Styling a Pinstripe Suit: One Suit, Three Ways

Most men have at least one suit hanging in their closet—but for a lot of guys, it’s a garment that only gets worn twice a year, if that. And if it’s a pinstripe suit? Some assume it’s only fit for boardrooms or vintage throwback parties.

But the truth is, the pinstripe suit is one of the most versatile, underutilized, and stylish tools a man can own. It’s not just for bankers or barristers—it’s for anyone who wants to dress with quiet confidence and classic flair. With the right fit, the right fabric, and a little imagination, one pinstripe suit can carry you from Monday’s meetings to Saturday’s wedding and Sunday’s brunch.

This guide is for the man who wants to do more with what he has. We'll show you exactly how to wear one suit in three ways—for work, weddings, and the weekend—and explore why the pinstripe has never gone out of style (and probably never will).

Why the Pinstripe Suit Never Goes Out of Style

Before we get into the styling, it’s worth understanding why this suit has stood the test of time.

A Suit Born in the Banks—Then Stolen by the Rebels

Pinstripes got their start in early 19th-century England, most notably in the banking world. Each bank had its own signature stripe pattern—a way to distinguish employees. But by the 1920s, the pattern had escaped the vault and entered the fashion mainstream. Jazz musicians picked it up. Gangsters made it glamorous. Hollywood stars gave it their stamp of approval.

It became a paradox: the pinstripe was associated with both authority and rebellion.

Fast forward to the 1980s, and the pinstripe came back as the uniform of power—Gordon Gekko, Michael Douglas’s infamous character in Wall Street, helped put it back on the radar. But today’s version is far more wearable. Softer fabrics. Slimmer fits. Less shoulder padding. More personality.

The Visual Trick That Works for Everyone

The vertical line is one of the oldest tools in a tailor’s arsenal. It elongates. It slims. It adds structure and definition without any effort from you. It’s flattering on tall, short, slim, and athletic builds alike.

A good pinstripe suit doesn't shout; it streamlines. And in a world of fast fashion and fleeting trends, that kind of consistency is powerful.

The Work Look: Modern Power Dressing

Let’s start with where most people think the pinstripe belongs: the office. And they’re not wrong—just incomplete.

The pinstripe suit at work does something special. It makes you look put-together, polished, and purposeful. But today’s office isn’t what it was twenty years ago. Whether you're meeting with clients, pitching to investors, or showing up for a casual Friday, the key is knowing how to adapt the pinstripe to your environment.

Choosing the Right Suit for Work

Stick with a navy or charcoal base. These colors are universally appropriate and easy to pair with your existing wardrobe. The stripe should be subtle—light grey or soft white. Avoid high-contrast pinstripes at work unless you’re in a high-creative field or intentionally making a bold statement.

Styling the Look

• Shirt: Crisp white is always safe. Light blue is a classic. For something a little different, try a fine bengal stripe or microcheck (just make sure the pattern scale doesn’t clash with your suit).

• Tie: Avoid bold patterns here. Stick with solid knits, silks, or small prints in muted tones—navy, burgundy, rust, or forest green.

• Shoes: Black oxfords are the traditional choice. Dark brown brogues or monk straps add a personal twist without breaking any rules.

• Accessories: A leather strap watch, a pocket square in white or muted tones, and matching belt complete the look. 

Modern Workplace Flexibility

In more casual workplaces, you can deconstruct the suit:

• Ditch the tie and go open-collar

• Wear the trousers with a fine-gauge merino crewneck or turtleneck

• Throw the jacket over a black t-shirt and dark jeans on casual Fridays

You’re signaling that you know how to dress well—but also how to dress right for the environment. 

The Wedding Look: Polished but Personal

Weddings are where you get to dress up—but you don’t want to look like you’re there to audit the bride and groom. The trick is dialing down the corporate vibe and bringing up the charm.

Pinstripes can feel bold, especially when everyone else is in solid navy or grey, but that’s exactly why they work. When worn right, they exude sophistication, individuality, and a bit of old-school romance.

