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Fashion Challenge: Overalls

Overalls
Photo Credits 1, 2, and 3

Overalls have always been on my “don’t” list, especially since I’m from a small farming town where everyone wears overalls, and not in a trendy way. However, this farming basic might be edging it’s way onto my “do” list, with a little nudging thanks to Ralph Lauren and Ms. Alexa Chung (photos above). Like it or not, overalls are definitely on the spring trend radar – and although they’re challenging, they’re more wearable than you think.

Keep in mind that the point of this series is to show fun ways to style more difficult-to-wear trends. A micro-trend by definition is a short-term development in fashion, so every trend might not appeal to everyone! The goal is to get you to be bold and try these out-there runway trends in real life. Don’t like the trend I chose but have one that you’re dying to see styled? Let me know in the comments!

Tips and Tricks

  • Moderation is key. Don’t pair your overalls with anything even remotely western inspired–you don’t want to look like you’re wearing a costume. Skip plaids, agriculture-y boots, and cowboy anything. As with any trend, going overboard can look tacky.
  • Step it up a notch - literally. If you choose a pair of overalls with full legs, like the look in Picture 1, opt for heels instead of flats on the bottom. A high heel makes the look intentional and feminine.
  • Ladies first. Overalls look masculine, so balance that out with something ultra-girly, like Tomeka’s lace shirt in Picture 3, or this tie-neck blouse and ladylike bag:

the vintage society overalls
Photo Credit

  • Try something new. Don’t be afraid to mix it up. Wear one strap unhooked, like the J. Crew model below, try folding the whole bib down, or throw on a blazer. Nothing is off limits, so be creative!

J. Crew spring lookbook 2010sparklyG overalls
Photo Credits 1 and 2

  • Find the right fit. Overalls aren’t flattering for every body type, so you might need to try different styles before you find a good fit. Although I’m a little iffy on this trend in general, if I were going to try it, I would go for a belted jumper: because of the stiff nature of denim, the skirt is a nice, flattering A-line. If you have amazing legs, show them off in a cut-off pair!

Get the Look

Overalls and Florals

Product Information: Overalls – Forever 21, Floral shirt – The Outnet, Cardigan – Miss Selfridge, Platform sandals – Piperlime, Nude fishnets – Nordstrom, Watch – Urban Outfitters

Add girly flair to light-wash overalls with a floral blouse. Sticking to neutral add-ons gives this outfit a light look, perfect for spring. Pairing denim with nude fishnets gives this outfit texture. Not keen on the heels? Substitute these flat booties for something a little less risque.

Extra-Credit Reading Assignment

Still can’t believe that overalls are “in” for spring (me either!)? Add these to your reading list:

So, what do you think?

Are you up for the fashion challenge? How would you style a pair of overalls? If you try this look out, take some photos and post links to them in the comments section! We may feature our favorite looks here. Would love to see how you guys tackle this challenge.

Also, if you have another item you’d like to see as a Fashion Challenge, let me know it the comments – I’d love to hear from you!

arrow27 Responses

  1. ieva
    38 mos, 2 wks ago

    I don’t know… Might be fun to try several times, but I don’t see myself wearing overalls neither today, nor later on. The one from F21 looks quite nice, though!

  2. Julie
    38 mos, 2 wks ago

    I think this is a good idea for a challenge. Overalls are always something I’ve wanted to try, but then I chicken out. Overall skirts (is that the right term?) and overalls with shorts would be easier to pull off than the mannish lumberjack overalls on some of the models, I think.

    I like the 2nd outfit at the top and I really, really like the outfit put together at the end. I’ll try the extra credit reading.

    Nice post!

  3. Anna
    38 mos, 2 wks ago

    I don’t think you give overalls enough credit. I have, like Julie, always been too chicken to try them, but I’ve always loved the way they looked on my bolder friends. For me, style has always been not what’s cool, but what’s fun and joyfully unique. I think overalls represent that pretty well.

    I especially love the skirt overalls, and the outfit you put together at the end was awesome! :) I agree that it’s all about being able to balance it out.

    (having said that, I can see how your farm experience may turn you away from this look)

    Great post!

  4. 38 mos, 2 wks ago

    I LOVE this! Last weekend, I went home to visit my parents and went through some old clothes I’d left at home.. I definitely snagged the overalls and overall skirts. So excited to wear them.. I love how things come back around into style.

  5. 38 mos, 2 wks ago

    I don’t know. Perhaps an overall skirt (a.k.a. jumper) could work, but it’s not the most flattering outfit for someone pear-shaped… Kind of emphasizes the weaknesses, if you know what I mean.

    Still, and intriguing idea. And the rest of your blog is great, too!

  6. Cathy
    38 mos, 2 wks ago

    Overalls are one thing I will never wear… unless I decide to be a hillbilly for Halloween one year or something…

  7. Nicole
    38 mos, 2 wks ago

    i’ve been looking for a good pair of overalls since last year! yes they can definitely be really cute if you style them correctly. i really like the one alexa chung has on.

  8. Zamia
    38 mos, 2 wks ago

    I’m almost wanting to give these a try, but like the others, a bit too chicken to do it. Would shorts and suspenders be somewhat of a compromise? Would the same rules still apply?

