Frilly socks, lunch boxes and chokers: How our editors would update their back-to-school outfits

Yahoo Style

Nostalgia has fueled sales for all things ’90s for a few years now, which inspired our Yahoo Style + Beauty editors to reflect on our own favorite back-to-school outfits (though many are pre-Kimmy Gibbler-esque, to be sure).

Some choices — no doubt the doing of an overly autonomous tyke — are relegated to the archives (see: mom’s photo album) in perpetuity. Others inspire their own modern takes, replete with a handful of retro jean jackets and a Gucci backpack or two.

Speaking of backpacks, a young Bianca Stratford, of 10 Things I Hate About You fame, may have put it best: “There’s a difference between like and love. Because I like my Skechers, but I love my Prada backpack.”

If you’re in need of your own back-to-school shopping inspiration, check out what we’d wear today if we could do it all over again.

<p>I wore a mix of offensive neon jean shorts and graphic T-shirts as a ’90s kid. Luckily, I outgrew the neon and kept the good bits: a love for denim and cheeky tees. —<em>Alexandra Mondalek, Yahoo Style fashion features writer</em><br><br><a href="https://www.net-a-porter.com/us/en/product/892120/frame/le-crop-mini-boot-distressed-mid-rise-flared-jeans" rel="nofollow noopener" target="_blank" data-ylk="slk:Le Crop mini boot distressed mid-rise flared jeans, $245" class="link rapid-noclick-resp"><span>Le Crop mini boot distressed mid-rise flared jeans, $245</span></a><br><a href="http://www.revolve.com/smythe/br/f2df94/?srcType=dp_des2" rel="nofollow noopener" target="_blank" data-ylk="slk:Smythe pinstripe blazer" class="link rapid-noclick-resp"><span>Smythe pinstripe blazer</span></a><span>, </span><a href="http://www.revolve.com/smythe-pouf-sleeve-one-button-blazer-in-navy-pinstripe/dp/SMYT-WO162/?d=F¤cy=USD&mkwid=%7Bifsearch:s%7D%7Bifcontent:c%7D_dc%7Cpcrid%7C114237047411%7Cpkw%7C%7Cpmt%7C&pdv=c&matchtype=&gclid=EAIaIQobChMIhL3O3OCz1QIVk1YNCh3BbQPFEAQYASABEgJKAfD_BwE" rel="nofollow noopener" target="_blank" data-ylk="slk:$695" class="link rapid-noclick-resp"><span>$695</span></a><br><a href="http://www.saksfifthavenue.com/main/ProductDetail.jsp?FOLDER%3C%3Efolder_id=2534374306624262&PRODUCT%3C%3Eprd_id=845524447111361&R=3610928072750&P_name=Chlo%26%23233%3B&N=306624262&bmUID=lSi53sn" rel="nofollow noopener" target="_blank" data-ylk="slk:Chloe Multi-Strap patent leather pumps, $880" class="link rapid-noclick-resp">Chloe Multi-Strap patent leather pumps, $880</a><br><a href="https://www.net-a-porter.com/us/en/product/914646/loewe/printed-stretch-cotton-jersey-t-shirt" rel="nofollow noopener" target="_blank" data-ylk="slk:Loewe printed white T-shirt, $325" class="link rapid-noclick-resp"><span>Loewe printed white T-shirt, $325</span></a><br><br><a href="https://www.net-a-porter.com/us/en/product/892185/see_by_chloe/olga-small-textured-leather-backpack" rel="nofollow noopener" target="_blank" data-ylk="slk:See by Chloe backpack, $425" class="link rapid-noclick-resp"><span>See by Chloe backpack, $425</span></a> </p>
Throwback-to-school shopping

I wore a mix of offensive neon jean shorts and graphic T-shirts as a ’90s kid. Luckily, I outgrew the neon and kept the good bits: a love for denim and cheeky tees. —Alexandra Mondalek, Yahoo Style fashion features writer

