How to Wear Your Denim Overalls 6 Different Ways

Slouchy, loose overalls give you that carefree and relaxed feeling, like you're vacationing in Maine or Vermont. This pair is perfectly cropped and distressed to give some subtle texture to the blue denim. Wear with a billowy peasant blouse and easy brown slides to get that effortless out-of-office look.

Shop the pieces: 1. Free people overalls, $115; 2. Leith Clark x Catbird ear climber, $178; 3. Madewell x Christy Dawn top, $148; 4. Chloé Faye bag, $795; 5. Sam Edelman slide sandal, $89

Don't play it safe with a standard-issue t-shirt under your overalls; layer a polka dot crop top underneath, instead. This will help you stay cool for summer and offer a sexy hint of skin without exposing more than you're comfortable with. These pearl hoops add a delicate touch, while a bucket hat and Birkenstocks make the outfit feel casual enough for a weekend at the park.

Shop the pieces: 1. Frame crop overalls, $330; 2. Topshop crop top, $22; 3. McQ Alexander McQueen bucket hat, $95; 4. Stone and Strand pearl huggies, $295; 5. Birkenstock sandals, $100

For a summer-into-fall transitional look, wear a lightweight sweater underneath your overalls. This Stella McCartney crew neck top complements the ultra distressed Balmain overalls (FYI this pair is quickly selling out, so add it to your cart asap) while the pops on the sleeves give the look some color. Style it with a crossbody bag and a pair of pinkish sandals to tie the whole look together.

Shop the pieces: 1. Balmain overalls, $598; 2. Astrid and Miyu shell huggies, $79; 3. Stella McCartney sweater, $925; 4. Marc Jacobs camera bag, $295; 5. Melissa sandals, $85

Fashion daredevils will want to trade in their blue overalls for this tiger stripe-meets-leopard spots pair. The material is still denim, but the overall design makes a fierce statement. Let the prints shine on their own by layering a black bodysuit underneath—I like turtlenecks—and dress it down with a pair of sneakers.

Shop the pieces: 1. Ganni overalls, $370; 2. Re/Done bodysuit, $70; 3. Nanushka belt bag, $335; 4. Golden Goose trainers, $460

If you feel like a little kid in denim overall shorts, try pairing them with "grown-up" pieces. My picks include this blousy white top from J.Crew, a Fendi rattan crossbody bag, and a smart pair of ballet flats from Stuart Weitzman. Add on a beaded and pearl combo bracelet, which gives off an air of playfulness without making you feel like you're in elementary school again.

Shop the pieces: 1. H&M overalls, $30; 2. J.Crew top, $52; 3. Fendi rattan bag, $3,390; 4. Catbird gold bracelet, $93; 5. Eliou bracelet, $76; 6. Stuart Weitzman ballet flats, $295

The New Yorker in me loves this almost all-black outfit. To give the look an interesting masculine feel, wear with a printed shirt from AllSaints (plucked from the mens section, just size down if you want it to be more fitted) and thick-sole combat ankle boots. A structured handbag and gold ring completes the outfit.

Shop the pieces: 1. Paige overalls, $279; 2. AllSaints shirt, $130; 3. AllSaints ring, $50; 4. MCM tote bag, $1,133; 5. 3.1 Phillip Lim, $650

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