Take option A: the evening drinks.
A swanky bar requires smart attire but unless you’ve come straight from work, avoid the suit. Suits are great but they lack individuality. A good shirt is essential (browse mrporter.com for a wide variety of options) but maybe leave the flamboyant patterns until you’ve really got to know one another… and she likes you despite some of your wardrobe. Once the shirt’s sorted, it’s really plain sailing. Chinos are always a hit: get a pair that are well fitted, choose subtle shades of navy or beige (I’ll even allow maroon) and you’re set. No need to look further than Zara for a smart, inexpensive pair that I promise will look good. Top it off with a good pair of shoes: Church’s leathers are always a good investment- just please leave the sock-less plimsolls at home. Pull it altogether with a smart blazer a la Paul Smith or sharp coat (a Burberry inspired trench will always be a hit) and you’ve got the perfect outfit. Simple.
Or try option B: the afternoon weekend coffee meet.
A casual, relaxed vibe calls for chilled clothing but still a cause for effort of course. Smart jeans, a tee under a jumper and quite honestly you’re onto a winner. Again Zara is a go-to for these basic pieces along with the likes of J. Crew and John Smedley for good quality knitwear. Looking good really is that easy. Even keep the stubble if you want, just loose the lumberjack inspired checked shirt, and don’t even think about a low scoop v-neck.