If you haven’t dated for twenty or thirty years, the question of what to wear can be surprisingly unsettling. Perhaps a partner used to help choose your clothes, or you’ve spent years in work suits, gardening gear or whatever was clean. Maybe your body has changed, or you’re not sure whether the shirts you’ve always worn still look right. And at the back of your mind may be the worry that you’ll look like you’re trying too hard, or not hard enough.
This guide covers dressing for dates after 50 in a way that’s comfortable, appropriate and still feels like you. It’s not about chasing fashion or trying to look younger. It covers how to start with what you’ve got, why fit and condition matter most, outfit ideas for different kinds of dates, shoes, grooming, glasses, dressing for a changing body, doing it on a budget, and what to wear in your dating profile photos.
The short answer
- Clean, well-fitting clothes in good condition matter far more than labels or fashion.
- Smart-casual suits most first dates after 50: good jeans or chinos, a shirt or knit, and a jacket.
- Dress for the date you're going on. A walk, a coffee and a dinner need different things.
- Shoes say a lot. Clean, comfortable, smart-casual shoes go with almost everything.
- Grooming counts: a recent haircut, tidy facial hair and clean nails make a real difference.
- Your profile photos should show how you'll look when you turn up, so wear things you'd actually wear on a date.
Why it matters, and why it doesn’t
Nobody sensible decides whether they like you based on your shirt. What people tend to remember is whether you were kind, interested in them, easy to talk to and good company.
But what you wear sends a simple signal: that you’ve made an effort and you’re taking the date seriously. Clean clothes that fit say “I respect your time”. It also affects how you feel. If you’re comfortable and reasonably confident in how you look, it’s easier to relax and focus on the conversation.
So the aim isn’t to impress. It’s to look like the best everyday version of yourself, and then forget about it. Our guide to how to feel attractive again after 50 covers confidence more broadly.
Start with what you have
Before buying anything, go through your wardrobe honestly. Many men find a few good outfits hiding among old favourites.
A simple wardrobe check
Try things on and ask:
- Does it fit me now? Not when you were last at your fittest
- Is it in good condition? Check for fraying collars and cuffs, faded colours, stretched necklines, bobbling and stains
- Does it look current enough? Very baggy or very dated cuts can make you look older than you are
- Is it comfortable to sit and walk in?
- Would I wear it to meet a friend for a pint or lunch? If so, it’s probably fine for a first date
Be ruthless with anything worn out. A faded shirt with a frayed collar undoes the effect of everything else. Clothes strongly linked to your marriage can go too, if you’d like a fresh start.
Pick two or three go-to outfits
From what’s left, put together two or three outfits you’d be happy to wear on a first date. Try them on with shoes and a coat. Ask a friend, sister or grown-up child for their honest view if you’re unsure. Having outfits ready removes a lot of last-minute stress.
Fit and condition matter most
If there’s one thing that makes the biggest difference, it’s fit. Many men carry on wearing a size they bought years ago, or buy everything a size too big for comfort.
Signs something doesn’t fit:
- Shirt buttons pull across the stomach or chest
- Shoulder seams hang off your shoulders, or sit too far in
- Sleeves cover your hands, or stop well short of your wrists
- Trousers bunch heavily at the ankles, or are too tight to sit comfortably
- Jackets won’t button, or swamp you
A tailor or alterations service can shorten trousers and sleeves, or take in a waist, for much less than the price of new clothes. Clothes that skim the body, neither tight nor baggy, look best on most people.
Outfit ideas for different dates
Most first dates after 50 are relaxed and often in the daytime, so smart-casual is usually right.
| Date | What tends to work | Things to think about |
|---|---|---|
| Coffee | Dark jeans or chinos, an Oxford shirt, polo or knit, a casual jacket | Keep it relaxed. A suit would feel too formal |
| A walk | Comfortable trousers, layers, a waterproof jacket, walking shoes or clean trainers | Check the weather and terrain |
| Lunch | Chinos, a shirt and a knit or blazer | Something you can sit in comfortably |
| Dinner | Smarter trousers, a good shirt, a blazer, smart shoes | Check the venue. Some restaurants are more formal |
| Drinks | Dark jeans, a shirt or smart knit, a jacket | Bring a layer if you might sit outside |
| Gallery, museum or market | Smart-casual with comfortable shoes | You’ll be on your feet |
| Theatre or concert | A shirt and jacket, smart trousers | Venues can be warm, so layer |
If you’re unsure, it’s fine to ask your date how smart the place is, or to look it up. Our guide to first date ideas over 50 has plenty of ideas for where to go.
