Classic, Not Costumey: How To Wear Vintage Goods with Style

Many of our long-time readers know that we’re all about classic style and high-quality stuff. We love vintage apparel and accessories that have stood the test of time, so today, we’ll discuss how to incorporate them into your outfits so that you look classic, not costumey or dated.

We believe that quite a few things, including certain aspects of fashion, are better the old-fashioned way. However, there are some things from the past that should actually just be left in the past. For example, a three-inch tall collar that is starched and stiff; that’s rather uncomfortable, and I’m glad we don’t have to wear this anymore.

If you ask our critics, they say, “Well, what are you talking about? You already look like from the 1930s” or “You dress like you’re right out of Downton Abbey.” I get the sentiment because we’re definitely more on the formal side of things. But, in men’s clothing, it’s all about the details, and in those, we’re definitely not true vintage.

The 1930s had great style inspiration that carried over until today, but a pair of spats, a top hat, or a cane will just make you look distinctly vintage. That being said, if you want a classic look, chances are you don’t want to be perceived as a Robert Crowley or Downton Abbey cosplayer.

At the same time, there are vintage pieces that you might want to wear, and we’ll help you out today. In general, you’re probably better off sticking to stuff from the 1920s and after. Everything before that can make you look distinctly vintage, or it’s at least a lot harder to incorporate into a modern wardrobe.

Don’t get me wrong. We fully support people who want to dress up like an Edwardian or a Regency gentleman. And that’s cool if that’s you, but it’s not something that most people feel comfortable wearing.

How To Wear Vintage Goods with Style: 1. Don’t Wear Costumes

It may seem obvious to you, but sometimes people want to get a certain item or a certain look, and they drift off on amazon and end up with a very cheap costume that is supposed to be something but really isn’t.

Often, these remakes of maybe a tailcoat or a morning coat are made of cheaper fabrics that wouldn’t have existed back then. They have odd buttons and weird cuts, and it’s simply not something you ever want that looks good on you and works well for your silhouette. I know sometimes it’s tempting to wear. If you wear stuff like that, it makes you look like you’re going to a Halloween party.

So, how do you know if something is a costume or not? Well, it’s a little harder to find out if you shop online. Easy giveaways are the sizing. If it’s small, medium, large, it’s not a vintage garment. Are the tags and size labels modern? It’s not a vintage garment. Is the fabric lightweight and flimsy? It’s probably not a vintage garment because they used to be much heavier. If the price is too good to be true, it probably is.

You may find some vintage items at a local thrift store. But, there’s a huge difference between a used clothing store and something that specializes in vintage clothing, and our guide to understanding the quality hallmarks of clothing can be helpful if you shop at those stores.

Overall, I’d say pick items that look good on you and work well for your silhouette. I know sometimes it’s tempting because the fabric is really nice, but that bell-bottom pair of pants will make you look distinctly 1970s, no matter how great and unique and unworn the fabric is.

2. Be Aware of the Vintage Details

Know the different cuts and patterns in clothing and the details. While the suit, in general, is a timeless garment that has stood the test of time. Not all suit styles are timeless. Be aware of cuts and patterns that make a look dated.

Suit Lapels

You might find a three-button jacket with a very high buttoning point and, therefore, very short lapels, which just looks a bit more dated, especially in combination with a lower gorge, which is also something that’s a bit more vintage looking. Likewise, if you have a sport coat or a jacket with an extremely wide lapel, that can also look very 1970s. Or maybe, there’s a suit with a somewhat dated pattern that gives its age away. 

Sometimes, those items can still be great for your wardrobe if they fit your style and physique. For example, higher-button jackets were popular in the 20s, and there was some resurgence in the 1970s. They can look good on taller gentlemen. Otherwise, it may look a bit stuffy.

For another example, let’s look at the lapels you can find, maybe, those skinny six-centimeter lapels that are between two-and-a-quarter and two-and-a-half inches. And likewise, a four-plus-inch-wide or 10-centimeter-plus-wide lapel will just look overpowering on a short or very slim guy. You can even make it look like a Tommy Nutter fanboy from the 1970s.

Currently, skinny lapels are more popular, and so you have a little more wiggle room there. But if you go too slim, it puts you right into the Mod Movement or Mad Men area.

If you look at more modern jackets, you can see the gorge; a split seam between the collar and the lapel can be quite high. With the peak lapel, sometimes, the peak actually is above the shoulder line. If you look at older garments from the 30s, it can be quite low. So, something like that can really give it away even though most people couldn’t pinpoint that the gorge height is what makes it feel vintage to them.

Suit & Jacket Patterns

There are also certain patterns like checks or madras that can look more like the 60s, for example. So, unless you really know how to confidently wear it, it will look costumey.

Waistcoat Cuts

The same concepts are also true for waistcoats. Some of them can be cut with a flare at the bottom and five or six buttons in a single-breasted version, or double-breasted waistcoats with shawl collar pals and deep cut v’s.

