Outfit Ideas for Entrepreneurs

If you’re like most of us entrepreneurs, we spent a lot of time at our desk, meeting clients or doing the in-between (desk-to-seeing-clients) and comfort is key.

And, like everything, please apply this guideline as just that- a guideline. 

Vest, Hanna Lee Style, www.hannaleestyle.com/blog

Let’s talk leggings

One of my most heated newsletters to date- leggings!

As a mom, especially during those chase days of a younger one, I totally get the love of leggings. An oversized sweatshirt and leggings? COMFY.

AND, they should not be worn as pants (because they are not pants).  Think of leggings as a thick pair of tights. 

I imagine you wouldn’t wear tights out of the house..as your pants.

Would you? 

Here are three outfit ideas to wear your leggings to look put together and still feel comfortable:

  1. Wear a sleeveless white tunic, long sweater and a funky belt
  2. Wear a printed dress (great in case stains happen) and complete with a denim jacket
  3. Sleeveless white tunic with an open sweater and a scarf.
Legging Outfit Ideas, Holiday Outfit Ideas, Hanna Lee Style, www.hannaleestyle.com/3waystowear
Legging Outfit Ideas, Holiday Outfit Ideas, Hanna Lee Style, www.hannaleestyle.com/3waystowear

Have you noticed a pattern here? Butt.is.covered! 

California entrepreneurs going from hiking to co-working

The quick switch (this is for your Kristen!)  Let’s say you’re super tight on time and you’ve just gotten done hiking a wonderful trail yet you have to meet clients or look presentable in your favorite co-working space.


Here are 3 outfits to go from cat-suit hiking to pulled-together-in-a-pinch.

Remember, the KEY here is to cover your butt.

1.  Add a long cashmere sweater, belt and finish with a silk scarf.  (Not a belter? Opt for a zip-up sweater here).

2. Add a sweater dress, scarf and shoes.

3.  Add your favorite shawl vest, cinch with belt and of course-shoes. 

P.S- simply changing these layers/ fabrics will work wonders to easily adapt to whatever climate you’re in.

Pull-on pants AKA legging alternatives that feel equally as comfortable 

Here’s the thing, you can be comfortable and look stylish.  When I saw my client Julie (hi Julie!) she had on these fabulous casual-but-pulled-together pants.  Obviously I asked her where they were from and she said Athleta. The same thing happened next time I saw her. I couldn’t believe how chic-but-simple they were. (That’s the magic people!)

Particularly pull-on pants. (Which, by the way, have come a long way in terms of style and there are one million available options right now).  

The key here, especially to upgrade your look quickly to go out and meet clients is wearing that layer or pull-it-all-together piece (in some cases, it may even be that ONE necklace that makes your outfits feel pulled together!)

For most folks I work with it’s that layering piece that makes you look professional but not stuffy (ahem, my favorite swazer as described here). 

Favorite Pull On Pants:

  • Fabrizio Gianni
  • Athleta has so many wonderful options
  • Brynn Walker
  • UP!

You’ve been buying the wrong size denim. Here’s why.

As a comfort freak I used to be pretty anti-denim until I found fits and stretches that were comfortable. I TRULY believe when you find that comfortable denim pant- game changer!

Click here to watch the video: The BIGGEST “SECRET” about finding denim that fits.

Watch this here to be blown away (I swear you’ve been buying the wrong size denim and this is why).

A few of my client favorites:

  • NYDJ particularly the Marilyn bootcut
  • Joe’s jeans
  • Levis
  • Jcrew
  • Mother
MixandMatch, Hanna Lee Style, www.hannaleestyle.com/shoppingtakestime

Paige denim is one of my favorites (especially for us short gals) and this denim was originally purchased three sizes bigger in the waist (yes THREE) but I purchased to fit my hips/thighs just as I encourage you to do. I hope you can tell from this picture that clearly these fit my hips/thighs.

Professional denim outfits you can copy:

Denim + white top + leather blazer 

Business Casual Outfit Ideas,Hanna Lee Style, www.hannaleestyle.com

Denim + white top + vest

Business Casual Outfit Ideas,Hanna Lee Style, www.hannaleestyle.com

Denim + blouse + open sweater


I LOVE a comfy jumpsuit.

Bathroom breaks are not the easiest but if you find the right one, it can feel like you’re in pajamas.  I love them because…duh, versatility!

Swap this heel for a mule and ditch the belt (but add necklace) for the ultimate comfortable look.

Why You Should Find a Style Uniform:

If I say what do you think of Steve Jobs and Mark Zuckerberg wardrobe? What do you think of? A uniform probably. A turtleneck and a sweatshirt…and I get it! 

While you don’t have to be, ahem, as boring as those two uniforms you can steal this wardrobe hack to get dressed easily—->The outfit uniform!

Sorry for the ridiculous amount of pictures of myself in here but I wanted you to get the drift.  Vests are one of my go-to’s (if you didn’t know by now..ha!) and I help women have equally-easy “outfit uniforms” so they can get dressed without much effort or thought and look absolutely put-together. 

How can you create a “uniform” to make your life easier?

Here are three uniforms you can steal:

  1. Blazer + scarf + skinny pant or wide leg and a boot 
  2. Vest + shirt + scarf + shoe
  3. (Maybe you have great legs..show them off!) Sweater-blazer + skirt + tights +boot
The best boot for winter

Alternatively, clearly I have a uniform when I have client fittings: