28 Days, 28 Raves: A Month's Worth of Chic Outfit Ideas

Day 1

Intimidated by mixing patterns? Take baby steps with a heathered sweater against soft-focus stripes. A jolt of poppy makes for a confident finish.

Kule top, $345;

Day 2

• Knit on knit is the new double denim (in a good way). Experiment with texture to avoid frumpytown, such as cabled up top and ribbed down below.
• ASOS sweater, $80; asos.com
• Sonia by Sonia Rykiel skirt, $540; net-a-porter.com
• See by Chloe bag, $595; bloomingdales.com
• Aldo shoes, $100; aldoshoes.com

Day 3

Take summery yellow into fall with a richer shade and heavier fabric a la this cozy midiskirt. It'll brighten the longest of workdays.

Reiss jacket, $465;

• reiss.com
• By Malene Birger blouse, $385; at Edit by LBP, 225-757-5905
• COS skirt, $135;

• cosstores.com
• Wouters amp Hendrix cuffs, $339 each; at Iona, 608-467-9489
• Want les Essentiels de la Vie bag, $595;

barneys.com
HampM heels, $60; hm.com

Day 4

Bring minimalist gray to life courtesy of an oversize cobalt coat. The slouchiness sets off sharp angles and imparts pared-back cool.

Trademark coat (worn on top), $498;

• www.trade-mark.com
• Vince coat, $675; vince.com
• ASOS sweater, $80; asos.com
• Mango pants with belt, $70; mango.com
• Bones and Feathers Collective rings, $60-$73; bandfcollective.com
• Clare V. bag, $483; shopbop.com
• Elie Tahari cutout lace-ups, $340; at select Elie Tahari boutiques

Day 5

A stealthy way to flash some skin on date night: Layer a sleeveless turtleneck over a skirt with alluring cutouts-it's a mini in disguise!

River Island tunic, $70;

Day 6

Some say pleats add bulk, but on slim-fit trousers, they make a high waist look ultra-flattering. Go ahead and tuck in that shirt.

By Malene Birger blouse, $385; at Edit by LBP, 225-757-5905
Mango pants with belt, $70;

Day 7

A stark palette sets the stage for sharp geometric lines. Temper a daring angular slit with crisscross heels for a modern happy-hour look.

Jonathan Simkhai sweater, $325;

• nordstrom.com
• Rodebjer shirt, $425; rodebjer.com
• Jennifer Chun skirt, $275; at Jade's Closet, 610-225-7290
• Lillot earrings, $63;

Day 8

Take on the role of sophisticated tomboy in a wide-leg jumpsuit and a slinky rust turtleneck. Play comfy sneaks against a structured bag.

Joseph jumpsuit, $835; at Joseph, 212-535-2503
Gap turtleneck; $60;

Day 9

Soften bold black-and-white with texture: A nubby sleeveless coat brings out the relaxed Baja vibe of a blanket skirt.

Demylee turtleneck, $84;

• revolveclothing.com
• Apiece Apart skirt, $375; apieceapart.com
• Alex Mika rings, $55--$106; alexmikajewelry.com
• Zac Zac Posen bag, $495; at select Dillard's stores
• Vince pumps, $350;

nordstrom.com

Day 10

Team a preppy sweater with an oxford shirt and a barely there mini for a winning boy-meets-girl formula.

Jil Sander Navy sweater, $560; at Jil Sander, 212-925-2345
Everlane shirt, $78;

Day 11

Tired of the LBD? Test-drive a fuller style that cuts a quietly elegant, hourglass figure. Gold-dipped stilettos do plenty of talking.

Theory coat, $695;

• theory.com
• Raoul dress, $400; at Effie's, 205-345-1814
• Eleanor Kalle rings, $195 each;

• eleanorkalle.com
• BCBG Max Azria pouch, $108; bcbg.com bcbg.com
• Diane von Furstenberg pumps, $375; at Diane von Furstenberg, 646-486-4800

Day 12

A tailored blazer never fails to sharpen feminine separates. Just slip it off to slide right into a post-work rendezvous.

Rhié blazer, $795;

• rhiestudio.com
• By Malene Birger blouse, $385; at Edit by LBP, 225-757-5905
• Apiece Apart skirt, $375;

• apieceapart.com
• Wouters & Hendrix cuffs, $339 each; at Iona, 608-467-9489
• Tote Faux leather, Shop Prima Donna, $45;

shopprimadonna.com
Nine West ankle boots, $149; ninewest.com

Day 13

Don't be afraid to clash a little. Slightly off pairings, like marigold and camel, bring a quirky feel to no-frills pieces.

