What to wear when you don’t know what to wear

I’m just going to go ahead and say it…I wear the same outfits A LOT. There’s been so much hype in the blogging world and concern from clients (before we get started,) about creating a brand new outfit (bloggers) or not worrying about others remembering outfits (clients.) But especially with our warm fall weather and being in a bit of a flux state with my weight (but losing, yay!) I feel absolutely fine about relying on my basics and repeating my favorite outfits fairly recently.

As my good friend and fellow San Francisco Bay area image consultant, Elena Daciuk, always says:

“It’s better to look good every day than to look different every day.”

I truly think this makes so much sense! And I gotta say I find a lot of comfort in Elena’s wisdom.

The truth of the matter is (and this might sound completely counterintuitive to what I do for a living,) people don’t pay as much attention to what you’re wearing as you think they do. 

What does matter is that you:

  • Feel confident in what you’re wearing
  • Your outfit is fully accessorized, coordinated and complete, i.e. it’s a great outfit!

Back when I used to work in an outside sales position (where we were required to go to the office each morning, ugh!) I remember being concerned about repeating a basic pair of black pants. No one ever made any comments on my black pants repeating. Co-workers only made comments on my more fashion forward, statement outfits. (It was truly only a couple of guys who didn’t understand the looks, and it drove me crazy that they felt as though they had license to comment on my style.)

The beauty of basics is they’re not memorable, and you’re able to change the look of an outfit with absolute ease!

At this point, you may be wondering, “So Dana, what have you been wearing.” I thought I’d share a few of my workhorse pieces/outfits that have been in heavy rotation lately. First off, I want to mention that I personally use the wardrobe sheets I make with my clients. If you’ve been reading my blog a lot, you know how much I believe in advance outfit planning.

Here’s a sneak peek at the basics that have been my lifesavers this fall:

My black fringed skirt. Okay, so not exactly basic, but a phenomenal skirt: a year round fabric, looks good with booties and over the knee boots.

My black flared skirt…that I’ve, no kidding, had since about 2005! I actually prefer it to my pencil skirt, as it’s easier to wear with flat shoes/boots (the key to lasting 5000 steps through the mall on my searches!)

My black Vince “ski pant” leggings. They are a thick fabric, seamed in the front and back and are a very thick fabric. Sophisticated and versatile, I usually wear mine with a long dressy sweater or leather trimmed tunic with the patent booties (which are also an elevated style.)

Black basic bottoms

My black blazer, (yep that exact one…I’ve had it a while.) It goes with everything! I wear it with jeans, grey pants, and just about everything else.

My black pencil skirt. As you can see from the photo below, it can be dressed way down as well as dressed up with a blazer for a bit more of a corporate look.

Of course, my jean jacket. This one is by Jag and by far the most flattering and comfortable one I’ve ever had. I’m not sure if they’re still available or not, but it’s super stretchy and soft.

denim and pencil


My black culottes. Believe it or not, I don’t have any black pants right now! These have been a perfect sub this fall. Very often I’ll wear them with a lightweight long sleeved blouse tucked in with my flat, black patent booties (yet another basic…most comfortable shoes I’ve ever owned!)

My dark, skinny jeans. Although rarely for work, I sometimes wear them pre-shopping (by myself) with the blazer.

And then I have a few knit tops, blouses and lightweight sweaters along with a couple of dresses (that I can’t wear as often because they require heels.) That’s about it. Now if the weather were cooler, I could definitely expand on these pieces, but truly I feel great in all of these outfits built on my favorite 3 season basics.

Give a variety of your basics beyond your everyday black pants a try. I promise even though you may repeat some outfits (like I do,) you’ll always look great and feel great each day.

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3 comments on “What to wear when you don’t know what to wear

  1. Great article, Dana! Like you, I have kept my work wardrobe super simple…a solid black dress, black flared skirt, black slacks, black jacket, and a black cardigan. I then brighten the look with different colored tops and accessories appropriate for the day. Keeping it simple has saved me time and allows me more purchasing power for those special occasions and “fun” events.

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