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When ugly becomes cool

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Date:
September 9, 2024

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Author:
Madison Joslyn

We talked about how to style a look around a specific item that you’re excited about, but what’s fun is when you can repeat the process time and time again. Once you’ve started to play around with styling a look around one item you can move onto the next level: styling something that’s quote on quote “ugly.” I believe that there exists this fine balance between ugly and cool; it’s like something can be so ugly that it becomes interesting the more you look at it then circles around to the other side of the spectrum and becomes cool. 

This isn’t the first time I’m saying we shouldn’t dress for anyone else, but that we should only dress for ourselves. The epitome of that is wearing an item that some people might find ugly, then rocking it. 

Take my super colorful sweater. While it’s not ugly it is loud and calling for attention. It has several colors and fabrics, and could seam hard to style. Do you pair it with a color in that’s already woven in? Do you wear it with neutrals, with other patterns? The answer is there’s no wrong way to do it. You get to style it however you would like. It’s your prerogative. 

What it means when something is “ugly”

Ugly doesn’t necessarily mean bad, it can be something that feels off putting or uncommon. I have a consigned tan Prada sweater with tassels coming out of it and it’s so unique one could say it’s ugly (someone on IG said I looked like Big Bird). I love it because it’s unique and I’d never seen anything like it before. It makes the whole outfit. I can wear it with jeans or sweats, or even over a skirt. I can throw on sneakers or flats, the possibilities are as endless as the number of tassels. Or take my JW Anderson mules with the oversized buckle detail. I have them in all silver and they are bold and loud. One might say ugly, but I say interesting and fabulous. I’ve never seen anyone wear the version of these shoes in silver, and anytime I’ve seen someone wear them in black it makes me pause and really think, do I like these? Are they ugly or are they cool?

That is the true precipice of fashion, when you’re forced to think about an item or a look and wonder how you feel about it. I might despise the shoes 20 years from now, but when I wear them I feel cool and different. I don’t feel like a canned version of a woman wearing this season’s popular BP sweater (if you know Nordstrom back in the aughts you know what I’m talking about). 

Now let’s something that seems ugly look cool

The feeling of “cool” is one that is so empowering. It makes you feel like you’re in charge, you’re confident; you know who you are. When you feel cool you feel special and important, it’s not a feeling most women ascribe to themselves, and I think we should change that. We should be able to feel empowered by our clothes. Perhaps you want to blend in, but perhaps you want to feel exceptional.

Maybe you don’t know which side of the line you want to be on, or you’re straddling both sides and you don’t know what sounds right–take a little walk with me.

Breaking it down

I love teaching through examples so let’s take my Nizhoni sweater. First off, it is arguably not ugly, but it is multicolored and full of pizzaz. It might seem like something that is overwhelming to wear. Or take my Morphew Chenille Beach Coat, it’s so colorful and filled with textures. When I first saw it on the racks at The Refind (catching a trend here? we’re obsessed) I was drawn to the colors, which if you know me that’s wild. (I need to do a whole analysis about the insanity that I’m attracted to color these days because I spent my 20s being revolved by it.) But when I first started looking at the coat I didn’t know what to think. The fabric almost felt like a towel and it took me awhile to realize that the colors made up a design of a peacock. How cool is that?

The more I looked at the coat I realized there was so much potential. It could be something that stands on it’s own, I wouldn’t even need to create an outfit around it. Think about this: if you’re wearing a full length coat that has it’s own personality, does it matter what you’re wearing underneath? Can you even see what’s underneath? Throw on an easy shoe and whatever you’re already wearing and you’re out the door. OR if you’re not sure about wearing it out, the coat is so cool to be able to wear around the house. TBH that’s how I’ve been styling it–for at home wear–but how chic is that? When I wake up in the morning and stumble downstairs to make coffee and I throw that coat on I feel put together. Like some artsy gal who lives in NYC and like miss Carrie Bradshaw is always wearing something fabulous, even when sitting at home curled up with a book, writing a blog, or binging TV (let’s be honest that’s a primary past time).

Fun through clothes

Whether you’re wearing a funky and colorful sweater or you’re donning a wild overcoat in your house, I always recommend adding some fun in your life, and you can do that through clothes. Again, you probably wouldn’t have heard me talk about “fun” when it comes to clothes a few years ago, but hey life changes you. I think I’ve become softer as I’ve gotten older, and experimenting with color has been super liberating. What would it do for you in your life to feel better about yourself at home, instead of being a couch gremlin? What would it do for you at work, or as a mom feeling more empowered in your clothes, in your body?

Whether you’re wearing a funky and colorful sweater or you’re donning a wild overcoat in your house, I always recommend adding some fun in your life, and you can do that through clothes

Tips to try out the “ugly” vibe

Use some or all of these tips to play with the ugly vibe. Let me know what questions you have or if you want to chat through styling a specific item!

  1. Confidence is Key: Start by wearing the item with confidence. If you own the look, it can shift how others perceive it. When you feel good in what you’re wearing, others will notice the cool factor more than any unconventional elements.
  2. Balance with Basics: Pair “ugly” pieces with minimalist, classic items. For example, wear bold shoes with a simple black dress, or an oversized sweater with tailored pants. The balance keeps the look intentional.
  3. Embrace Uniqueness: What may seem odd to one person can be a trendsetter to another. Find one unique feature of the piece and emphasize it. If it’s an unconventional color, let that color shine with a monochrome look or subtle complementary tones.
  4. Accessorize Strategically: Accessories can elevate an outfit. Pair your “ugly” item with statement jewelry or trendy bags that align more with current styles. It creates a contrast that draws attention to the outfit as a whole rather than any one item.
  5. Mix Textures and Patterns: Sometimes the “ugliness” is just a matter of perspective. Experiment with layering different textures or mixing patterns to shift focus and create a more fashion-forward look. For instance, a strange-colored jacket might look great with textured fabrics or graphic prints.
  6. Lean Into the Quirkiness: Some items are meant to be quirky or eccentric. Highlight their uniqueness rather than hide it. If something is unusual, like chunky shoes or asymmetrical clothing, play it up with an equally bold or offbeat styling choice.
  7. Stay True to Your Style: While it’s fun to experiment, stay true to what resonates with you. Incorporate the piece in a way that reflects your style, whether you’re minimalist, boho, or edgy.

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