How to Wear: Overalls In Your 20’s

Developing Security In My Clothing Choices.

Recently I had been talking to my roommate about personal style and how I feel like I’m finally nearing a place where I have a consistent sense of it. In this past year, I’ve felt significantly more confident about my clothing decisions, and I think it has a good deal to do with my environment. This doesn’t mean that you have to move to a cool neighbourhood to wear the clothes that you want, but surrounding one’s self with inspiration is definitely beneficial to nurturing a sense of style. Living on trendy West Queen West, inspired by fashion-forward neighbours, and flanked by my eccentric and self-assured roommate Dana, there are very few things that I’m afraid to wear anymore. Overalls lead by example because I recall being very anxious to wear them in public this time last year. It sounds silly but it took practice to feel comfortable in them, as well as many other staple pieces of my current wardrobe. In fact, developing a feeling of security towards my clothing choices, in general, has been an endeavour 9+ years in the making.

Since the 7th grade, I’ve been trying to pinpoint what my style is. Of course, back then, I had no concept of what was ‘fashionable’ other than what I could reference in Seventeen magazine and what my peers were wearing at school. So I defaulted to general preadolescent trends, toting Abercrombie t-shirts, West 49 ‘Boobies’ braceletsLulu lemon leggings, and the notorious Birkenstock sandal.

It wasn’t until high school that I began personally experimenting with my outfits, and I don’t recall those years fondly. I have a particular memory of wearing a pair of oversized Levi’s in grade 10, and being laughed at by a boy in the staircase who sarcastically asked if I could possibly wear a baggier pair of pants. I destroyed them that night, a regretful thought now that such jeans are a key component of my current wardrobe. And to think that I bought them for less than $5 from the local thrift store, when the exact same styles are sold today at Brandy Melville and Aritzia for $50 or more.

Still, you’ll note that those jeans were technically a step forward in the process of developing my fashion sense. Though my ventures were not well received, the first two years of high school did see a variety of mismatched outfits, perhaps necessary to the overarching understanding of how I wanted to dress (denim shorts with tights underneath and turquoise pants with a floral top come to mind). But I never felt confident in those clothes and going forward, I was increasingly scared to wear something out of the norm. When I did feel that I’d reached a place where I could start to feel comfortable with my self-expression, later in high school, it was largely in part because I conformed to a conventional look (I started wearing push up bras for the first time in my life, sporting crop tops and tight jeans on a regular basis).

By the time I moved to Toronto for University, you could say I had learned how to fit in with my clothing, and even how to use it to accentuate certain features of my body (i.e. my waist, small boobs, etc.) But I still didn’t know what my style was, let alone how to wear the things I really wanted to wear. I’ve always had an appreciation for bohemian looks and desperately wanted a pair of flare jeans, but I didn’t think I could pull them off. It wasn’t until last summer that I bought a pair for the first time, about a month after I moved onto Queen West.

Flare Jeans from Free People

In the past, I shied away from bohemian styles because I was worried that I looked silly in oversized tops, or that the colours and patterns were too bold for my personality. I thought that it was more important to accentuate my frame then wear something ‘fashionably oversized’. I often told myself to try to look “hot,” baring a perception of the word that I didn’t realize was not my own. This aspect of style is still something I struggle with, in trying to create an “attractive look”. I sometimes feel split between what I think is fashionable and what I imagine my boyfriend will think I look good in.

Not to say that my boyfriend makes me feel pressured to dress a certain way- in fact, he’s very supportive when I sport a more adventurous outfit. But it’s undeniable that I’ve grown up with a certain perception of what he as a boy, will consider good looking, and the insecurity to cater to it sometimes threatens to override my personal style. My roommate, who prefers a style less feminine than my own, shared with me that she sometimes endures the same insecurity. While her outfits often depend on her mood, she tries to maintain a look that is neither too ‘masculine’ or too ‘feminine’ (making a point to accessorize a baggier outfit with earrings/necklace and a more feminine outfit with sneakers/ denim/ etc.) Every once in a while, the fear of appearing conventionally less attractive creeps into her mind, and she wonders if the guys she likes would prefer her more feminine. But as she reminded me, the kind of people we should find ourselves attracted to are not ones that will prefer a girl in tight clothes over one in overalls and a bucket hat.

That being said, I think the solution to all of this, is to try to remain as true to yourself as possible when it comes to your clothes. About a day after our discussion of personal style and the pressures that implicate it, my roommate sent me this video, a kind of how-to detailing the main points for a) identifying your style and b) finding the confidence to wear it. The Youtuber advises viewers to start by sourcing clothing inspiration online, noting the Instagram explore page, and Pinterest, as well as further inspiration from fashion magazines and books, before curating the inspiration you find onto a mood board. I’ve personally been a dedicated Pinterest user since 2013 so I’m in favour of that platform. Next, she suggests that you take the 5 pieces that appear most on your mood board and seek them out on your next shopping trip, while being careful not to get distracted by pieces that are trending or on sale. This is another one of my weak spots, as I often get excited by clothing items that I don’t currently need or don’t fit into my overarching style. Over the years I’ve made countless impulsive purchases that I later regret.

I like to think that I’ve improved my shopping decisions since then, but it’s only because I’ve learned to practice constraint. Now when I shop, I try on everything I like in order to gauge how a piece will fit into my wardrobe, but will only purchase something if I absolutely love it (and even then there’s a certain amount of thought that goes into deciding whether or not I need it).
Finally, on the point of being able to confidently wear your clothes: Once you’ve sourced the inspiration, and you’re ready to debut your new whatever it is to the world, you may have to get over a small bump (the initial discomfort). When it comes to integrating a piece into your wardrobe that isn’t so natural to you, you sort of have to break it in. Take my overalls for example- you start by finding the right outfit pairing for them…
IMG_8499 copy
(in my current case: a solid coloured t-shirt to go underneath and a cute pair of sandals) These overalls were $10 at the Black market closing sale
…and then you take a breath, and walk them out into the world! And honestly, you just keep doing this until you feel comfortable wearing them. I can’t even begin to tell you how nervous I was the first time I wore my overalls on the street, or my flare jeans to the grocery store, and now I go everywhere in both of them. If you get a weird look from someone passing by, remind yourself that you’re wearing whatever you’ve got on because you love it. If you don’t feel comfortable in an article of clothing after a few wears, it might be an indication that it’s not for you. As it’s taken me so long to learn, comfort is just as important to your style as fashion is, because comfort determines how you’re going to feel in your clothes. If you feel good, your look will reflect it.
Security about your clothing choices comes with time, but I think it’s the biggest indicator that you’ve established a sense of style specific to yourself. I’ve found this security to be true of my style, and every day I see it reflected more and more in the clothes I own, and the confidence in which I wear them.


2 thoughts on “How to Wear: Overalls In Your 20’s

Leave a Reply