In this insights article, our owner and principal personal stylist and shopper, Natalie Tincher, shares how to avoid some common everyday wardrobe mistakes by taking a little extra time to consider your day.

I was recently out and about (like I often am) in New York City. This particular day looked like this:

Two morning meetings in different neighborhoods
A client shop, which means I’m going to be on my feet for 3 or 4 hours while being present with sales associates and the client
Dinner with a friend after

When I was getting ready in the morning, I wanted to wear a cute pair of flats. It was a warm day, and we move fast in NYC! By the time I got to the Shop my feet had swollen and were killing me. I score high in the Relaxed style personality, and it took all I could muster to be my usual upbeat, present self for the physically painful four hours. I had to take a cab instead of the subway to get to my dinner—and even then the walk from curb to cab was pain-stricken each step!

Yes, that may sound dramatic (and I may be over-dramatizing a bit)— but being able to focus on the people around me and the situations I’m in is a big focus and joy point in life for me. These precious moments with my people are what fill my cup, and I want them to have the best of me always. My barking dogs were getting in the way of this.

Dress for Your Day

I should have known better, but I got rushed and careless. I didn’t take the extra beats to be more thoughtful. So in order to help you avoid my mistakes, here is a quick checklist to help you dress for your day.

When picking out your wardrobe each day, take 30–60 seconds to consider the following:

The Weather: Look at the forecast. What are the highs and lows? Is there precipitation in the forecast?
Now look at your outfit choice. . . .
- Are your shoes going to withstand the weather?
- Do you need layers for the temperature swings?
- Is your fabric sweat-friendly?
Your Settings: Think about the settings in which you’ll be. What do you know about them? Or not know and want to be prepared for?
Now look at your outfit choice . . .
- Are you prepared for an intense air conditioner or no air conditioner?
- Will you need to sit or stand for long periods? If so, is your outfit comfortable for that scenario?
Your Schedule: Picture you going about your day’s plan and what it will look like in your chosen outfit.
Now look at your outfit choice . . .
- Do your shoes fit the bill for your activities? (I’m asking myself this now every day!)
- Does your outfit feel “right” for all of the people you’ll be meeting and spaces you’ll be inhabiting?
- If it’s a long day, can you picture yourself feeling good wearing all of the elements in this outfit all day? Are you missing anything? Do you need to make any swaps?

Note that if you are like me and pick your outfit each morning, do this each day. If you select your outfits at the beginning of each week, run through this list each day. Do a quick final check each day to make sure none of your considerations have changed.

So I hope this helps you dress for your day in a way that avoids some practical and common outfit misjudgments, so you can stay focused on your plans and not be distracted by your wardrobe choices! In fact, I hope you always feel great about them!