I don’t know what I was thinking when I decided to do today’s One Item Five Fashionable Ways on looking stylish in overalls.  First, is it even possible to take this utilitarian garment and style it fashionably?  If you asked the me of 15+ years ago my answer would be yes because, after all, you couldn’t be a twenty-something of the 90’s without owning a pair.  Working on this post, I thought about how often I wore mine (stylishly, of course), that my friends owned them, and that they were a perfectly fine garment to wear just about anywhere.  I won’t disclose the name of my friend who actually wore them to a bar in the 90’s and used the front pocket of her overall bibs to hold a Zima (she was really drunk).  She even walked away with a phone number from a guy that night….and, no he wasn’t a farmer.  Yes, at one time, wearing overalls in a stylish manner was completely commonplace and, because fashion is cyclical, it seems that this may be true again.  At least according to current trends and those who don’t remember this trend the first time.

As a 40 year old woman I don’t have the same relationship to overalls that I did the last time they were popular.  In fact, looking at the photos of young girls wearing them, pretty much the same way my friends and I did when we were their age, makes me feel old, in that smug “been there, done that” sort of way.  Will I be wearing overalls again?  Doubtful.  I usually heed my mom’s advice: “If you did a trend the first time, you don’t do it again.”

So why am I doing a post on how to look stylish in overalls?  I don’t really know.  I started working on it, the whole time wondering if I was crazy.  However, because these posts take hours to put together, I had to commit.  I was too far long into it to go back and start something new unless I wanted to scrap a few hours of work.  So be it for the sake of nostalgia or be it because you’re seriously wondering how to look stylish in overalls, below are some outfits to check out along with some styling tips.  I am using this pair from The Gap because, unlike the classic bib style that are on most pairs of overalls, I liked that these looked more like a jumpsuit.

If you don’t like overalls and wouldn’t even be caught dead in them, the good news is you can easily swap out the overalls in the outfits below for a pair of jeans and still have some attractive fall outfits to consider.  If you are someone who plans on embracing overalls, please don’t let my attitude towards them stop you.  Like you now, the me of many years ago was once enthusiastic about them.  Just trust me on this: In 15 years you will be laughing at yourself too.

Stylish in Overalls Without Looking Five, Like a Farmer or a Fool

Outfit #1

In the first outfit I styled them simply.  It seems there are two ways to go with overalls, in a basic manner or overly layered.  For this clean look I added a striped long sleeve t-shirt from Boden, a pair of Steve Madden slip on sneakers, and for a splash of color, a red cross body bag.  Finishing the look is a pair of fun elephant stud earrings from Modcloth.  While these are super cute, I want to give some words of caution on the cute thing when wearing overalls.  Be careful.  Cute and modern is one thing, but anything frilly, like bows, ruffles or even pigtails worn with overalls is taking the cute thing a little overboard.  Avoid girly, juvenile touches.

Outfit #2

It wasn’t uncommon to see people (and when I say people I mean men and women) wearing blazers over overalls in the 90’s, nor is it uncommon now.  By doing it there is the play on tailored with casual that is created that, when done right, can actually look sort of cool.  If you’re wondering what to wear as an outerwear piece with a pair of overalls try a tailored tweed blazer.  It also will add some shape.

In this outfit I added this tweed jacket from the Gap and layered a basic long sleeve white t-shirt.  For some casual polish, I added a necklace from Anthropologie, a burgundy scarf from Banana Republic, leopard Lucky Brand flats and cognac Tory Burch bag.

Outfit #3

Another way overalls have been worn is with a printed blouse, like this one from J. Crew, a slouchy cardigan, like this one from Anthropologie, and heeled booties, like these.  It’s even okay to add long necklaces, like this one from Stella & Dot.  In this outfit, I finished the outfit with a olive suede handbag from LAUREN Ralph Lauren.  To avoid looking like a homeless person in all these layers, choosing quality items and pieces that are relaxed but not too baggy.

Outfit #4

Cropped tops lend themselves perfectly to overalls.  In fact, we did this all the time with our baby tees and overalls in the 90’s.  The benefit of wearing a crop top this way is you show a touch of skin on the side but the tummy is covered with the bib.  Here I took a grey knit crop top from Topshop and kept the outfit uncomplicated with a printed scarf, pair of peach oxfords, colorful earrings and teal bag from Foley.

Outfit #5

Lastly, if your overalls are making you feel too blobby and like you have zero shape you can add a belt, like this one from Ralph Lauren.  This casual Boho look was created with a burgundy Modcloth tank, a slouchy chunky boyfriend cardigan from The Gap, heeled lace-up boots in cognac, a pair of gold earrings from Anthropologie and a beanie from Forever 21.  The last touch is the plaid infinity scarf.  Plaid and overalls are a common mix.  If you don’t want to look too retro-grunge, small doses are better.

Shop for overalls

If you’re all over this trend, check out these other overalls styles, at a variety of price points, from around the web.