6 Easy Outfits You Can Wear From Work to Dates: Button-Front Shirts

I was charged with the task of finding outfits that could transition smoothly from work to date nights. I’m going to be honest; it was an extremely difficult task. When I picture what I usually would wear to work, it seems quite different from what I would wear for a night out on the town. As you probably know, I am a kindergarten teacher. I don’t always dress this snazzy when I teach. In fact, I have a dozen pairs of flats, favorite pair of green chinos, and an unbelievably fuzzy sweater that I love to wear with everything. Not exactly the most flattering outfit to go out in afterwards. On the other hand, I didn’t want to be wearing something sexy to go and teach a bunch of 5 and 6 year-olds… that would just be weird! After some reflection on my own wardrobe and research on Pinterest, I found one clothing item that kept reoccurring in photographs of work and date wear…it was so simple, but it was button-front shirts!

In general, I don’t show my button-front shirts enough love, and mostly because I think they are too masculine for me, especially when I wear them with pants. I also picture myself wearing one when I first interviewed for a teaching job. At that time, I had the whole interview suit, complete with button-front shirt underneath. Never mind that it was 80-90 degrees in the sweltering summertime! So, they can seem a little stiff and masculine, which is maybe the opposite from what you want to wear at a date (I like to be feminine and soft, but to each her own!). However, after my scouring of Pinterest, I did find multiple outfits using button-front shirts that would be a great flow from work to a date. I also have some other ideas for quick ways to make your button-front shirt look more professional or flirty.

1. Tied Button-Front Shirt Over Dress

  • For work: Wear your button-front regularly buttoned, or tie the front. Make sure your midriff is not showing by wearing the shirt over a dress or skirt with an undershirt. This look works best for midi skirts and A-line dresses, but you could also try it with a pencil skirt. Many work places insist on closed-toed shoes, so I found a pair of Mary Janes that are just adorable from Red Velvet Memphis.
  • For dates: Tie the front of your button-front. Make sure the bottom 2 or 3 buttons are undone to make this easier. Check for your tag sticking out, so that you don’t look like a dork (which I forgot! LOL). For your date, you can wear the rest of your buttons open or closed… oooh la la!

2. Button-Front Tucked into Pencil Skirt

  • For work (Top and bottom left): I chose shorter heels with a closed toe. I also wore an understated pair of crystal earrings. I liked this button-front with this skirt, even though both are patterned. The horizontal stripes in both tied the whole outfit together.
  • For dates (Middle and right): If you drive from your work to date or carry a large tote bag, you can change out your jewelry and shoes for something a little sexier. I am wearing black mule heels, a statement necklace, and matching earrings in place of the work accessories. No matter how conservative your outfit is, if you add bright, bold jewelry and heels, you are going to look fierce.

3. Button-Front With Lace or Leather

  • For work: Choose a “sexier” fabric like lace or leather. Make sure it’s an appropriate length. I love this two-tone pumps. They worked with almost all of the outfits!
  • For date: You don’t have to change anything! Isn’t that fabulous?!

4. Wrap the Shirt Around Your Waist

For work: Wear the button-front normally. Underneath, have on a solid tank or tee. I wore this look over top of an A-line dress. I coordinated the print on the top with the red in the dress. You can find out more about A-line dresses here, if you’re wondering what I’m talking about. They really do work for everyone, and are so versatile!
For dates: Tie the button-front around your waist. It could be a more casual look with sandals, or as you see here, more formal; it almost looks like a beautiful layer to the dress.

5. Make it a One-Shoulder Top

For work: Just wear the button-front normally. I would tuck it into the midi or pencil skirt.
For dates: Wear your button-front shirt as a one-shoulder top. I saw this in Glamour Magazine for July 2017. They gave credit to a fashionista named Tamu McPherson for styling her shirt this way. First, put one of your arms into the shirt. Then, button a few of the buttons underneath your opposite armpit. Wrap this sleeve around your waist and knot with the unbuttoned section at the bottom of the shirt. I loved how this looked, but I could see my boyfriend saying, “What’s wrong with your shirt??” Haha!
By the way, you can also make it into a STRAPLESS shirt. Place the collar of the shirt above your chest (don’t put your arms in!). Button the second from the top button so that it’s buttoned right between your breasts. Button the shirt the rest of the way down, then take the sleeves from around the back of the shirt and tie in the front. Voila!

6. Make it an Off-the-Shoulder Top

For work: Again, wear normally and tuck into your skirt.
For dates: Button 3 or 4 of the buttons in the middle of your shirt. Fold the collar of the shirt back and over your shoulders slightly (it will probably slide forward a tiny bit). Roll the sleeves up to help the shirt stay in place. I could see a fun bra or camisole slightly peeking out under this. I think this was my favorite look. πŸ™‚

To sum it all up…

  • You can simplify your accessories for work if you want a more streamlined, chic look, and brighten them up for your dates if need be.
  • Choose a “sexier” fabric for the skirt (leather or lace).
  • In general, wear your button-fronts over appropriate-length dresses or skirts (Remember the finger tip rule??).
  • You can tuck them in, tie them in front, button normally…wear them however your little heart desires.
  • Wrapping your shirt around your waist can either make your look more casual or formal, depending on how you style it.
  • You can wear re-style your shirt so that it is an off-the-shoulder top, strapless top, or one-shoulder top.
  • One more tip is that you can always make your button-front more professional by adding a blazer on top.

That’s all, folks! Tell me which look was your favorite. Was there anything that you found surprising or interesting? Lastly, let me know if you have another way that you love to style your button-front shirts.

Until next time…


36 thoughts on “6 Easy Outfits You Can Wear From Work to Dates: Button-Front Shirts

Add yours

    1. It really is nice to be able to use pieces in different ways! I think #1 is the one I would wear most for teaching. It’s most “me.”


    1. Thank you! Most of them are actually dresses, believe it or not, other than the black and white striped skirt. I should wear these shoes more often


  1. As a teacher I also find it hard to dress for going out right after work. I loved these ideas especially the first look with the full skirt!

    Liked by 1 person

    1. Yes, that look is the most teacher friendly for sure! I would wear it in a heartbeat. Then you don’t have to change a thing about it!


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