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Middle Aged Guy’s Date Wardrobe for Summer 2015

By Carolyn J. Woodruff, JD, CPA, CVA

Today, let’s deal with the “date” wardrobe you should build over time (depending on your budget). This wardrobe selection is for Summer 2015 for dinners out, movies, theater, concerts and similar activities.

Find your own look and make it your own.  Be creative.  It will make you feel good about yourself.  Be your own person and have your own identity.  Here are some suggestions:

For dating after separation, the first item you need is the summer sport coat in one of the new great looking seersuckers, maybe a subtle plaid.  If your budget allows for three blazers in your wardrobe, you should also have a pinstripe jacket and an off white or white, all one color, in your dating wardrobe.

Next the shirt.  I recommend your date wardrobe contain two shirts that pop for each blazer. Look at solid bright colored cotton or cotton/linen shirts in nontraditional colors like lime, pink, orange or blue. A half dozen of these shirts would be great. Let your skin tone, eye color, and hair take you in the direction of the right bright colors. Take your jackets and find shirts that “pop” with the jacket. Generally, wear your shirt tail in your pants at fifty.  If you are really thin and fit, you can do a tee shirt under the blazer; otherwise, stick to the shirt. The level-hemmed shirt with the big palm tree on it is out.

Now the jeans—three to five pairs of the most expensive jeans you can afford. These do not need to be blue jeans, but jeans in gray, navy, and taupe.  But, please don’t just buy khakis. If you must have “blue jeans”, please have something unusual about them like shredded. The khaki jean is okay, but not the business casual khaki, which is moldy for a date unless the date is a business event where jeans are a “no-no”.  Buy jeans two inches longer in length, because you need to roll them up.  So if you generally buy a 32 inseam, buy 34 so you have the two inches to roll up.  The rolled cuff gives nice “sloppy” look.

Shoes, and it is all about the shoes. The pants will highlight the shoes. Casual oxford wingtips are popular now.  Don’t think simply brown or black.  Light gray and canvas with white soles and white laces will go with most of your dating wardrobe and look hot. Get a second set of laces. Stay away from black shoes for summer 2015. Combination of light and brown wingtips are versatile. Get a complimentary belt, maybe two-toned.

A pocket square adds a splash of color and can be the final spice of your outfit. Buy the solid color pocket squares in all colors. Buy multiple pocket square holders. These are little “wallets” that hold the pocket square in place and are inserted with the pocket square in the front pocket.  Pocket squares wilt without the pocket square holder.  If you are busy, buy enough pocket square holders for your pocket squares, so you are always ready to go with the pocket square. The pocket square must contrast with the jacket or you do not see it.

A great summer date outfit example:  subtle blue seersucker jacket, lime green shirt, gray jeans, light gray oxford wingtips with off white soles and laces, off white belt, and finish with a lime green pocket square.

In the end, you still have to be yourself. So if this doesn’t appeal to you, find a trend that does appeal. Look at the Duck Dynasty guys. They all ended up with pretty good-looking ladies!

Thanks to my husband, Dwight Ensley, for input on this blog.