button up shirt front

There’s nothing more versatile or universal than the classic button up shirt. Made popular for women by Katherine Hepburn, the top goes by many names, shapes, lengths and cuts. As the era of fashionable androgyny continues on, the lines of men and women’s fashion become ever more blurred. On today’s “How-to-Style” series, I created three looks with one very classic piece.

button up intro

Traditionally, shirt dresses were always worn by men and boys whereas women wore blouses. Most stores will label the button up a blouse versus a shirt. Now, both men and women benefit from the button up and it is a standard item that should be in everyone’s closet as a staple item. I wore my favorite monochrome button-up from Forever21 that I purchased a few years ago (a testament to Forever21 making clothes that last despite what critics say) and styled it according to my 3 main lifestyle focuses: casual, work and going out.

Button Up Shirt: Casual Look

button up shirt casual two

I partnered up with accessories brand, MissCo Girl for this casual look. I believe in understated style to make big statements. Monochrome and/or muted tones need attitude to back them up, the Ying to a minimalists Yang. Button up shirts are perfect for the pre-fall season.

button up shirt casual one

Shop Similar Look:
Hat $12, Necessary Clothing | Shirt $40 H&M
Shorts $30 Zara | Boots $90 Zara

For a casual element, button up shirts shouldn’t be taken too seriously. A loose fit is fine and not worrying about whether to tuck or not tuck is okay, too. As summer comes to a close, mixing shorts and booties is a great way to style this pre-fall look.

button up shirt missco

If I’m wearing all black and white, I like to add a pop of color or print and I love the alien print on the Digital Print Backpack by MissCo Girl! Weekends are very on-the-go for me and I try to carry as little things as possible, so this bag is great for my lifestyle. Added bonus: use my code SITTINGPRETTYSTYLE10 to receive a fun surprise on your first MissCo Girl order!

Tips for Casual Wear:

  • Looser fit tends to feel more relaxed
  • Don’t button your collar
  • Leave half the shirt tucked in, half tucked out

Button Up Shirt: Work Look

button up shirt work one

A nod to one of my favorite fashion icons, Audrey Hepburn, I love pairing cigarette pants and/or black skinny jeans with a classic button up. Work outfits should have a bit more of a structured look to them and adding a blazer never hurts, but during the summer heat you can still get away without one. I button my shirt all the way to the top adding a fun necklace and a bright, bold lip for some personality.

button up shirt work two

Loafers are one of those amazing shoes that are both a staple and a trend. Once considered a casual shoe, the loafer is a chameleon going from weekend casual to city lounges. Loafers are amazing shoes for work. In a lot ways, work can feel like a very “gender neutral” place depending on the type of career you have. For many, dressing “too feminine” or “too masculine” can have negative connotations, no matter how wrong they are. I feel like loafers and other similar shoes break those connotations by creating a space that is neither masculine or feminine, yet both because it’s all about how they are styled.

button up shirt work three

Shop Similar Look:
Pants: $39 Urban Outiffters | Lippie Stix in Bossy $5 Colourpop.com
Loafers $50 Zara

Tips for Work Wear:

  • Button up your shirt – it’ll look and feel more professional
  • Add a statement piece – we tend to repeat many articles of work clothing, accessories make them feel fresh
  • When in doubt, tuck it in

Button Up Shirt: Street Style

button up shirt look three one

I like to wear my trendier pieces to go out. It’s fun to be a little bold, whether it be with a leather skirt or funky shoes. Let me say, you can totally wear a button up for a night out! I’m all about standing out in a crowd and we all don’t have to wear tight dresses for a fun evening. I kept it classic with my button up tucked into my shirt for a clean look.

button up shirt three two

Adding the leather skirt and bag gives the polished look a little edge. Fun fact: I wore this skirt for both my 23rd and 24th birthday – two great nights! It’s totally fine to wear trendy pieces and mini skirts as long as you feel comfortable and it looks good on you.

button up shirt suede

Shop Similar Look:
Skirt $40 Nastgal.com | Bag $48 Nastygal.com
Shoes $198 Nastygal.com

Suede, lace up and blocked heel – hitting three major trends for Fall! Just as in my casual and work looks, I love to add a pop of color and these shoes finish pulling off the look without trying too hard. Living in New York, I walk around a lot and unless absolutely necessary I will choose a comfortable heel to go out in. Thank goodness for fate: these shoes are a little pricey, so I held off on them for the longest time. Then, I get an email from Nasty Gal (which is why you should totally sign up for my newsletter, I announce this kind of stuff!) that they were having a mega shoe sale and wound up getting these with a 70% discount (the end).

Tips for Street Style:

  • Pair a classic button down with a trending piece
  • Add a fun item for visual interest
  • Roll up the sleeves for an even edgier look

Have a favorite way to style your button up? Leave a picture or comment in the comment section below! Don’t be afraid to mix things up and don’t think button ups have to come in a specific style. Just like us, they come in all shapes, sizes and colors. Until next time.


Check out more “How-to-Style” Series below:

How to Style A Pajama Shirt Dress

How to Style Relaxed Skinny Ankle Jeans

Product was sent as a gift but all thoughts and opinions are my own**


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