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5 Tips for Changing Your Personal Style


Have you ever looked up a recipe for air frier brussels sprouts?

I (Nathan) did that last week and found something I didn’t bargain for: 12 (twelve!) paragraphs of personal dissertation and historical editorial, which was only distracted further by a virtual Times Square barrage of ads and pop ups. After what felt like hours of scrolling past the origin story of brussels sprouts and otherwise inconsequential (to me) familial diatribes, I found what I came for: 3 steps for making myself a smelly little green to go with out dinner. The result was delicious and simple, but the process was more arduous than it should’ve been.

With that said, rather than entertain you endlessly (which I surely could) with paragraphs of allegories and narratives, I’ll get straight to what the title infers: How do we change our personal style? We talk a lot on TPE about the value of focusing on personal style, rather than chasing trends. But what if you’re unhappy with your personal style and ready for a wholesale change?

This week someone mentioned they were ready for a shift from their athleisure uniform to a more put together look. They’re not looking to go full Y2K or chase TikTok trends, and they even had inspiration in mind for the changes they wanted to make, but they were looking for advice on where to start, and how to find more inspiration.

Here are 5 ideas I thought would help anyone who’s looking for a wardrobe shift, tweak, or even wholesale change!

1 | Self Scout

The idea of “scouting” is a sports term that essentially means studying an opponent (or even a prospect you want on your team) to understand their strengths, weaknesses, and tendencies. The idea is that the more you understand these things, the better you can plan to take advantage of them and ultimately win. Anna and I occasionally try to “self scout” in an effort to understand ourselves better. It’s a tongue-in-cheek exercise that helps us laugh at ourselves, become more self aware, and ultimately find ways to better ourselves.

When it comes to clothes, self scouting is a bit more simple but way messier. “Self scouting” first and foremost means trying on all of your clothes — yes, all of them. Drag out all of your stuff, try it on, see what fits, what you hate, and what your wardrobe “tendencies” are. The goal with this exercise (which we’ve recommended variations of over the years) is to “know thyself”, or at least your closet. Know what your closet does well, where it needs help, and what needs to go in the trash.

Donate what you hate or what doesn’t fit or what you haven’t worn in 3 seasons, and keep the rest. By the end of this process, you should know exactly where to start with your new wardrobe venture!

2 | Start Slow

When it comes to first steps, take your time.

You may have ideas in your head or inspo you’re ready to copy and paste into your life, but don’t invest heavily in an overnight overhaul. Why? Because you may find yourself spending hundreds of dollars on extremely cool individual pieces that you struggle to style together in a cohesive look. This inevitably leads to buyers remorse and dissatisfaction, which may lead to wasted money on pieces you never wear.

Start with staples, get 1-2 pieces that really stand out for the vibe you’re trying to achieve, and then sit with it for awhile. Let some time pass, let things marinate, and you’ll be better for it in the long run.

It’s important to remember that personal style is — in many ways — a lifelong hobby. In the same way that goals unexpectedly lend themselves to new objectives, every idea leads to another idea. Even the most consistent uniform wearers shift their perspectives over time, so don’t rush the process!

3 | Start from the Bottom (Your Bottom)

One thing you’ll notice about anyone who has great personal style is they have killer pants.

Big knits, nice coats, and loud jackets may catch the headlines, but well-made pants are legitimately (and literally) the foundation of dressing well. So if you’re going to invest more money in something on the front end of your style transformation, we recommend covering your ass first!

It’s not a stretch to say great pair of pants can make a $10 t-shirt look awesome, and a cheap-looking (important to emphasize “looking”, because more expensive does not always equal nicer) pair of jeans can make even the most luxurious and well-crafted top look lame.

With pants, comfort is everything. If you don’t feel comfy, you just won’t wear them. Focus on fit (what makes you feel confident and comfortable), material (something that will last a long time), and versatility (pants you can realistically wear often because of your lifestyle, job, and wardrobe), and you’ll find yourself excited to try new combinations with your favorite pants.

*3 specific notes on how to spot “well-made” stuff:

  • Origin: Made in China doesn’t always mean bad, but the reality is we just don’t know because there’s very little transparency. If something says made in Italy, Portugal, India, USA, or Japan, it’s almost always a well-made garment.
  • Material: Some people love stretchy pants, and while we don’t blame you, most high quality stuff is made with natural materials. Look for cotton, wool, linen and other similar fibers, and you’re likely to see something that’s more thoughtfully sourced and will last longer.
  • Fit: A lot of times (though not universally), higher quality clothes fit better. Why? Because achieving a certain look or cut takes more design work, which is a higher investment by the brand or designer. That said, if you find something that fits you right, then that’s all that matters! Just make sure you’re comfortable in the clothes you wear.

4 | Double Down on What You Love

When you find a look you love, whether that be a singular creator, brand, or “vibe” that seems to stick with you more than others, or an aesthetic that speaks to you, seek it out. Try to get details on what it’s called (the keywords that make it searchable), and then use tools like Pinterest to find more of it. This helps build inspiration to use what you have today as a stepping stone to recreating looks you love, while also giving you ideas for pieces you may want to buy in the future.

We talked about this concept recently, but don’t be afraid to stock your closet with what you love and wear most. We sometimes conflate variety with the sensible choice, but doubling down on what you want (and what you’ll actually wear more often and get the most use out of) can often be the best use of your budget and closet space. When you find looks, pieces, and styles that you can’t wait to wear, throw out the rulebook (within your means, of course), and trust what your instincts are telling you that you want to wear!

5 | Your Errands Are Your Runway

When you’re turning over your wardrobe or trying something different, you may find yourself feeling a little shy about wearing certain pieces or looks out and about. Maybe it doesn’t drape on you how it did on the model, or maybe the lighting in your room isn’t helping you feel the confidence you felt in the dressing room. Whatever the case, sometimes it can be hard to push yourself to wear something that feels “not me” on a date or out with friends.

This is where your errands come in handy. When you go for a coffee run or to the grocery, throw a ‘fit. Put on that jacket that feels too loud, that dress that has a different cut, or those pants that feel way too big. Most of us run errands in our sweats anyways, so it’s not like fear of judgement should be a massive deterrent (if you feel it is at other times). This gives you a low risk way to see how something makes you feel, whether it’s comfortable, and whether it feels as part of your personal style as you hoped.

This exercise could either confirm your doubts or give you the confidence you need to commit to this new look — either way, that’s a good thing! In the end, we imagine you’ll be surprised at not only how good you feel, but also how many compliments you get when going all out for a quick trip to the bodega.

*Oh, just don’t forget to keep the tags on when you can — just in case things don’t go as you hope.

We hope these simple tips help you sharpen your wardrobe, whether you’re looking to make wholesale changes, your just hoping for some fun tweaks in the new year!



• leave a comment •

  1. Rebecca R Pappas says:

    Very helpful! I especially like the part about where the clothes are made and trying out your new outfit when running errands. Thank you!

  2. Babs says:

    Love the wear it on errands. Never heard that piece of advice.

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