Looking for tips on how to choose shorts that not only fit well but also make you feel confident? Stephanie Rumble, professional fashion stylist and accountability coach from Bright Red, shares her expert advice on selecting the right shorts for every body shape, size, and age. Drawing from her years of styling experience and a passion for empowering women, Stephanie helps you embrace your style and feel fabulous in your shorts.

Shorts are more than just a practical summer garment. They represent freedom, comfort, and personal style. However, many women hesitate to wear them, often due to self-consciousness or not knowing how to find the right pair. This guide will help you choose the perfect pair of shorts that flatter your figure, suit your lifestyle, and boost your confidence.

If you’d like personal help with your wardrobe or style choices, explore Bright Red’s tailored personal and commercial styling services, designed to help women feel confident and fabulous in their clothing.

Why Shorts Are for Everyone?

Many women avoid wearing shorts, believing they are too old, too big, or just not "right" for shorts. Stephanie believes that shorts are for any age, any size, and any season. It's time to shift your mindset and embrace the idea that looking and feeling good in shorts is achievable for everyone.

Confidence is the most fashionable thing you can wear. So whether you're 25 or 75, shorts can be a staple in your wardrobe with the right selection and styling. Don't let outdated ideas hold you back from feeling cool, comfortable, and stylish.

How to Choose Shorts: Start with Your Comfort Level

The first step in understanding how to choose shorts is to assess your comfort level:

Are you comfortable wearing shorts at all?
Do you prefer a longer length initially, like three-quarter styles, to ease into showing more leg?
Can you start by wearing them around the house to build confidence?

Four stylish women wearing different shorts outfits, smiling and standing together in a bright room, showcasing confidence and diverse fashion choices. — Choosing the right shorts starts with how you feel. There’s no perfect body type—just your comfort zone. Try styles that make you feel confident, one step at a time.

The journey to wearing shorts confidently begins with how you feel in them. There’s no “perfect” body type for shorts—only what feels right for you. Everyone’s comfort zone is different, and it's okay to take small steps towards expanding it.

“Start by wearing them around the house and then think, actually, it’s not so bad after all.” ~ Stephanie Rumble

How to Choose Bike Shorts: Fabric and Fit Matter

If you’re wondering how to choose bike shorts, pay close attention to fabric and fit:

Choose materials that suit the climate and your lifestyle: denim, linen, cotton, or stretch fabrics.
Look for shorts that provide structure if you prefer a tailored look, or opt for soft fabrics for a relaxed vibe.

Three diverse women wearing stylish bike shorts and crop tops in a modern indoor setting, confidently posing together and showcasing different body types and fashion choices. — When choosing bike shorts, fabric and fit matter. Look for comfort, flexibility, and styles that help you feel confident—whether for workouts or everyday wear.

Bike shorts are not just for the gym—they’ve become a casual fashion favourite too. Keep in mind that shorts that are too short or too tight can be uncomfortable and distracting. Aim for a balance between style and practicality.

If you’d like to learn more about how style choices impact confidence, check out Stephanie's speaking engagements, where she shares tips on personal presentation and wellbeing.

Length Shorts: Finding the Perfect Hemline

Choosing the right length shorts can dramatically change your look:

Longer shorts (Bermuda or knee-length) offer more coverage and can flatter many figures.
Mid-thigh lengths often work well for most body types.
If you have heavier thighs, a slightly shorter cut can actually help elongate your legs.

Sometimes just a few centimetres can make a big difference. Don’t be afraid to try different lengths, experiment, and see what makes you feel your best.

Fitting Shorts: Waist and Width Are Key

Proper fitting shorts are essential for comfort and style:

Consider the waistband: high waisted shorts are great for tummy coverage and waist definition.
Check leg width: shorts should be slightly wider than your thigh for a flattering silhouette.
Avoid shorts that cling too tightly or create discomfort.

A well-fitted pair of shorts can make you look polished and feel fantastic. Don’t hesitate to tailor them if necessary—it’s a small change that can make a big difference.

