10 Shoes for Men Over 40 That Look Grown, Not Old

After 40, your shoes start to matter more. Your feet want comfort, your budget wants pairs that last, and you don't want to look like you're dressing for a retirement party or trying to look 25.

These 10 shoes for men over 40 solve that. Each one shows a real pair on a real guy, tells you what it works with, and says where to wear it. Some are smart, some are sporty, and a few are made for cold days and long walks.

1. Black Leather Derbies With Khaki Chinos

Black lace-ups are the safest pair you can own. Here they sit under straight khaki chinos with a clean break at the ankle, so the shoe is easy to see. The sole is a little thick, which gives you comfort and keeps the shoe from looking too dressy.

Wear it to: the office, dinner out, a family event.

Swap: brown derbies with the same chinos look warmer and a bit more relaxed.

2. Black Leather Loafers With Olive Chinos

Loafers are the easiest dress shoe to live with, because there are no laces to fight. These have a plain top and a thick sole, which feels sturdy and not too formal. The olive chinos are cuffed above the ankle, so the shoe and sock line show.

Wear it to: work, a restaurant, a long day of meetings.

Swap: wear thin black socks in colder months and no-show socks when it's warm.

3. Dark Sneakers With a Field Jacket and Black Trousers

Sneakers look old when they're bright, bulky or beaten up. Plain dark grey ones with a slim sole look the opposite. Wear them with straight black trousers and a field jacket, and you get a sharp outfit that is still easy to walk in.

Wear it to: a walk, errands, a casual lunch.

Swap: black leather sneakers dress the same outfit up a little.

4. Black Slip-On Loafers With Dark Jeans and Patterned Socks

This is a simple weekend pair. Slip-on leather shoes go with a plain tee and dark jeans, and they take two seconds to put on. The patterned socks are the only detail, and they show just enough when you sit down.

Wear it to: a park, a market, lunch with friends.

Swap: keep the socks in the same dark family as the shoes if you want it quieter.

5. Worn-In Brown Leather Lace-Ups With Grey Trousers

Brown leather gets better with age, and these have the soft creases of a pair that has been worn for years. Brown shoes with grey trousers and a brown quilted jacket is a calm, earthy mix. The trousers are a bit long here, so a small hem would make the shoes show more.

Wear it to: a cold day in town, a market, a casual lunch.

Swap: polish them with a neutral brown cream to bring the color back.

6. White High-Top Trainers With Shorts for the Gym

At the gym, you want support and a pair that doesn't look like it belongs to a teenager. These white trainers have a high cut and a flat sole with black side panels. The crew socks with navy stripes finish the look.

Wear it to: the gym, a home workout, a yoga class.

Swap: keep white trainers for the gym only, and wipe them clean after each use.

7. Lace-Up Walking Shoes With Corduroy Trousers

These are sturdy lace-up shoes with a thick sole and a leather top, the kind you can wear for hours. Corduroy trousers fall almost straight to the shoe, with only a small fold at the hem. You get a pair that looks neat and is built for walking.

Wear it to: city walks, travel days, long errands.

Swap: a plain black pair looks more dressed up, a brown pair more casual.

8. Black Sneakers With Grey Joggers and a Navy Jacket

Black sneakers with a white sole are the cleanest casual pair. They don't show dirt, and they go with grey, navy and green. Light grey joggers with a navy jacket keep the outfit relaxed and easy to move in.

Wear it to: a cold-weather walk, a quick trip out, a casual day.

Swap: slim grey chinos instead of joggers make it a bit smarter.

9. Grey Running Shoes for Walking and Training

If you run, walk fast or train, get a real pair of running shoes. These are light grey with a thick cushioned sole and a mesh top. The soft color goes with black shorts, and the shoe doesn't scream sportswear.

Wear it to: the track, a morning jog, a fast walk.

Swap: save running shoes for sport. For daily wear, pick a plainer sneaker.

10. Black Leather Shoes With a Warm Parka for Winter

On cold days, grip and warmth come first. Here a man in a navy parka walks with trekking poles in plain black leather shoes. If you walk outside a lot in winter, look for a rubber sole with deep tread and room for thick socks.

Wear it to: winter walks, the park, cold commutes.

Swap: a leather boot with a rubber tread sole gives more grip and keeps your feet dry.

How to Pick Shoes After 40

Comfort comes first. Look for a cushioned insole and a sole with a little give. Try shoes on in the afternoon, when your feet are at their biggest, and walk around in them before you buy.

Leave a thumb's width at the toe. Your heel should not slip. If your feet have gotten wider, look for brands that sell a wide fit.

Keep the shape simple. A rounded or slightly almond toe looks classic. Very pointy and very square toes both look dated fast.

Choose colors that go with everything.

Shoe	Goes with	Best for
Black leather derby	Khaki, grey, navy, black	Work, dinner, events
Black or brown loafer	Chinos, dark jeans	Work, weekends
Dark sneaker	Jeans, black trousers	Everyday
Brown leather lace-up	Grey, navy, olive	Cooler months
Running shoe	Shorts, joggers	Sport

Look after them. Clean and condition leather every few weeks. Replace sneakers when the sole is worn flat, since old soles hurt your knees and back.

Match the shoe to the trouser. Straight, ankle-length trousers show off any shoe. If the hem bunches over the laces, get it taken up. A good fit helps your shoes look right, and our formal chinos outfits show how much a clean hem changes things.

FAQ

What are the best shoes for men over 40? Black leather derbies or loafers for smart wear, and dark, plain sneakers for everyday. A good pair of walking shoes with cushioning covers the rest.

Should I wear sneakers after 40? Yes. Pick clean, simple ones in dark grey, black or white with a slim sole, and wear them with trousers or dark jeans. Skip very bright colors and bulky chunky soles.

What shoes make a man look older? Worn-out soles, scuffed leather and very square toes. Shoes that don't fit well also make you walk and stand differently.

How many pairs of shoes do I need? Three is a good start: black leather lace-ups or loafers, plain sneakers, and a brown pair. Add a boot for winter. For more casual outfit ideas, see our spring jeans outfits for men.