9 Timeless Stripe Shirt Outfits to Wear This Fall

Can we talk about stripe shirt outfits for a minute? A striped shirt is one of those pieces I reach for when I want to feel instantly pulled together. Whether it’s a crisp button-up or a classic Breton, it’s a wardrobe staple that just works. Wear it buttoned, tucked, or layered under something cozy. It’s the kind of piece that makes getting dressed easier, especially as we transition from summer into early fall.

There’s something about stripes that feels polished yet effortless. Striped shirts are one of those pieces that can lean classic and feminine, or structured and modern, depending on how you wear them. They pair effortlessly with tailored staples like blazers, denim, and soft knits- and has a way of grounding a look while still feeling fresh.

If you’re looking for new ways on how to style yours this season, I’m sharing 9 timeless stripe shirt outfits to try. The kind you can actually wear now, and all season long.

9 Timeless Stripe Shirt Outfits to Wear This Fall

Before we get into the outfits, let’s get into why stripes are such a timeless wardrobe essential. I wear stripes all year long but style them a slightly differently for fall.

Why Striped Shirts Are the Ultimate Fall Wardrobe Staple

Because they go with everything. Striped shirts add just enough interest without overpowering an outfit, and they’re easy to style with everything from denim and trousers, to knits and blazers. You can even mix them with florals. In fall, when layering is key, they work great under cardigans or trench coats while still looking polished on their own. I love that they’re both classic and versatile. Something you can wear on repeat without it ever feeling tired.

What To Wear With A Striped Shirt In The Fall

A striped shirt is easy to build outfits around. For fall, try pairing it with:

Classic straight or wide-leg denim

You can’t go wrong with denim, especially in fall. A stripe shirt with a great pair of jeans is one of the most timeless, casual outfits you can wear. Think polished button-up shirts or easy Breton stripes styled with loafers or a block heel. I tend to favor darker denim as we shift into colder weather.

These are a few of my favorite jeans:

Layered cardigans or sweater vests

Layering a cozy knit like a sweater vest, over a striped button-up shirt with the collar peaking out is a classy way to wear layers in fall. The stripes paired with the texture adds visual interest and keeps your outfits from being ordinary. Wear this stripe shirt outfit with chinos or jeans and a great pair of ankle boots.

Lightweight blazer

While you can wear both button-up shirts or striped tees under a blazer, for comfort reasons, I prefer a tee. It lays nice under a blazer and if you’re choosing horizontal stripes, the blazer helps to break it up a bit.

Midi skirts in neutrals

Cozy neutrals like shades of camel, beige, ivory, brown, gray, and black all set the tone for a chic and ladylike outfit. Adding a pair of knee-high boots makes this perfect for fall. These slip skirts are a favorite of mine. I have them in several amazing colors. And they look amazing with striped shirts!

Trench coats or jackets for cooler days

Fall style is all about layering smartly. Light coats keep you warm on chilly fall days, and add another bit of texture to your outfits. Opt for neutral coats for all of your striped shirts, or for a modern touch, try a navy coat styled under a blue stripe shirt and jeans. Finish it off with a pair of black or brown boots.

This trench coat comes in three colors and is so petite friendly! I wear it in size 0. If you prefer a shorter jacket for fall, I highly recommend this one. It’s chic yet effortless (I have it in size 2).

Loafers, ballet flats, or sleek boots

Shoes always make the outfit. Thats probably why I have way too many pairs of shoes. The same outfit can have a completely different vibe by swapping out your shoes. My most worn fall shoes are timeless loafers, classic ballet flats or Mary Janes, and awesome boots. Both ankle boots and knee-high boots are a must for a truly timeless fall capsule wardrobe. Check out my previous post for a full list of all the great fall shoes for women. They all look great with stripe shirt outfits.

How To Style a Stripe Shirt And Look Timeless This Fall

Striped Shirt with Wide-Leg Jeans and Heels

A striped button-up and wide-leg jeans make the perfect pairing for early fall. It’s easy, timeless, and just structured enough. Tuck in the shirt to define your waist, slip on a pair of heels, and suddenly it’s elevated without trying too hard. It’s classic with a modern twist: the crisp shirt balances the volume of the jeans, while the heels add length and refinement. Petite tip: A slightly cropped jean or a sleek heel helps keep proportions clean and elongates the leg with wide-leg styles.

Outfit details: Wide-leg Jeans | Stripe shirt | Heels (take half size up in this style and save 15% with TARA15)| Suede bag

Layer a Striped Shirt Under a Sweater Vest with Jeans for Fall

Sweater vests add cozy sophistication to a striped shirt and jeans outfit- perfect for crisp fall days. Petite tip: Choose a cropped or belted vest to keep your silhouette balanced and avoid looking bulky.