Le Crop mini boot distressed mid-rise flared jeans, $245
Smythe pinstripe blazer, $695
Chloe Multi-Strap patent leather pumps, $880
Loewe printed white T-shirt, $325

See by Chloe backpack, $425

<p>This beloved first-day-of-preschool outfit was entirely made by my mom! I love the mixing-and-matching of purple and red, and absolutely coveted that Snoopy lunchbox. I would just update the look to suit modern lines and to be more age-appropriate. —<em>Beth Greenfield, Yahoo Style + Beauty senior editor</em><br><br><a href="https://www.net-a-porter.com/ca/en/product/875823/a_p_c__atelier_de_production_et_de_creation/therese-denim-skirt" rel="nofollow noopener" target="_blank" data-ylk="slk:APC denim skirt, $190" class="link rapid-noclick-resp"><span>APC denim skirt, $190</span></a><br><a href="https://www.gilt.com/brand/helmut-lang/product/1175873786-helmut-lang-cap-sleeve-placket-top?origin=search" rel="nofollow noopener" target="_blank" data-ylk="slk:Helmut Lang cap sleeve top, $99.98" class="link rapid-noclick-resp"><span>Helmut Lang cap sleeve top, $99.98</span></a><br><a href="http://shopmelissa.com/sale/melissa-strips#272=557" rel="nofollow noopener" target="_blank" data-ylk="slk:Melissa Strips chunky red gel heels, $80" class="link rapid-noclick-resp"><span>Melissa Strips chunky red gel heels, $80</span></a><br><a href="http://mattandnat.com/shop/handbags/all-handbags/sheenan-koala" rel="nofollow noopener" target="_blank" data-ylk="slk:Matt & Nat handbag, $108.50" class="link rapid-noclick-resp"><span>Matt & Nat handbag, $108.50</span></a> </p>
Throwback-to-school shopping

This beloved first-day-of-preschool outfit was entirely made by my mom! I love the mixing-and-matching of purple and red, and absolutely coveted that Snoopy lunchbox. I would just update the look to suit modern lines and to be more age-appropriate. —Beth Greenfield, Yahoo Style + Beauty senior editor

APC denim skirt, $190
Helmut Lang cap sleeve top, $99.98
Melissa Strips chunky red gel heels, $80
Matt & Nat handbag, $108.50

<p>I actually love my look here, and would wear some iteration of it today. Unfortunately, I was likely wearing my favorite pair of white capris with athletic socks peeking out of my camel Merrell’s, but at least my accessory game is on point. My DIY seed bead choker and tiny braid are the epitome of my late ’90s style. I just wish I still had that huge gap between my two front teeth. —<em>Devon Kelley, Yahoo Beauty editor</em><br><a href="https://staud.clothing/collections/all/products/berto-top?variant=29381370315" rel="nofollow noopener" target="_blank" data-ylk="slk:Staud Berto Top, Berry Blue" class="link rapid-noclick-resp"><span>Staud Berto Top, Berry Blue</span></a><span>, $80</span><br><a href="https://www.modaoperandi.com/rachel-comey-ss17/ticklers-frayed-crop-jeans" rel="nofollow noopener" target="_blank" data-ylk="slk:Rachel Comey Ticklers Frayed Cropped Jeans" class="link rapid-noclick-resp"><span>Rachel Comey Ticklers Frayed Cropped Jeans</span></a><span>, $370</span><br><a href="https://mnzstore.com/collections/shoes/products/palma-low-pink-metallic-maryam-nassir-zadeh-ss17" rel="nofollow noopener" target="_blank" data-ylk="slk:Maryam Nassir Zadeh Palma Low, Pink Metallic" class="link rapid-noclick-resp"><span>Maryam Nassir Zadeh Palma Low, Pink Metallic</span></a><span>, $420</span><br><a href="http://www.susanalexandra.com/shop/fd2mv1cjgl9yzgxm33gg63mu90u4i4" rel="nofollow noopener" target="_blank" data-ylk="slk:Susan Alexandra Tiny Joys Necklace" class="link rapid-noclick-resp"><span>Susan Alexandra Tiny Joys Necklace</span></a><span>, $138</span><br><a href="https://www.gucci.com/us/en/pr/women/womens-handbags/womens-backpacks/gg-supreme-backpack-p-473875K9RHT8856?position=9&listName=ProductGridComponent&categoryPath=Women/Womens-Handbags/Womens-Backpacks" rel="nofollow noopener" target="_blank" data-ylk="slk:Gucci GG Supreme Backpack" class="link rapid-noclick-resp"><span>Gucci GG Supreme Backpack</span></a><span>, $1,750</span> </p>
Throwback-to-school shopping

