How to Wear Denim Overalls, Even If You Think You Hate Them

My favorite thing about fashion is that moment when you find yourself happily wearing a trend you used to hate.

Aug 14, 2014 at 4:00pm | Leave a comment

My favorite thing about fashion -- and I don’t mean high fashion, but just picking out clothes every morning and seeing what other people on the street are wearing -- is that moment when you find yourself happily wearing a trend you used to hate.
 
Believe me, it’s not that I like to admit that I was wrong. It’s just the same feeling that I get when I suddenly can’t get enough of a food I used to hate. I never understood why people like sushi and onion rings until this summer, when I'm suddenly into both. There’s a little bit of embarrassment about vehemently holding out for years, but mostly I’m enjoying the thrill of something new, something that I never thought would be for me. It’s the little surprises in life, you know?
 
So yeah, all that to say: I’ve started wearing denim overalls, to mixed reception. Some people think they're cute, while other people (*cough* boyfriend *cough*) can't even look at me when I'm wearing them without wincing. I honestly still haven't decided how I feel about them myself. All I know is one day I was walking through the children's section at Target, as one does, and saw these perfect dark wash overalls in a size XXL. Basically I think that means that I stopped growing (vertically, anyway) around the age of 16, which sounds about right. 
 
Since I got these overalls, I've been enjoying wearing them around the house barefoot with nothing underneath. That doesn't make for much of a fashion article, though, so I came up with four of my favorite ways to wear overalls without looking like a farmer. 
 
1. With a striped T-shirt and sneakers.
 
 
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This is Overalls 101. Easy, simple, can't go wrong. I have at least a dozen striped T-shirts in my closet (although this particular one happens to be a dress from Asos) because they go with everything, and overalls are no exception. My sneakers are Commes des Garcons Play for Converse. 
 
2. With a crop top and platform wedges. 
 
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I realize that I’m so pale it’s not immediately obvious that I’m even wearing a crop top. 

 
Remember when I said "Hey, platform wedges are totally awesome!" and everyone agreed? Well, good news: They're still totally awesome, especially when paired with cuffed overalls. Although I'm not really the crop top type, I feel comfortable wearing this trend with overalls because I'm still pretty covered up. You could also switch out the crop top for a bikini and the wedges for sandals (but be advised, this outfit is more for country lake swimming than beach swimming). 
 
3. With oxfords heels and a floral top.
 
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A silk floral blouse helps to elevate denim overalls a lot -- not as far as work wear (unless your workplace is the most casual ever) but definitely nice enough for your niece's birthday party or whatever. Balance out the country look even further with a pair of preppy brown oxford heels. I found these at Payless a few weeks ago and love them. Just be careful when pairing overalls with heels because it can look a little too unbalanced if you're not careful. I’ve seen girls look really cool wearing strappy heels or pointy pumps with overalls, but maybe don’t go overboard with sky-high Louboutins.
 
4. With a sheer lace shirt layered on top. 
 
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Any kind of sheer or lace shirt, or one with an open back, will add an interesting dimension to your overalls. It won't be immediately obvious that you're wearing overalls, but then the straps peek out in the back and it's just really cute and unexpected, okay? Trust me. I also like the idea of putting a sweater on top of overalls so they look like regular jeans, but most people think this defeats the point of wearing overalls so maybe that's something we can debate in the comments. I paired the overalls with heels again here, but a nice pair of flats would work too. 
 
As always, I have a few guidelines for purchasing and wearing this trend. One strap undone is okay if you're the sort of person who can pull it off (I am not); both straps undone and flapping around is kind of silly. If you want to look more put together, choose a pair in a dark wash with a slightly snug fit. If you like the light-wash, destroyed, baggy kind then go for it. It’s just a different look and can be harder to pull off. 
 
You could also get short overalls but I prefer the long pairs because they’re more versatile; you can wear them year round. Don’t get the striped train conductor kind, please. There’s no need for that (although Forever21 appears to think differently). Finally, you can get overalls in various colors, patterns and even materials like leather and velvet. However, I strongly recommend that you start out with denim and proceed slowly, so as not to hurt yourself or others.
 
I rounded up a few acceptable options for those of you who are feeling brave. I tried to include mostly overalls around $50 because they don’t seem like the sort of thing anyone needs to spend a ton of money on. That said, I did include the $300 pair because it seemed like a really nice option for a stylish woman who has cash to burn on a fancy pair of denim overalls for her summer getaway to Cape Cod or Vermont or something. I’m sure that woman exists and if I were her I would totally buy those overalls. If you ARE her, buy them! 
 
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I just realized that so far I've written about coming around on overalls, platform wedges, leopard print, plunging necklines, and thigh high boots. Some of them were a success, some of them...well, not so much. But I've had a lot of fun experimenting with each and every one. So if there's a trend out there that you're curious or on the fence about (or just plain scared of), suggest it in the comments and I'll give my best shot at styling it in a future article. 
 
All photos by Joshua Kirby