Skip to Main Content

Your browser’s Javascript functionality is turned off. Please turn it on so that you can experience the full capabilities of this site.

SHOW ’EM WHO’S BOSS

From cool two-piece suits to comfy one-and-done sweater dresses, these styles have just the right amount of profesh polish. Think hardworking meets easygoing. Consider this our version of power dressing for the season.

/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=NH079&cgid=featuredshops-laid-back-tailoring&maxprice=148%2e0&minprice=148%2e0&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop

Denim Straight-Leg Jumpsuit

$148.00

25% off with code FIRSTLOOK
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=99106735316&cgid=featuredshops-laid-back-tailoring&maxprice=178%2e0&minprice=178%2e0&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop
Best Seller

Drapeweave Caldwell Double-Breasted Blazer

$178.00
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=99106735301&cgid=featuredshops-laid-back-tailoring&maxprice=178%2e0&minprice=178%2e0&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop
Best Seller

Drapeweave Caldwell Double-Breasted Blazer

$178.00
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=NG528&cgid=featuredshops-laid-back-tailoring&maxprice=98%2e0&minprice=98%2e0&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop
Best Seller

Drapeweave Carley Wide-Leg Pants

$98.00
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=NG700&cgid=featuredshops-laid-back-tailoring&maxprice=92%2e0&minprice=92%2e0&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop
Best Seller

Carmon Crop Cardigan Sweater

$92.00

25% off with code FIRSTLOOK
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=NG698&cgid=featuredshops-laid-back-tailoring&maxprice=59%2e5&minprice=59%2e5&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop
Dearing Square-Neck Crop Sweater Tank

$59.50
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=NG674&cgid=featuredshops-laid-back-tailoring&maxprice=158%2e0&minprice=158%2e0&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop
Best Seller

The Bradley Lugsole Loafer in Leather

$158.00
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=NG625&cgid=featuredshops-laid-back-tailoring&maxprice=178%2e0&minprice=178%2e0&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop

Best Seller

Caldwell Double-Breasted Blazer in Palmyra Plaid

$178.00
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=99106703224&cgid=featuredshops-laid-back-tailoring&maxprice=108%2e0&minprice=108%2e0&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop

Carley Wide-Leg Pants in Plaid

$108.00
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=ND787&cgid=featuredshops-laid-back-tailoring&maxprice=48%2e0&minprice=48%2e0&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop
MWL Sweatshirt Bralette

$48.00 select colors $34.99

25% off with code FIRSTLOOK
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=NG684&cgid=featuredshops-laid-back-tailoring&maxprice=158%2e0&minprice=158%2e0&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop
The Claudie Heeled Lugsole Mary Jane in Leather

$158.00
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=NG570&cgid=featuredshops-laid-back-tailoring&maxprice=128%2e0&minprice=128%2e0&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop

Best Seller

Brushed Knit Redford Blazer in Houndstooth Check

$128.00

25% off with code FIRSTLOOK
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=NG628&cgid=featuredshops-laid-back-tailoring&maxprice=188%2e0&minprice=188%2e0&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop

Best Seller

Montrose Belted Trench Coat

$188.00

25% off with code FIRSTLOOK
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=NG251&cgid=featuredshops-laid-back-tailoring&maxprice=128%2e0&minprice=128%2e0&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop

Best Seller

The Perfect Vintage Straight Jean in Mayfield Wash

$128.00
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=NH027&cgid=featuredshops-laid-back-tailoring&maxprice=198%2e0&minprice=198%2e0&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop
The Piazza Oversized Tote

$198.00
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=NB334&cgid=featuredshops-laid-back-tailoring&maxprice=55%2e0&minprice=45%2e0&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=true&gridtype=four-up&skipCategoryShotType=false

desktop
Best Seller

Supercrop Long-Sleeve Tee

$55.00 select colors $45.00

25% off with code FIRSTLOOK
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=NG693&cgid=featuredshops-laid-back-tailoring&maxprice=69%2e5&minprice=69%2e5&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop
Best Seller

