People notice whether an outfit was put together or just thrown on. Who did the putting together matters a lot less than whether anyone did.
Mistake 3: wearing clothes bought for a younger body
I still own T-shirts I bought because they were what I wore in my twenties, when I was about 30 pounds lighter. Tight band tees looked fine on me then. They don't now.
If you've changed shape, your clothes need to change with you. A shirt that fits the body you have looks better than one that fits the body you remember.
The piece that changed everything: Chelsea boots
For decades I owned two pairs of shoes that mattered: one for dressing up and a pair of sneakers. Then my wife at the time bought me a pair of Chelsea boots, and it changed everything.
They let me dress up without looking like I was about to put on a suit. With dark jeans they look sharp, and British shoemaker John White calls Chelsea boots and dark jeans a pairing with real longevity. If you only buy one thing after reading this, make it a pair of Chelsea boots.
What I actually wear now
I don't have a go-to outfit, and that's on purpose. I'd rather not have to remember which combinations work on me. My app, DRESSED, picks a complete outfit from my own closet each morning, so I don't have to think about it.
Because of what I own, a few combinations come up often:
- Work or going out: a gingham shirt, dark jeans and Chelsea boots.
- Dates, back when I was dating: chinos, a shacket, and a collared shirt or T-shirt underneath.
- A weekend with my kids: today it was black jeans, black Chelsea boots, a light green V-neck sweater and a black gingham shirt underneath.
None of these are fashion statements. They're just clearly chosen, and that's most of the battle.
What the professional stylists say
I'm not a stylist, so here's what the people who dress men my age for a living agree on.
Fit comes first. Style Girlfriend interviewed tailors, costume designers and stylists about style for men over 50, and every one said tailoring is what separates a guy wearing clothes from a well-dressed man. That's my band-tee problem: clothes that fit the body you had at 25 work against you now.
Skip the trends. In Mr Porter's guide to dressing when you're past 50, William Gilchrist, who has styled the Rolling Stones and Cillian Murphy, says men at this age should avoid trends and should have developed a style of their own by now.
Dress for who you are, not your birth year. In the same piece, Julie Ragolia, stylist to Pedro Pascal and Mads Mikkelsen, says dressing in your fifties is no different from your forties or twenties: it comes down to your state of mind.
Start with the basics. Catherine Hayward, former fashion director of GQ and Esquire, tells Mr Porter that making an effort starts before the clothes: a proper haircut and a neatly clipped beard. Polishing your shoes and having them reheeled is another easy win.
Find what works and repeat it. Jeremy Langmead, former editor-in-chief of British Esquire, told Esquire that in his 50s he found the pieces that work, stocked up on them and mostly sticks to a uniform, in The Secrets to Dressing Well in Your 50s. I do the same thing a different way: DRESSED rotates combinations that work on me, so I'm never starting from scratch.
That last one is the reassuring part. You don't need a separate set of rules for being older. You need clothes that fit, a few pieces that are clearly yours, and the habit of choosing them.
Why bother at our age
The most common mistake I see in men my age is not caring. We're older, not dead.
Dressing better helps in the relationships you have and the ones you're starting, including professional ones. It matters when you're looking for a job, meeting a client or going on a first date. Too many dads, divorced or not, pick cargo shorts and a T-shirt because they're easy, not because they look good. You don't need to become a fashion person. You just need to look like you meant it.
Why I built DRESSED
After my divorce I was confused about what looked good and why. I didn't want to show up to dates or business meetings looking like I didn't care, so I started asking an AI chatbot what to wear.
It did well when I sent photos of what I owned. But by the third time I asked, it started inventing clothes, because it had forgotten my closet. When I asked how to make this work long term, it told me to build a database of my closet and connect it to AI.
So I did. That's DRESSED: you add the clothes you own, and Vera, the AI stylist, builds a complete outfit from them each day using your weather and calendar. It turned out more people needed it than just me. You can try it free for 7 days, or rate today's outfit without signing up.
For more on how much effort good outfits really take, read this piece.
How this was written: I drafted this with help from AI, using my own answers to interview questions about how I dress. I reviewed and edited every line, and the experiences are mine. Style claims were checked against menswear sources. Corrections are welcome at feedback@trydressed.com.
DRESSED looks at your actual wardrobe, the weather, your calendar, and what you've worn recently — and gives you one answer for what to put on today. Not options. The answer. The formula-finding happens in the background.
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