That being said, a waistcoat or vest is typically worn underneath a jacket, so it’s not too prominent, and you can typically get away with it and people not thinking of you as, “Oh! This is the vintage gentleman.”

Pants Pleats & Rise

In the 1930s and ’40s, pants for men were cut a lot roomier with pleats, and so if you wear that, it’s definitely a statement piece. Some of you feel that high-waisted trousers may feel odd or costumey when worn without a jacket, but I assure you they’re super comfortable, and once you go that route, you likely won’t go back to shorter rise or lower rise trousers.

Of course, there are other specific styles like the zoot suit, which are quite dated or, let’s say, the Nehru jacket. By the way, that’s something that I wore for my high school graduation. It was a white Nehru jacket suit, like this mile collar. It’s one of the fashion mistakes I committed, and it’s just terrible.

3. Combine Vintage with Modern Pieces

My third suggestion is to combine a vintage item with modern items and not with many other vintage items because that makes you look more rooted in the present day, rather than the 1930s or 40s or 50s or 60s. It often involves making the outfit less formal.

For example, I’d wear a black vintage jacket with a white shirt, but I chose a spread-collar shirt rather than a classic-collar shirt. I could have worn a very traditional silver and black silk tie. But, I chose a pink and black knit tie. It has more texture, it’s more casual, and it’s bolder. Rather than going with a classic plain white pocket square in a TV fold, I chose a printed paisley pocket square with tones of blue, yellow, and magenta that picks up the color of the tie and the blue of the waistcoat.

I could also wear plain black socks with a cap-toe Oxford or maybe even a button boot, which would have been distinctly vintage. But, if you switch it out for a pair of light pink socks that pick up the colors of the tie and a black double monk strap, it just looks more youthful.

I could also skip the cufflinks and go with a barrel cuff. But, personally, I like wearing cufflinks, and so I just stuck with it. Of course, I could have gone even bolder. Let’s say if I would have worn a camo or flower tie with this outfit, it would have definitely made it more modern. 

4. Know About the “Cumulative Costume Effect” of Accessories

One might think, “Cool. The best way to wear vintage is to just add lots of accessories.” However, that is not true. There’s something called the “cumulative costume effect,” which happens if you add more and more, especially vintage accessories. We already made a guide that highlighted the pitfalls of adding too many accessories to an outfit or the so-called “over-accessorizing.”

The same is true, of course, in the context of vintage clothing and vintage accessories. Too much is just too much. For example, take the image below: I’m wearing a jacket from the 1930s or 40s, a nice kind of medium brown tone with a herringbone pattern. It has shorter, wider lapels for modern tastes, and it has patch pockets, particularly a patch chest pocket, which has a shape that reminds me a lot of It Happened One Night and what Clark Gable wore, and that’s a movie from 1934.

However, I’m also wearing a big boutonnière, a pocket square, a scarf, a Panama hat, and sunglasses. It’s just over the top.

Meanwhile, if I pair the same suit with a light blue shirt, a purple madder silk tie with small paisleys, a simple gold tie bar, and even the same purple pocket square, the tasteful quantity and color palette of the ensemble allows everything to harmonize in an elegant way.

The same is true in reverse. I can take a standard navy suit with a white shirt and then change things up. So, rather than a regular tie, I can wear a vintage short tie. Rather than no boutonniere, maybe a small one, I can go with a really big one. Rather than the traditional white linen pocket square, I can wear a patterned one. Rather than black Oxford, you can go with button boots. Or you can add a bowler hat or a pocket watch with a watch chain.

Of course, you can also add a collar bar or a collar clip, or even a walking cane. Once you do that, your very standard modern suit will now look totally vintage. In less than five minutes, you can set back this ensemble by about a hundred years! All these accessories are perfectly easy to combine into a regular modern-day outfit, but it’s the cumulative effect of wearing them that makes it look dated.

That being said, not all accessories have the same vintage feel. A top hat or a cane is very vintagey. A collar clip or pin maybe looks somewhat vintagey. But, if you wear it with a club collar, it’s very Boardwalk Empire.

Vintage ties can have great patterns and colors, but if you go with a 30s tie that is super short, that’s just very, very dating. My tip: don’t wear a short tie and mid-rise trousers because it just looks like Sean Connery in Diamonds Are Forever. On the other hand, if you wear a short tie and you like the pattern, and you combine it with the vest, and you don’t see how short it is, it can work.

If you start wearing capes or spats or white gloves with your outfits, it definitely has a more vintage flair that comes immediately by adding those items. But, if you have a White Tie ensemble, having those white gloves is what completes the look, and it’s just the icing on the cake.

5. Keep the Dress Code in Mind

Ignoring a dress code will usually make you stand out, no matter if you’re under or overdressed. Many formal vintage-inspired items like a stroller suit or a morning coat may be totally appropriate for a classy, formal wedding in England, but it may look very dated outside of that realm.

