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Trendy Back-To-School Outfit Ideas For High School & College

Windsor has trendy back-to-school outfits for high school and college students! Find inspo for cool outfits or cute and preppy looks. Get back-to-school outfits from trendy high school apparel to stylish college clothes. Shop jackets, tops, jeans, skirts, dresses, fall shoes, and bags!

Discover the basic tanks and tees you need in your wardrobe that you can layer with this fall season. Shop sleeveless fitted bodysuits, cropped tanks, short sleeve tees, and long sleeve tops you can pair with denim and your fave jackets. Layer on jean jackets, cropped corduroy jackets, trendy plaid shackets, and oversized blazers for cool outfits for school.

For an elevated vibe, create effortlessly stylish looks with cropped sweaters, cardigan and top sets, collared button-down tops, and chic blouses. Style your sweaters and cardigans with plaid mini skirts and ankle booties, and collared tops and blouses with wide-leg pants and mules. Windsor has the latest selection of jeans and a curated collection of Denim by Windsor to create college outfits you’ll love. Shop classic skinny jeans, boyfriend jeans, mom jeans, flare jeans, and other styles of denim in a range of trendy washes and levels of destruction. Bring the cool-girl vibes to your back-to-school fashion with relaxed-fitting joggers paired with cropped hoodies in new fall colors and ankle booties, or oversized sweaters with leggings and knee-high boots.

Rompers and jumpsuits make the perfect first-day-of-school outfits since they offer a dressier vibe while still keeping it laid back and chic. Explore flirty skater rompers you can layer with jean jackets, or cute denim jumpsuits styled with layered necklaces. Get the breakdown of trending outfits with these 5 Core Aesthetics for Back-To-School Fashion.

Transition into the fall season with basic ruched knit mini dresses paired with shackets and booties. Shop preppy collared dresses, cozy sweater dresses, and classic long sleeve dresses you can pair with flats, sneakers, boots, or mules to create outfits for school. Discover adorable matching sets, floral dresses, and marble print dresses that will level up your college fashion. Make Windsor your go-to for all your back-to-school shopping to create outfits you’ll love.

  • Stretch The Rules Mesh Denim Print Crop Top

    Stretch the rules in this Y2K-inspired mesh crop top perfect for concerts and backyard parties! It features fitted long sleeves, a mock neck, and a fitted hem on denim printed sheer mesh fabric. Complete the look with a seamless bralette and your favorite bottoms!

    Fit & Features

    • Fitted long sleeves
    • Mock neck
    • Fitted crop hem
    • Denim print
    • Sheer mesh fabric, minimal stretch
    • Runs true to size

    Style Number/Barcode: 06002-1643

    Category Name: Back To Campus Outfits

    Price: $6.97 $22.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Casual Cool Vibes Hoodie Bomber Jacket

    Layer on the casual cool vibes with this nylon hoodie bomber jacket offering a relaxed fit perf for everyday wear.

    Fit & Features

    • Nylon-blend fabric with woven lining, no stretch
    • Drawstring hooded neckline
    • Zip-front design
    • Long sleeves with cinched hems 
    • Mid-length cinched hem
    • Relaxed fit
    • Runs true to size

    Style Number/Barcode: 06204-2077

    Category Name: Back To Campus Outfits

    Price: $42.90

    Availability: In Stock

    Available Color: TAUPE

    Available Size: S, M, L, XL

  • High-Rise Distressed Boyfriend Jeans

    Create a dramatic moment with distressed jeans that add an edge to your look! The medium-wash denim jeans feature a flattering high-rise waist and a boyfriend silhouette with trendy knee slits. Complete the look with a crop top and combat boots.

    Fit & Features

    • High-rise waist
    • Boyfriend silhouette 
    • Knee slit accents
    • Multi-button down closures
    • Five-pocket styling, belt loop accents
    • Medium-wash denim, slight stretch
    • Runs true to size

    Style Number/Barcode: 06602-0240

    Category Name: Back To Campus Outfits

    Price: $42.90

    Availability: In Stock

    Available Color: MEDIUM, DENIM

    Available Size: 1, 3, 5, 7, 9, 11, 13

    Product Badge:
    • Best Seller
  • Attention Please Cargo Mini Skirt

    Capture everyone's attention in this trendy cargo mini skirt perf for the new season! It features a high-rise waist with belt loops and dual front snap button closures, large cargo-style side pockets with adjustable straps, dual back pocket flaps, and a mini-length hem with a fitted silhouette. Style with the matching cropped jacket for a cool-girl vibe.

