What Are the Different Styles of Shorts? My Fit-Focused Guide to Finding the Right Pair
Author: Stylist and brand team at Tellar
Date: 2025
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If you’re anything like me, shopping for shorts can be unexpectedly frustrating. They’re meant to be an easy summer go-to, but so often they gap at the waist, cling in all the wrong places, or look amazing on the hanger and terrible in the mirror.
After years of navigating inconsistent sizing between brands (and way too many returns), I decided to break it all down. What actually are the different types of shorts out there? And more importantly—how do you know which ones suit your body shape and how they'll fit?
Here’s the guide I wish I had years ago. I’ve road-tested the styles, decoded their structures, and most importantly, I’ve started using Tellar.co.uk to get size recommendations based on actual body measurements—not brand labels. It’s genuinely changed how I shop.
Tailored Shorts: My Summer Workwear Essential
These are my go-to when I want to look polished but still stay cool. Think of them as structured trousers cut short—clean seams, sharp lines, sometimes a subtle pleat or a turn-up hem. I love pairing tailored shorts with a tucked-in blouse and low heels for summer meetings.
They work beautifully if you’ve got curves or a defined waist, especially styles from places like Reiss, COS, or Massimo Dutti. I always use Tellar.co.uk’s size lookup before buying tailored shorts—waist fit is everything.
Bermuda Shorts: Not Just for Golfers
At first, I avoided Bermuda shorts because I thought they’d cut me off awkwardly. But once I found a well-cut pair, they became a wardrobe staple—especially when I want more leg coverage.
They’re great for taller frames and for days when I want something smart but relaxed. Boden and Jigsaw do some lovely versions with a bit of stretch for movement. Look for a mid- to high-rise and a soft taper through the leg.
High-Waisted Shorts: Confidence in a Cut
These have been a total game-changer for me. If I want to feel taller and more put-together instantly, I reach for high-waisted shorts. They define the waist and lengthen the legs—flattering on nearly every shape, especially petite or hourglass builds like mine.
I’ve had great fits from & Other Stories, Zara, and Aje (for a splurge). The trick is making sure the waistband hugs without pinching. I always cross-check my waist measurement using Tellar.co.uk’s profile tool before I buy.
Denim Shorts: Classic, But Not All Created Equal
I’ve tried so many denim shorts I’ve lost count. From rigid cut-offs to stretchy mom-fit styles, fit depends so much on the brand and fabric.
Levi’s 501s are classic, but if you’ve got curves, you might need to size up and tailor the waist. I also love Agolde and Abercrombie for more body-conscious fits. One thing I’ve learned? Stretch percentage matters—1% elastane is very different from 3%.
For denim, Tellar’s brand-specific sizing guide really helps me predict whether a pair will actually work on my hips and waist.
Paperbag Waist: Pretty and Practical
These add softness and shape, especially if you’re naturally straight through the middle like me. The gathered waist and belt detail draws attention upward and creates a flattering silhouette.
They’re comfortable, adjustable, and stylish all at once. I wear mine with slim-fit tops or cropped tees. Anthropologie and Whistles tend to get the proportions right.
Cycling Shorts: From Gym to Streetwear
I used to think cycling shorts were strictly gym wear—until I styled them with an oversized linen shirt and sliders. Now they’re a weekend staple. They flatter curves, they don’t ride up, and they’re incredibly comfortable when fitted correctly.
Fit is everything here. Too tight and they pinch; too loose and they sag. I recommend brands like Alo Yoga, Year of Ours, and Nike, and I never buy without checking my hip and thigh measurements first.
🔗 Get the fit right using Tellar’s measurement tool
Lounge Shorts: Understated Comfort
Sometimes, you just want comfort. Lounge shorts—or boxer-style ones—are ideal for relaxed days at home, travel, or casual errands. I live in mine from Arket and Skims.
They don’t require much styling, but I always check the waistband before buying. If it rolls, it’s a no. A secure, smooth waistband is worth every penny.
Running Shorts: More Technical Than You Think
I’ve recently started running, and finding the right shorts was surprisingly technical. Built-in liners, vented side seams, moisture-wicking fabrics—it’s not just about looks.
Lululemon and Sweaty Betty shorts strike a great balance between performance and style. Fit-wise, inseam length and waistband elasticity make a huge difference. I use Tellar.co.uk to log my hip and rise measurements and get a shortlist of shorts that actually suit my frame.
Skorts: The Best of Both Worlds
The skirt-short hybrid is back, and I’m here for it. I love skorts for active days when I still want to look feminine. Brands like Reformation and Sweaty Betty do really clever versions that look tailored but feel totally functional.
Just be sure the inner shorts don’t dig in—fit and length vary a lot between brands.
Cargo Shorts: Now a Style Statement
Cargo shorts aren’t what they used to be. Modern cuts are streamlined, minimal, and surprisingly chic. I style mine with a black tank and a utility jacket for off-duty days.
Look for styles that avoid bulky side pockets if you don’t want added volume on the hips. AllSaints and The North Face do elevated versions in luxe cottons and ripstop fabrics.
Pleated Shorts: Subtle Volume and a Bit of Vintage
Pleats can be tricky, but when done right, they add elegance and movement. I like pairing pleated shorts with slim tops or a lightweight knit.
These work best if you want to soften a straight frame or create shape. COS and Sandro often get the balance right—refined but relaxed.
Board Shorts: Not Just for the Beach
I bought my first pair for a surf trip, but now I wear board shorts regularly in summer. They’re water-friendly, comfortable, and long enough for real coverage.
Look for secure waistbands and lightweight, quick-dry fabric. Billabong and Patagonia make great technical versions with a flattering silhouette.
What I’ve Learned About Fit
Honestly, the biggest lesson in all of this? The label is meaningless unless the fit is right. I’ve been a size 8, 10, and 12 in the same brand, depending on the cut or fabric.
That’s why I use Tellar.co.uk. It matches my chest, waist and hip measurements to sizing data from over 1,500 brands—so I know what will fit before I click "buy." No more guesswork. No more size drama.
Want to Shop Smarter?
Join Me on the Fit Revolution
If you’re tired of guessing your size, try Tellar—it really is free and easy. And if you want to stay up to date with the best styling advice, fit tips, and sizing hacks:
I hope this guide helps you find your perfect pair. There’s a short for everyone—you just need the right tools to find it.