No question…shorts can be tricky. If you’ve ever tried on pair after pair and thought “Nope, not happening”, you are not alone. As we age, our bodies and style preferences shift. Finding flattering, sophisticated ways to wear shorts may become more challenging. I know it has for me over the years.
But here’s the good news: you absolutely can wear shorts and look chic and classy, at any age. It’s all about choosing the right silhouettes and hemlines as well as being strategic about styling.
Below, I’m sharing my favorite tips for looking polished, put-together, and confident in shorts—yes, even if you’ve sworn them off for years!
Ready to simplify your style this summer? Our summer capsule is the answer to effortless, chic style!
classy tips for wearing shorts
1. Go for a Longer Inseam
One of the simplest, yet most impactful style tips for looking classy in shorts? Choosing the right inseam length.
💡 Why it works: A longer inseam offers just enough coverage to feel confident and elevated, without compromising style. It keeps your look modern and refined—never veering into teen territory.
General rule of thumb:
Petite (5’4″ and under)? Look for a 3–5″ inseam.
Taller? A 5–7″ inseam flatters beautifully.
And if you’re ever in doubt? Try the fingertip test: Stand tall, arms relaxed at your sides. If the hem of your shorts hits at or just beyond your fingertips, you’re golden.
✋ Just a reminder—this is a guide, not a rulebook. I’ve certainly worn shorter styles when they felt right. The goal is to find that sweet spot where you feel most comfortable, confident, and polished.
In the look above, I’m wearing a sleek pair of faux leather cuffed shorts (similar options linked below!). Notice how they hit mid-thigh? That’s a universally flattering length that visually elongates the legs and keeps things looking chic and put-together.
2. Choose an A-Line or Relaxed Fit
When it comes to looking chic in shorts, fit is everything.
Look for A-line silhouettes or slightly looser fits around the thighs. The a-line shape will create the illusion of smaller thighs and balance hips beautifully. It’s a subtle design that delivers major style impact—especially if you’re curvy or have strong, athletic thighs. But this fit really works on most body shapes.
In contrast, Shorts that cling too tightly can actually make your legs appear larger. And while we’re all about embracing and celebrating your body as it is, I haven’t met many women who want to look larger. My job? To help you feel like your most confident self—not self-conscious.
💡 Style Note: The pair I’m wearing here is a few years old and no longer available, but I’ve linked several current styles with this flattering A-line silhouette below. Even denim shorts can feel elevated and elegant with the right fit—it really is a game-changer!
3. Don’t Be Afraid to Size Up
One of the most underrated style secrets for looking polished in shorts? Size up. A slightly looser fit instantly adds sophistication—and keeps you comfortable all day long.
Tight waistbands or snug leg openings can make shorts look (and feel) unflattering and frumpy. But a bit of extra room? It creates that effortless drape that reads elevated, not overworked. No one wants to be tugging and adjusting with every step, so if you’re between sizes… go ahead and choose the bigger one.
💭 And please—don’t stress about the number on the tag. No one can see it, and it absolutely doesn’t define you. What does define you? Feeling confident, comfortable, and classy in your clothes.
👗 Style Spotlight: This pair by Frank & Eileen is a perfect example—featuring a chic 4.5″ inseam and a relaxed fit. I styled them with a sleeveless collared top instead of a basic tee and added some polished denim mules. It’s those small, but thoughtful swaps that really elevate a summer outfit.
4. Opt for Elevated Fabrics
One of the fastest ways to elevate your entire look? Choose shorts in high-quality, structured fabrics. Skip the paper-thin, clingy materials and opt for linen blends, twill, cotton, or a wrinkle-resistant crepe. These fabrics drape beautifully, hold their shape, and—bonus—help smooth everything out for a more flattering fit. No visible panty lines, or lumps and bumps.
👗 Style Tip: Look for tailored details like front pleats, a subtle cuff, or trouser-style silhouettes. A pair of pleated crepe shorts styled with a white top looks stylish—and is incredibly easy to pull together.
All three pairs of shorts featured above are great examples of how structure + shape + fabric = a more sophisticated look. These are the kinds of pieces you’ll find yourself reaching for again and again…
5. Add a Blazer
Styling matters! If you really want a classy look with your shorts this summer, turn it into a chic suit. Add a blazer for instant polish. In the 2 outfits above, the blazer is really the star of the show. Even with relaxed raw hem denim shorts, a blazer adds instant class to the look. Now I know, many of you are going to think, “Really Erin? It’s WAY too hot for a blazer in the summer!”. And I get it… I lived in south Texas for eight years. But, even living there I wore jackets and light blazers because I always FROZE in the air conditioning. So unless you’ll be outside, in the extreme heat all day, then I would consider adding a chich blazer with your shorts.
I just picked up this light tan ruched sleeve blazer by Veronica Beard, above left, a few months ago and let me tell you…It’s a winner! Perfect color and weight for summer, the sleeves are already pulled up (no style hack necessary!), and you can add in zip in/out dickeys come fall to give the blazer a whole new, more cozy vibe. And the white ruched sleeve blazer above is one I’ve had for years now and wear every summer. I just love the Old Money vibes you get from pairing this blazer and these affordable white shorts together.
Think you don’t need jackets in the summer months? Think again!
6. Try a Matching Set
For those of you who really value simplicity… go with the done-for-you matching set! Matching shorts sets are so easy to wear, elevated, and classy. I suggest sticking to one color (no prints) for a more fail safe and classy option. The bonus with sets? You can wear them as separates for a totally different look too. So if you’re in a style rut, and want more ease with your style, try a matching set!
This summer I’m really loving the simplicity of whites and blacks. I wore this beautiful white embroidered short set on a recent trip to Europe and loved it (pictured left above)! It’s a set that will make you feel put together no matter where you are going from the beach to brunch.
The black set above is another elegant, easy summer set. The exact top is no longer available, but I linked some similar options below!
If you are a color lover through and through, take a look at this beautiful matching set by Farm Rio. This brand keeps knocking it out of the park.
style it with confidence
Let’s be clear: Shorts don’t come with an expiration date—no matter what anyone says.
Because true style isn’t about age… it’s about confidence.
When you find the right cut, length, and fabric that flatter your body and express your personal style, shorts can be every bit as chic and powerful as a tailored skirt or trouser.
So go ahead—explore new fits, play with color and matching sets, and embrace the pieces that make you feel amazing.
It’s time to let go of the outdated rules… and start wearing what we truly love.
