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Shorts that Will Take You into Fall, Plus Our Cowboy Boots Winner

Don’t forget to enter our Hazel & Harlow necklace and t shirt giveaway! Tomorrow is the last day to enter!

So, here in Florida we’ve got a couple more months of shorts wearin’ weather to get through, but those of you lucky enough to be experiencing a cool down definitely don’t have to pack away your shorts! Consider rockin’ them with some tights! They’re a fabulous alternative to a skirt. Don’t mind me…I’ll just be sitting here in Tampa…jealous that you get to sport tights. I’m afraid that I would pass out if I tried to put on a pair right now. HA!

Wearing shorts over tights is definitely not a new style concept, but I thought I would throw it out there since I tend to forget about it myself. I have a gorgeous pair of tweed shorts that totally didn’t make it out of my closet last fall. For shame! I, in fact, posted about this “trend” last winter and still forget to try out the look myself.

theory iselin plaid shorts

Theory Iselin Plaid Shorts at shopbop.com

topshop sequin bloomer shorts

Topshop Sequin Bloomer Shorts

forever 21 casual classy trouser shorts

Forever 21 Casual Classy Trouser Short {BonBon Deal of the Day at $15.80}

ella moss sedona shorts

Ella Moss ‘Sedona’ Shorts at Nordstrom

topshop gold button shorts

Topshop Gold Button Shorts

milly satin belted shorts

Milly Satin Belted Shorts at Net-A-Porter

forever 21 wool blend shorts

Forever 21 Wool Blend Shorts

p.s. The winner of our Corral Cowboy boots giveaway from Langston’s is Jamie from La Vie…J’aime! Email us with your contact email lady and we’ll get the ball rolling! Thank you so much to everyone who entered. We’ll have another fabulous giveaway for ya’ll tomorrow!

Disclosure: We select all our giveaway winners using the random.org integer generating service.

  • Grace

    It’s already too cold for shorts where I live! 🙁 Maybe with some tights, though. I do love the Theory and Forever 21 ones.

    September 20, 2010 at 7:37 pm Reply
  • Snuggle Wasteland

    I used to rock this look back in 1990 (ish). I was so thin. *sigh*

    September 20, 2010 at 7:49 pm Reply
  • Phoenix Peacock

    this is a cute but really bold look that I’m not sure I have the courage or the body for

    September 20, 2010 at 7:51 pm Reply
  • Blair @ Wild & Precious

    i’m way jealous but SO excite for Jaime!!

    i need to find out if i can wear shorts with tights at work…i hope so!!

    September 20, 2010 at 8:07 pm Reply
  • JAS

    Cute! Not sure I could pull if off with a 30 (+5) mom body, but I do like all of these!

    September 20, 2010 at 8:14 pm Reply
  • Heidi

    Yeah…I’m not sure I’m brave enough to try this look. So cute, though!

    September 20, 2010 at 8:14 pm Reply
  • doodlesbylauren

    Okay, so I sported short winter shorts, tights and heels on my very first date with my hubs…Jan.1993. And, I still love, love that look! Not going to be sporting it now, just because of my age, but it’s so cute!

    September 20, 2010 at 8:15 pm Reply
  • Candi @ Candace Rose

    Congrats, Jamie! 🙂

    September 20, 2010 at 8:16 pm Reply
  • Jaime @ la vie..j'aime

    OMG I am SO EXCITED!!!!!! Thanks Ladies! I will email you shortly 🙂

    PS: Obsessed w/ the sequined shorts here!

    September 20, 2010 at 8:44 pm Reply
  • Ashley

    love these shorts!

    September 20, 2010 at 8:48 pm Reply
  • Midtown Girl

    The sequined number has my name written all over it!!

    September 20, 2010 at 9:01 pm Reply
  • Wanderlusting

    As you know, I JUST got into the whole shorts thing… not sure if I could give it a go for winter… maybe with tights and boots though!

    September 20, 2010 at 9:05 pm Reply
  • Kristina

    Thanks for such a fun chat on BlogFrog! So glad to have “met” you! Umm can I just say that shortly after the chat ended I traipsed over to H&M and Forever 21 and spent $$$ on clothes & accessories? BUT one of the items was a camel colored blazer!! YAY!

    September 20, 2010 at 9:05 pm Reply
  • Katie

    Congrats to Jaime!

    September 20, 2010 at 9:13 pm Reply
  • Josie

    LOVE those Ella Moss shorts! Stunning.
    xo Josie
    http://winksmilestyle.blogspot.com

    September 20, 2010 at 9:14 pm Reply
  • Gracie

    I quite like shorts and tights although I never worn them in our winter. These shorts would be perfect for it though.

