Now that the winter months are finally drawing to a close, it’s time to start looking toward the warmer months.  I live in Dallas, where we get about a whole month of Spring and then it’s Summer.  And so, I’m giving out what I consider to be must have items for the next few months.

First up is the Boat Shoe:

This shoe is perfect for the upcoming warm weather.  It looks great during the morning, lunch, happy hour and casual dinners.  I love it for the Hamptons-esque summer vibe that it gives.  When you wear this shoe, you could go from a leisurely coffee on a Saturday morning to a night out on a hot summer night.  Also, this is a great shoe for those men who want to hide their ugly feet.  A lot of men have ugly feet and toenail issues and this shoe keeps the rest of the public (read: me) from having to see your gnarled toes in flip flops.

The shoe above is available at Sperry for $85.  Not a bad price for a shoe that will take you from happy hour on a cool April evening to a late dinner in September.  Historically, it doesn’t get too cold in Dallas until October, so I can’t beat $85 for 6 months of wear.  You can find cheaper versions of this shoe out there, but when buying shoes, I always think that quality is a better reason for buying than price.  However, if you’re only going to wear them a few nights of the spring/summer, then go for the cheap ones.  No sense in paying a lot for a shoe you know you won’t wear.

What to wear these with?  You can’t go too wrong on these.  Though, I will advise that they look best with a khaki pant/short and a nice button-down shirt or a vintage t-shirt.  Will you look like a douche in these?  If you stick with a classic, preppy outfit, you’ll look fine.  But pair them with Dad Jeans and tucked in polo shirt and you’ll like a laid-off banker.

When should you stay away from these?  If you are going to a place that’s outside, then these are perfect.  If you’ll be sitting in a dark steakhouse with a glass of red wine?  Avoid.  These shoes are more for being outside and having fun, then they are selecting a wine to go with your porterhouse.  Also, don’t wear these to the office, even on a casual Friday.

Next post:  Umbrellas.

Stephen Trendy

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