A reliable first-date outfit
If you want one combination that works almost anywhere: dark, well-fitting jeans or chinos, a plain shirt in white, light blue or a soft check, a navy or grey jacket or knit, and clean leather shoes or smart trainers. It’s hard to go wrong.
Shoes
People notice shoes, and scruffy footwear can let down an otherwise good outfit.
- Keep them clean and in good repair. Polish leather shoes and clean trainers before a date
- Smart trainers in plain leather, suede desert boots, loafers and Chelsea boots all work with smart-casual clothes
- Avoid worn-out running trainers unless you’re going on an active date
- Make sure they’re comfortable. You may walk further than you expect
- Match the occasion. Walking boots for a hill walk, smarter shoes for dinner
Dressing for British weather
Being cold, wet or overheated makes it hard to relax.
- Check the forecast on the day
- Layer up. A knit or overshirt under a coat lets you adjust indoors and out
- Choose a decent coat. A navy or dark overcoat, a waxed or quilted jacket, or a smart waterproof can all work
- Carry a compact umbrella or wear something with a hood
- In summer, choose breathable fabrics such as cotton and linen, and avoid anything that shows sweat badly
Colour and fabric
You don’t need to be adventurous. A few simple principles help.
- Navy, grey, white, light blue, olive and brown are easy to wear and combine
- A bit of colour near your face, such as a blue shirt or a green knit, can be more flattering than all grey or black
- Simple patterns such as small checks or stripes are fine. Keep it to one pattern at a time if you’re unsure
- Natural fabrics like cotton, wool and linen feel comfortable and wear well
- Avoid novelty prints and slogan T-shirts on a first date, unless you’re confident they reflect your personality
Grooming
Grooming often makes more difference than clothes. Small things are noticed.
- Get a haircut a few days before, so it’s fresh but not just-cut
- Facial hair: if you have a beard or moustache, keep it trimmed and tidy. If you’re clean-shaven, shave on the day
- Trim nose, ear and eyebrow hair, which many men find grows more with age
- Clean, short nails
- Fresh breath: brush your teeth, and consider mints. Avoid heavy garlic beforehand
- Aftershave or cologne: a little goes a long way. Many people find strong scents off-putting in a small space
- Clean glasses, if you wear them
Hair loss and grey hair
Grey hair is common and many people find it attractive. Thinning or losing your hair is also very common. A short, tidy cut usually looks better than trying to disguise it, and many men find that a closely cropped or shaved style suits them. Whatever you decide, a good barber can advise on what will work for your hair.
Glasses
If you need glasses, wear them. Being able to read the menu and see your date clearly matters more than anything else. If your frames are very old or you don’t like them, a new pair can be a worthwhile update, as they sit right at the centre of your face.
Dressing for a changing body
Many men’s bodies change after 50. Weight gain, weight loss, health conditions or mobility issues can all affect what’s comfortable.
- Buy for the body you have now. A comfortable, well-fitting shirt looks far better than a straining one
- If you’ve gained weight around the middle, a shirt worn untucked (if it’s designed to be) or a jacket worn open can be more comfortable
- If you’ve lost weight, clothes that hang off you can look sloppy. Having a few things taken in, or buying one or two items in your new size, helps
- If you have a health condition or disability, choose comfort and practicality. Easy fastenings, stretch fabrics and supportive shoes can still look smart
Our guide to dating with a health condition covers the wider picture.
A small date wardrobe
If you’d like to build a few reliable pieces, this list covers almost every date. You may already own most of it.
- Dark, well-fitting jeans
- A pair of chinos in navy, stone or olive
- Two or three shirts, such as white, light blue and a subtle check
- One or two knits, such as a crew neck or quarter-zip
- A navy or grey blazer, or a smart casual jacket
- A good coat for colder weather
- One pair of smart leather shoes or boots, and one pair of clean, smart trainers
- A decent belt that matches your shoes
These combine into many outfits.
Style on a budget
You don’t need to spend a lot.
