I am a lazy girl. I want to put the least amount of effort in, for the maximum return. In business school, we teach our students to avoid the point of diminishing returns. During the productivity phase, all the effort you put in gives you value. So you work harder and harder but at a certain point the return gets smaller until one day you realize you aren’t getting anything back and in fact the returns are negative.

Let’s apply this to getting dressed: My goal is to look great, feel confident and use as little of my brain-share (and budget) as possible.

That’s why I buy Workhorses Only.

I never want to panic about “what do I wear” as I stand in a bulging closet trying on item after item, left with not only the frustration about how long it takes to get ready but also with a closet to clean. That is the definition of not just diminishing returns, but negative returns.

For me, dresses are the unsung hero of my life.

Maximum return for time spent. It’s a one-and-done. No shirt coming untucked. No hard pants (also, pants are just a nightmare—to buy and wear— for all but like 3% of the population). A dress presents you as put-together and chic all while giving you comfort and confidence.

If I could only have one word to define my style it would be Classic.

This is important! Note, my word is not Stylish. Or Edgy. Or Minimalist. Those might be your words. They’re all lovely! What I love about having ‘Classic’ as my overall style goal is that things I bought 8 years ago still serve me today. Things I buy tomorrow will serve me in the year 2030. Keeping up with trends has never worked for me. I know my body type and I dislike feeling like I’m trying too hard.

After many years, I’ve figured out how to stay in the “productivity phase” referenced above when it comes to getting dressed. I spend about 1-2 minutes, at most, to select an outfit. As I select an outfit, I think to myself, “when I have to go to this, I wear this.” To make this more sticky, I pulled scenarios from real-life and the dress that I reach for. The events themselves might be different for you, so I included the vibe too.

1. Casual Friday | “Here to conform”

2. Baby or Wedding Shower | “Here to celebrate”

3. Tennis match | “Here to play”

4. Running Errands | “Here for ease”

5. Date Night | “Here to charm”

   

#1 Casual Friday | “Here to Conform”

There are days when you don’t want all eyes on you. Maybe you’re exhausted or don’t want to be in the spotlight or you actually don’t want anyone thinking too much about what you are wearing. Sometimes I want to blend in and have anyone’s passing glance just register “she looks nice” and move on.

For those days a navy dress—in a cotton/linen/jean—will do the trick.

My buy reco: Boden while the sale is going on and it’s under $100. The combo of Tencel and modal cotton makes this wrinkle-free and machine wash. The length is both flattering and appropriate for work, for almost all heights.

#2 Baby or Wedding Shower | “Here to Celebrate”

It’s helpful to have a few go-to dresses that are happy.

A navy or black dress is great, but not for this occasion. It’s so wonderful to celebrate those big moments with our loved ones and dressing for their special day is a sign of respect for the occasion. Something I read years ago by Gretchen Rubin really stuck with me which is to “act the way you want to feel.” I find the same to be true for what we wear.

Putting on something happy gets you in the celebration mood! Green is my happy color.

My buy reco: The splurge from Tuckernuck. This dress could flex into any shower, brunch or graduation event. I like that it’s lose in the stomach and gives you comfort to enjoy the celebration.

#3 Tennis Match | “Here to Play”

Tennis is vital to who I am as a human. It’s provided a way for me to shutdown my brain and stop making lists. I play as much as I can. On a good week, 4 times. On a bad week, twice (I start to wallow if it’s any less than that). I can either wear a tennis skirt, top and sports bra or simply a tennis dress (with shorts). Voila!

My buy reco: scallops all day. I’ve had this dress for 4 tennis seasons. It is holding up beautifully. One of my most successful Amazon buys.

#4 Running Errands | Lunch “Here for Ease”

When I don’t even want to spend 60 seconds getting dressed, yet I want to dupe people into believing I’ve got it together, I reach for this dress. This dress is lovely when I’m bloated or tired or happy. If someone asked me to pack only one dress, it’s this one. Fit note: if you’re taller than 5’8 this will be pretty short on you.

Buy reco: choosing between the chambray and sea green? I can’t. I won’t.

#5 Date Night Out | “Here to Charm”

A little black dress does have its uses. It’s rare for us to have a dinner night out so I like to elevate the occasion by wearing something more sophisticated. I’m not sharing anything revelatory—a black dress can live in your closet for a decade or more! To make it feel new, you can add a belt like I’ve done below. Exchange the sandals for heels. Add a blazer (and boots) in colder weather. The trick to having a black dress stand the test of time is simplicity. Look for a simple shape without too many embellishments and a more synthetic fiber. I typically prefer cotton/linen, but in the case of black, it won’t hold up. Look for some viscose/nylon/elastane/spandex to be in the material.

To see all the items I linked in this post, you can go here. (I make a small affiliate revenue if you use these links and that helps support the work I do, so thank you).

Take Home Assignment For You

1. Identify 3 occasions that are a common occurrence in your life.

2. Think about what you’ve worn that makes you feel confident at each of these occasions and create a shortcut for yourself of “when I do this thing, I wear this.”

3. Shop for the occasions you listed as a priority over one-offs. If you go into the office a lot, but dresses for the office versus a bi-annual brunch.

Shopping smart is fun and I’m rooting for you.

Confidently Yours,
Marina

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