Honestly, you might even be mistaken for a Christmas caroler if you wear a top hat and a tailcoat. Or if you’re invited out with friends, maybe it’s not the best time to put on your Black Tie ensemble. Maybe leave the tuxedo at home. 

One could argue that a gentleman in Black Tie, among other gentlemen in Black Tie, looks very charming and like he fits in. But a gentleman on his own wearing a Black Tie is going to be trying too hard to look like James Bond. Unless, of course, you love black tie and dinner jackets just like I do, and then it’s okay to wear them even though others don’t dress up and you enjoy it.

Just make sure your clothes don’t become a barrier for others to talk to you because they put you on a pedestal and think you want to be better than them.

6. Practice Inspiration, Not Duplication

Get inspired by vintage style icons, don’t try to copy them. I mean, nearly everyone can recall a scene from a movie or maybe a vintage fashion illustration that they thought, “Wow! This looks stunning. I want to look like that.”

And yes, you might be tempted to exactly take the individual items that you saw in that outfit and try to recreate them for yourself. The problem is if you can’t wear it confidently, it just makes you look like someone who’s trying to look like someone else, and it doesn’t fit your personality.

You won’t look like Cary Grant just because you’re wearing the gray flannel suit, and you won’t have the elegance of Fred Astaire just because you wear a White Tie ensemble. I also don’t look like Steve McQueen just because I wear his Persol sunglasses and his waxed jacket.

Most people won’t think of you as stylish, but just someone who watches many movies and wants to emulate their style icon while not having found their own true style.

Sure, I get it. You may watch Casablanca and think Humphrey Bogart looks really cool in that fedora. So, you go out there. You buy a fedora. You don’t think about if it really works with your face shape, and you have no idea how to wear it properly because you haven’t read the guides on the Gentleman’s Gazette.

The key to picking up on those items is to take individual parts of them and make them your own. To truly look your best, you have to feel your best, and it has to be genuine, which transitions us nicely to our next suggestion.

7. Be Confident

Be confident in the way you dress. Trust me: I’m no stranger to getting looks or attention when I enter a room or a grocery store. But, the alternative would be just to wear sweatpants and a hoodie, and that’s just unacceptable to me.

Frankly, it takes some confidence to pull up a classic look, particularly for a vintage look. And someone who does it really well is a guy named Vintagebursche, who has a YouTube channel. He’s from Germany, and he loves vintage wear, and he wears it on an ongoing basis.

At the end of the day, even if you have a wonderful bespoke or vintage outfit, but you don’t have the confidence to wear it, the clothes wear you, and you look more like a sheep rather than a confident gentleman.

I know when you’re just starting out in your style journey, this kind of confidence may just not be there yet for you even though you strive to have it. We understand that, and we made a guide about what it’s like when your friends and family don’t understand your style, but you secretly want to go that route.

You may gain confidence from the fact that your vintage item is actually a quality garment that has a timeless style, which has great value, and that you participate in protecting the environment from just throwing away old stuff and wasting resources. Frankly, I believe a classic wardrobe is an inherently sustainable and green wardrobe.

Conclusion

With all that, we hope you found our tips helpful, and you can now create outfits that put you in the history books, not make it look like something that is from a history book.

Outfit Rundown

The jacket is actually part of a vintage stroller suit, which is the equivalent of a tuxedo for formal day wear. It’s black with jetted pockets and a peak lapel. I combined it with a more modern white shirt and an extreme spread collar, a tie that is knitted in magenta and black from Fort Belvedere, which you can find in our shop here. Just like this pocket square in paisley. Rather than the traditional gray waistcoat, I went with a mottled light blue one. And instead of the typical cashmere-striped or sponge bag striped trousers, I went with black and white houndstooth trousers. I still got pleats because I have big thighs and that’s what works for me.

Skinny or slim pants just don’t. I also chose pink and gray shadow-striped socks from fort belvedere, because they’re a little more playful and pick up the colors in the pocket square and the tie. My shoes are black double-monks from Ace Marks and they’re just more youthful and sporty than a black cap-toe Oxford or a pair of balmoral or button boots.

Yes, I could have skipped the cufflinks, but I like to wear cufflinks so these are silver monkey fist knot cufflinks from Fort Belvedere which you can find in our shop here. I also added a pinky ring, which to a lot of people is something that is vintage-y or maybe mobster-like, but I personally like them and it’s part of my style and you can see my entire ring collection here. And to learn more about pinky rings and signet rings, we got you covered. Last but not least, I’m wearing a vintage Reverso watch, which is a style that’s originally from the 30s and I like the aesthetic. But, you can still get that style today and it’s not dated at all.

What’s your favorite vintage piece, and how do you like to wear it? We’d like to know how classic (and hopefully not costumey) your style is, so share it in the comments.