I actually love my look here, and would wear some iteration of it today. Unfortunately, I was likely wearing my favorite pair of white capris with athletic socks peeking out of my camel Merrell’s, but at least my accessory game is on point. My DIY seed bead choker and tiny braid are the epitome of my late ’90s style. I just wish I still had that huge gap between my two front teeth. —Devon Kelley, Yahoo Beauty editor
Staud Berto Top, Berry Blue, $80
Rachel Comey Ticklers Frayed Cropped Jeans, $370
Maryam Nassir Zadeh Palma Low, Pink Metallic, $420
Susan Alexandra Tiny Joys Necklace, $138
Gucci GG Supreme Backpack, $1,750

<p>I pretty much like my back to school throwback here, but I might update it so it’s a little edgier. —<em>Jacqueline Laurean Yates, Yahoo Beauty editor</em><br><a href="http://www.nastygal.com/elena-vegan-leather-moto-jacket/AGG99437.html?color=105" rel="nofollow noopener" target="_blank" data-ylk="slk:Elena Vegan Leather Moto Jacket, $90" class="link rapid-noclick-resp"><span>Elena Vegan Leather Moto Jacket, $90</span></a><br><a href="https://www.dhgate.com/product/2017-chic-punky-metal-rivets-shoes-women/391843719.html" rel="nofollow noopener" target="_blank" data-ylk="slk:Chic Punky Metal Rivets Ankle Boots, $40" class="link rapid-noclick-resp"><span>Chic Punky Metal Rivets Ankle Boots, $40</span></a><br><a href="http://www.barneys.com/product/chlo-c3-a9-marcie-small-crossbody-503359549.html?utm_source=google&utm_medium=cpc&cmpgntype=pla&campaignid=345512835&adgroupid=31887928635&product_partition_id=309025959354&product_id=00505033595504&cmpntype=pla&campaign=%5BPLA%5D%20-%20Product%20Types%20-%20Tier%202&adgroup=Womens%20-%20Bags%20-%20Shoulder&k_clickid=a5a813da-dc3c-4e5f-8ecd-7a7095761ecc&gclid=EAIaIQobChMI_4T8i8i01QIVD5t-Ch1ZqARtEAQYASABEgLlDfD_BwE" rel="nofollow noopener" target="_blank" data-ylk="slk:Chloe Marcie small cross body, $890" class="link rapid-noclick-resp"><span>Chloe Marcie small cross body, $890</span></a> </p>
Throwback-to-school shopping

I pretty much like my back to school throwback here, but I might update it so it’s a little edgier. —Jacqueline Laurean Yates, Yahoo Beauty editor
Elena Vegan Leather Moto Jacket, $90
Chic Punky Metal Rivets Ankle Boots, $40
Chloe Marcie small cross body, $890

