Choose your top according to the climate. If it’s snowing outside, your favorite sweater is a perfect option. If it’s sunny and 75, a colored t-shirt will complete your look perfectly. For weather somewhere in between, layer a leather or denim jacket on a t-shirt for effortless vibes. Avoid tank tops at all costs. 

For shoes, try something relaxed like Converse sneakers or casual Oxford loafers. When it comes to shoes, much of the dressiness is based on material, so suede or cloth is the way to go for a casual date. Like tank tops, avoid sandals. Only wear sandals to the beach, unless you don’t want a second date. 

A Business Casual Date Look

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Sometimes dates are scheduled for the middle of the week, in the middle of a workday, or immediately after the workday is done. This isn’t common, but it happens, and you need to be prepared if it does. Luckily, this is an easy look to achieve. It’s basically what you’d wear to work, but on the days you have an important meeting or presentation. 

On important days at work, you’re trying to impress someone, just like you are on a first date. A pressed shirt and a good looking sport jacket are the easiest way to impress someone. Keep your bottoms dressy as well. If you can, schedule your big presentation for the same day as your first date. Two birds, one handsome stone. 

A Dressy Date Look

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Like business casual, dressy is a rarity in date looks. It’s not often you attend an opera or a charity gala on a first date, but it could happen. A tuxedo is probably not necessary, but a three-piece suit, or at the very least, a suit jacket, is required, as is a tie. And if you don’t know how to tie a tie, find a tutorial on YouTube. 

Accessories make or break a dressy outfit, so wear your best watch, tie clip, and matching pocket square to complete the look. You’re sure to get a second date. If not, you’ll get another first date with someone else for sure.