Fashionable Shorts: Embracing Current Trends

To keep your look fresh with fashionable shorts, consider:

Trying trending styles like wider-leg Bermuda shorts or tailored designs.
Pairing shorts with tucked-in blouses or structured tops.
Choosing colours that complement your skin tone, especially if your legs are on the paler side.

A stylish woman stands confidently on a bright veranda, wearing vibrant pink tailored shorts, a crisp white blouse, and holding a floral straw bag, showcasing a fashionable and fresh summer look. — Stay fresh with fashionable shorts by choosing trending styles, playful colours, and flattering silhouettes—while always putting comfort and confidence first.

Trends come and go, but personal comfort and confidence should always come first. Let your individual style guide your choices.

Fashion with Shorts: The Right Shoes and Tops

To elevate your fashion with shorts:

Choose shoes that work with the length of your shorts: flats, sandals, or low-profile trainers.
For guidance on what shoes to wear with high waisted shorts, neutral footwear can elongate your legs.
Select tops that balance your look: fitted tops for looser shorts, or looser tops for fitted shorts.

Shoes and tops can transform your outfit, making shorts versatile for different occasions—from casual days to relaxed evenings.

Look Good in Shorts: Boosting Confidence

One of the biggest barriers to wearing shorts is mindset. To look good in shorts:

Use positive self-talk and kindness towards yourself.
Focus on comfort and fit over unrealistic ideals.
Remember: when you feel good, you look good.

Confident man and woman smiling in casual summer outfits—both wearing denim shorts, white tops, and relaxed expressions—showing comfort and style at any size. — Looking good in shorts starts with confidence and comfort. Focus on fit, positive self-talk, and wearing what makes you feel great—because when you feel good, you shine.

Confidence builds with practice. Try wearing shorts around the house first, then venture out when you’re ready. If building confidence is something you're working on more broadly, consider Stephanie’s accountability coaching, which supports mindset shifts for lasting change.

“There’s no perfect body type for shorts—only what feels right for you.” ~ Stephanie Rumble

What Size Cycling Shorts Should You Choose?

For those wondering what size cycling shorts to pick:

Aim for a snug but comfortable fit.
Choose stretchy, breathable fabrics.
Ensure they stay in place without pinching or rolling.

When thinking about how to choose cycling shorts, keep your activities in mind. The right pair will offer both comfort and freedom of movement.

Different Types of Shorts for Women

Here are some popular different types of shorts for women:

Bermuda shorts: longer and polished.
Boyfriend shorts: relaxed and casual.
Denim shorts: versatile classics.

Owning a few styles can help you create looks for every occasion. Don’t be afraid to mix it up.

How Should High Waisted Shorts Fit?

Many women ask how should high waisted shorts fit:

They should sit at or just above your natural waist.
They shouldn’t dig in or create discomfort.
They pair beautifully with cropped or tucked-in tops.

High-waisted styles can highlight curves while providing comfort. Adding accessories like belts can complete the look.

Flattering Shorts for Women: Additional Tips

To find flattering shorts for women:

Balance your silhouette with the right top.
Opt for fabrics that hold their shape.
Choose colours that complement your complexion.

What’s most flattering is what makes you feel most like yourself. The mirror—and your confidence—will guide you.

Best Comfortable Shorts for Everyday Style

Everyone deserves a pair of best comfortable shorts for daily wear:

Elasticated waists offer easy comfort.
Soft fabrics like cotton or linen feel great in warm weather.
A relaxed fit keeps you comfortable without sacrificing style.

Even casual shorts can look polished with the right accessories and thoughtful styling.

Style with Shorts: Adding Personality

To style with shorts:

Add accessories like belts, jewellery, or hats.
Mix textures and patterns for interest.
Experiment with proportions and layers.

Injecting personality into your shorts outfits lets your unique style shine. Don’t be afraid to have fun with it.

Final Thoughts: Feel Confident and Enjoy the Sunshine

Finding the right pair of shorts isn’t about perfection—it’s about comfort, confidence, and self-expression. As Stephanie Rumble reminds us, anyone can look stylish in shorts with the right approach. Choose what makes you feel good and step out with confidence this summer.

