His: Winter Date Night

Winter date nights.  Especially hard down here in the South,  as we tend to overdress and over-prepare for cold weather.  A threat of snow will cancel school 24 hours in advance, and empty out the grocery store shelves.  It’s like a bad version of Red Dawn.  Well, just because the weather is cold doesn’t mean that there isn’t time for the ladies.

Winter dating is fine, but it takes some planning.  The culture in the South is built around outdoor activities (every restaurant has a deck), so in the winter, you have to look for indoor activities.  One of my favorite things to do in the winter is go see concerts, specifically at the smaller venues.  So let’s play out that scenario: a winter date night at a concert.  Small bites beforehand, hopefully something to make you look forward to the next date afterwards. Here’s what I’d wear to pick her up:

From top left:

1. Randolph Engineering Sportsman Sunglasses:  The sun goes down earlier, which gives you all the more reason…especially if you are heading west.  These Sportsman sunglasses from Randolph are an awesome pair of aviators with some bells and whistles.
2. Lumina Graham Charcoal Oxford Shirt:  How many white, blue, and pink oxfords do you have in your closet?  Expand your pallet a bit and go for charcoal.  It goes with everything, and is a nice hue for the winter months.
3. Creed Millesine 1849 Cologne:  When picking out the smell good in the winter, look for something woodsy.  And no, this cologne is not a product of your favorite band of the same name.  These folks actually know what they are doing.
4. 1958 Rolex Explorer 1 6610:  I love the look of adding something so classic to a quasi-casual outfit.  Granted a vintage Rolex, like this Explorer 1, will go with anything, but it changes the theme of the outfit for the better.  If you don’t have a vintage watch, get it on your wish list ASAP.
5. J. Crew Cashmere Colorblock Sweatshirt:  It’s cold, and you’ll need to layer.  Go a little sideways with J. Crew’s take on the sweatshirt, made out of cashmere in a navy and gray colorblock style.
6. Levi’s Made & Crafted Tack Selvedge Jeans:  Why not grab a new pair of jeans with some of that Christmas money?  There are a bunch of affordable options (especially in the after-Christmas sales).  She’ll appreciate the well fitting jeans, and you’ll get an early start on the break-in process.
7. Martin Dingman Woodrow Houndstooth Belt:  Belts add flare, and this option from the Ozarks has a tortoise shell detail on the buckle.  Not much cooler than that.
8. Smart Turnout Felsted Striped Socks:  Cool socks for a cold night.  Keep your toes insulated.  She may not see these…but she might…
9. Dubarry Kerry Chelsea Boots:  Let’s call these ‘dress boots’.  They look great with just about everything, and have a more updated style when done right.
10. Filson Guide Jacket in Soy Wax:  Your outer layer should have plenty of pockets to stow away all your (and her) stuff.
11. Cash Money:  Don’t ever open a tab at a concert.