Heels and shorts: cute or tacky?

I’ve got some cute black shorts that are almost knee length. My shoe choices include simple flat brown sandals and super-comfy black slides with a heel of about an inch and a half. The black shoes are cuter– the brown sandals are just kinda blah. But I’m hesitant about pairing heels with shorts. Is it stylish or tacky? (esp for someone who is normal sized, not model-thin.) I’m soooo clueless– help!


  1. In my honest opinion, heels with shorts are tacky. But what do I know? I’ve never had the term “trend setter” linked with my name. 😉

    To each his own. Fashion these days seems to be pretty much anything goes.

  2. Personally I wouldn’t pair them together. I have seen lots of people do it but I just don’t really care for it. Maybe others will have better advice. Afterall, the last time I wore heels was on a night out with hubby 2 years ago. LOL.

  3. Definitely the heels, primarily because they’re also black. Unless you’re doing the whole “brown and black” look, I wouldn’t pair brown sandals with a black outfit.

    And I would totally wear heels with shorts – probably not pointy toe dressy heels, but I’d wear those sandals in a heartbeat!

  4. I think it depends on the top you are wearing and the function to which you are wearing the outfit. If it is more casual, I might not do the heels. But, like Heidi said, I wouldn’t mix the black and brown either, unless you are carrying it through the whole outfit. I think heels with shorts is totally fine.

  5. I would only do a wedge heel or espadrille. Otherwise a no-go.

  6. I would wear the heels especially since the shorts are knee length. I wouldn’t do the brown black thing.

  7. This guy says…I..don’t…think..so.

  8. I’d go with the super-comfy black slides that match your black shorts.

  9. I think if where you are going and what your a pairing the shoes is more dressy than …um..the grocery store…then I would wear the black slides. Heels make your legs look longer and as long as you aren’t wearing running shorts…

  10. I agree that because the shorts are knee length, the heels are fine. They are a more casual shoe, not patent leather or anything. The longer shorts are more dressy than short jean shorts would be, so you’ll look great!

  11. Heels are very good with longer shorts–and those are adorable.

  12. Open toed heels are okay, though I would go with more of a kitten heel than a higher, or clunky heel. I have a pair that sort of look like a flip flop with a small heel that I wear with just about everything!

    You could also do an espadrille with a heel.

    Of course, that’s just my opinion. 😉

  13. I think you should try both on with the shorts and see what you think, how comfortable you are. With that length of shorts they might look cute- and the fact that the heel is so modest!


  14. Mmmm, I’m in the no heels with shorts camp.

  15. Do the heels. It’s trendy, but not faddish. And like someone else stated, it’s best to not mix black and brown unless you’re going for an obvious, intentional look.

  16. I count it as I do a facial piercing. It is a RARE person that can pull it off and if you have to ask, you are probably not the person. Sorry.

  17. No heels with shorts, sorry. It’s not trendy. Heels would work if they were past the knee (like a capri pant) made out of a dressier material. If they are at knee length I’d stick to flat shoes for sure.

  18. If the shorts are almost knee length, I think the heeled black sandals would look cute. I also agree that brown sandals and black shorts would not match at all. The black shoes pictured look more like sandals with a little heel than official dress heels. I think you’d be fine (and cute) wearing them!

  19. Those sandals are fine! It’s not like you’re rockin’ 4″ heels with shorts – those are fine.

    Of course, I live in the south where some of the finer ladies at my pool definitely rock 4′ heels with shorts that don’t come close to knee length, lol.

  20. I just saw someone the other day wearing heels with long shorts and was amazed at how cute it was. Very stylish and nice looking, not “daisydukeesque” or anything. It looked very classy(if you were wearing tushy length denim shorts and pantyhose, I would definitely have a different opinion :)….)

  21. Heels are great with long shorts- it is in style right now and it will make your legs look longer and thinner!

  22. I’d go for the black slides. Heels with long shorts just doesn’t seem a great combination to me.

    I’m no fashion guru though 🙂

    Cheers, Wilm

  23. Those heels aren’t super-dressy, they’re chunky & cute. I have some leather flip-flops with a chunky heel that I wear with skirts & shorts both. I’m sure no one will even notice! 🙂

  24. My gut reation would be tacky but cute. Or would it be cute but tacky? 😉

  25. i’d go with the heels, as long as the shorts are around knee-length.

  26. My honest opinion? Cute, but only up to a certain age. And I think we’re both past that certain age. ;^)

  27. I think the heels work if the shorts are longer. Besides, I’d rather err on that side than with brown shoes with a black outfit.

    Either way, though, it is SO important for YOU to feel comfortable with what you where. Otherwise you’ll spend the entire day second-guessing yourself. Or at least I would!

  28. Only if you have exteremly nice legs……I do agree with the capri with those heels, I may wear mine today…..feeling inspired !

  29. I think no. But I also think no to the brown shoes. But then, what do I know, I wear the same pair of navy sport sandals with everything all summer long. Sorry, I’m no help.

  30. Heels are perfectly acceptable with long shorts as long as the shirt you are wearing is dressy, otherwise, it’s a no-go. Definitely no black shorts with brown sandles. Of course, it just MHO…

  31. For sure those shoes would pair great with a long pair of shorts. Those look like sandles to me, dressy sandles. Be a little sassy.

    And remember, add a stylish pair of $15 sunglasses and no matter what you have on, people will think YOU are stylish. I live by this motto.

    A cute handbag always helps that theory as well.

  32. oh boy. now i have to weigh in. first of all, it is OKAY to wear those heels with knee-length shorts…40 years old and up = no problem. where it gets tricky is making the entire look work. so, the shorts have to the type that would lend themselves to heels (the right cut and style) and being worn with the right kind of top. THEN, it looks very on point and stylish. do not wear a regular tee shirt with it, ya know? get a cute top, dare i call it a “dressy” top, put on the knee-length shorts and heels and go for it. I do it ALL the time. it’s all about getting the elements right. it’s not hard. a few more pictures on your end would make our assessment job easier, mary! LOL.

  33. Tacky.


  34. I think it depends on the heels. I am very conservative when it comes to wearing heels since I never really wore very feminine things until I got past my teens, but I think so sandals would look cute with shorts even with the heel. IMO.



  35. Go with the heels. I’m not a fan of brown shoes with black pants or shorts so that would be a big faux paus in my opinion. Heels with shorts, especially longer shorts are fine. And the heel seems to be low enough that it’s not as though you were wearing 5 inch stilettos with them.

    Go for it! I’d tell my mom to wear an outfit similar to that and she’s 46! Age is just a number. Respectable and classy is timeless. And there is nothing not respectable or classy about low heels with longish shorts. Trust me!

  36. I say tacky and not practical for a mom. At least that is what I tell my self when I see this look on someone else and I start to think maybe I should do the same.
    Frugal Carol

  37. I love the way heels and shorts look but knee length shorts “No Way” I am 20 and im all about looking cute but sexy and those shoes are not cute I wear shorts above the knee not slutty!! and a pair of cute 2 1/2 or 3 inch heels that match the shirt or shorts but not both……wish i had a pic id so post it.

  38. I say go with those slides with either capris or shorts. I think it would look AWESOME! Those heels are not too high to make it look unfashionable.

  39. musicislove says:

    I love the ide of Booties with shorts! Heavyset women should be careful when pulling off this look because the leaner the leg the better it looks (in my opinion).
    I would go for a loose dressy top, fitting short, and booties with no more then a 4″ heel.