All the wardrobe myths that are keeping you from looking your best.

You don’t need a trust fund, life of leisure or personal stylist.

This is a free preview of our paid content. Paid subscribers will receive a weekly newsletter containing an in-depth lesson to cultivating an exquisite wardrobe while saving you time, money and answering the age old question of “what should I wear today”.

That feeling of mixed messages on what you should buy and wear today.

A few weeks ago in Venice we were seated at a lively dinner party filled with accomplished people from a variety of backgrounds. The conversation could’ve taken many paths, as interesting and mysterious as the small winding alleyways of that mystical city.

Or instead, on this occasion, Philip and I were asked our opinions on the celebrities with the best personal style.

We’ve come to expect this line of questioning, though we do excel at other topics, I promise! While Philip was able to name a few good examples, mainly men - and that wasn’t easy without dipping into the realm of old Hollywood - there wasn’t any name that just jumped out as an obvious answer. To which I added my contribution: it’s a fool's errand because almost all of today’s celebrities use stylists. Are we talking about red carpet outings or press appearances? A stylist’s work. Having lived in Los Angeles for a few years, it’s surreal to run into a celebrity at the grocery or pharmacy because they blend in with the hoi polloi. There are a few exceptions, of course, but many celebrities are just like us, struggling to figure out what to wear on a day to day basis, the stakes being much higher for them, of course.

A few days later in the charming South Tyrol region of Italy, we were enjoying lunch with a spectacular view of the Dolomites. Philip called my attention to a gentleman seated in the room behind us. An elegant man, enjoying a quiet Sunday reading the paper. Simply dressed in a tonal Prince of Wales check jacket and turtleneck, with a dash of personality in the form of a bright orange pocket square. Effortless. Comfortable. Understated.

After he departed, another exquisite man entered and sat, again, behind me. Slightly younger than his predecessor, he wore a beautifully tailored blue-grey jacket, light beige crewneck sweater, light blue French cuff shirt, a darker orange trousers, a darker blue sock and brown loafers. A hint of personality came through in his African beaded bracelet and his round, horn-rimmed glasses. He, too, had a newspaper, where he was working through the crossword.*

We were able to see him exit the restaurant in his field jacket, a mossy green with a subtle orange windowpane that complimented his trousers.

I wish I was the type of person who could kindly ask to take a stranger’s photograph. Alas, I am not.

Both of these gentlemen are examples of the lessons to be learned about building wardrobes that work for you and put you in the best light, regardless of the occasion. Two men, out for solitary Sunday lunches with their newspapers. They aren’t following trends. They didn’t have a studied approach to dressing as if they spend hours scouring the menswear forums. While they are both wearing classic foundational pieces, they also have elements of individual self-expression. They’ve invested in items that stand the test of time, in construction as well as timelessness. They elevated the atmosphere they inhabited, bringing a sense of occasion to an otherwise ordinary moment. Can you imagine having that impact on others around you? That’s more than I can say for the celebrities I’ve encountered at the grocery store.

*It occurred to me how much more chic it is to sit at a table for a meal with a newspaper as your entertainment than using your phone.

It is our fundamental belief that everyone, or at least most everyone, wants to look good every day. Great, even! Before some of you mutter under your breath that it’s too much effort for every day, etc etc, let me phrase it another way. Nobody wakes up in the morning and wants to look their worst. Nobody goes out of their way and puts effort into looking their worst. Do I have your attention now?

Yet we hear all the reasons and excuses why people choose to show up in a way where they don’t look or feel their best. The truth is that most people are simply lost. They don’t have the tools, both knowledge and clothing in their wardrobe, to look effortlessly fantastic on a daily basis. And they are swimming in a sea of influencer content that muddies any sense of individuality they may have.

If the tools were available, wouldn’t you want them?

In this space we will tackle the wardrobe myths and challenges you face through weekly tutorials. A wardrobe that costs you less money over time. One that makes dressing a pleasure that takes very little time or effort. One that pays back in compliments from complete strangers.

I’ve put some thought to the myths we tell ourselves about dressing well and looking our best. Here are a few off the top of my head:

Myth #1 - I need to be wealthy to have a beautiful wardrobe.

Myth #2 - A disciplined or uniform wardrobe is boring and limiting.

Myth #3 - Looking my best every day will take too much time.

Myth #4 - Dressing my best isn’t comfortable.

Myth #5 - I need to lose weight before I can have a beautiful wardrobe.

Myth #6 - Sales are a great way to build a wardrobe on a budget.

