Date Night in Madison

It’s summertime in Madison! And that means concerts on the square, lazy afternoons on Mendota terrace, and plenty of opportunities to meet someone special – and with all of the other activities around town to enjoy; sailing, biking, and our many beer gardens, it should be no trouble coming up with ideas for date night. There’s just one catch: what are you going to wear on the first date night?

The answer to this question will depend on many factors…what your date’s interests are, where you plan on going and what you plan on doing.  No matter what the situation it is important to keep in mind that overdressing probably won’t hurt your chances but under-dressing almost certainly will.  

Besides eyes, smile, and hair style, the first thing women look at when they meet a man are his shoes. What shoes you wear will say a lot about your attitude, your aspirations, and whether she can expect to enjoy an evening at L’etoile or McDonalds. If the setting calls for slacks then it’s best to go with brown or black leather. If you’ll be wearing shorts steer away from flip-flops or sandals; instead try to find a pair of Dockers or a similar flat-bottom, lace-less shoes which come up to just below the ankle. This will allow you to eschew socks and look good in the process. As always, it’s important to match the belt to whatever footwear you select, and a knit belt with a pair of canvass loafers will never let you down.

An Evening Date Downtown

For an evening spent downtown enjoying our vibrant food scene or one of our many local bars or nightclubs it is a good idea to wear a light jacket when the weather permits. Not only does it provide a place to keep your keys, phone, and wallet that isn’t your pants’ pocket (to avoid that awkward bulge), but you never know when a 75 degree day will turn into a 60 degree night and your date will have forgotten her sweater or pull-over.  

For a formal date night, you might try spicing things up by including an ascot as an alternative to the usual necktie. This is especially recommended in the hotter July and August months as it sits beneath the open collar, allowing for better air-flow while keeping the chest covered. Your date will be impressed by your confidence and it will be a great conversation starter.

One essential piece of advice is this: when meeting someone for the first time, wear something that you feel confident in! If you’re uncomfortable it will show so aim for a look that highlights your best qualities. Look good, feel good, do good!

By: Christopher Dally