<p><span>I had the Dorothy Hamill ’do, at least according to my mom. I think it was really because I had an aversion to hairbrushes. Because people often mistook me for a little boy, my mom dressed me very feminine. And I really wanted my ears pierced, so she let me. —<em>Allison Trimbell, Yahoo Style + Beauty video producer</em></span><br><span><a href="https://www.yoox.com/US/38650499/item?cod10=38650499GB&tp=48213&utm_campaign=Blouse%20%24200-399_desktop&utm_medium=shopping&utm_source=polyvore#cod10=38650499GB&sizeId=&sizeName=" rel="nofollow noopener" target="_blank" data-ylk="slk:L’Autre Chose silk blouse, $239" class="link rapid-noclick-resp">L’Autre Chose silk blouse, $239</a></span><br><a href="https://www.zara.com/us/en/woman/skirts/view-all/check-miniskirt-c733908p4841074.html" rel="nofollow noopener" target="_blank" data-ylk="slk:Zara check mini-skirt, $35.90" class="link rapid-noclick-resp"><span>Zara check mini-skirt, $35.90</span></a><br><a href="https://www.baublebar.com/product/20173-celestial-drops-gold?sku=20173" rel="nofollow noopener" target="_blank" data-ylk="slk:Celestial drop earrings, gold $36" class="link rapid-noclick-resp"><span>Celestial drop earrings, gold $36</span></a><br><a href="https://www.net-a-porter.com/us/en/product/853105/Gianvito_Rossi/suede-mary-jane-pumps" rel="nofollow noopener" target="_blank" data-ylk="slk:Gianvito Rossi suede Mary Jane pumps, $448" class="link rapid-noclick-resp"><span>Gianvito Rossi suede Mary Jane pumps, $448</span></a> </p>
Throwback-to-school shopping

I had the Dorothy Hamill ’do, at least according to my mom. I think it was really because I had an aversion to hairbrushes. Because people often mistook me for a little boy, my mom dressed me very feminine. And I really wanted my ears pierced, so she let me. —Allison Trimbell, Yahoo Style + Beauty video producer
L’Autre Chose silk blouse, $239
Zara check mini-skirt, $35.90
Celestial drop earrings, gold $36
Gianvito Rossi suede Mary Jane pumps, $448

<p>Nothing says fall like a classic, cozy staple. Mine was most likely L.L. Bean in this photo, and I wouldn’t trade that in for a different version. I also like my Sketchers — but I love my Chloe backpack. —<em>Casey Hollister, Yahoo Style photo editor</em><br><a href="https://www.llbean.com/llb/shop/611?originalProduct=91402&productId=1523489&attrValue_0=Paperwhite&pla1=0&mr:device=c&mr:adType=plaonline&qs=3126415_google&lsft=qs:3126415_google&gclid=EAIaIQobChMIzaTpseiz1QIV0YuzCh2MhwVVEAQYAyABEgLqnfD_BwE&gclsrc=aw.ds&dclid=CKrjgMHos9UCFUoENwod8IIPUg" rel="nofollow noopener" target="_blank" data-ylk="slk:L.L BEAN, Cable knit sweater, $39.99-$44.95" class="link rapid-noclick-resp"><span>L.L BEAN, Cable knit sweater, $39.99-$44.95</span></a><br><br><a href="https://www.net-a-porter.com/us/en/product/895768/helmut_lang/checked-wool-mini-skirt" rel="nofollow noopener" target="_blank" data-ylk="slk:Helmut Lang, Checked wool mini skirt, $425" class="link rapid-noclick-resp"><span>Helmut Lang, Checked wool mini skirt, $425</span></a><br><a href="https://www.net-a-porter.com/us/en/product/896968" rel="nofollow noopener" target="_blank" data-ylk="slk:Chloe, Faye small leather and suede backpack" class="link rapid-noclick-resp"><span>Chloe, Faye small leather and suede backpack</span></a><br><br><a href="https://www.net-a-porter.com/us/en/product/800516/gucci/queercore-embellished-leather-brogues" rel="nofollow noopener" target="_blank" data-ylk="slk:Gucci, Queercore embellished leather brogues, $1,450" class="link rapid-noclick-resp"><span>Gucci, Queercore embellished leather brogues, $1,450</span></a> </p>
Throwback-to-school shopping

Nothing says fall like a classic, cozy staple. Mine was most likely L.L. Bean in this photo, and I wouldn’t trade that in for a different version. I also like my Sketchers — but I love my Chloe backpack. —Casey Hollister, Yahoo Style photo editor
L.L BEAN, Cable knit sweater, $39.99-$44.95

