Despite its cool factor, incorporating vintage into your style can be tricky to navigate.
After all, not everyone wants to look like their grandfather. You certainly don’t want to be caught in an irrelevant cut or fit, or look like you’re in a costume.
Don’t let these very real concerns deter you though. Old classics add a lot of character to outfits, regardless of your personal style.
The secret is sticking to the following eight vintage pieces. They’re fool-proof, always look good, and don’t require expert styling to pull off.
A Vintage Watch
I’m a huge proponent of vintage watches. In fact, some of the watch world’s tried-and-true classics are models that haven’t changed much in the decades they’ve existed.
Most American brands or formerly American brands, like Timex, Bulova, and Hamilton, constantly churn out models from their archives.
Besides, we don’t wear watches to tell time anyway. They’re, ironically, an anachronism in and of themselves. Even the oldest, most retro-looking wrist watch has a place in a modern man’s wardrobe. As long as they fit your wrist, they’ll never look weird.
Here are two other cool things about a vintage wristwatch. They’re easy to find on a budget. And, they’ll have a lot more street cred than most modern mid-priced timepieces.
Plus, one of the reasons I, and other watch nerds, love watches is the lore and stories behind them. Vintage timepieces are rife with those.
Classic Cool-Weather Outerwear Like Trench Coats and Overcoats
Here’s a situation in which vintage would (usually) be a better choice than modern.
A lot of vintage trench coats, capes, overcoats, peacoats and topcoats were made long before the days of fast fashion and synthetic materials.
Most older cool-weather outerwear is made from natural materials, whether that’s dense, durable gabardine or classic wool.
And the thing about men’s coats is that they haven’t changed a lot. Or rather, they haven’t changed to the point that they’d ever look irrelevant. This is because despite fits constantly changing in tailoring, one thing that remains the same is the necessary fitted, strong shoulders.
This is why Cary Grant is such a tailoring icon. Sure the button number on his suit jackets or the fit of his pants go in and out of style. But the shoulders are always the same, which is why he always looks dapper.
With coats, it’s all about the shoulder fit. So go ahead and raid your grandfather’s closet for your next topcoat.
Vintage Ties
First of all, there’s nothing wrong with modern ties. Second, I’m not talking about the polyester ones from the mid-’70s or the huge bigger-is-better ties from the ‘90s.
If you go as far back as the ‘40s, the ‘20s even, you’ll find bold yet classy designs that were truly works of art.
I’ve seen silk bird motifs that remarkably don’t look cheesy because of how well-woven it is, geometric foulards that actually look better in a wide design, and so much more.
They’ll definitely be a statement, but not a loud one.
Here’s the thing though, if you tie your tie incredibly tight, I’m talking pull extra hard with every maneuver of the tying process, you can get a pretty small knot.
A lot of old ties are made of thin, but strong, silk. If your tie is thicker than modern conventions dictate, the small knot will temper that.
And don’t forget, tie thickness goes in and out of style too.
Vintage Cufflinks and Tie Clips
Is it me or are cufflinks these days either just straight-forward formal ones or interestingly-designed but fast-fashion produced?
I love sifting through men’s cufflinks and tie clips at vintage stores. I’ve seen every design under the sun, from art deco abstractions to stately lion’s heads, to tasteful diamond encrusting on tie clips.
Like women’s jewelry, vintage cufflinks and tie clips can be instant heirlooms, which add meaning and character to your outfit.
A Pair of Vintage Corduroys
I know this sounds counterintuitive, but hear me out. Yes, vintage pants in general are hit or miss because of constantly changing cuts and fits. And yes, fashion has a weird, conditional relationship with the corduroy material—when it’s in, it’s so in, when it’s out, it’s a joke.
But, if you wear them with intention and confidence, they perfectly balance coolness with elegant class. And what’s cooler than not caring what’s in vogue and just going with what looks good on you?
Plus, corduroy pants are a fall staple. So at the very least, you can wear them then.
As with most golden era practical wear, they look purposeful in most cuts, can be paired with workwear, knit polos, and tweed jackets. Basically, they can be incorporated into any personal style.
And like vintage jackets, older corduroys were built before the fast fashion era.
Vintage Suit Vests and Waistcoats
Vintage suit vests and waistcoats are superior for all of the reasons older jackets are.
They’re made with high-end materials, are often handcrafted, and, since they need to sit comfortably under a suit jacket, their fits never change. There has never been a skinny suit vest era or baggy waistcoat fad.
You can often find a vintage suit vest that’s higher quality than a brand new one in the same price bracket.
If you’re willing to go a bit dandy with your style, you can go really far back to find a waistcoat. I’m talking late 1800s back. They often have beautifully unique cuts and artistic embroidery.
Vintage Tuxedo Jacket
If you don’t mind a slight retro slant with your formalwear, I highly recommend going for a vintage tuxedo jacket. Again, in the golden era of fashion, every tuxedo jacket was made bespoke.
That means old tuxedo suit jackets were built with specificity and durability. All you need to do is get it tailored.
And trust me, that’s still going to cost less than a brand new full bespoke tuxedo.
And besides, tuxedo jackets came in all styles in the ‘20s, ‘30s, and ‘40s. Some look less retro than others. Some exude an old world charm, which never looks bad on formalwear.
Military Attire
Your local military surplus store is your friend.
Why buy that cheap utility-style shirt from H&M when you can get one for just as cheap at a vintage store or military surplus? And, you’ll know it was built to soldier-approved specs.
Remember. Most menswear classics have roots in the military. It’s a cycle. The military develops clothes and gear for practical purposes. They evolve past that to something more advanced and technical, but the past iterations trickle into the general public.
Our past men in uniform wore several garments that are common in a stylish man’s closet today. I don’t doubt that the sartorial standard issues today will become menswear staples decades from now.
Go the vintage military route for pilot jackets, cargo pants, utility shirts, safari jackets, service boots, chinos, the list goes on.
I know I’m biased. I’m the kind of guy who constantly says, “the old ways are better.”
However, I’d never discount the value of modern creature comforts. With certain garments and accessories though, not much improvements have been made. Need I evoke fast fashion one more time?
By going vintage in these eight categories, you’ll find high-quality, good-looking pieces, and often at a decent price.
