Myth: Your pair of steel-toed work boots are great on the job but have no place at the local watering hole on a Friday night.
Truth: With the right jeans, jacket, and attitude, any pair of work boots can make you the best dressed working man at the bar on the weekend. You just need to know how to pull it off.
Just please wash the dirt off before you go out….
There’s nothing wrong with wearing a good pair of boots to the bar, club, or restaurant with your friends. Honestly, if you do it right, you’ll look dapper. Not only will you stick out from the crowd, you’ll look like a man that’s comfortable in his own skin (even if you’re only wearing them out because you can’t afford nice shoes!).
The only problem is that most men do it completely wrong. Nothing looks better than a sharp-dressed man whose outfit is perfectly complemented by his boots. On the flipside, nothing looks worse than a guy who looks like he walked in the door from work, threw on a t-shirt, and didn’t even bother to clean up his boots before heading out.
Here’s how to build an outfit that makes you look like the working man’s version of Prince no matter the venue.
Pros of Wearing Boots Out
Choosing the Perfect Jeans
If you’re rocking a pair of black combat boots (not our first choice for the bar), a pair of slim fitting black jeans is perfect. If you’re wearing a pair of dark brown hiking boots, consider a pair of red or green Chino’s. The mixing and matching game starts with the kind of boots you’re wearing. They are the foundation for your entire look. When in doubt, nothing screams “classic cool” more than a pair of boot-cut jeans with standard, all-purpose construction boots (except for maybe Fonzi punching a Jukebox to turn it on, but we can’t all be that cool).
To Cuff or Not to Cuff
Cuffs are a bit risky. Get them right and you look like Old-World Royalty. Get them wrong and you look…well…let’s not ruin the night by bringing THAT up.
A general rule of thumb is to do a single or a double cuff based on your height. If you are on the short side (5’10” or shorter), you want to have a cuff that’s 1.5 inches or narrower. A narrow cuff will make you look taller (for all those girls on SnapChat that have height requirements!), and a wider cuff will make you look shorter. Of course, you can mix this look up depending on what kind of pants you are wearing.
Never Tuck Your Pants Into Your Boots
Unless you ride horses for a living (playing Red Dead Redemption doesn’t count), you should always keep your pants cuffed above your boot (or draped over them). When you’re going out, you always want to consider fashion over function. If you want to be the guy at the bar that tucks his pants into his socks, you might as well also pin your mittens to your jacket and wear a sign that says “please don’t give me your phone number”. Even if it is slightly less comfortable it is well worth keeping your dapper look intact.
Matching the Top to the Bottom
If you’re going for the classic casual look, any solid color crew neck t-shirt will go great with a pair of bootcut jeans. If you walk with purpose and confidence, your outfit will speak for itself. Remember, nothing screams confidence more than a man who goes against the grain and pulls it off.
If you go the button-up or flannel route, you can always work into a taller pair of boots with a pair of blue skinny jeans. This will add some attitude to your look (not the kind your parents hated when you were younger either!).
What About Jackets?
If you want add some edge to your look, pair a bomber jacket with combat boots. For a more business casual look, a blazer and a pair of sharp hiking boots will get you all the job interviews. Maybe you want to look a little more rugged but don’t know how to grow a beard. In that case, throw on a denim jacket to compliment your construction boots. A smart pairing of your boots and jackets will always take your look to the next level. Who knows, maybe we’ll see you in those annoying Facebook ads selling L.L Bean boots leading up to winter.
Whether you’re trying to look sharp for an upcoming job interview, or tough for a night at the clubs in a rough part of town, a pair of boots will always add to your look. Feel free to use your imagination, and try a few things out. You’ll be surprised how much you can elevate your look with a sharp pair of work boots. Just remember, being comfortable in your own skin is all that matters…. except tucking your pants into your boots. That’s just dumb.