How to Style Shorts in 2025 For Every Occasion But One?

How to style shorts in 2025 to look chic and feel comfortable? With something fashionable, obviously! You want to style shorts with something trendy yet sophisticated. With something that will make shorts appropriate even for church. Oh yes, you can wear shorts for the church and even for a job interview, if you know how. Worry not; you will know that in a minute. Scroll down to discover the best shorts outfits and see how to wear shorts no matter the season or occasion. From the street to the office and the club, shorts are almost always a good idea for ladies.

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HOW TO STYLE SHORTS IN 2025

As always, all the collages in this article are hyperlinked and available for immediate purchase. You can shop for all the shorts outfits presented in this article as you read. To shop for the shorts outfits presented, simply click on the item you want to buy. One simple click will take you to the store (I only link to the stores I shop from and know they are trustworthy) where you can purchase that item.

We are adding new outfits constantly – make sure you subscribe to Brunette from Wall Street Substack to make sure you don’t miss a new shorts outfit. Also, become a paid Brunette from Wall Street Substack subscriber if you want to leave a comment, ask a question, or find out why we style shorts with those shoes and that top. And what is more, we let you know about the IRL sizing and fit.

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1 SHORTS OUTFITS WITH A BLOUSE

TAILORED NAVY TURNUP SHORTS WITH HIGH NECK SLEEVELESS FLORAL SATIN BLOUSE AND EMBELLISHED DENIM KITTEN HEEL SLINGBACK PUMPS AND BLACK HAIR BOW

WHITE PLEATED SHORTS WITH CORAL BOW TIE SHORT SLEEVE SATIN BLOUSE AND PLATFORM SANDAL WEDGES

BLACK PLEATED SHORTS WITH PINK SILK RUFFLE BLOUSE AND POINTY CHERRY LACQUER RED PATENT LEATHER KITTEN HEEL SLINGBACKS

BLACK PLEATED SHORTS WITH CORAL BOW TIE SHORT SLEEVE SATIN BLOUSE AND HIGH HEEL SANDALS

BLACK PLEATED BERMUDA SHORTS WITH BLUE POLKA DOT BLUE BLOUSE AND CHERRY LACQUER PATENT LEATHER KITTEN HEEL SLINGBACKS WITH PINK JACQUARD HEADBAND

DARK TWEED SHORTS WITH RED SILK BLOUSE AND POINTY BALLET FLATS

NAVY BLUE TURN UP TAILORED SHORTS WITH RED SILK BLOUSE AND BLACK APTNET LEATHER MID HEEL MARY JANE PUMPS WITH SEMI-SHEER BLACK TIGHTS

DARK TWEED SHORTS WITH BLACK SHEER BLOUSE AND BLACK KNEE HIGH BOOTS

2 SHORTS OUTFITS WITH A SHIRT

WHITE BUTTON SHORTS WITH WHITE OVERSIZED SILK SHIRT ON A WHITE CROCHET BIKINI TOP AND BLACK ESPADRILLE WEDGES WITH A BRAIDED FAUX LEATHER HEADBAND

BUTTER YELLOW SHORTS WITH WHITE OVERSIZED SILK SHIRT AND BIRKENSTOCK WITH POWDER PINK JACQUARD TURBAN

NAVY BLUE LINEN SHORTS WITH SILK NAVY SHIRT AND BLACK ESPADRILLE WEDGES AND RAFFIA TOTE BAG

DARK TWEED SHORTS WITH A STRIPED SHIRT UNDER A STRIPED CARDIGAN AND TRANSCENDENT PINK SUEDE POINTY BALLET FLATS WITH DARK NAVY SATIN BRAIDED HEADBAND

