Back to Basics: A Simple Work Outfit

Today’s outfit is from Cupcakes and Cashmere circa 2015.  It’s simple, easy and perfect for a business casual office.  But let’s punch it up for a professional office and bring it into the 2020s.

Blouse // Emily is wearing an abstract print camp shirt, but I wanted to choose something with a little more whimsy.  This Equipment star-print shirt is a popular choice.  This floral shirt from Scotch and Soda is also a nice option.  If you want something more like the inspiration photo, the look for you is this ecoWish top from Amazon.  Plus-size?  Couldn’t find a button-up, but this printed Eloquii tie neck is lovely.

Pants // I don’t care what Gen-Z says, slim-fitting pants are fine.  Those super high-waisted, cropped, wide legs they’re wearing work on almost no one.  I like these Ryan-fit pants from Banana Republic because they’re Audrey Hepburn slim as opposed to aughts-denim skinny.  They’re also washable, which is great.  And they go up to size 20, and are available in long and short inseams.

Blazer // Epic work jackets can still be found on sale racks throughout the web.  This $400 Alice + Olivia jacket is now under-$100.  So if there are brands that you have long admired but never been able to afford, dip over to their site, hit the sale rack and see what you find.  Hugo Boss is a great place to start.  Rebecca Taylor and Reiss are also worth a stop.

Bag // I run into so many ladies who tell me they struggle to find simple, modern work bags.  There is only one solution: Matt & Nat.  These vegan leather bags are designed for working women, and they’re almost all under-$200.  This small satchel is very cool, and it’s made from recycled materials.

Shoes // The inspiration photo has the menswear-inspired lace-ups that were popular in 2015.  If it were 2019, I’d put in a pair of cap-toe flats.  But since most of us are still wearing slippers, I decided to stick to a simple neutral flat.  I like these Naturalizer flats.  If you’d like something in black, these Malone Souliers mules are the perfect shoe for summer, or stick to a basic with these Bandolino hidden wedge flats.

Sunglasses // The round sunnies aren’t on trend right now, so I chose my favorite pair of frames: these Ray-Ban black and gold aviators.  I get so many compliments when I wear them out.  Yesterday, a woman chased me out of a nail salon to ask where I got them.  They’re very cool.

{this post contains affiliate links that may generate commission for the author}



  1. Allison says:

    I like this approach! Take an old favorite and update. Very helpful.

    July 1, 2021/Reply
    • Lee says:

      Agreed! Such a great way to freshen up my perspective.

      July 1, 2021/Reply
    • Cait says:

      +2 This is exactly what I need! It’s really helpful and practical to see ways to update outfits that I would’ve worn in the past but that feel a little off now.

      July 1, 2021/Reply
    • N. says:

      Also agreeing with this! Love the idea of taking something old and making it new!

      July 2, 2021/Reply
  2. Rachel says:

    +1! These types of styling tips are exactly what I need. I have a lot of clothes from 5+ years ago and I’d love to learn more about how to update things. I really appreciated this!

    July 2, 2021/Reply
  3. Cait says:

    Amen! High-waisted, wide-legged, cropped pants flatter no one. I love that you’re still styling some options with much more flattering pants options!!

    July 13, 2021/Reply