  9. Erinn
    38 mos, 2 wks ago

    Oh god… once when I worked in retail, the store I was working at got a giant shipment of overalls. It was horrifying. Someone from our head office even took the time to write “Fugly Overalls” on the side of the box in Sharpie. That pretty much summed up my opinion of the garment. (And our shoppers seemed to agree… we sold one pair over the course of 4 months)

    Although I have to admit that the skirt overalls are almost cute!

  10. Paula
    38 mos, 2 wks ago

    This takes me back to my elementary school days. I don’t think I’d look cute in overalls anymore lol.

  11. Jess
    38 mos, 2 wks ago

    there’s more than just jean overalls to! i recently purchased an overall skirt but it is in a flower print and totally adorable…keeps it from looking too ” country” even though I am a country girl at heart..if you can pull the overall look off..more power to ya! remember..confidence is the key! :D

  12. Rebecca
    38 mos, 2 wks ago

    Overalls aren’t very flattering for petite people I find… I look like a little kid in them.

  13. melanie
    38 mos, 2 wks ago

    I think they look great as shorts or as a skirt
    but idk if I can sport the long ones.

  14. 38 mos, 2 wks ago

    I’m hesitantly liking the skirt ones. I had on in high school and junior high, but I never wore it because I felt self conscious about it. Now I sort of wish I had kept it!

    As for the pants and shorts, I feel the same way about them as I do about rompers: why constrict myself so much! Such a hassle just to go to the bathroom or anything!

    Also, with my small boobs and bigger hips, I feel like this trend just isn’t very flattering! The only one I’ve seen that doesn’t make the girl look like a box is that middle one alexa chung is wearing.

  15. Sharon
    38 mos, 2 wks ago

    yea i’d agree that long ones may be quite hard to pull off, unless you are thin and tall. lol :P

    but i think overalls are adorable! i remember once in high school i did dress up too “cowgirl-like”, so i definitely know what youre talking about! balance is the key. If wear it right, it can look really stylish and cute :)

    I like pairing it with shirt, i think it actually looks really classic and creative. :)
    plus, it looks really summer! gotta love the season!

  16. 38 mos, 2 wks ago

    style some brightly colored dr. marten high tops!!! I just bought a pair and I’m clueless on how to wear them! :)

  17. Denise
    38 mos, 2 wks ago

    No. Period. LOL. Though I commend the styling on the suggested outfit. Overalls are cute but I think its just not appropriate for the city.

  18. Annie
    38 mos, 2 wks ago

    No way…I feel like you need to be model-thin in order to look good in these. Plus, i’m very petite, and I look young enough as it is so wearing overalls would only make me look younger!

  19. Margo M
    38 mos, 2 wks ago

    I remember getting a skirt version a about three years ago. I used to wear them with leggings and a tube top….it looked okay..and did not require any body shape.

  20. winnie
    38 mos, 2 wks ago

    I really like the skirt overalls and the way the outfit is put together in the second picture, but I don’t think the regular denim overalls like those pictured in the other photos are really all that flattering on anyone. I imagine they would make your butt look really weird.

  21. Lauren
    38 mos, 1 wk ago

    I actually really adore the Get the Look section. Put with a cardigan, I wouldn’t see it as just plain old overalls. It’s nice to see them fashioned in a way that doesn’t make you look… old. Or shapeless. Or both.

  22. Emily
    36 mos ago

    When I was in middle school I sometimes wore overalls with a tanktop. the tanktop would be striped or have some sort of design. This made it look girly and comfortable and not really country. I don’t know if I could pull that off now at 26.

  23. 35 mos, 4 wks ago

    oh . nice piece . thanks for sharing .

  24. ovrlzgrlzrlz
    35 mos, 4 wks ago

    If you ladies want the opinion of a 23 year old heterosexual male, I personally think/overalls look dead sexy on the majority/of the female/populace. I can only hope/this/trend sticks around longer/ than it did last/time (early 2000′s). Ps. The bibskirt (jumper) was not popular in the US last time amongst the over/12 year old ladies, and I really hope that chan ges.

  25. Maria
    35 mos, 3 wks ago

    I’ve been wearing overall in all styles (skirt, shorts, long…etc) for a long time now and I have never tired of them. In fact, living in NYC all my life and being around fashion concious individuals ALL time. I’ve learned that you HAVE to take chances, I enjoy them because they are super comfortable and have a certain cuteness about them. My favorite way to wear them is with a brite body hugging top, like a t-shirt or tank top. I am nicely endowed on top so it really balances me out. Loosely fitting, soft and worn denim overalls with a cute top, my sandels and one of my favorite casual couture bags and Im ready to go. Also, try them with a baseball hat and hoop earrings, a couple of bangles. Again keep the top really cute, pretty and sexy. Anything goes in NYC BUT there IS a golden rule you should never break: Always keep things in balance. When I wear this look I cant get the guys eyes off of me! Its a very “yeah Im wearing overalls and look hot and Im not even trying” kind of look…lol. Have fun!

  26. Maddie
    33 mos, 2 wks ago

    Maybe if it was a skirt one in a navy or dark green like Alexa’s. Otherwise, no.

  27. Jess
    1 mo, 1 wk ago

    I’m a 17 year old girl. I just got overall shorts because I think they’re really cute! Mine have cross straps in the back.. So they look more like shorts with suspenders from the back. How do I make them look cute for school?

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