How to Choose and Style Striped Shirts Based on Your Personality Dressing Style

How to Choose and Style a Striped Shirt Based on Your Personality

Styling striped shirts by personality dressing style is a fun and expressive way to take a classic wardrobe piece and make it completely your own. Striped shirts may be timeless, but that doesn’t mean they need to look identical on everyone. By aligning your stripes with your personality style, you transform a staple into a signature.

Here’s how to approach styling striped shirts by personality so they look and feel true to you. As with all choices, there are countless ways to express your personality and even your combination of personality and dressing styles. Here are just a few examples of approaches you could take to style a striped shirt (and when you look at the options that don’t feel right, it may give you a clue as to why you’ve felt uncomfortable in the past).

Classic Style: Traditional Appeal

A classic wardrobe thrives on structure and simplicity. Striped shirts are a fashion classic as well as a classic personality dressing style garment. This means you should feel right at home wearing and styling a striped shirt. Your striped shirt should be:

Symmetrical and neat—think fine stripes in a crisp cotton, button-down
In navy, white, or neutral tones

Pair it with tailored trousers or dark jeans, leather loafers, pumps and a blazer or trench coat. Add pearls or minimal gold jewellery for polish.

Relaxed Personality Style: Effortless Comfort

For the relaxed personality, comfort is queen. Your ideal striped shirt is a knit rather than woven version, you’ll find those classic button up styles uncomfortable and constrictive, for you it’s a tee-shirt version and the Breton style may be a wardrobe staple for you:

Made from breathable cotton or bamboo
Easy-care with a loose or boxy cut
In calming hues like traditional Breton blue and white or more natural colours like oatmeal, faded blue, or sage

Wear with joggers or stretchy jeans, a casual denim skirt, a soft cardigan, and slip-on flat shoes. Keep jewellery simple and functional.

Feminine Style: Soft and Romantic

The feminine personality loves details and softness. Choose a striped shirt that highlights you feminine shape and has some delicate details:

Blouses with puff sleeves, lace trims, or pastel stripes
Lightweight or flowing fabrics

Pair with a midi skirt, ballet flats or sandals, and delicate jewellery. A floral scarf or soft pink lipstick can enhance the romantic vibe.

Dramatic Style: Bold and Confident

If you love to turn heads, look for:

High-contrast stripes in black and white or bold colours
Unusual cuts or asymmetrical designs

Wear with wide-leg pants, or a leather skirt and structured blazers. Finish with statement accessories such as a wide red belt and shoes, and bold makeup.

Creative Style: Artistic Expression

For creatives, standard stripes need a twist. Either you’ll style your Classic style in a completely new way or look for a style that’s unique and unusual. Try:

Unexpected stripe combinations, mixed patterns, or deconstructed silhouettes
Unusual colour palettes or textures

Layer with patterned trousers or under a sleeveless dress. Play with proportions and accessories to make it uniquely yours.

Striped shirt - was classic except the bows at the elbows add in an element of both feminine and creative, paired with relaxed denim skirt, feminine ballet flats and a dramatic brooch

This striped shirt is the only one I’ve ever felt like me in! This is because of the bows at the elbow that take an otherwise classic garment and make it more creative and feminine (both part of my personality) in one move!

Rebellious Style: Edgy Subversion

Rebels don’t follow the fashion rules. Look for:

Oversized or distressed striped tops, or choose a sexy, alluring version
Pieces with raw hems or zips

Pair with ripped jeans or a leather skirt and chunky boots. Add layered chains or studded accents for edge.

Elegant Chic Style: Understated Sophistication

Elegance is all about refinement. Your ideal striped blouse features:

Fine pinstripes in monochrome tones in a sophisticated cut
Luxe materials like silk or satin

Wear with tailored trousers, elegant heels, and gorgeous pearl jewellery. A slick bun and red lip complete the look.

Your Personality, Your Way to Style Stripes

When you style striped shirts with your personality in mind, they stop being basic and become a true reflection of you. It’s not about following trends—it’s about knowing yourself.

Want to understand your style personality better? My 7 Steps to Style program dives deep into how personality influences every style decision—from patterns to silhouettes and accessories.

Curious about how your personality influences your style? Try my free Personality Style Quiz to discover your core personality dressing style. It’s the perfect starting point to understand what works for you and why, so you can build a wardrobe that truly reflects your unique essence.

Remember everyone is a mix of the personality dressing styles (at least 3) which is why getting and education in personal style is so integral in understanding what really works for you both physically and for your personality as it stops you from continuing to make expensive mistakes, or just never feeling at home in your clothes.