What to Wear on a First Date: A Guide for Men

Style guru Rudi Jotikasthira offers some crucial advice for any man hoping to end up in the pink —so to speak.

February 11, 2017
So you’ve scored yourself a date for this Valentine’s Day. Well done. Time to stop the back patting and figure out what you’re going to wear. Style guru and fashion designer Rudi Jotikasthira gives tips on making the right impression on the all-important first date.

1. Make an effort:
Yes, personality, wit, and charm are important, but they aren’t worth a damn if she wrote you off the moment you walked through the door. Make an effort to present yourself well and show that you are a complete package. Most first dates take place somewhere casual, but that doesn’t mean you should turn up looking scruffy. Let’s be clear: appearances matter, as women notice things. Show her you know the meaning of personal hygiene even if you’re the five-o’clock-stubble type of guy —that means washing your hair and making sure your nails don’t look like you’ve been digging up the garden.
Jude Law and Matt Damon in Talented Mr. Ripley (1999)
2 Footwear: She will notice your feet before anything else. Many a man loses out on a second date because of a shit pair of shoes. Wear decent leather lace-ups or loafers. You can dress them down with plain, dark jeans. Keep the color of the shoes neutral, and clean or polish them before the date. Sneakers are allowed but only if they’re plain and not too sporty. Dress them up with smart trousers and a crisp white shirt to avoid looking too casual.
illustration by Napisa Leelasuphapong

3. Don’t wear a suit: With the exception of very posh restaurants or occasions with dress codes, skip the suit. Other than looking like you’ve come straight from work, you’ll also appear as much fun as a newsreader about to announce the latest terrorist atrocity. Always opt for smart separates such as a blazer and slim, tailored trousers instead.

4. Subtle details: Pay attention to small details that add to the bigger picture —she will appreciate it. Wear a simple but good quality leather belt with a plain buckle, and carry a nice leather wallet. Forego obvious logos and let her appreciate the quality of the leather rather than its price tag.

(From top left) Cary Grant in Alfred Hitchcock’s Notorious (1946), Casablanca with Humphrey Bogart (1942), Risky Business with Tom Cruise (1983), illustration by Napisa Leelasuphapong

5. Wear some color: Wearing plain black or neutral colors is boring. Don’t be scared of highlighting your look with color. Colored socks or a jewel-tone T-shirt under a black or navy jacket can create a more sophisticated look.

6. Less really is more: Keep it simple. This is no time to experiment with new trends from the runways of Paris or Milan. No girl wants to be with a guy who takes more time getting ready than she does. This also applies to the amount of cologne or aftershave you put on. Spray sparingly to draw her in quietly, not to leave her desperate to escape the table —and you— in search of non-carcinogenic air.

To Catch a Thief with Cary Grant (1955)
At the end of the day (and for a promising end of the date), it should really be about you and her. Put your best self forward by wearing clothes that fit you well, which will not only enhance your features and figure but also make you feel comfortable and confident. Lastly, don’t forget your lucky pants, because you just never know. —R.J.