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

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.

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1 of 29

Day 1

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; kule.com
Apiece Apart skirt, $375; apieceapart.com
Echo Design snood, $48; echodesign.com
Arme de L'Amour bracelet, $420; armedelamour.com for info
Marc by Marc Jacobs bag, $298; marcjacobs.com
Ann Taylor ankle boots, $248; anntaylor.com
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2 of 29

Day 2

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

3 of 29

Day 3

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
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4 of 29

Day 4

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; 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

5 of 29

Day 5

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; us.riverisland.com
Nonoo skirt, $625; shopbop.com
T+J Designs ring, $24/3; tandjdesigns.com
Time's Arrow bag, $525; times-arrow.com
Topshop mules, $110; topshop.com

6 of 29

Day 6

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; mango.com
Clare V. bag, $483; shopbop.com
George Frost x Michael Bastian keychains, $130 each; lulufrost.com
Tory Burch pumps, $350; toryburch.com
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7 of 29

Day 7

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; lillotnyc.com
GiGi New York clutch, $165; giginewyork.com
COS heels, $225; cosstores.com

8 of 29

Day 8

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; gap.com
ALC bag, $645; intermixonline.com
A.V. Max ring, $28; avmaxaccessories.com
Converse sneakers, $55; converse.com

9 of 29

Day 9

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; 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
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10 of 29

Day 10

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; everlane.com
T by Alexander Wang skirt, $325; shopbop.com
Vrai amp Oro ring, $65; vraiandoro.com
Clare V. bag, $483; shopbop.com
G.H. Bass amp Co. loafers, $98; ghbass.com

11 of 29

Day 11

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 29

Day 12

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
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13 of 29

Day 13

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; 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; shopbop.com
Tory Burch pumps, $350; toryburch.com

14 of 29

Day 14

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

15 of 29

Day 15

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; 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
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16 of 29

Day 16

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; 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

17 of 29

Day 17

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; asos.com
Gap turtleneck; $60; gap.com
Trademark pants, $298; trade-mark.com
Mia heels, $59; miashoes.com

18 of 29

Day 18

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; anntaylor.com
Loft sweater, $80; loft.com
Banana Republic sweater (around waist), $90; bananarepublic.gap.com
Chinti and Parker trousers, $285; net-a-porter.com
Coach watch, $198; coach.com
Missguided sandals, $36; missguidedus.com
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19 of 29

Day 19

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; asos.com
Edun skirt, $395; barneys.com
Coach watch, $198; coach.com
Danielle Nicole bag, $98; piperlime.gap.com
Joie sneakers, $179; joie.com

20 of 29

Day 20

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; 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

21 of 29

Day 21

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; lacoste.com
Novis skirt, $895; novisnyc.com
Joie sneakers, $179; joie.com
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22 of 29

Day 22

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 29

Day 23

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; tibi.com
McQ Alexander McQueen dress, $790; alexandermcqueen.com
Efva Attling rings, $185-190; efvaattling.com
Treesje clutch, $145; treesje.com
Nine West ankle boots, $149; ninewest.com

24 of 29

Day 24

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
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25 of 29

Day 25

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; theonne.com
Iris amp Ink shirt, $195; theoutnet.com
Reece Hudson clutch, $695; reecehudson.com
Chinese Laundy pumps, $70; chineselaundry.com

26 of 29

Day 26

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; 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

27 of 29

Day 27

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; coach.com
Saskia Diez ring, $242; openingceremony.us
Mansur Gavriel bag, $610; bergdorfgoodman.com
Nike sneakers, $120; nike.com
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28 of 29

Day 28

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; uniqlo.com
ALC bag, $645; intermixonline.com
Nine West boots, $149; ninewest.com
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