These topics and more will be covered, in depth, in the weeks and months ahead. Every week we will offer at least one actionable tip or tutorial that can put you on your way to looking your best

Welcome to our new series of actionable tips & tutorials! Let’s start with some mythbusting.

MYTH: Sales are a great way to build a wardrobe on a budget.

The sales season is upon us, friends.

Is it just me or has the onslaught of sales messaging this holiday season gone off the rails? It kicked off earlier and with such an intensity that some days I don’t want to open my inbox.

Let’s be clear, these discounts have nothing to do with you or what you need. It’s all about end of year numbers, happy shareholders and then starting 2025 strong. If the emails and ads popping up in your social feed weren’t already too much - there is the wave of gift guides that are packed full of sponsored content and affiliate links to not only make money for the retailers and brands, but also the influencers who are pushing them.

So with that, let’s all take a deep breath.

I’m going to tell it like it is: sales can be a wardrobe disaster, blowing through all your best intentions. Sales are a means of psychologically manipulating you into thinking you must have something now because it will absolutely be going away soon, or at least the tempting price will. The old “sense of urgency” scheme. It’s the same tactic used at the beginning of this email to get you to convert to a paid subscription. Ha!

How do we best survive the sales season with our dignity intact?

Here are tried and tested rules to follow when you’re feeling vulnerable and ready to buy that heavily discounted jacket that goes with absolutely nothing you currently own:

Rule #1 - Did you even know about this item before it was forced into your consciousness during the sale?

If you weren’t already aware of something before you started seeing ads for it, then you don’t need it. If you didn’t have a hole in your wardrobe that you needed to fill with this item - this exact, specific item down to color, material and style - then you don’t need it.

Do not negotiate with yourself on these points. Most bad decisions have been made on a “great deal”. The Louisiana Purchase is an exception to this rule.

Rule #2 - Ask yourself, would you have purchased this item at full price?

Is there a reason why you haven’t purchased it? Perhaps it’s a bigger financial investment and you were saving up to pay in cash?

In some cases there are things we mull over. Is it essential? Does it fill a need? You’ve been asking these questions for weeks or months and haven’t arrived at an answer. Don’t let the sale be the answer. If you couldn’t convince yourself of the value that item could bring to your wardrobe (or life!) before the price was discounted, it’s not going to serve you well in the long run.

Rule #3 - Is there ever a good time to buy during a sale?

Yes, there absolutely can be wardrobe (and life!) enhancing values to be found during sales.

Say you’ve been watching an item because you have a need and it is well-made and of good quality but is just out of reach financially. Suddenly it’s available at a lower price, in the exact size and color you need. By all means, jump on that opportunity!

Note: I mention size and color you need. There are a lot of mental gymnastics that you can do to convince yourself that the bright yellow sweater in a size larger will be just as good as the light blue one you need in the proper size. It won’t be. Don’t compromise.

Rule #4 - Double check the details

Are you really getting a great deal? It’s good to double check the details on the product before you add it to your cart.

I was recently served an ad for a suede safari jacket. In multiple places. This jacket was following me around the internet like the eyes of a portrait. I was curious about the price since we also offer a safari jacket. What was advertised as a suede jacket was revealed to be “Italian stretch suede” and described as “100% suede”. While we will go into more details on textiles in another post (or many), it only takes a quick Google search to learn that Italian stretch suede is 100% polyester. As Philip said, “real suede only stretches when it’s still on the animal.” Touché!

Okay, fine. It’s not suede. But is it then worth the $1300 price tag? Or even 20% off that?

Treat your purchases, even those on sale, as investments. Will this pay out over the long term? Is it truly a good value?

Remember, it’s not saving you money if it’s not something you need or it isn’t exactly what you needed, especially if it sits in your closet with the tags attached.

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Welcome to our new weekly series featuring actionable Wardrobe Tips & Tutorials.

Paid subscribers will get weekly in-depth emails featuring tips and tutorials that will:

Save you money in the long run while vastly improving your wardrobe.

Save you time by making buying clothing and dressing effortless and enjoyable.

Eliminate the headaches of a closet full of clothes and nothing to wear.

The cost is $8 a month (or for a savings at $80 a year) which is the equivalent of one overpriced, over-sugared caffeinated beverage or a cocktail at a mid-range eatery - quite a value for 52 installments of looking great, buying less and saving time. That comes to only $1.84 an installment!

Free subscribers will receive a biweekly Sunday edition of our Acquired Taste newsletter including a quick tip to cultivating a beautiful wardrobe, as well as previews of our weekly paid newsletter.

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