Stephanie Rumble, stands confidently in a colorful patterned top and matching shorts against a vibrant pastel background with the quote: “Confidence is the most fashionable thing you can wear.” — With confidence, every outfit shines—Stephanie Rumble, Founder of Bright Red

If you’re also looking to build resilience or improve workplace wellbeing, explore Stephanie’s education workshops, which cover topics like stress management, resilience, and personal development.

This article was inspired by Stephanie Rumble's "Style for Life" podcast. Learn more about styling and personal development at Bright Red.

Listen on Spotify

Frequently Asked Questions

How do I start feeling comfortable wearing shorts?

The best way to start is by wearing shorts around the house to build your confidence in a private setting. This allows you to get used to the feeling without worrying about how others might perceive you.

Gradually, as your confidence grows, you can start wearing them out casually. Remember, confidence is something that builds over time, and the more you wear them, the more natural it will feel.

What length of shorts is most flattering?

The most flattering length varies depending on your body shape and personal comfort. Mid-thigh shorts are often the most versatile and flattering for many women because they provide enough coverage while still showcasing your legs.

If you prefer more coverage, Bermuda shorts that end just above the knee can also look great and feel comfortable. The key is to choose a length where you feel confident and balanced.

How should high waisted shorts fit?

High waisted shorts should sit comfortably at or just above your natural waistline without digging in or feeling restrictive. The waistband should provide gentle support and create a flattering silhouette.

This style often pairs beautifully with tucked-in tops or slightly cropped blouses, helping to define your waist and elongate your legs.

What are the best shorts for heavier thighs?

If you have heavier thighs, look for shorts with a slightly wider leg opening to avoid clinginess. Mid-thigh lengths are often flattering as they balance the proportion of your legs without cutting them off at an awkward spot.

Soft fabrics with a bit of stretch and structured waistbands can help you feel both comfortable and confident. A personal styling consultation with Stephanie at Bright Red can help you find the perfect cut for your body.

Can older women wear shorts?

Absolutely! There’s no age limit on wearing shorts. In fact, in the podcast, Stephanie shared that her own mother still wears shorts and looks great doing so. The idea that shorts are only for younger women is simply a myth.

Choosing a style, length, and fabric that make you feel good is far more important than your age. Confidence truly has no expiry date.

What shoes work best with high waisted shorts?

High waisted shorts work well with shoes that visually elongate the legs. Neutral-tone sandals, flat sneakers, or wedges are all great choices depending on the occasion.

To balance proportions, avoid heavy or chunky shoes unless they are styled intentionally. The right footwear completes the outfit and helps create a polished look.

How do I choose the right fabric for shorts?

The fabric you choose should reflect both your lifestyle and the climate. Lightweight cotton, linen, and denim are popular choices for casual wear, while structured fabrics work well for dressier shorts.

If comfort is your top priority, look for materials with a slight stretch or an elasticated waistband. Stephanie’s styling services can also help you choose the ideal fabrics for your needs.

Are cycling shorts suitable for everyday wear?

Cycling shorts have become a casual fashion staple in recent years and can certainly be worn for everyday activities. Pair them with an oversized tee, a fitted tank, or a blazer for a trendy look.

The key is to balance the tight fit of cycling shorts with looser or more structured tops to create a flattering silhouette.

How do I find shorts that boost my confidence?

Confidence comes from wearing clothes that make you feel good, regardless of trends. Start by identifying what lengths, fabrics, and cuts feel most comfortable on you.

If you need support in discovering your personal style, booking a styling consultation can help you feel more empowered and confident in your wardrobe choices.

Should I worry about cellulite when wearing shorts?

No, you shouldn’t let cellulite stop you from wearing shorts. Most women have some level of cellulite, and it’s completely natural. The focus should be on comfort and confidence, not perfection.

Choosing the right length and fit can help you feel more comfortable, but the most important thing is embracing your body as it is.

Fashion Styling

Stephanie Rumble

Jul 10

9 min read