You are likely seeing it everywhere. Grandpa core is in. What does that mean? It means that what used to be cool in your dad’s day, your grandfather’s day, maybe even your great grandfather’s day is cool again. We’re going old school in the style world, causing people to flock to thrift stores or raid their ancestor’s closets for authentic vintage clothes so they can put together nostalgic looks from the 30s, 40s, 50s, 60s, 70s, 80s, 90s — get the idea? If it is old, it is new.
But that doesn’t mean everyone is doing it right. Sometimes it looks downright silly. We have seen guys in legitimate zoot suits. Women dressed as flappers. TikToks and Instagram reels are overflowing with people trying to make a name for themselves and going over the top by looking like a Peaky Blinder. Now, while we all wish we could look like a Peaky Blinder, there is an art to doing this in a way that makes you look stylish and not like you are in a cosplay.
Less is more
First thing’s first, let’s get one thing straight. Less is more. When you look at the picture above, you likely get two separate thoughts. The first is, “those guys were the epitome of cool and tough in their day.” The second is, “if I dressed like that today, nobody would take me seriously.” You are right in both instances.
Dressing like you are a part of this mafia family may seem pretty fantastic in theory, but the truth is in practical application you come across looking like a cartoon character. You look like you are a henchman of Judge Doom in Toon Town. Instead of going all out and cosplaying a tough and rugged man from the past, here are some ways to treat your wardrobe so you can present and updated version of what was cool back then, so it fits today.
Loosen up
Step one, when you are looking for an old school look is to loosen up. This is both figuratively and literally. You need to have fun with this or you won’t come across genuine. So do yourself a favor shake off the rigidity, and start playing with what you love about the vintage look and how you can incorporate it into your modern wardrobe.
The literal way to loosen up is in the fit. Start investing in dad jeans, looser in the hips and the legs and sitting higher on the waist. Dump the ultra slim fit suits and start wearing something a little roomier to give yourself that middle of the century vibe to go along with the modern day fabrics.
One garment at a time
Here is the trick: when you start moving one item at a time into your wardrobe, you will gradually start adopting a specific look and it will start to feel more natural. For instance, if you want to capture a sexy vintage look, invest in (or inherit if you are lucky enough) a leather flight jacket from WWII and start wearing it with your modern day wardrobe. You will start to see the effect it has on the outfit and the people around you.
You can also add smaller accessories like a vintage Vietnam War watch or a signet ring from your grandfather’s fraternity. Something that takes you back but doesn’t overwhelm the look. Small steps like this allow you to integrate these items into your every day wardrobe without abandoning your current styles.
Own your tux
You know what vintage men did well? They black tied better than any of us today. Sure, you can go back to the Victorian Age and say that the coat tails and white tie is the way to go, but the early 20th Century was the cream of the crop when it comes to dressing for a party. Think The Great Gatsby, nobody did it better. But what was it about those men, and why can’t we replicate those looks today? There is a simple answer.
Back then, even the less fortunate owned their clothing. If you were wearing a tuxedo, it was fit for you. It is tailored to your body, and the fit is perfect. Around the 70s and 80s, men stopped owning their tuxedos and started renting them. Why do that? Two reasons. The first is we don’t go to that kind of party anymore, and the second is, it feels like a money saver. Save money a different way. Buy the tux, tailor it to you, throw the party, wear it, be Jay Gatsby.
Embrace a flat cap
Alright all you Peaky Blinders out there, this one is for you. There are really only two things you need to look like a Peaky Blinder without being over the top. The first is an undercut haircut, which still looks great and is easily maintained. The second is a good flat cap. Some people call them newsboys, but this is the cap you should switch to.
If you are a guy that typically wears a ball cap or no cap at all, wait until you see what this does to your casual looks. If you are a fedora kind of guy, then this will take your suit looks to the next level. If you keep the suits modern and the cuts closer to today’s standard, you can embody the aura of a Peaky Blinder without people thinking you stopped off after a Comic-Con.
Get suspenders
Here is one for the fellas looking to emulate their great-grandfather’s style more than anything. If you want to really bring a vintage look to your wardrobe, adopt suspenders into your style. These have been around forever and they are the pinnacle of turn of the 20th Century style. From the plains to the cities, every man wore these, what do they call them across the water, braces?
Here is a tip for all you guys just now thinking about doing them: Please, for the love of everything, don’t use the clips. Go to your tailor and have them put suspender buttons on the inside. You aren’t twelve any longer so if you want to do it, do it right. As a matter of fact, ditch the old dress pants and get some new dress pants with no belt loops, because you don’t need a belt anymore.
Go back to old-world colors
Finally, color theory in menswear is a divisive topic. Some men think you should stay subtle, mature. Other people think you should challenge the drab colors of the past and embrace bright colors and stand up. For the purposes of adopting a vintage style, you should do the latter. Focus on the browns, blues, grays, and olives. These were easy to come by through the 1900s and the bright colors of the 70s and 80s signified a huge shift in style.
Now, if you are more Stranger Things and less Mad Men, then by all means go all out with the neons and bright colors. Whichever one suits your vintage personality. Now, go perfect this and pass on the knowledge with better TikTok and Reels for the next generation of vintage men.