Nanushka coat, $750; at Corridor Store Inc., 201-363-4600
Creatures of Comfort dress, $449;

• shop.creaturesofcomfort.us
• With amp Wessel turtleneck, $130; withandwessel.com
• Wouters amp Hendrix cuffs, $339 each; at Iona, 608-467-9489
• Clare V. bag, $483;

Day 14

Rocker accessories, such as snakeskin booties and a chunky chain-strap bag, lend some major edge to a pretty pastel blue.

ASOS sweater, $62;

• asos.com
• Topshop skirt, $76; topshop.com
• M Missoni bag, $595; at M Missoni, 212-431-6500

donaldjpliner.com

Day 15

Prevent an oversize cuddly cardi from swallowing you whole by wearing a body-skimming sweaterdress underneath.

Elizabeth and James cardigan, $395; at Jet Black Boutique, 315-475-9601
Steven Alan dress, $495;

• stevenalan.com
• Kenneth Cole New York bag, $178; kennethcole.com
• Falke socks, $36; herroom.com
• Stuart Weitzman brogues, $398; at Stuart Weitzman, 212-750-2555

Day 16

For a casual Friday that steers clear of sloppy, match a slouchy sweater to a colorful coat-it's cohesive with minimal effort.

Trademark coat, $498;

• www.trade-mark.com
• Svilu sweater, $285; www.svilu.com
• Lauren Ralph Lauren shirt, $70; bloomingdales.com
• Mango pants, $70; mango.com
• Wouters amp Hendrix cuffs; at Iona, 608-467-9489
• Cuyana tote, $150;

cuyana.com
Nine West wedges, $129; ninewest.com

Day 17

All white looks just as breezy as (but feels a lot warmer than) it did in August. Counter the ease with sophisticated greige heels.

ASOS sweater, $80;

Day 18

A few devil-may-care details—a sweater tied around the waist, jaunty slides—take traditional menswear into cute territory.

Ann Taylor coat, $278;

Day 19

What's better than PJs? Polished yet comfy head-to-toe knits in a color combo that has sporty, all-American appeal. Brunch, anyone?

ASOS sweater, $80;

Day 20

Give a classic pencil skirt a badass attitude adjustment by mixing in a wool moto jacket. Tough without being try-hard.

Assembly New York jacket, $784;

• assemblynewyork.com
• Gap Turtleneck, $60; gap.com
• COS skirt, $125; cosstores.com
• Paige Novick pendant necklace, $405; paigenovick.com
• A.P.C. Calfskin belt, $205; at A.P.C., 212-966-0049
• Tory Burch pumps, $350;

toryburch.com

Day 21

An unexpected keyhole plus a built-in waist tie makes this look street-style catnip. Push the envelope with charcoal kicks.

Lacoste top, $150;

Day 22

Coquettish lace-up kitten heels play against type when paired with a straitlaced, schoolgirl-inspired ensemble.

Rag amp Bone dress, $450;

• neimanmarcus.com
• By Malene Birger blouse, $385; at Edit by LBP, 225-757-5905
• Wouters amp Hendrix cuff ($449) and ring ($299); at Iona, 608-467-9489
• Kate Spade New York clutch, $598;

katespade.com
Nina Originals heels, $168; ninashoes.com

Day 23

Surprise a dinner date by skipping the girlie trappings in favor of a graphic black-and-white study in clean lines.

Tibi coat, $595;

Day 24

Lazy Sundays call for comfy sweats. Give them the gamine treatment with French-girl stripes and a flirty little ruffle.

L.L. Bean coat, $249;

• llbean.com
• Clu Too top, $99; shopbop.com
• Allude pants, $435; at Carleen Ligozio, 631-204-0104
• Ampersand as Apostrophe tote, $698;

net-a-porter.com for info
Joie sneakers, $179; joie.com

Day 25

Featherweight wool meets silk faille for a whole new spin on evening. Even more unpredictable? The lush blue and subtle stripes.

Theonne dress, $225;

Day 26

Toughen up a simple sheath with utilitarian touches: A sleek backpack and combat-ready booties will do the trick.

Trademark coat, $498;

• www.trade-mark.com
• J.Crew dress, $228; jcrew.com
• Coach watch, $198; coach.com
• Six Eleven for Aritzia backpack, $475; aritzia.com
• L.L. Bean socks, $12; llbean.com
• Robert Clergerie boots, $695; at Robert Clergie New York, 212-207-8600

Day 27

Trendy metallic sneakers and an of-the-moment bucket bag elevate jeans and a sweatshirt for an errand-packed day.

AYR coat, $395;

• ayr.com
• MiH sweater, $345; mih-jeans.com
• American Eagle Outfitters shirt, $40; ae.com
• J Brand Jeans, $235; at select Neiman Marcus stores
• Coach watch, $198;

Day 28

Channel a present-day Mary Tyler Moore in a slim-fit turtleneck under a belted dress. Swingy confidence at its best.

Raoul dress, $400; at Effie's 205-345-1814
Uniqlo turtleneck, $80;