    September 20, 2010 at 9:17 pm Reply
  • Beth

    I haven’t been brave enough to rock this in the past but definitely want to try it this year… perhaps for a fun night out 🙂

    September 20, 2010 at 9:18 pm Reply
  • Allison

    I haven’t found a cute pair of dress shorts on me in a while. I hate my thighs, so they have to be the oh so perfect length, or I’ll hate them! Not too short and not too long!

    September 20, 2010 at 9:35 pm Reply
  • Annemarie @ Brunch at Saks

    Those sequin bloomers are so mine! Heading there right now! We are going to a wedding on NYE and while the ceremony will be traditional, the reception is going to be a big party- so these might be a contender for the night! xoxo

    September 20, 2010 at 9:38 pm Reply
  • Traci B

    Love shorts & tights! I don’t think I can pull it off but it’s really cute. There’s a really good chance we’ll be wearing shorts on Christmas Day!

    September 20, 2010 at 9:43 pm Reply
  • gigiofca

    I thought I’d do tights w/shorts last winter & it didn’t happen. I have issues w/leg & footwear. Me no likey. I think if I put the tights over the shorts, on the hanger, it’ll happen.

    Yay for the boots winner. That’s so cool.

    September 20, 2010 at 9:57 pm Reply
  • Leeann @ Join the Gossip

    All cute shorts! I just don’t look good in them myself. Boo to me!

    September 20, 2010 at 10:04 pm Reply
  • slamdunk

    Congrats to Jamie.

    I am still clinging to the shorts and short-sleeved gear as long as possible, but will have to face cold reality soon enough.

    September 20, 2010 at 10:07 pm Reply
  • Johanna

    I {heart} booties with short shorts & black fishnets…super sassy 🙂

    September 20, 2010 at 10:21 pm Reply
  • Ellen

    That’s a cute look, but you’re right – it’s too hot in Florida for it. Congrats to Jamie!

    September 20, 2010 at 10:22 pm Reply
  • Mimi

    haha yes I must do this! congrats to the winner! 🙂

    http://vivalabreee.blogspot.com/

    September 20, 2010 at 10:33 pm Reply
  • Bree

    omg wth?! haha idk why Mimi’s info came up on my comment. I tried to delete it but I don’t know how to!

    weird!

    anyways, I definitely must do this! congrats to the winner!

    http://vivalabreee.blogspot.com/

    September 20, 2010 at 10:37 pm Reply
  • Krysten

    Congrats to Jaime!

    September 20, 2010 at 10:40 pm Reply
  • savvy gal

    I love the pair by ella moss. : )

    September 20, 2010 at 10:53 pm Reply
  • won

    Congrats to Jaime!

    September 20, 2010 at 10:57 pm Reply
  • ilene

    love this look – esp with a pair of leggings and a cute pair of high heels or boot-wedges!!!

    September 20, 2010 at 10:58 pm Reply
  • Dancing Branflake

    I am so jealous! This was the best giveaway ever!

    September 20, 2010 at 11:00 pm Reply
  • Holly

    Those Ella Moss shorts are just too too cute! Love this post–except for the fact that I didn’t win…oh well, maybe next time 🙂
    xoxo,
    http://www.hollyinheels.com

    September 20, 2010 at 11:16 pm Reply
  • lindsay

    I love that these shorts will carry us into fall 🙂

    September 20, 2010 at 11:21 pm Reply
  • McKenzie

    Just DYING for the nude booties in the fourth picture. Love this trend for fall!!

    September 20, 2010 at 11:33 pm Reply
  • jami

    Cuuuute! shorts are tough! gotta find the perfect fit without looking too old lady!

    xo – jami
    i m a g i n e

    September 20, 2010 at 11:58 pm Reply
  • Daphne

    Love the concept of tights with shorts. Here in southern CA we also are not ready for tights just yet but I can’t wait. I love the sequin one but probably won’t wear it enough to justify the price. I have been lusting after a cord pair from VS but hoping F21 would bring a cheaper version soon.

    September 20, 2010 at 11:59 pm Reply
  • Samantha

    I love the idea of shorts with tights but I’m always too afraid to try it myself. That last picture is so chic and cute though..I might have to throw caution to the wind and try it this fall!

    -Samantha
    http://sincerelysamantha.com

    Ps- Thanks for your sweet comment today. I really appreciated it : )

    September 21, 2010 at 12:31 am Reply
  • Marchmusings

    Shorts with tights look great and keep you warm too!

    September 21, 2010 at 12:38 am Reply
  • bananas.

    ooh i can use a few sequin shorts but where’s the leather!?! it’s not listed. hmmm…

    and a big congrats to jamie for winning the coveted boots. yeehaw!