3 SHORTS OUTFITS WITH A T-SHIRT

FLORAL LINEN SHORTS WITH WHITE T-SHIRT AND BLACK ESPADRILLE WEDGES WITH A WRAP KNOT HEADBAND

NAVY BLUE LINEN SHORTS WITH WHITE T-SHIRT AND BLACK ESPADRILLE WEDGES WITH A BLUE HEADBAND

4 SHORTS OUTFITS WITH A TANK TOP

WHITE TAILORED BUTTON SHORTS WITH RED RIBBED TANK TOP AND BLACK POINTY FLAT MULES WITH PEARL HAIRPINS

SUPER SHORT YELLOW SHORTS WITH PINK TANK TOP AND WHITE HIGH TOP AIR JORDANS

DARK NAVY LINEN SHORTS WITH PINK TANK TOP AND AIR JORDAN SNEAKERS

5 SHORTS OUTFITS WITH A CROP TOP

WHITE TAILORED SHORTS WITH WHITE TANK CROP TOP AND POINTY FLAT MULES WITH WIDE-BRIM HAT AND SEASHELL CHARM NECKLACE

FLORAL LINEN SHORTS WITH WHITE CROP TOP AND BLACK POINTY FLAT MULES WITH A BUCKET HAT

NAVY LINEN SHORTS WITH WHITE CROP TOP AND BLUE SLIPPERS

6 SHORTS OUTFITS WITH A PEPLUM TOP

WHITE TAILORED SHORTS WITH WHITE PEPLUM TOP AND EMBELLISHED DENIM KITTEN HEEL POINTY SLINGBACK PUMPS WITH NAVY LINEN BRAIDED HEADBAND

WHITE TAILORED SHORTS WITH WHITE PEPLUM TOP AND BLACK POINTY SLINGBACK PUMPS WITH NAVY LINEN BRAIDED HEADBAND

POWDER PINK LACE SHORTS WITH BLACK PEPLUM TOP AND BIRKENSTOCK SLIDES

7 SHORTS OUTFITS WITH A BIKINI TOP

NAVY LINEN SHORTS WITH LEOPARD PRINT BIKINI TOP AND WIDE-BRIM SUNHAT

8 SHORTS OUTFITS WITH A SLIP TOP

MINT GREEN SILK LACE SHORTS WITH MATCHING MINT GREEN SILK SLIP TOP AND SLIPPERS

9 SHORTS OUTFITS WITH OFF THE SHOULDER TOP

10 SHORTS OUTFITS WITH A POLO TOP

FLORAL LINEN SHORTS WITH BLACK NAVY KNIT 3/4 SLEEVE POLO TOP AND BLACK ESPADRILLES WITH FUCHSIA PINK SATIN KNOT HEADBAND

11 SHORTS OUTFITS WITH A TURTLENECK TOP

NAVY BLUE LINEN SHORTS WITH BLACK TURTLENECK 3/4 SLEEVE TOP AND BLACK ESPADRILLES

12 SHORTS OUTFITS WITH A SWEATER

TWEED SHORTS WITH BLACK MERINO WOOL TURTLENECK SWEATER AND AIRY BLUE SATIN TOP KNOT HEADBAND WITH BLACK KNEE HIGH BOOTS

13 SHORTS OUTFITS WITH A CARDIGAN

BUTTER YELLOW SHORTS WITH WHITE LACE CARDIGAN ON A WHITE T-SHIRT AND POINTY FLATS

NAVY BLUE TURN-UP SHORTS WITH STRIPED CARDIGAN AND TRANSCENDENT PINK SUEDE POINTY BALLET FLATS

14 SHORTS OUTFITS WITH A BLAZER

WHITE TWEED SHORTS WITH WHITE DOUBLE BREASTED BLAZER ON A WHITE BOW BLOUSE WITH MID HEEL LOAFER PUMPS

NAVY BLUE TAILORED SHORTS WITH MATCHING NAVY BLUE DOBLE BREASTED BLAZER ON PINK SILK BLOUSE AND BUTTER YELLOW ANKLE BOOTS WITH OFF WHITE POWDER BRAIDED LEATHER HEADBAND

NAVY BLUE TAILORED SHORTS WITH MATCHING NAVY BLUE DOBLE BREASTED BLAZER AND BLACK KNEE HIGH BOOTS AND BLACK SHEER SOCKS WITH PEARL HAIRPINS

NAVY BLUE OVERSIZED BLAZER WITH DARK TWEED SHORTS AND STRIPED BUTTON DOWN SHIRT WITH TRANSCENDENT PINK SUEDE POINTY BALLET FLATS AND GREEN SATIN TOP KNOT HEADBAND WITH BLACK TOP HANDLE BAG

