Fashion regrets: We’ve all had them. And because my job is in fashion, well, I’ve had enough for the both of us. Since I teach about having a classic wardrobe, developing your personal style, and looking timeless, it would be remiss of me not to share the beginning of a normal style journey. You know, the beginning where you don’t know what your style is or what to buy so you jump on every trend and your wardrobe is a mish-mash of random colors, styles, and prints…yep, been there!
I scrolled through the archives for these styles that I used to wear that not only make me cringe, but surprisingly, also make me feel thankful too. Thankful because it’s normal to make style “mistakes” because they get you closer to your own personal style, which in turn boosts your confidence and self-esteem.
And keep in mind that though these are things I don’t like on myself, I’m not shaming anyone for liking or wanting to wear these items. These are personal regrets because they do not fit my personal style, but they may fit yours!
1. Chunky Bauble Statement Necklaces
Just call me the (former) chunky necklace queen. Because if necklaces were treasures, I would have had enough to buy a country and swear myself in. I found a pack of cheap statement necklaces at a thrift store and I remember feeling super cool wearing them. Never mind the plastic jewels kept falling off and the gold chains tarnished in about a week…
They make me cringe now because they just look so fake. And huge! Plus, they instantly date my outfits to when these were in style. I eventually grew out of my love for chunky necklaces and have since replaced them with dainty necklaces that are a lot more subtle. 😉 I don’t mind a good chunky necklace; it’s the baubles that are very 2000s.
What to try instead:
2. Things I Wore for Other People
At the beginning of my business and website, I was not confident in who I was and what I liked, leading me to be quick to jump on every trend that people loved in an effort to seem “with it”.
Additionally, I tried to reach every age group, which I’ve learned you just can’t do! As an example, when it was “back to school” season, I would highlight school looks for the younger crowd. This Gen Z style is just not me and I cringe now when I look back at my low-rise jeans with crop tops, gingham mini dresses, and fake glasses. Like, who is this girl?
What to try instead:
3. Cold Shoulder Tops
Are you a tank top? Are you a shirt? Reveal your true purpose!
Showing skin without showing skin seemed like a great compromise at the time. But now, this style doesn’t make a lot of sense to me. And though I don’t normally care about what’s “in”, these “flash in the pan” trends are super popular for that time and when worn after, they date your outfit and look out of style.
What to try instead:
4. Jeans With Rips in the Knees
Why oh why did I take all my perfectly good jeans and cut them up? File that under things I’ll never understand. I don’t mind a subtle distressing here or there, but this reproduced and trendy look of my knees falling out is simply not a style I’m into and I think it downgraded some of my looks. Plus, why the knees? That’s one of the least attractive body parts on well…anyone!
What to try instead:
5. My Repurposed Clothes
You can’t blame a girl for trying. My repurposed clothes were born out of part necessity (believe it or not, a newlywed 20-year-old does not have a lot of money) and the desire to have fun (being creative with a clothing project is exciting to me).
But what started off with good intentions quickly became a disaster. I would take my sister’s, husband’s, and mom’s old clothes and try to turn them into new, cute things. Oh, and with possessing no real sewing skills or equipment I should add!
The end result was me wearing clothes that were glued together or tied around my body. Extra points for creativity, but yes, it looked about as unsophisticated as it sounds.
What to try instead:
6. Chokers
My sister said I looked like a cat in the choker with a pom pom and I didn’t want to believe her. Now? Well, I believe her.
That choker makes me cringe the most and it’s another one of those styles, like cold shoulder tops, that make you instantly think of a certain time period. Atemporal clothes and accessories are what I want to focus on now!
What to try instead:
7. Flared Sleeves
Are you a voluminous sleeve or not? Though there’s nothing inherently wrong with a flared sleeve cuff, this look seems to have stopped halfway and is another one of those trends that were super popular in its time that now seems outdated to me. But of course, I wouldn’t be surprised if this came back!
Instead, I like shirts that commit and go all the way with a balloon sleeve. It seems a lot more intentional!
What to try instead:
8. My Cheap Fast Fashion Purchases
One reason why you don’t see “Shein Hauls or “Amazon Hauls” from me is that I am simply tired of the cheap fast fashion purchases. Not saying they don’t have some good quality items and not saying I never shop here, but at the beginning of my style journey, places like Romwe and Zaful were all that I shopped from.
These clothing items didn’t fit well, stained easily, and would rip within a week or two, and I remember when taking pictures, I would have to pose in such a way as to hide a giant hole. Part of my drive to create a classic, high-quality wardrobe is that I was so sick of wasting money on these types of clothes!
What to try instead:
9. Floppy Hats
Just like flared sleeves, there’s nothing wrong with a floppy hat but I cringe because it’s just not me! It fits a more bohemian aesthetic, plus, I do think they are a little outdated now. Instead, I love a beret, newsboy cap, baseball hat, straw hat, or fedora.
What to try instead:
We all love a good style before and after. Here’s mine:
Everyone at one point wore something that would now make them cringe. Your style evolving over time is normal and expected! But if you’re looking to get started on your style journey, check out my 50+ page eBook which will help you develop your style and build a wardrobe from scratch!
You were, and probably still are, extremely cute and those things were probably worn at the height of BoHo chic being in. Make no apologies! You have found your style and we all have a couple of stops on the way to finding ours.
Thanks for the enouragement!
You have great style now and I really appreciate all your articles. I so look forward to the next one & am so happy when I see a message from you in my email. Thank you for all your hard work!
Received numerous compliments on my dress style when I was in Paris last September. Many thanks
Well, I like the chunky bauble necklaces and I wouldn’t label any of the outfits as “mistakes”. It was who you were at the time and that’s ok! Style is about whatever you feel good in and who knows, that might gradually evolve as well. Your website is really handy for basics/neutrals inspo even if I tend to wear more colour – thanks!
That is a great article! What is good to keep in mind that making mistakes (even thought these aren’t real mistakes) are essential to learning. It also means that you are open to trying new things. If you aren’t making mistakes, then it means you are not trying new things and therefore not learning.
Hm…I get most of your points, but thinking floppy hats are “ehh” and preferring fedora made me chuckle. Fedora is one of the most weirdly worn hats I’ve encountered. And generally, it just looks funny instead of chic.
And I see that your style is more polished now, but that huge Chanel logo pin(?) on your coat looks tacky.
I agree with her on the floppy hats being cringe. They are sort of a class and race marker: only light skinned rich women wear them, for one. You supposedly use them to keep sun off your face but they are overkill: some women wear these things in a way that looks like a personal tent, while everyone else simply wears a bit of sunblock on their nose, a visor, shades and a lightweight hoodie.
That’s what is off-putting about that style. The writer may have a different view.
I agree with with you 100% on every single one of these items.
Every single one of these fashions seems to work on a rotation highlighting a different angle of a woman’s body. Men love our soft shoulders, hips, thighs, chests, buttocks, you name it ..
And we are stuck with strappy heeled sandles that give us blisters and make us trip, and an itchy, off-the-shoulder knit top that is drafty and requires an uncomfortable bra. How about a short dress that makes you worry about your bottom making direct contact with a vinyl chair?
Worst thing – everybody thinks I would look so much nicer in these fashions than in the sensible, well-fitting ones that I have hanging in my closet. So I come home to find a clingy polyester black miniskirts hanging in my closet – hand-me-downs. And Stilettos.
Anyway I am up to here with it.