Classic Camel Blazer and Striped Tee Outfit with Straight-Leg Jeans

A camel blazer paired with a striped tee and straight-leg jeans offers effortless Parisian chic. Petite tip: Go for a fitted or cropped blazer to accentuate your waist and maintain proportion. And to elongate your look even more? Opt for pointed toe shoes like these.

Tucking a Striped Shirt into a Midi Skirt with Heeled Boots

This feminine fall look pairs a tucked-in striped shirt with a flowing midi skirt and knee-high boots for elegant versatility. Fir effortless texture and warmth, tie a sweater over your shoulders. Petite tip: Choose an A-line or pleated midi skirt that hits just below the knee to elongate your frame.

Wearing a Striped Breton Shirt with a silk Scarf for French-Inspired Fall Looks

A striped Breton shirt paired with a silk scarf is effortlessly chic and very French. Tuck it into high-waisted pants or denim, knot the scarf at your neck or on your bag, and you’ve got a timeless look with just the right amount of detail. Petite tip: Choose a slimmer-fit shirt and tie the scarf close to the neck to keep proportions balanced.

Fresh Fall Outfit Idea: Blue Striped Shirt with White Jeans and a Neutral Cardigan

White jeans and a neutral cardigan soften the striped shirt for a fresh, early fall vibe. Petite tip: Choose cropped white jeans paired with ankle boots or flats to create the illusion of longer legs and a balanced silhouette. If you need just a little boost, these ballet heels are so comfortable and classy!

Elegant Fall Style: Striped Shirt with Camel Trousers and a Structured Bag

Pair navy-and-white stripes with warm camel pants for a polished fall outfit. Navy is a neutral so feel free to pair it with warm accessories like cognac, burgundy, and taupe. Petite tip: Opt for high-waisted trousers with a tailored fit to elongate your legs and define your waist.

Fall Outfit Idea: Striped Shirt Paired with a Belted Trench Coat and Dark Denim

A belted trench over a striped shirt and dark denim is a classic, polished fall uniform. Petite tip: Choose a trench with a defined waist for a flattering petite-friendly fit. For a great petite friendly option, this trench is great and fits true to size.

Outfit details: Jeans | Blue striped shirt | Trench coat | Ankle boots (15% off with SF-TARA-15) | Suede bag

Parisian-Inspired Look: Striped Shirt Tucked into High-Waisted Pants with Silk Scarf and Slingbacks

Tuck your stripe shirt into high-waisted pants and add a silk scarf for a refined, editorial-inspired outfit. Petite tip: High-rise pants and delicate slingbacks help elongate your frame.

FAQ: Your most Frequently Asked Questions on Striped Shirts

Do Striped Shirts Look Good In The Fall?

Yes striped shirts look great in the fall! The beauty in stripes is their classic appeal that can lean soft and feminine or more modern and edgy, depending on how you style them. They’re endlessly versatile, pairing effortlessly with solids, florals in the same color family, polka dots, and even animal prints for a fun twist. Plus, their graphic pattern adds visual interest to layered looks, making them the perfect foundation for fall outfits that are both timeless and modern.

Are Striped Shirts Flattering On Petites?

Yes, absolutely, especially when you choose the right stripes and fit. Vertical or narrower stripes can create the illusion of length, helping to elongate a petite frame. It’s also key to focus on the shirt’s proportions- think well-fitted cuts, cropped lengths, or styles that tuck nicely to define your waist. Avoid overly wide or boxy shapes that can overwhelm a smaller silhouette. With the right styling, striped shirts can be a super flattering and versatile wardrobe staple for petites.

How Do You Dress Up a Striped Shirt?

The secret to dressing up a striped shirt lies in the details, especially your accessories. Opt for luxe materials like soft leather shoes, which have a subtle sheen that catches the light better than suede. Choose bold yet understated jewelry; for me, a pair of small but statement-making hoop earrings instantly elevates even the simplest outfit (These are my go-to pair and you can take 20% off with TARATMV). A textured statement bag in a buttery soft leather or a woven design, adds just the right touch of sophistication. And don’t forget a belt. Whether you’re wearing jeans or a dress, a well-chosen belt pulls everything together and adds polish to your look.

Where to Find the Best Timeless Stripe Shirts

For more classic fall style, you might love my post on building a fall capsule wardrobe you will love for years!

9 Timeless Stripe Shirt Outfits to Wear This Fall

9 Timeless Stripe Shirt Outfits to Wear This Fall

Why Striped Shirts Are the Ultimate Fall Wardrobe Staple