💌 Style Mail: The question you should be asking when you get dressed

Because it's not just about the clothes...

May 15, 2025

I talk about clothes (a lot). Because I love clothes. I’ve built a business around clothes. Almost my entire career has been about clothes (in a few different ways). And it all goes back to when I was little & I hand-sewed clothes for my dolls. And when I was the only boy in my neighborhood reading GQ at age 14.

I specifically love the transformational nature of clothes. Because when you change your clothes, other things change as well. You wear certain clothes to go to work. You wear different clothes to exercise. You wear other clothes to go to bed. And you select special clothes for certain occasions & celebrations.

But here’s the real truth - it’s not about the clothes. It’s about how the clothes make you feel.

Yes, clothes are a visual medium. You assess whether you like them or not based on what you see in the mirror - but it doesn’t stop there. Because even though you check yourself out in the mirror in the morning (and maybe in the bathroom at work), you feel your clothes on you all day long. And those feelings impact what you do, what you say & how you move about your day.

So, the next time you look in the mirror & ask yourself, '“how do I look?” Go one step further & ask yourself, “how do I feel?”

Let’s get into it.

✍️ Style Scoop

When I talk to clients, I tell them that our work together is about the clothes, but it’s not about the clothes (how’s that for an oxymoron?). Because clothes are just a tool. Some clients want to focus on clothes to advance in their career. Other clients want to update what they wear for social occasions (meeting friends, date nights, etc.). I have clients who just want to evolve how they dress for their everyday casual lifestyle. But there’s a commonality among all my clients - they want to feel better in clothes.

How you feel in clothes shows up in different ways - it can show up in how you feel physically, how you feel mentally & how you feel emotionally.

As I often say - no one knows what size you’re wearing, unless you’re wearing your clothes inside out. But they do know when your clothes feel uncomfortable.

HOW YOU FEEL PHYSICALLY

The physical aspect of clothes is pretty obvious. Do your clothes fit? Do they feel comfortable? Is there anything that bothers you? But I can’t tell you how often I’m in a client’s closet & we find clothes that don’t fit, that aren’t comfortable & that have something that annoys them. So, here are a few things to remember:

You deserve clothes that fit you right now. No matter your current size & no matter what size you used to be. If you’ve experienced a shift in size (or shape) & you’re not sure what to do, read this.

Accept that tailoring your clothes will happen. Because (to repeat myself) you deserve clothes that fit. So, if the waist gaps on your pants, get them taken in. If your pants are too long (or too short), fix the length. If something is a little tight or a little loose, see what your tailor can do. And before anyone says, “tailoring is expensive” - it can be. So, if you need a $15 hem on your dress & your budget is $100, buy the $85 dress to stay within budget. And then read this for a few things to know before you go to the tailor.

Be realistic & don’t buy things hoping they’ll get more comfortable. Yes, you can break in a pair of shoes & certain fabrics will soften with time. But shoes won’t magically get bigger (or smaller). Itchy fabrics may always itch. And you shouldn’t have clothes that annoy the heck out of you & you suffer through wearing because of how they look.

It becomes much easier to get dressed when you stop thinking, “what will they think of my outfit?” & start thinking, “how do I feel about my outfit?”

HOW YOU FEEL MENTALLY

I’ve found that a lot of people are ‘clothes over-thinkers.’ You wonder if what you’re wearing is appropriate to the situation (is this dress right for a baby shower?). You think about whether people will judge what you’re wearing (if I wear a blazer, will my boss ask if I’m interviewing?). You ponder if you’re conveying the message you intend (does this print look too showy?). And I’m not saying to ignore appropriateness or intention - but I am saying to not let it get in the way.

Because here’s something that’s great to learn - people don’t think as much about what you’re wearing as you do.

So, don’t let any over-thinking get in the way of wearing what you love & just enjoying your clothes & your day. And instead, put all that mental energy into thinking of different ways to enjoy what’s already in your closet.

All these outfits are from the April VIP Lookbook - which you can access immediately when you become a Style Mail VIP!

HOW YOU FEEL EMOTIONALLY

Clothes are deeply tied into our emotions. Because your relationship with clothes often reflects (no pun intended) the relationship with who you see in the mirror. So, in other words - clothes can tie directly into your self-image.

Think about it. How often have you looked in the mirror & said, “I feel fat?” How often have you said, “I feel great?” And most importantly - how often have you said, “this feels like me?”

Authenticity is the goal with clothes & style - because ideally, your outside reflects your inside. But clothes can also reflect your mood. Some days you may feel bold, other days you may feel quiet. Some days you may feel perky, other days you may feel relaxed. But here’s the amazing thing - you can use clothes to express how you feel. And you can also use clothes to effect how you feel.

A pop color top can lift your mood (on one of those totally blah days). A structured jacket can help you feel powerful (when you have a big presentation). A fun pair of boots can make you feel cool (on a girls’ night out with your stylish friends). And this is how you can use clothes as a tool - to feel how you want to feel when it’s not coming naturally.

Clothes can also have emotions tied to them - good or bad. So, if something negative is getting in the way of your enjoying an item, maybe it’s time to let someone else love it.

Do you think about how your outfits feel (in addition to how they look)? Comment on this post to let me know. Because you can be wearing what seems to be the cutest outfit – but if it doesn’t feel good, how it looks doesn’t really matter.

In one of last month’s VIP posts, I shared a specific strategy to start noticing & addressing how you feel in clothes. So, if you’d like to get monthly style motivation to challenge how you think about your wardrobe - plus 30+ outfit examples per month as inspiration, links to the items I recommend to my clients (and more!), upgrade to my paid VIP subscription.

Once you upgrade, you get immediate access to all existing paid subscriber-only posts (including the one from last month). And then, for less than 2 Starbucks drinks a month or 2 moderately priced tops (that you probably didn’t need) per year, you’ll continue to get concrete ideas & strategies to use what you have & evolve your style.

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🕶️ Style Tip

Have you ever been getting dressed & you put on something, but it doesn’t work? It doesn’t fit or it’s stained or it needs a repair? When this happens, don’t put it back in your closet!

Set it aside for the tailor. Treat the stain and/or put it in the laundry. Find the missing button. In other words - do something with it that will make it wearable. Otherwise, you’ll just be in the same situation the next time you put it on.

💡 Client Spotlight

Carrie’s style mood board - aka our initial vision for aligning her style with the different facets of her lifestyle.

A focus with many of my clients is the alignment of their style & their lifestyle. Because it’s not about having a closet filled with great clothes - it’s about having a closet filled with great clothes that make sense for your life. And this was very evident with a recent client, ‘Carrie’.

Carrie has a really fun & expressive style. Her vibe leans into boho & she loves pieces with details - color, print, embroidery, trims, etc. And one of her main priorities was how to show up for high profile work meetings. Because she had no idea how to merge her personal style with a visible role in a conservative corporate environment.

I believe that everyone’s style can be consistent - so it’s not about changing your style to match the occasion. It’s about turning up (or down) the volume on different aspects of your style, based on what you’re doing. So for Carrie, we turned up the volume on boho ideas for her everyday, but we turned them down for corporate meetings. So, she always feels authentic, but still appropriate.

Carrie lives in a small town a few states away (so she’s a virtual client), but she really wanted to shop in person - so she flew in to the SF Bay Area to meet me for her shopping session. She’s on the border of plus sizes (generally 14-16 in bottoms & XXL in tops), which can make shopping in person challenging. But I’m happy to say that we found a bunch of options that she loves. And I created over 35 outfits for her, that make her feel great in all the facets of her life.