Helmut Lang, Checked wool mini skirt, $425
Chloe, Faye small leather and suede backpack

Gucci, Queercore embellished leather brogues, $1,450

<p>I actually don’t mind my outfit too much other than the obvious clashing of colors and prints. For a redo, I would still wear a floral printed dress, but trade out the plaid jacket for an on-trend denim one. As for my footwear, I’d swap out my slingback flats for a chic pair of mules. —<em>Julie Tong, Yahoo Style fashion market editor</em><br><a href="http://us.topshop.com/en/tsus/product/clothing-70483/dresses-70497/floral-print-button-front-skater-dress-6790374?bi=60&ps=20" rel="nofollow noopener" target="_blank" data-ylk="slk:Topshop, Floral Print Button Front Skater Dress, $100" class="link rapid-noclick-resp"><span>Topshop, Floral Print Button Front Skater Dress, $100</span></a><br><a href="https://www.mytheresa.com/en-us/000895-denim-jacket-789156.html?utm_source=affiliate&utm_medium=polyvore.us" rel="nofollow noopener" target="_blank" data-ylk="slk:Balenciaga Denim Jacket, $995" class="link rapid-noclick-resp"><span>Balenciaga Denim Jacket, $995</span></a><br><a href="http://www.mercedescastillo.com/Farrah/MC-FARRAH,default,pd.html?dwvar_MC-FARRAH_colormaterial=001%20GRAINED%20CF%2fNAPPA%20CF&cgid=shoes-mc#start=1" rel="nofollow noopener" target="_blank" data-ylk="slk:Mercedes Castillo Farrah, $595" class="link rapid-noclick-resp"><span>Mercedes Castillo Farrah, $595</span></a> </p>
Throwback-to-school shopping

I actually don’t mind my outfit too much other than the obvious clashing of colors and prints. For a redo, I would still wear a floral printed dress, but trade out the plaid jacket for an on-trend denim one. As for my footwear, I’d swap out my slingback flats for a chic pair of mules. —Julie Tong, Yahoo Style fashion market editor
Topshop, Floral Print Button Front Skater Dress, $100
Balenciaga Denim Jacket, $995
Mercedes Castillo Farrah, $595

<p>I was ready to drive myself to school like the independent woman I have always been! Only now I’d probably wear a mini dress like this one, an oversized jean jacket, mules, and a cool backpack. —<em>Cindy Arboleda, Yahoo Style + Beauty Intern</em><br><a href="https://www.ripndipclothing.com/collections/accessories/products/lord-jermal-backpack-black" rel="nofollow noopener" target="_blank" data-ylk="slk:Lord Jermal Backpack, $80" class="link rapid-noclick-resp"><span>Lord Jermal Backpack, $80</span></a><br><a href="http://www.levi.com/US/en_US/womens-clothing-jackets-vests/p/299440029" rel="nofollow noopener" target="_blank" data-ylk="slk:Levi’s x Rolling Stone Ex-Boyfriend Trucker Jacket, $298" class="link rapid-noclick-resp"><span>Levi’s x Rolling Stone Ex-Boyfriend Trucker Jacket, $298</span></a><br><a href="https://www.urbanoutfitters.com/shop/kimchi-blue-lilyanna-linen-button-down-dress?category=dresses&color=068" rel="nofollow noopener" target="_blank" data-ylk="slk:Kimchi Blue Lilyanna Linen Button-Down Dress, $59" class="link rapid-noclick-resp"><span>Kimchi Blue Lilyanna Linen Button-Down Dress, $59</span></a> </p>
Throwback-to-school shopping

I was ready to drive myself to school like the independent woman I have always been! Only now I’d probably wear a mini dress like this one, an oversized jean jacket, mules, and a cool backpack. —Cindy Arboleda, Yahoo Style + Beauty Intern
Lord Jermal Backpack, $80
Levi’s x Rolling Stone Ex-Boyfriend Trucker Jacket, $298
Kimchi Blue Lilyanna Linen Button-Down Dress, $59

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