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

28 Days 28 Raves
Photo: Styled by Ali Pew; Photo by Time Inc. Digital Studios

Falling into a fashion rut? Hit a winning streak with a month's worth of outfits that are simple to style. For InStyle's October issue, we created 28 super-chic ensembles that we promise will make choosing your outfits in the morning a cinch. The secret to these foolproof looks lies in 14 versatile yet far from basic pieces, including everything from a cozy cable sweater (perfect for fall) to wear-with-anything ankle boots—all of which will work with what's already in your closet.

PHOTOS: Shop a Month's Worth of Chic Outfits

For more, pick up the October issue of InStyle, available on newsstands and for digital download now.

01 of 28

Day 1

28 Days 28 Raves
Styled by Ali Pew; Photo by Time Inc. Digital Studios

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;

02 of 28

Day 2

28 Days 28 Raves
Styled by Ali Pew; Photo by Time Inc. Digital Studios
  • 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
03 of 28

Day 3

28 Days 28 Raves
Styled by Ali Pew; Photo by Time Inc. Digital Studios

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

04 of 28

Day 4

28 Days 28 Raves
Styled by Ali Pew; Photo by Time Inc. Digital Studios

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;

05 of 28

Day 5

28 Days 28 Raves
Styled by Ali Pew; Photo by Time Inc. Digital Studios

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;

06 of 28

Day 6

28 Days 28 Raves
Styled by Ali Pew; Photo by Time Inc. Digital Studios

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;

07 of 28

Day 7

28 Days 28 Raves
Styled by Ali Pew; Photo by Time Inc. Digital Studios

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;
08 of 28

Day 8

28 Days 28 Raves
Styled by Ali Pew; Photo by Time Inc. Digital Studios

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;

09 of 28

Day 9

28 Days 28 Raves
Styled by Ali Pew; Photo by Time Inc. Digital Studios

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

Demylee turtleneck, $84;

nordstrom.com

10 of 28

Day 10

28 Days 28 Raves
Styled by Ali Pew; Photo by Time Inc. Digital Studios

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;

11 of 28

Day 11

28 Days 28 Raves
Styled by Ali Pew; Photo by Time Inc. Digital Studios

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
12 of 28

Day 12

28 Days 28 Raves
Styled by Ali Pew; Photo by Time Inc. Digital Studios

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

13 of 28

Day 13

28 Days 28 Raves
Styled by Ali Pew; Photo by Time Inc. Digital Studios

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;

14 of 28

Day 14

28 Days 28 Raves
Styled by Ali Pew; Photo by Time Inc. Digital Studios

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

ASOS sweater, $62;

donaldjpliner.com

15 of 28

Day 15

28 Days 28 Raves
Styled by Ali Pew; Photo by Time Inc. Digital Studios

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;

16 of 28

Day 16

28 Days 28 Raves
Styled by Ali Pew; Photo by Time Inc. Digital Studios

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;

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

17 of 28

Day 17

28 Days 28 Raves
Styled by Ali Pew; Photo by Time Inc. Digital Studios

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;

18 of 28

Day 18

28 Days 28 Raves
Styled by Ali Pew; Photo by Time Inc. Digital Studios

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

Ann Taylor coat, $278;

19 of 28

Day 19

28 Days 28 Raves
Styled by Ali Pew; Photo by Time Inc. Digital Studios

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;

20 of 28

Day 20

28 Days 28 Raves
Styled by Ali Pew; Photo by Time Inc. Digital Studios

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;

toryburch.com

21 of 28

Day 21

28 Days 28 Raves
Styled by Ali Pew; Photo by Time Inc. Digital Studios

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

Lacoste top, $150;

22 of 28

Day 22

28 Days 28 Raves
Styled by Ali Pew; Photo by Time Inc. Digital Studios

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

23 of 28

Day 23

28 Days 28 Raves
Styled by Ali Pew; Photo by Time Inc. Digital Studios

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

Tibi coat, $595;

24 of 28

Day 24

28 Days 28 Raves
Styled by Ali Pew; Photo by Time Inc. Digital Studios

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

25 of 28

Day 25

28 Days 28 Raves
Styled by Ali Pew; Photo by Time Inc. Digital Studios

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

Theonne dress, $225;

26 of 28

Day 26

28 Days 28 Raves
Styled by Ali Pew; Photo by Time Inc. Digital Studios

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

Trademark coat, $498;

27 of 28

Day 27

28 Days 28 Raves
Styled by Ali Pew; Photo by Time Inc. Digital Studios

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;
28 of 28

Day 28

28 Days 28 Raves
Styled by Ali Pew; Photo by Time Inc. Digital Studios

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;

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