The best shorts are the pair you stop thinking about five minutes after getting dressed. That is the real answer to how to choose relaxed shorts: find a fit that gives you room to move, a fabric that suits the forecast, and a look that feels like you. Beach plans, coffee runs, backyard hangs, road trips - relaxed shorts should be ready for all of it.
They are not meant to look stiff, overly tailored, or like you are headed to the gym. The right pair has an easy shape but still looks intentional. Think weekend ready, not worn out.
How to choose relaxed shorts by fit
Start with the waist. Relaxed shorts should sit comfortably where you naturally wear your pants, without pinching when you sit or sliding down when you walk. An elastic waistband, drawstring, or a combination of both adds flexibility, especially on days when the plan includes a big lunch, a long drive, or nothing more ambitious than the couch.
A relaxed fit does not mean sizing up until the shorts lose their shape. The goal is a little breathing room through the seat and thigh, not excess fabric bunching at the waist. If the waistband fits but the legs feel tight when you sit down, move to a roomier cut rather than simply going up a size. If the shorts balloon around your hips, the fit is probably too big.
Look for a leg opening that falls away from the thigh instead of gripping it. This creates that clean, laid-back silhouette that works with a tee, polo, sweatshirt, or lightweight button-up. You should be able to take a full stride, sit cross-legged, and move through your day without constantly tugging at the hem.
Let the inseam set the mood
Short length changes the whole feel of an outfit. A shorter inseam, often around 5 to 7 inches, gives a casual, active look that feels right for warm weather, beach days, and easygoing weekends. A mid-length inseam around 7 to 9 inches is the dependable middle ground - relaxed without feeling too short, polished without looking formal.
Longer shorts can work well if you prefer more coverage or have a taller frame, but avoid hems that hit too far below the knee. They can make a relaxed outfit feel heavy and dated. A good rule: choose a length that lands above the knee or around the top of it, then wear it with confidence.
It also depends on where you are wearing them. A breezy 5-inch pair might be perfect for a coastal getaway, while an 8-inch pair can be your everyday choice for casual lunches, travel days, and neighborhood plans.
Pick a fabric for the day you actually have planned
Fabric is where comfort becomes real. The best choice depends on your climate, your schedule, and the kind of worn-in ease you want from your shorts.
Cotton is the classic everyday option. It feels familiar, softens over time, and pairs naturally with the rest of a casual wardrobe. Cotton jersey shorts bring the cozy feel of your favorite sweatshirt to warm-weather dressing. They are made for slow mornings, quick errands, and post-beach downtime.
French terry offers a little more structure while keeping the same relaxed energy. It is especially good for cooler summer nights, travel, and transitional weather when lightweight shorts feel too bare but sweatpants are too much. The looped interior gives the fabric texture without making it overly heavy.
For hot, humid days, lighter cotton blends and breathable woven fabrics usually win. They allow more airflow and tend to look a touch cleaner if you want shorts that can move from a patio lunch to evening drinks. Linen blends bring an easy beach-life feel, though they will wrinkle more. That is part of the charm for some people and a deal-breaker for others.
Avoid choosing based on the label alone. Feel the fabric, consider its weight, and picture where it will go. A heavier, plush short can be your go-to for cooler evenings, but it may feel like too much during a July afternoon. One pair does not have to do every job.
Choose colors that get more wear
Neutral colors make relaxed shorts easy to repeat, which is exactly what a great casual staple should do. Navy, black, gray, cream, olive, and faded blue work with most T-shirts, hoodies, polos, and sneakers already in your closet. They also give you room to play with a graphic tee or brighter top without the whole outfit feeling busy.
That said, summer is a good time to loosen up. Washed coral, seafoam, soft yellow, or a sun-faded red can bring personality to a simple outfit without becoming a costume. The key is choosing colors that feel natural to your style, not colors you think you are supposed to wear on vacation.
If you are buying your first pair, start with a versatile neutral. If you already have the basics covered, add one color that feels like a change of scenery. The Bulldog Factory approach is simple: casual clothes should carry some spirit. A good color can do that before you say a word.
Prints should feel easy, not loud
A subtle stripe, small pattern, or heritage-inspired graphic can work well when the rest of your outfit stays simple. Pair printed shorts with a solid tee or sweatshirt and let one piece lead. If you tend to reach for graphic tops, solid shorts will give your look more balance.
There is no rule against a bolder choice. Just make sure the shorts fit your real rotation. A fun print that only works once a year is less useful than a color or pattern you will wear every weekend.
Build the outfit from the shorts up
Relaxed shorts are simple, but proportions still matter. Roomier shorts look best with tops that have some shape, even when the overall outfit is casual. A classic-fit T-shirt, a slightly oversized tee with a clean hem, or a relaxed polo all work well. If you wear a sweatshirt, choose a lighter layer or push up the sleeves to keep the look suited to the season.
Shoes set the final direction. Clean sneakers keep the outfit sporty and social. Slides make sense for pool days, beach walks, and low-key lounging. Canvas shoes or casual loafers can make a woven short feel a little more pulled together for dinner outdoors. Socks are personal territory, but if you wear them with shorts, keep the choice deliberate - clean crew socks for a sportier look or no-show socks for a quieter finish.
Pay attention to pockets, too. Deep side pockets are useful, but bulky items can pull down soft fabrics and ruin the line of the shorts. Keep your phone, keys, and wallet light when possible. Comfort is easier when you are not fighting a sagging waistband.
Know when relaxed should still look polished
Relaxed shorts are not a replacement for every warm-weather bottom. For a dressier restaurant, work event, or occasion with a stated dress code, chinos or tailored shorts may be the better call. But for most casual settings, relaxed does not mean careless.
Choose shorts that are clean, in good condition, and free of stretched-out waistbands or curled hems. Fit them well. Pair them with a fresh tee or polo. That is enough to look put together without losing the comfortable, confident energy that makes casual style worth wearing.
The pair you reach for most will not always be the trendiest or the boldest. It will be the one that fits your plans, feels good from the first step, and makes a regular Saturday feel like the start of a great weekend.