Quick answer: Choose overalls with adjustable straps and room through the hips, and wide-leg pants with a waist that sits comfortably at or above your natural waist. Balance their volume with a fitted or tucked top, and switch shoes and layers with the seasons.
Why relaxed bottoms work
Overalls and wide-leg pants are made for real days. They let you crouch, carry, cycle and sit cross-legged without anything digging in, and they leave room for a layer underneath when it is cold. They also look effortlessly put-together, because the straight drape of the fabric does the styling for you. If you have only worn skinny jeans for years, a pair of relaxed bottoms will feel like a holiday for your legs.
Getting the overall fit right
Look for adjustable straps first; they let you set the bib at the right height whatever your torso length. The hips and seat should feel roomy, not tight, and you should be able to sit down without the straps pulling on your shoulders. Most overalls are cut relaxed, so take your usual size for a classic fit or size up for a slouchier look. Roll the hems if they are long; it is part of the charm.
What to wear under overalls
A fitted tee or a ribbed tank is the classic choice, and stripes are always a good idea. In cooler weather try a thin long-sleeve top or a turtleneck, and when it is really cold, a chunky sweater worn under the bib. A button-up shirt with the sleeves rolled looks sharp and works for errands or a casual office. Keep the top close to the body so the overalls stay the main shape.
Wide-leg linen pants basics
Wide-leg pants should sit comfortably at your natural waist or a little higher, with enough room through the thigh that the fabric falls straight from the hip. Drawstring and elastic waists are easier to wear all day, while a button front looks a bit more polished. Linen is the best fabric for warm days because it breathes, and soft wide-leg linen pants crease beautifully rather than messily.
Balance the volume
The golden rule with relaxed bottoms is to keep one part of the outfit close to the body. Tuck in a blouse, knot an oversized shirt at the waist or wear a cropped knit so your waist still shows. A fitted tee works with overalls; a body-skimming top works with wide-leg pants. If you want everything loose, use a belt or a contrasting color at the waist to give the eye a place to rest.
Shoes for every season
Canvas sneakers and leather sandals are the easiest summer partners, and they suit both overalls and linen pants. In spring and fall, try loafers or ankle boots, which look good peeking out from a cropped wide leg. In winter, chunky boots and thick socks keep you warm under a full-length pant. Avoid very high heels with overalls; the outfit wants to be grounded and comfortable.
Layering in cool weather
On cold days, layer leggings or thermal tights under wide-leg pants; nobody can see them and they make linen wearable longer into the season. Add a chunky cardigan over overalls and a striped button-up shirt under them for a very easy cool-weather look. A long cardigan with wide-leg pants creates a long, relaxed line that suits most heights.
Care for relaxed bottoms
Denim overalls can be washed inside out in cold water and hung to dry to keep the color. Linen pants are best washed cold on a gentle cycle; hang them straight from the waistband while damp and most creases will fall out. If you prefer them crisp, iron linen while it is still slightly damp. Corduroy should be turned inside out and never dried on high heat, which flattens the ribs.
Building your set
One pair of overalls and one pair of wide-leg pants cover a remarkable range of outfits when you rotate tees, shirts and knits on top. Start with neutral colors such as denim, sand or black, then add a color you love. Browse our pants and overalls along with our tops and shirts to build combinations that work every day, all in sizes S to XL with free U.S. shipping.
Frequently asked questions
Are overalls flattering?
Yes — adjustable straps and a fitted top underneath keep them looking intentional on any body shape.
Do linen pants wrinkle?
A little; hang them while damp and the natural creases soften.
What shoes go with wide-leg pants?
Sneakers or sandals in summer, loafers or ankle boots in cooler months.
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