Striped Shirts + Patterned Ties: A Shortcut to Vintage Style

If you don’t have a desire to wear vintage tailoring but want to achieve a vintage look, don’t worry- it’s as easy as wearing a striped shirt and patterned tie.

Instantly looks old school and displays a mastery over classic style, while still looking easy!


This essay was written on 10/29/2017 and elements were revised on 8/14/2020.

By now, I’ve written quite a bit on dissecting golden era (1920s-1960s) style and how to wear it today. It all started with a guide to each era (even with a StyleForum guest article) and even had a how-to for the way Spencer and I generally approach menswear.  However, this essay is a quick one to demonstrate and easy way to look vintage; it’s one that I do quite regularly as a part of my everyday style!

Obviously, I definitely understand that vintage clothing isn’t always accessible to everyone.  Perhaps it’s that you can’t find the right size, there aren’t any dealers/eBay listings where you are, or you simply don’t like to wear used clothing. Or you just find it best to wear contemporary things like Ring Jacket or Ascot Chang bespoke. As this blog has come to demonstrate in recent years, there’s nothing wrong with wearing a contemporary tailoring while incorporating vintage styling. But what exactly is vintage styling?

It’s definitely not wearing a baggy zoot-esque suit with crazy ties like Jim Carrey in The Mask.  I mean, people did wear bold swing ties back in the day, but that’s not really the approach we have here.  We like to go against the vintage grain (who usually love bold stuff) and instead opt for something “classic”.  Luckily for you, it’s pretty darn easy.  All you need is a striped shirt and a patterned tie. 

I’m not going to talk too much about this, as it speaks for itself, but you’ll see that striped shirts and patterned ties (which I count as stripes, checks, and prints) really dominated menswear of the 1930s-1940s. You’ll note that while some of the patterns can be abstract, they’re not too far off from foulards, repeating geometric shapes, or variations on repps.  It’s nothing too crazy and it’s something that definitely has been echoed in classic menswea today. without being overly modern (I’m looking at you, floral ties).  Just check out these examples!

As you can see, it’s a subtle way to give your outfit some throwback vibes., as well as providing some fun to a sartorial outfit. You don’t have to buy a tweed suit or a pinstripe DB when you can start simple add some flair to your shirt and tie!  The most interesting thing is that it stands out because people seldom dress like this anymore.  Either guys dress too boringly (plain shirt, plain ties) or they put too much emphasis on the outside pieces like their jacket or hat.  I’m serious; simply pairing a striped shirt and a patterned tie is enough to be vintage inspired.

Wearing It


Let’s use my Ascot Chang suit as a great example. As I stated before, this suit is cut with references to both contemporary Neopolitan and vintage tailoring, through it’s use of wide lapels, high rise trousers, and soft shoulders. However, those are all things that are quite common in the tailoring world today- just look at guys wearing Ring Jacket, Drake’s, or Liverano. The difference is in the shirt and tie.


To give it an overt vintage styling, I have a pink reverse stripe shirt and a fun foulard tie, with contrast each other well; it’s important to remember scaling when mixing patterns. This combination not only livens up the plain navy suit, but it directly references those examples from the 1930s-1940s. It’s playful and less strict, especially when compared to stripes on stripes, which can be lean preppy.

If I was a decidedly more modern dresser, i’d wear something less busy. Here, the foulard and thick stripes look inherently old school, even if people can’t exactly place it as Golden Era inspired.

Of course, the use of a spearpoint collar and collar clip help point it in my vintage favor as well, but I think the pattern choice is equally as important, since “plain” attire wasn’t much publicized in the 1930s-1940s.


You can push the vintage connotation further by literally wearing a vintage tie.  As I’ve written before, vintage ties just have a way with fun patterns that present a lot of personality when compared to modern print ties.  The blue tie above is my favorite and it’s soft-edged, abstract square motif is much more interesting than the straight forward foulard I wore with the Ascot Chang suit. Because of this, the separates outfit looks even more vintage, despite the jacket and trouser being modern (but they look vintage too, no?).