Bouclé Sweater Vest

$69.50

25% off with code FIRSTLOOK
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=NG229&cgid=featuredshops-laid-back-tailoring&maxprice=138%2e0&minprice=138%2e0&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop

The Perfect Vintage Straight Jean in Meaford Wash: Seamed Edition

$138.00
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=99106690528&cgid=featuredshops-laid-back-tailoring&maxprice=158%2e0&minprice=158%2e0&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop
The Bradley Lugsole Mule in Nubuck

$158.00
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=99106687060&cgid=featuredshops-laid-back-tailoring&maxprice=158%2e0&minprice=158%2e0&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop
The Bradley Lugsole Mule in Nubuck

$158.00
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=NG626&cgid=featuredshops-laid-back-tailoring&maxprice=178%2e0&minprice=178%2e0&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop

Best Seller

Caldwell Double-Breasted Blazer in Hedden Plaid

$178.00
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=NG689&cgid=featuredshops-laid-back-tailoring&maxprice=59%2e5&minprice=59%2e5&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop

Kendale Button-Front Crop Sweater Tank

$68.00 $59.50

Extra 25% off with code FIRSTLOOK
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=NG690&cgid=featuredshops-laid-back-tailoring&maxprice=59%2e5&minprice=59%2e5&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop

Kendale Sweater Biker Shorts

$69.50 $59.50

Extra 25% off with code FIRSTLOOK
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=NH091&cgid=featuredshops-laid-back-tailoring&maxprice=110%2e0&minprice=110%2e0&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop
Best Seller

Button-Front Midi Shirtdress

$110.00

25% off with code FIRSTLOOK
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=NH025&cgid=featuredshops-laid-back-tailoring&maxprice=158%2e0&minprice=158%2e0&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop
Best Seller

The Piazza Crossbody Bag

$158.00
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=NG910&cgid=featuredshops-laid-back-tailoring&maxprice=88%2e0&minprice=88%2e0&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop

Best Seller

Oversized Ex-Boyfriend Tunic Shirt

$88.00
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=NG511&cgid=featuredshops-laid-back-tailoring&maxprice=138%2e0&minprice=138%2e0&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop
The Perfect Vintage Straight Jean: Faux Leather Edition

$138.00
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=NG541&cgid=featuredshops-laid-back-tailoring&maxprice=158%2e0&minprice=158%2e0&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop

Tapered Overalls in Clybourn Wash

$158.00
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=NH481&cgid=featuredshops-laid-back-tailoring&maxprice=98%2e0&minprice=98%2e0&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop

Carmon Crop Cardigan Sweater in Gingham Check

$98.00

25% off with code FIRSTLOOK
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=NH140&cgid=featuredshops-laid-back-tailoring&maxprice=98%2e0&minprice=98%2e0&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop

Gingham Midi Sweater Skirt

$98.00
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=NG521&cgid=featuredshops-laid-back-tailoring&maxprice=118%2e0&minprice=118%2e0&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop
Best Seller

Harlow Wide-Leg Pants

$118.00
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=NH480&cgid=featuredshops-laid-back-tailoring&maxprice=92%2e0&minprice=92%2e0&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop

Carmon Crop Cardigan Sweater in Stripe

$92.00

25% off with code FIRSTLOOK
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=NG699&cgid=featuredshops-laid-back-tailoring&maxprice=62%2e0&minprice=62%2e0&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop

Dearing Square-Neck Crop Sweater Tank in Stripe

$62.00
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=NG438&cgid=featuredshops-laid-back-tailoring&maxprice=69%2e5&minprice=69%2e5&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop

The Momjean Short in Streamside Wash

$69.50
/on/demandware.store/Sites-madewellUS-Site/default/Product-HitTile?pid=NA919&cgid=featuredshops-laid-back-tailoring&maxprice=128%2e0&minprice=128%2e0&showpricing=true&showpromotion=true&showrating=true&showcompare=true&pricerange=false&gridtype=four-up&skipCategoryShotType=false

desktop

Best Seller

The Perfect Vintage Jean in Haight Wash

$128.00