5 Outfit Mistakes I Promised Myself Not to Make Again

Hi, I'm Anna, and I'm a repeat offender of these five outfit mistakes. (Phew, it feels good to get that off my chest.)

I'm by no means a perfect outfit composer (as good as I am at spotting great outfits), but for some reason, I frequently catch myself running into the same few sartorial issues and I'm pretty darn sure I'm not alone in making them, so I'm finally ready to put an end to these simple but common outfit mistakes.

Why now, you ask? Maybe it's a belated attempt at formulating a New Year's resolution, or maybe all this time at home has me considering all the ways I can improve my style for future outings. Regardless of the motivation, I'm putting these resolutions in writing to hopefully make them stick.

What better way to hold myself accountable than to publish these style-related blunders to an audience of thousands? In all seriousness, though, these mistakes are nothing major (i.e., skipping comfortable shoes for a painful but trendy pair or carrying a tiny bag that doesn't fit any of your essentials), but I wouldn't be surprised to learn that you've also been guilty of a few of them, too. In the interest of self-improvement, keep scrolling to learn what I'm doing (and shopping) to avoid these blunders for next time.

1. Going for Uncomfortable Shoes

It's hilarious how many times I glance at my sneakers and flats when getting dressed and still look the other way. Want to know what's not funny at all? When those trendy sandals pinch or those chic heels wobble when I walk.

Don't get me wrong, I'll still be wearing heels, but I'm vowing to prioritize comfortable shoes when I know I'll be walking a lot that day. Doing this will also help identify the most comfortable shoe trends so my outfit always feels current. Right now, I'd include retro sneakers, chain-embellished flats, sleek loafers, and sporty sandals in that list.

Instead: Prioritizing Shoes That Are Comfortable and Stylish

2. Wearing Jeans I Can't Sit Down in for Long Periods of Time

Do you have a pair of jeans that look great when you put them on but don't work as well the moment you sit down? Because same. High-rise rigid jeans are one of my go-to denim styles, but I've learned the hard way to skip them if when I'm spending the day sitting at my desk and instead save them for most other occasions. Luckily, looser-fitting styles are trending right now, so there are more than enough options to choose from, but I'm also turning to stretch jeans when I'm still in the mood for something high-waisted.

Instead: Reaching for Looser-Fitting Styles and Jeans With Stretch

3. Carrying Too Small of a Bag

Tiny bags were trending so hard in the past few seasons, so I know for a fact I'm not alone with this one. While they certainly have their charm and add a cool element to a look, every time I carried one, I frustratingly ended up stuffing my pockets with all the items that didn't fit. Instead, I'm shopping for spacious bags that offer something just as stylish to my outfits.

Instead: Investing in Spacious Bags

4. Stepping Out in Wrinkly Clothes

This is one of the easiest mistakes to avoid since all it takes is a few extra minutes to steam said wrinkly garments. I just ordered the below handheld steamer on Amazon in the hopes of leaving this style mistake in the past for good, but another easy way to avoid them is to look for fabrics that don't wrinkle very easily. My favorite accents are plissé and smocking, but knit pieces and jacquard are also foolproof (plus they hold up well if you pack them for travel).

Instead: Wearing Wrinkle-Resistant Fabrics (and Taking the Extra Time to Steam Delicate Fabrics)

5. Not Dressing Appropriately for the Weather

As someone who just moved to New York from California, the concept of dressing for the weather was lost on me. Suffice it to say that I wasn't used to carrying an umbrella everywhere I go or taking the concept of layering very seriously, but that's all changed now and my shopping list includes items like a trench coat, lug-sole shoes, and yes, a chic umbrella.

Instead: Checking the Weather Forecast and Dressing Accordingly

Next up, the spring outfits that feel so right now (and the pieces to re-create them for under $200).