Ask Anton: Dashing Date Style

Dear Anton, I’m set to go on my first date with a girl I’ve had my eye on for a while, but I have no idea what I’m supposed to wear. Do you have any tips I could follow?
-Sam

Dear Sam,
To help you get a handle on first-date dressing, I’ve outlined a few of the most common situations and what you should wear in each one. With the knowledge that you look smokin’ hot in your first-date fashion, you can relax a little and focus on letting your personality shine through.
On a first date, many people stick to the traditional lunch or dinner meeting. First impressions set the tone for the rest of the date, so it’s vital that you make a good one. If you’ve made a reservation at an uber-chic restaurant, your outfit will likely involve a slim-fitting suit along with elegant dress shoes. On the other hand, if you show up looking like you’re red-carpet ready when you’re just grabbing a hot dog, it's more than a little inappropriate, and rather than enjoying her meal, she’ll think you’re totally out to lunch.
Another standard first date destination is the movies. If you’re in the habit of dressing sharply, then put some effort into choosing your outfit. On the other hand, guys who tend to favor jeans and sneakers should avoid sprucing up too much. After all, if you wear more tailored clothing when your style is usually more loose and laid-back, you’re setting the standard for how your date will expect you to dress in the future. So unless you’re prepared to get dressed up every time you leave the house, don’t bother.
Essentially, aim to dress in a way that makes you feel comfortable and just be yourself when it comes to fashion at the movies. For a look that’s both hot and easy to wear, try a pair of dark straight-leg jeans, like the Wilhelm Jean from Monarchy, and throw on a graphic printed top, like Kentucky’s Birds Tee. On your feet, either sneakers or sporty-looking loafers are appropriate with this outfit.
Obviously, you know you shouldn’t wear a three-piece suit for a picnic-style date. However, don’t think that you can wear shorts with sneakers or ripped-up jeans and a baseball cap just because you’re spending time outdoors. Instead, focus on coordinated pieces that show her that you didn’t just pull on the clothes from your bedroom floor for this occasion.
Since picnics imply decent weather, try a khaki pant or even a pair of linen pants. Pair them with a light-coloured casual collared shirt, Like Ben Sherman’s Corgi Shirt in Optic White. Finally, brown sandals will complete your relaxed yet elegant ensemble.
Hopefully you’ll have a successful first date. If not, at least you’ll be dressed for it.
I hope this helps,
Anton