Dressing It Up for the Ceremony

Stick with a navy or charcoal base. These colors are universally appropriate and easy to pair with your existing wardrobe. The stripe should be subtle—light grey or soft white. Avoid high-contrast pinstripes at work unless you’re in a high-creative field or intentionally making a bold statement.

Styling the Look

• Shirt: White works across seasons, but in spring or summer, soft pastels like sky blue, lavender, or blush elevate the look without overwhelming it.

• Tie: Here’s where you have permission to play. Try florals, silk knits, or vintage-style patterns. A burgundy floral tie against a navy pinstripe? Gorgeous.

• Pocket Square: Don't skip this. A pop of color or pattern ties the whole look together. Coordinate with your tie, but don’t match exactly.

• Shoes: Brown leather dress shoes feel warmer and more relaxed than black. Oxblood works beautifully for weddings, especially in fall.

Optional Add-Ons

• Vest: Adds a layer of refinement. Choose one in a solid neutral or tonal match.

• Overcoat or scarf: For winter weddings, a camel or charcoal wool overcoat can be incredibly elegant.

For Less Formal Celebrations

Skip the tie, leave the top two buttons undone, and

The Weekend Look: Effortless Style

This is where a pinstripe suit really earns its keep. Forget the formality—you’re going casual, creative, and cool.

The key to pulling off a suit casually is contrast. If your suit is tailored and sharp, everything else should be softer, more relaxed, and a little unexpected.

Option 1: Jacket as a Blazer

Pair it with:

• A white crew neck tee or long sleeve Henley

• Slim, dark denim or light grey chinos

• Casual leather sneakers or suede desert boots

Finish it off with:

• A knit beanie or baseball cap

• A scarf or soft layering piece

• Sunglasses and a watch with a fabric strap

Option 2: Trousers on Their Own

The trousers of a pinstripe suit are surprisingly versatile. Pair them with:

• A solid black turtleneck

• A charcoal zip-up knit

• A denim jacket or chore coat

Shoes? Low-top white sneakers or even clean boots. You’re dressing down the stripes, but keeping the edge.

Option 3: Full Suit, No Rules

Yes, you can wear the full suit. Just strip away the formality:

• No tie

• T-shirt or thin crew neck knit

• Leather sneakers

• Optional: baseball cap or crossbody bag for a street-style edge

This is how modern menswear lives: tailored, but not rigid. The rules are yours to rewrite.

Suit Maintenance: Keep It Sharp

A suit this good deserves care. Here's how to make sure it stays in top form for years.

Do:

• Use a suit brush or lint roller after each wear

• Hang it on a wide, structured wooden hanger

• Give it 24–48 hours between wears
• Steam it rather than iron it (it’s gentler)
• Spot-clean minor stains before they set

Don't:

• Dry clean too often—2–4 times a year is plenty

• Leave it crumpled or folded

• Store it without a breathable garment bag if it’s seasonal

And don’t forget: if your body changes, your suit can too. A great tailor can let it out or take it in to keep the fit perfect.

The Rex Cox Advantage

At Rex Cox Menswear, we know a great suit isn’t just about the brand or the label—it’s about the fit, the fabric, and the feeling it gives you. We’ve been outfitting men in Mission and across the Fraser Valley for nearly 100 years. When you walk into our shop, we don’t just hand you a suit—we help you discover one that feels like it was made for you.

Why shop with us?

• Modern, high-quality pinstripe suits from brands we stand behind

• Tailoring to fine-tune the fit

• A staff that knows how to style a suit six ways to Sunday
• Honest advice—no upselling, no pressure

We’ll help you build a wardrobe that works harder. One suit at a time.

The One Suit You’ll Actually Wear

Too often, we treat suits like occasion-only wear. They get dusted off for weddings or job interviews, then shoved to the back of the closet. But it doesn’t have to be that way.

A well-chosen pinstripe suit isn’t just something you own. It’s something you live in. You wear it to pitch your best ideas. To celebrate with friends. To turn a Saturday lunch into something special.

You don’t need a closet full of suits. You just need one really good one—and the confidence to wear it.

So come visit us in downtown Mission. Try one on. Let’s talk fabric, fit, and all the ways you’ll wear it. Because one suit, when it’s the right one, is all it takes.


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