- Charity shops often have good-quality jackets, coats and knitwear
- Resale apps and sites such as Vinted and eBay are handy for finding specific items
- Look after what you have: proper washing, ironing and shoe polish make clothes look newer
- Get things altered rather than replaced
- Buy fewer, better pieces that go together
- Ask for help. Some department stores offer free personal styling appointments, with no obligation to buy
What to wear in your profile photos
Your photos should show how you look now, dressed as you would be on a date.
- Use several outfits across your photos, such as one smart, one casual and one outdoors
- Plain colours photograph better than busy patterns
- Avoid sunglasses and caps in your main photo
- Avoid photos in work uniform or high-vis, unless your job is a big part of who you are
- Show what you enjoy, such as walking, cycling, cooking or travel
Our guides to dating profile photos after 50 and dating profile examples for men over 50 can help.
What to avoid
A few things tend to work against you:
- Worn-out or stained clothes
- Clothes that are too tight or far too big
- Very dated outfits, such as the suit you got married in
- Trying too hard to look young, such as very skinny jeans or loud designer logos, if that’s not you
- Strong aftershave
- Leaving it to the last minute
After divorce or bereavement
For some men, choosing clothes for a date is unexpectedly emotional. A partner may have bought most of your clothes, or you may feel guilty making an effort for someone new. Some men find that buying one new item for themselves feels like a positive step. Others are happier in familiar clothes. Both are fine.
If getting ready brings up grief or anger, give yourself time. Our guides to dating after divorce and dating after losing a wife may help.
Second dates and beyond
Once you’ve met once or twice, it’s natural to relax a little. You don’t need to dress up more each time, but it’s worth keeping up the basics: clean clothes, good grooming and something suited to the plan.
- A different outfit from the first date shows a bit of thought, though repeating a favourite is fine
- Meeting their friends or family: aim for the smarter end of smart-casual, as you would for a first date
- A weekend away: pack a mix of casual and slightly smarter clothes, comfortable shoes for walking and something warm for the evenings
- Staying in: comfortable but clean clothes. There’s no need to put on a show, but tired old jogging bottoms send a message too
As the relationship grows, your partner will see you in every state, from gardening clothes to a wedding suit. That’s part of getting close. Making a little effort when you see each other, though, is a small way of showing you still care.
Getting ready on the day
- Lay your outfit out the night before, including shoes and coat
- Iron your shirt and check for marks
- Give yourself time, so you arrive calm rather than rushed
- Plan your journey, allowing for delays
- Check you have your phone (charged), wallet, keys and an umbrella
- Follow good first date safety habits, such as meeting somewhere public
Our guide to first date conversation tips can help if you’re nervous about what to talk about.
Common situations
“My wife always chose my clothes”
That’s very common. A friend, family member or free personal styling service can help you work out what suits you. Start with a few simple, well-fitting basics.
“I’ve only got work suits and gardening clothes”
Chinos or dark jeans, a couple of shirts, a knit and a casual jacket will cover most dates.
“I don’t want to look like I’m trying too hard”
Smart-casual clothes that fit well look relaxed but considered. That’s the sweet spot.
“My kids say I dress like a granddad”
Their view may be worth hearing, but it’s your choice. You might try one more modern piece, such as a better-fitting pair of jeans, and see how you feel.
“She suggested a smart restaurant”
A shirt, a blazer, smart trousers and polished shoes will work almost anywhere. A tie is rarely needed, but you can check the venue’s website.
Frequently asked questions
What should a man over 50 wear on a first date?
Smart-casual clothes that fit well: dark jeans or chinos, a shirt or knit, a jacket, and clean shoes.
Should I wear a suit on a first date?
Usually not, unless the venue is very formal. A blazer with chinos or smart trousers is more relaxed.
Do I need new clothes to start dating?
Not necessarily. Most men can put together a couple of outfits from what they have, perhaps with one or two well-fitting new pieces.
Is aftershave a good idea?
A little, yes. Strong scents can be off-putting.
Should I shave off my beard?
Not unless you want to. A well-trimmed beard looks good on many men.
What should I wear in my dating profile photos?
The kind of clothes you’d wear on a date, in a few different outfits, so people can see how you look now.
Related guides
- How to feel attractive again after 50
- Dating profile photos after 50
- Dating profile examples for men over 50
- First date ideas over 50
- Style tips for women dating after 50
- First date safety checklist
Sources
- Hearts Again editorial guidance on first dates and confidence.