The type of restaurant will usually dictate the kind of clothes and accoutrements you should be focusing on for your dinner date. You can keep it simple with a sweater and dress pants match, or you could pair a nice suit with a matching tie, or even dust off that old dinner vest. It’s not unusual for men to wear downy blazers over their dinner suits, or quilted parkas over their shirts, but bear in mind that the fewer pockets you have on a jacket, the more suitable it is to wear for dinner. On sunny days, you could also ditch the jacket altogether and wear a nice dress shirt. Since you want to look your best, make sure your dress shirt is properly fitted.
If it’s drinks you’re after, then there’s no need to show up dressed to the nines, but you should make sure your get-up is dashing and smart. You could go for a rolled back sleeve shirt and dress pants as you may not have time to get changed if you’re going out straight after work. Or you could opt for an even more casual outfit, with an anorak and sneakers. If the weather’s nice, a plain shirt and bomber jacket ensemble should be easy to slip into when you’re pressed for time. A hoodie would never be appropriate for this type of occasion, unless it’s made to resemble a waistcoat, or it’s made of wool, or other types of material smarter and firmer than most cotton blends.