Introducing a third pattern, like a brown checked jacket (which always tends to look vintage as well), is a great way to play with the other two patterns.  Some guys make take the opportunity to wear a plain knit tie, but I love leaning into it. It just looks vintage and yet, laid back and slouchy.  It’s like jazz, where despite the improvised notes being carefully chosen in the moment, still feel natural and flow into each other, as if they were always meant to be there.

As a guy who refuses to look overly formal or corporate, a striped shirt and patterned tie help mitigate that and present me as a guy who dresses purely for pleasure.


Now I’ve been doing this a while.  Just look at this old photograph from when this essay was first written!

I’m wearing a softly constructed wool/cashmere suit from Suit Supply, which I’ve since sold to my friend Jay.  Like my Ascot Chang suit, one of the reasons why this suit works so well for a “contemporary vintage” outfit is due to the construction, details, and fabric.  Firstly soft tailoring works well with a lot of people.  The natural shoulders make a jacket comfortable and timeless, while padding can come off as too “formal” or dated.  There’s nothing wrong with a structured look, but I really prefer a garment that I can relax in!  Sprezzatura, ya know?

Apart from the fit, it already looks “vintage” due to the wide lapels (surprising for a mall-brand in 2017) and the flecked brown fabric. As I’ve said here and here, brown suits are really uncommon compared to navy or grey suits and look “old” as a result. But even so, wearing a striped shirt and vintage tie help add to it.


Here’s where the 1930s-40s shines through!  Who would’ve thought that a simple combination of geometrics shapes and lines could be the difference between a modern and vintage look?  I’m still aghast at why guys don’t mix patterns like this; I find it way more interesting than a plain shirt and tie.  But we can take a step further to see exactly how this pairing is “vintage”.

Here’s a modern example of a brown suit with a checked tie.  Can you see how adding in this specific type of checked tie with a 30’s striped shirt make it different? Dan’s tie, while still great, is pretty “normal” and is something you’d expect from any modern dresser. Let’s not forget that vintage ties can help create a vintage look, since mainstream tie designs seldom come close to the old ones. Just notice how my 1930’s checked tie is pretty odd compared to “regular” ties.  The shapes are different and there are a multitude of colors in it.  The way it plays with the red/white of the shirt is beautiful and interesting enough without being too bold!

I will say that following accounts like Drake’s, who routinely pair their fun takes on foulards and repps with striped shirts, providing a great example of my trope in action within the contemporary menswear world.

Other Examples

I’ll finish off this article with some more examples of how wearing a striped shirt and a patterned tie is the best way to  approach vintage style without looking like a costume.  Some of the suits are vintage I think the general idea is there.  Vintage inspired style is pretty easy to do, even if your attire isn’t completely vintage.

Whether its a foulard, stripes, or checks, it’s use with a striped shirt just looks old school and fun! Who needs to be plain and corporate all the time?



Red striped OCBD with foulard tie.


Purple stripe OCBD with green block stripe tie



Ultra vintage: blue stripe spearpoint with green foulard tie.


A prep look, but a bit more vintage.


Pink university stripe with blue/red print.


Tan stripe with blue/red diagonal check






Bold striped tie on a pencil stripe shirt.



Works with jeans too!





Triple pattern mixing again!


Paisley is a fun pattern that contrasts with stripes well, if foulards are too tricky for you.


Big squares!









Don’t all of those examples look vintage? See how it easy it is to do?  So please don’t spend your money on buying cheap flat caps, clip on suspenders, and tweed jackets, when you can really get that classic, non-costumey vintage style by simply adding a striped shirt and a patterned tie.  It’s a shortcut that works every time.

Also I just want to remind you guys that I will be giving a short presentation at the Dapper Day Expo this saturday, November 4.  I’m the only one taking about menswear, and will mainly focus on vintage ( and where to get it and style it). The seminar (and the rest of the Expo) will be in the Disneyland Hotel, which is accessible through Downtown Disney.  Tickets are $10, but that ticket get you into the expo on both days, which is a great alternative to going into the Disney Parks (since it can be expensive).  You can find out more by going to the official website. 

I really hope to see some of you there!

Always a pleasure,

Ethan W.


Street x Sprezza

Photography by Ethan’s Tripod 


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