Have you ever had that gut-wrenching moment when you step into a room and realize that your outfit isn’t meshing with the overall vibe? As your eyes scan the scene, it hits you — you’ve totally misjudged the atmosphere and now feel like you’ve overdone it with your look. You tried too hard.
So what’s the deal with this whole “trying too hard” thing?
After styling thousands of women, I’ve uncovered 2 main factors at play:
- Fear of being judged: We worry that others might criticize how we look or what we wear.
- Wanting to fit in: We want to feel like we belong and worry that our outfits might make us stand out in a bad way.
YUCK! Nobody wants to feel like they’re trying too hard!
So how do we prevent it from happening in the first place?
The answer is simple: catch yourself WHILE getting dressed! This way you’ll change your clothes BEFORE heading out and experiencing the vibe mismatch.
To help you get started, I’m sharing why you end up feeling like you tried too hard. Pay attention to this guidance WHILE getting ready to go out to avoid feeling like you’ve overdone it.
Keep reading for:
3 Signs You’re Overdone Or Trying Too Hard With Your Outfit
1. You’re not aligned with your surroundings
Individuality is highly regarded in my styling practice. My motto is: get dressed for how you want to feel, not what others think.
AND ALSO I believe in acknowledging where you’ll be and who you’ll be with.
This isn’t about taming your style or self expression…
It’s about reading the room which conveys cultural competence so you make well informed decisions with tact, empathy and respect.
It’s like “I see you.”
“I acknowledge your presence.”
“I recognize what’s going on here.”
So if you choose to wear a gold sequin top to your work breakfast meeting — go for it!
Just be sure it’s in good taste. Because aesthetics also play a role here.
Here’s what I mean by that…
Recently, I was getting ready to go out and felt VERY excited about the outfit I had in mind — a colorful long sleeve bodysuit, black shorts, black ankle boots, gold belt and fishnets.
After putting it on, I looked in the mirror and saw that I was dressed to go dance a Chorus Line at the club. Not the swanky 50th birthday party on the Upper East Side!
The outfit said daring and sexy — which was fun! But the event’s location — elegant and classy — wasn’t coming across in this look.
Plus, let’s be real — trying too hard can make your outfit look a bit tacky. In my case, the fishnets were too much.
The take-away here is to prioritize your individuality, but always consider context and aesthetics.
2. You’re Clearly Uncomfortable Or Dressed Impractical
Have you seen the show Pretty Little Liars? I’m binging it with my daughter. (A bonding thing for us.) Anyhow, the show is set in high school, at least in the current season we’re watching. (This series spans years!) And the main characters dress…omg — I have SO many thoughts on this!
First, they’re dressed like 30 year olds. But that’s not even my point. They wear 6” stilettos to school! How is this comfortable or practical? It’s not!
It looks like they are trying to prove something which is the core of trying too hard. You feel like you need to show people something to feel like you belong. I think for Pretty Little Liars, it was like “Let’s make fashion a subplot to keep viewers talking and entertained.” (It’s working for me!) There’s no way those shoes make sense in real life.
Think of it like this: if you’re going to climb Mt Everest, would you wear your wedge sandals? No. That would be trying too hard to show people you’re stylish. (Or whatever you want people to believe about you.) This doesn’t mean you can’t have stylish climbing shoes that you love. You just choose something more practical so you’re not uncomfortable.
So unless your primary intention is the same as a tv costume designer and you want fashion to be your subplot, leave the 6” stilettos out of the high school. (Or perhaps the grocery store is the middle age version of this.😊)
3. You’re Over Accessorized
Another thing I love looking at in Pretty Little Liars is their accessories. Every single outfit has a belt worn around the waist and depending on which character, there are big dangly earrings, piles of chain necklaces, brooches, hair accessories, and statement shoes (in addition to the 6” stilettos, they do a lot of knee highs or thigh high boots.)
Often they’ll wear all these accessories in the same outfit. Are they overdoing it? For their trendy, maximalist lives, I don’t think so.
For the rest of us who don’t consider ourselves slaves of fashion, it’s too much, and can become distracting. I talked about this in an instagram post where I used Brene Brown’s Netflix show as an example. 👇
The bottom line: choose your statement, then make it.
There’s no need to keep adding exclamation points to drive home your message. The more you pile on, the more cluttered you look which dilutes your style and can feel like you’re trying too hard.
How To Stop Trying Too Hard With Your Look
When I think about that outfit I tried on for the 50th bday party, sure — not wanting to feel judged or like I didn’t belong definitely played into my decision. But at the core, I felt like I was straying too far from how I wanted to feel at the event. It wasn’t the ME I wanted to bring forward in those circumstances. Perhaps on date night with DH when we’re out seeing a band, I’ll wear it (and replace the fishnets with black sheer tights.)
If you want to stop feeling like you’re trying too hard, get in touch with how you want to feel in your clothes, but don’t forget to read the room and consider your aesthetics. Also make sure you don’t sacrifice your comfort in such a way that’s impractical and always accessorize with intention.
If you want a straightforward approach to boosting your styling skills so you put together dynamic outfits with ease, checkout my DIY styling bootcamp. This program is designed to help you make the most of your current wardrobe so that you create new and exciting outfits using what you own in 21 days. Perfect to get a bunch of new looks for summer without buying anything new!
Or if you prefer a more individualized, high touch experience — go here to book a complimentary call and let’s discuss how I’ll help you create a captivating style that highlights your body and feels undeniably YOU!