    Shop Matching Top: Attention Please Cargo Cropped Jacket

    Fit & Features

    • High-rise waist, belt loops
    • Dual front snap button closures
    • Large cargo-style side pockets, strap details
    • Dual back pocket flaps
    • Mini-length hem, fitted silhouette
    • Cargo twill fabric
    • Runs true to size

    Style Number/Barcode: 06301-0170

    Category Name: Back To Campus Outfits

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Charming Direction Sleeveless Plaid Romper

    A sleeveless plaid romper features a square neckline adorned with a velvet bow and a flattering form-hugging fit that leads to the flared short-length hem. Perfect for back-to-school styling.

    Fit & Features

    • Plaid print, knit fabric, minimal stretch
    • Square neckline, velvet bow, shoulder straps
    • Form-hugging fit
    • Flared short-length hem
    • Shorts lining
    • Romper in size small is 29" shoulder to hem with an 8" front rise and a 1.5" inseam
    • Runs true to size

    Style Number/Barcode: 06503-1214

    Category Name: Back To Campus Outfits

    Price: $6.97 $39.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Cute And Classic Cuffed Denim Jacket

    Layer on this cute and classic denim jacket over all your casual summer 'fits. It features a collared neckline, three-quarter length sleeves with buttons to cuff, a complete button-down front, and a cropped, fitted silhouette. Style with simple hoop earrings.

    Fit & Features

    • Collared neckline
    • Three-quarter length sleeves, buttons to cuff
    • Button-down front
    • Buttoned chest pockets, side pockets
    • Cropped fit
    • Light wash denim fabric, no stretch
    • Runs true to size

    Style Number/Barcode: 06203-0193

    Category Name: Back To Campus Outfits

    Price: $14.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • High Fashion Under-The-Knee Faux Leather Boots

    Strut in these fashionable faux leather boots for insta-worthy looks all season! They boast a sleek pointed toe and block heel, an inner zipper closure to secure the style, and the perfect under-the-knee length shaft for styling with short dresses, skirts, or midis. Complete the look with a chic tote bag.

    Fit & Features

    • 3" Block heel, 7.5" leg opening, 14" shaft height
    • Faux leather material
    • Pointed toe
    • Inner zipper closure
    • Under-the-knee length shaft
    • Runs true to size

    Style Number/Barcode: 07402-1015

    Category Name: Back To Campus Outfits

    Price: $9.97 $45.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Chicly Defined Halter Button Vest

    Define your chic look with this halter button vest to elevate your favorite denim!

    Fit & Features

    • Stretchy knit fabric
    • Halter V-neckline
    • Back zipper closure
    • Button front accents
    • Front faux pockets
    • Cropped hem
    • Runs true to size

    Style Number/Barcode: 06005-2228

    Category Name: Back To Campus Outfits

    Price: $39.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M, L

  • Sleek Perfection Patent Faux Leather Handbag

    The chic patent faux leather material of this small handbag makes it sleek perfection! It features a square shape with a fold-over flap, snap-button closure, a top handle strap, a detachable crossbody strap, and a spacious leopard print lined interior with a zipper pocket. Style with a rhinestone ring set.

    Fit & Features

    • Small handbag design
    • Square shape
    • Fold-over flap, snap-button closure
    • Top handle strap
    • Detachable faux leather crossbody strap
    • Patent faux leather material
    • Spacious leopard print lined interior, zipper pocket

    Style Number/Barcode: 07203-1286

    Category Name: Back To Campus Outfits

    Price: $12.97 $26.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • Sunday Leisure Oversized Graphic Sweatshirt

    Lounging has never looked so comfy and cute than this oversized graphic sweatshirt! With a 'Sunday Leisure Club' and '23' graphic design a soft fleece lining to help keep you warm.

    Fit & Features

    • Cotton knit fabric, soft fleece lining
    • Crew neckline
    • Long sleeves
    • '23' and 'Sunday Leisure Club' graphic design
    • Oversized fit

    Style Number/Barcode: 06002-2015

    Category Name: Back To Campus Outfits

    Price: $34.90

    Availability: In Stock

    Available Color: NAVY

    Available Size: S, M, L

  • So Obsessed Marble Print Crop Top

    A wear-everywhere kind of crop top you'll be obsessed with! It features fitted long sleeves, a sexy plunge V-neckline with adjustable drawstring ties with cutout accents, and a cropped hem on marble print brushed knit fabric. Complete the look in wide-leg pants for brunch with the girls or a casual get-together!