NAVY TURN UP SHORTS WITH AN OVERSIZED NAVY BLUE BLAZER ON A BLACK TURTLENECK TOP AND BROWN TIGHTS WITH BROWN KNEE HIGH RIDING BOOTS AND LEOPARD PRINT HEADBAND

15 SHORTS OUTFITS WITH A BOMBER JACKET

16 SHORTS OUTFITS WITH A TWEED JACKET

NAVY BLUE TURN UP SHORTS WITH A CROPPED BUTTER YELLOW TWEED JACKET ON A FLORAL BLOUSE AND CHERRY CODED PATENT LEATHER KITTEN HEEL SLINGBACKS AND A SMALL TOP HANDLE BUTTER YELLOW BAG WITH NAVY BRAIDED HEADBAND

BLACK SHORTS WITH TRANSCENDENT PINK TWEED JACKET ON A PINK RUFFLE SILK BLOUSE AND POINTY PASTEL BALLET FLATS AND PINK JACQUARD HEADBAND

17 SHORTS OUTFITS WITH A LEATHER JACKET

TWEED SHORTS WITH BLACK CROPPED LEATHER JACKET ON BLACK MERINO WOOL TURTLENECK SWEATER AND BLACK KNEE HIGH BOOTS WITH AIRY BLUE SATIN TOP KNOT HEADBAND LAYERED WITH SHORT CAPE

18 SHORTS OUTFITS WITH A DENIM JACKET

19 SHORTS OUTFITS WITH A TRENCH COAT

TAILORED TURN UP NAVY SHORTS WITH CAMEL KNEE LENGTH TRENCH COAT ON RED CARDIGAN SWEATER AND BLACK TIGHTS WITH PATENT LEATHER MARY JANE PUMPS

DARK TWEED SHORTS WITH BROWN BURBERRY TRENCH COAT ON A BLACK TURTLENECK TOP AND BROWN TIGHTS WITH BROWN KNEE HIGH RIDING BOOTS

NAVY TURN UP SHORTS WITH BROWN BURBERRY TRENCH COAT ON AN OVERSIZED NAVY BLUE BLAZER AND BROWN TIGHTS WITH BROWN KNEE HIGH RIDING BOOTS AND LEOPARD PRINT HEADBAND

20 SHORTS OUTFITS WITH A WINTER COAT

TWEED SHORTS WITH PINK SHORT DOUBLE BREASTED COAT ON GREEN DOUBLE BREASTED BLAZER AND CROP TOP WITH MARY JANE PUMPS

NAVY BLUE TAILORED SHORTS WITH PINK SHORT DOUBLE BREASTED COAT ON NAVY BLUE DOUBLE BREASTED BLAZER AND BLUE SILK NECK TIE SHIRT WITH BLACK TIGHTS AND BLACK COMBAT BOOTS

TWEED SHORTS WITH PINK SHORT DOUBLE BREASTED COAT ON BLACK MERINO WOOL TURTLENECK SWEATER AND BLACK TIGHTS WITH RED HEADBAND

21 SHORTS OUTFITS WITH HEELS

BLACK PLEATED SHORTS WITH HIGH HEEL SANDALS AND PINK TANK TOP

NAVY BLUE LINEN SHORTS WITH CHERRY LACQUER PATENT LEATHER POINTY SLINGBACK KITTEN HEELS AND OVERSIZED WHITE T-SHIRT WITH DARK GREY BRAIDED HEADBAND

22 SHORTS OUTFITS WITH FLATS

WHITE PLEATED SHORTS WITH POINTY FLAT MULES AND 3/4 SLEEVE RIBBED WHITE TOP

WHITE FLORAL LINEN SHORTS WITH POINTY BALLET FLATS AND RUFFLE SHORT SLEEVE KNIT TOP

WHITE FLORAL LINEN SHORTS WITH POINTY MULE FLATS AND WHITE FLORAL CROPPED BLOUSE AND WIDE-BRIM HAT

BEIGE BELT TIE LINEN SHORTS WITH SLIDE FLATS AND LINEN TOP

BEIGE BELT TIE LINEN SHORTS WITH SLIDE FLATS AND ONE SHOULDER BIKINI TOP

DARK TWEED SHORTS WITH POINTY BALLET FLATS AND STRIPED BUTTON SHIRT WITH GREEN SATIN TOP KNOT HEADBAND AND MINI BLACK TOP HANDLE BAG