    September 21, 2010 at 12:45 am Reply
  • sssDawna

    congrats Jaime! can i borrow them sometime?? *hehe*

    i love the forever21 shorts = ]

    September 21, 2010 at 12:58 am Reply
  • Carole

    Congrats, Jamie.

    I’m afraid the shorts, even with tights, wouldn’t be a good look for this northerner.

    September 21, 2010 at 1:17 am Reply
  • Fifi Flowers

    Hmmmmm… love the look… but not pour moi

    September 21, 2010 at 2:08 am Reply
  • Sherin

    I think I need a nice new pair of shorts for the autumn, to wear with tights. All these look so cute.

    September 21, 2010 at 3:34 am Reply
  • Betty Manousos

    Well, they are all fabulous! Love shorts with tights.
    Congrats to the winner.

    Have a great day!

    B xx

    September 21, 2010 at 3:45 am Reply
  • Wrecked Stellar

    Especially out here in LA, I love the notion of wearing shorts with tights- it’s all about layering 🙂 xo, mel

    September 21, 2010 at 5:04 am Reply
  • Stéphanie

    I adore !

    September 21, 2010 at 7:04 am Reply
  • Stéphanie

    I adore !

    September 21, 2010 at 7:05 am Reply
  • Stéphanie

    So adorable post as always !

    September 21, 2010 at 7:13 am Reply
  • carolina - patagonia gifts

    love, love, love shorts. especially the sequined ones! congrats lucky winner! xo

    September 21, 2010 at 7:31 am Reply
  • Heather

    I love the Ella Moss shorts!

    September 21, 2010 at 9:34 am Reply
  • Jill@TeenageBride

    Congrats to the winner!!!

    I often forget about the whole shorts and tights thing as well, I really want sequined shorts haha.

    September 21, 2010 at 9:45 am Reply
  • Marie

    I love all the shorts you chose to feature here! Congrats to Jamie!

    September 21, 2010 at 10:36 am Reply
  • Meli

    I am so gonna try and rock this look this fall….but I am in TX so it will be “a minute” if you catch my drift!

    Congrats to lucky lady Jamie. You better WERK those boots!!!!!

    September 21, 2010 at 10:48 am Reply
  • sharon rose

    Hi there-fabulous picks, really love the khaki colour ones!! x

    September 21, 2010 at 10:50 am Reply
  • Holly

    I have a love affair with tights that began when I was a little girl and just never went away. I love them with skirts especially, but I think I’ve been neglecting the idea of pairing them with shorts. It looks SO cute though! I’ll have to give that a try now that the cooler weather is just around the corner. Thanks for the inspiration!

    September 21, 2010 at 11:04 am Reply
  • Salt

    I am ordering a pair of those Forever 21 shorts right now. Those are SO CUTE!

    September 21, 2010 at 11:24 am Reply
  • Lucky Dame

    I just ordered more tights yesterday from We Love Colors. Amazing stuff! Go see!!!

    http://www.welovecolors.com/

    September 21, 2010 at 12:59 pm Reply
  • isabel

    i LOVE the ella moss shorts

    September 21, 2010 at 1:34 pm Reply
  • livin wide

    loooove the shoes in the first one…i might need some black booties now.

    September 21, 2010 at 3:39 pm Reply
  • HauteWorld

    Love that sequined pair! Not sure I’m into the whole shorts with tights trend, but it does look good on some girls!

    September 21, 2010 at 3:53 pm Reply
  • Jamie Pickle

    Love the sequin shorts!!

    September 21, 2010 at 5:28 pm Reply
  • carma

    I have vowed to sticking to wearing shorter shorts. They just look so much cuter than bermudas which I think age those of us of a certain age 😉 You’ve got some excellent choices, and with tights – looks fabulous — congrats to your winner *wipes away tears*

    September 21, 2010 at 5:54 pm Reply
  • Shea

    I love the shorts with tights trend! Any way to extend the wear of summer pieces AND cover up my pasty legs!

    September 21, 2010 at 7:24 pm Reply
  • Cheryl

    these are all so adorable. i would like to wear some of these cute shorts with tights for fall. and congrats to jaime! she has a great blog.

    http://ohtobeamuse.com

    September 21, 2010 at 7:48 pm Reply
  • Annie Spandex

    I remember my mom saying something negative about shorts over tights being tacky and because of that, I have a hard time with the look, even though I tend to defend “tacky” things as redeemable. It’s just one of those deeply ingrained kinds of things!

    September 22, 2010 at 4:31 am Reply
  • Rachel

    Um, I NEED those Theory shorts! They’re perfect.

    September 22, 2010 at 11:45 am Reply
  • Anaiz

    I am super excited to wear shorts this fall! I’ve never done it before but this year is the year. I love the look with black tights 😀

    September 22, 2010 at 4:55 pm Reply

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