    Fit & Features

    • Fitted long sleeves
    • Plunge V-neckline
    • Adjustable drawstring ties, cutout accents
    • Cropped hem
    • Marble print
    • Brushed knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06001-4895

    Category Name: Back To Campus Outfits

    Price: $6.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Codi High-Rise Dad Jeans by Windsor Denim

    Your best silhouette yet is to be experienced in the Codi dad jeans by Windsor Denim! They feature a flattering ultra-high-rise waist, a slim hip-hugging fit, front distressed accents for a trendy look, and split sides along the hem. The dad jeans are crafted from a premium medium wash denim fabric with a color fading and slight stretch. Complete the look in a sleeveless bodysuit for a casual backyard dinner!

    Fit & Features

    • Ultra high-rise waist
    • Slim curve-hugging fit, dad-style leg
    • Front distressed accents, split sides along hem
    • Front button and hidden zipper closure
    • Five-pocket styling, belt loop accents
    • Medium wash denim fabric, color fading, slight stretch
    • Runs true to size

    Style Number/Barcode: 06602-0419

    Category Name: Back To Campus Outfits

    Price: $6.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Sleek Allure Curved Open Hoop Earrings

    These alluring curved open hoop earrings create a unique and undeniable style! Complete the look with a cute sweater top and jeans.

    Fit & Features

    • Open-hoop
    • Double-row curved metal design
    • Post-back closure, rubber stopper


    Earrings are final sale and may not be returned or exchanged.

    Style Number/Barcode: 07001-2100

    Category Name: Back To Campus Outfits

    Price: $8.90

    Availability: Out of Stock

  • Basic Ribbed Knit Long Sleeve Mini Dress

    Make a sleek statement with this long-sleeve mini dress, the epitome of chic simplicity. This figure-hugging silhouette, crafted from a soft ribbed knit fabric, offers both warmth and style. Featuring a high turtleneck for a touch of polished sophistication, this mini dress is perfect for transitioning from day to evening. Layer this ribbed knit mini-dress with an oversized faux leather blazer or stylish trench coat and knee-high boots for the perfected layered outfit.

    Fit & Features

    • Mock neckline
    • Long fitted sleeves
    • Mini-length hem
    • Curve-hugging fit
    • Ribbed knit fabric
    • Plenty of stretch
    • Runs true to size

    Style Number/Barcode: 06002-0703

    Category Name: Back To Campus Outfits

    Price: $6.97 $29.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Check Me Out Plaid Bodycon Mini Dress

    You'll be the object of everyone's gaze in this trendy plaid bodycon mini dress! It features a sleeveless square neckline, bungee spaghetti straps, a stylish lower back cutout, a mini-length hem, and a bodycon silhouette that will hug your natural curves. The stretchy brushed knit fabric features a chic windowpane plaid print. Complete your look with clear mules!

    Fit & Features

    • Sleeveless square neckline
    • Bungee spaghetti straps
    • Lower back cutout
    • Mini-length hem, bodycon silhouette
    • Plaid print
    • Brushed knit fabric, lined bust, plenty of stretch
    • Runs true to size

    Style Number/Barcode: 05102-5230

    Category Name: Back To Campus Outfits

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • In It To Win it Vintage Moto Graphic Tank Top

    With this graphic tank top, you'll be in it to win it serving up a vintage-inspired edge! The tank top features a sleeveless crew neck, front slashed detailing, a script that reads "Road Race/Ride or Die Vintage" and a fitted crop hem on stretchy knit fabric. Complete the look in boyfriend jeans for a trendy style.

    Fit & Features

    • Sleeveless crew neck
    • Front slashed detailing
    • Script reads "Road Race/Ride or Die Vintage"
    • Fitted crop hem
    • Stretchy knit fabric
    • Runs true to size

    Style Number/Barcode: 06002-1584

    Category Name: Back To Campus Outfits

    Price: $11.97 $19.90

    On Sale: Yes

    Availability: Out of Stock

  • Confident Flirt One-Shoulder Crop Top

    This crop top is exactly what you need to make your crush stop and stare! It boasts a flirty one-shoulder neckline, a fitted silhouette, and a cropped hem that flaunts your cute figure on smooth knit fabric. Complete the look in trendy distressed jeans.

    Fit & Features

    • Smooth knit fabric, moderate stretch
    • One-shoulder neckline
    • Fitted crop silhouette
    • Runs true to size

    Style Number/Barcode: 06001-5379

    Category Name: Back To Campus Outfits

    Price: $10.97 $24.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Ships Free
  • City Sleek Satin Cargo Joggers

    Look sleek in the city wearing these satin cargo joggers to elevate your style! They feature a flattering high-rise waist, hidden side pockets, a relaxed fit, cargo flap pockets with pull tabs, and an elasticized drawstring cuff. Complete the look in a long sleeve crop top for grabbing cocktails and appetizers!