NAVY BLUE TURN-UP SHORTS WITH GOLDEN ROUND BALLET FLATS AND WHITE SILK SHIRT UNDER A STRIPED CARDIGAN WITH LILAC PINK BRAIDED HEADBAND AND MINI BLACK TOP HANDLE BAG

23 SHORTS OUTFITS WITH BOOTS

WHITE TWEED SHORTS WITH WHITE KNEE HIGH BOOTS AND THIN BLACK MERINO WOOL TURTLENECK SWEATER LAYERED WITH OFF WHITE KNEE LENGTH DOUBLE BREASTED COAT AND PEARL HAIRPINS

NAVY TURN UP SHORTS WITH BROWN RIDING BOOTS AND BLACK TURTLENECK TOP UNDER BLACK TWEED JACKET AND BLACK CAPE WITH BROWN BELT AND PINK JACQUARD HEADBAND WITH BLACK TIGHTS

TWEED SHORTS WITH BLACK RIDING BOOTS AND PEACH TURTLENECK TOP

TWEED SHORTS WITH BLACK KNEE HIGH BOOTS AND BLACK SEMI-SHEER BLOUSE LAYERED WITH SHORT PINK DOUBLE BREASTED COAT

24 SHORTS OUTFITS WITH ANKLE BOOTS

DARK TWEED SHORTS WITH WHITE WESTERN ANKLE BOOTS AND GREEN DOUBLE BREASTED BLAZER ON A BLACK SILK BLOUSE

25 SHORTS OUTFITS WITH SNEAKERS

WHITE TAILORED SHORTS WITH TAUPE SUEDE SNEAKERS AND NAVY SILK SHIRT WITH WHITE AND BLACK STRIPE SWEATER

YELLOW TWEED SHORTS WITH DUNK SNEAKERS AND WHITE STRIPED CARDIGAN SWEATER

YELLOW TWEED SHORTS WITH DUNK SKATE SNEAKERS AND CREAMY CROCHET SHORT SLEEVE SWEATER WITH ORANGE BUCKET HAT

NAVY BLUE LINEN SHORTS WITH WHITE AIR JORDAN MID AND LIGHT PINK SHORT SLEEVE CARDIGAN SWEATER

26 SHORTS OUTFITS WITH ESPADRILLES

BLACK PLEATED SHORTS WITH BLACK WEDGE ESPADRILLES AND BABY PINK CARDIGAN WITH CHAIN BRACELET

NAVY BLUE LINEN SHORTS WITH BLACK WEDGE ESPADRILLES AND CROCHET TOP

NAVY BLUE LINEN SHORTS WITH BLACK WEDGE ESPADRILLES AND NAVY BLUE SILK SHIRT

NAVY BLUE LINEN SHORTS WITH BLACK ESPADRILLE WEDGES AND NAVY BLUE SILK SHIRT WITH RAFFIA TOTE BAG

27 SHORTS OUTFITS WITH WEDGES

WHITE PLEATED SHORTS WITH PLATFORM WEDGE SANDALS AND CORAL BOW TIE SHORT SLEEVE SATIN BLOUSE

WHITE PLEATED SHORTS WITH PLATFORM WEDGE SANDALS AND 3/4 SLEEVE RIBBED WHITE TOP

28 SHORTS OUTFITS WITH SANDALS

NAVY BLUE LINEN SHORTS WITH WHITE BROWN SUEDE BLOCK HEEL SANDALS AND 3/4 SLEEVE BOATNECK KNIT TOP

29 SHORTS OUTFITS WITH OPAQUE TIGHTS

NAVY BLUE TURN UP TAILORED SHORTS WITH BLACK OPAQUE TIGHTS AND BLUE BLOCK MID HEEL SLINGBACK PUMPS WITH AIRY BLUE MOHAIR SWEATER AND DARK GREY HEADBAND

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