    Fit & Features

    • High-rise waist, back elasticized band
    • Hidden side pockets, cargo flap pockets, pull tabs
    • Relaxed fit
    • Elasticized drawstring cuff
    • Front button and hidden zipper closure, belt loop accents
    • Smooth satin fabric, slight stretch
    • Runs true to size

    Style Number/Barcode: 06402-1360

    Category Name: Back To Campus Outfits

    Price: $20.97 $49.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Clearance
  • Too Cute to Pleat Strapless Romper

    Low effort, high impact. This strapless lace romper accentuates the waist and flares with pleated drama—aka, your new going-out obsession.

    Fit & Features

    • Smooth knit fabric, moderate stretch
    • Strapless neckline
    • Pleated mini-length hem
    • Shorts lining with mesh lace trim
    • Runs true to size

    Style Number/Barcode: 06503-000096

    Category Name: Back To Campus Outfits

    Price: $44.90

    Availability: In Stock

    Available Color: BLACK

    Available Size: S, M, L

    Product Badge:
    • New Arrival
  • Tequila Shot Time Embroidered Baseball Cap

    Live your best life in this trendy baseball cap, a must-have for happy hour with your squad! It features a traditional baseball cap design with a curved brim, a contrasting embroidered script that reads, "Tequila," and a contrasting embroidered lime, salt, and shot glass design. Style with hoop earrings and a cute crossbody bag!

    Fit & Features

    • Traditional baseball cap design
    • Curved brim
    • Embroidered script that reads, "Tequila"
    • Embroidered lime, salt, and shot glass design
    • Adjustable back strap

    Style Number/Barcode: 07302-1519

    Category Name: Back To Campus Outfits

    Price: $5.97 $12.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Paisley and Playful Halter Skater Dress

    Flirty, floaty, and made for dancing under the sun. With a smocked bust and ruffled skater fit, this halter mini dress is your go-to for festivals, vacays, or just looking way too good for no reason.

    Fit & Features

    • Paisley print, woven fabric, bust lining
    • Halter V-neckline, spaghetti strap tie
    • Stretchy smocked bust
    • Open tie-back detail
    • Flowy skater silhouette
    • Ruffled trim short hem
    • Runs true to size

    Style Number/Barcode: 05102-000065

    Category Name: Back To Campus Outfits

    Price: $42.90

    Availability: In Stock

    Available Color: BLUE

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Attention Please Cargo Cropped Jacket

    Capture everyone's attention in this trendy cargo cropped jacket perf for the new season! It features a collared neckline, short sleeves, a complete snap button-down front, dual chest pockets with adjustable straps, and a fitted cropped hem. Style with the matching mini skirt for a cool-girl vibe.

    Shop Matching Bottoms: Attention Please Cargo Mini Skirt

    Fit & Features

    • Collared neckline
    • Short sleeves
    • Snap button-down front
    • Dual chest pockets, strap details
    • Fitted cropped hem
    • Cargo twill fabric
    • Runs true to size

    Style Number/Barcode: 06204-1619

    Category Name: Back To Campus Outfits

    Price: $9.97 $38.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale
  • Too Cute To Catch Belted Ruffle Skort

    Catch her if you can—she’s booked, busy, and best dressed. This ruffled mini skort brings all the bounce for brunch, day parties, and spontaneous Insta moments.

    Fit & Features

    • Woven fabric
    • High-rise belted waist, belt loop accents
    • Hidden side zipper and hook-eye closure
    • Ruffled skirt overlay, shorts lining
    • Mini-length hem
    • Runs true to size

    Style Number/Barcode: 06403-000025

    Category Name: Back To Campus Outfits

    Price: $44.90

    Availability: In Stock

    Available Color: IVORY

    Available Size: XS, S, M, L

    Product Badge:
    • New Arrival
  • Casual Trendsetter Collared Bodysuit

    Show off your casual trendy style in this ribbed sweater knit bodysuit that is perf for fall! It features a johnny collar neckline leading to a partial button-down front, cap sleeves, a thong bottom, and a form-hugging fit. Complete the look with faux leather pants and booties.

    Fit & Features

    • Johnny collar neckline
    • Partial button-down front
    • Cap sleeves
    • Thong bottom, dual snap button closure
    • Form-hugging fit
    • Ribbed sweater knit fabric, moderate stretch
    • Runs true to size

    Style Number/Barcode: 06005-1244

    Category Name: Back To Campus Outfits

    Price: $6.97 $32.90

    On Sale: Yes

    Availability: Out of Stock

    Product Badge:
    • Sale