How I Changed My Style and Became a “Dress Person”

How I Changed My Style and Became a “Dress Person”

Do you ever wish you could adapt to a new style but aren’t quite sure if you should or could? Here’s how I changed my style and started to regularly wear more dresses. The same concepts apply to other style changes like scarves, accessories, hairstyles, etc.


When I was pregnant with Carter, I saw all sorts of cute maternity dresses. I even bought a few, but I never wore them. It can be hard enough with your changing body during pregnancy to feel stylish, but since I never really wore dresses (except on special occasions/events) before being pregnant I felt uncomfortable and felt like I looked strange. Those cute casual maternity dresses never got worn. After I had Carter and went back to work, I decided to try to start incorporating more dresses into my wardrobe so I had more options.

Really, what it comes down to is if you feel confident in whatever you’re wearing, then the style is a good fit for you. That was my problem… I felt uncomfortable so the different style didn’t look good. You know, the old… “it’s not you, it’s me.”

Because I traveled for work a fair amount during the time, I decided to start out by wearing dresses more during my work travel. It gave me time to get used to the new style when I wasn’t necessarily seeing the same people everyday. Plus, dresses are easier to pack.


Now, I more often wear dresses than pants to the office. I find I have a lot more versatility with dresses – I can switch around cardigans, accessories and shoes which provide more wardrobe options.

Other pros to wearing dresses: Less Ironing. Easy to dress up or down. Dresses are more forgiving if you gain a few pounds (also a con!).

I even chose to wear a dress for our family pics this year.


Tips for Transitioning to a New Style:

  • Start gradually.
  • Try it out at a time you won’t be in your normal environment so you won’t feel self conscious around people you know – like on the weekends, traveling, etc. I often try out new hairstyles on the weekends.
  • Don’t depart too much too soon from your current style. Example: If you generally wear more solids than patterns, don’t choose a patterned dress.
  • Choose your best colors. Don’t go too far out of your comfort zone. If you normally wear black, choose black, gray or navy to start with, then work your way in to other colors or add color with accessories.
  • Enlist help. Take a friend with you, or find ensembles you like online through Polyvore or Pinterest. Show them to salespeople in your favorite stores and have them help emulate the style for your body type.
  • Remember that you’re likely to be the one to notice the change more than anyone else, so work on feeling confident with your new look.

At first I only wore dresses late spring to early fall because I thought I hated wearing tights and pantyhose (can we all agree, that’s a weird word!). Eventually I came around though and realized tights, hose, and leggings could be comfortable – if they were the right fit and quality.


Recently Kushyfoot, a brand of premium tights, reached out to me and wanted to send me some new tights to try out. The first time I put them on I was impressed with the fit, they were thick and tight – in a good way – and the feet are patterned on the underside with ridges that make it them almost massage-like as you walk. I wore them one day on my recent work trip to NYC. 10,000 Fitbit city steps later and my feet were still going strong!

12200A_3 kushyfoot

They also sent me these cute Flats to Go. I keep them in my work bag. They are more slipper like than real shoes, but they’ve come in handy a few times when my heels were really hurting my feet or when I was in my hotel room and needed to get something in the lobby quickly.


My favorite places to buy dresses for work or casual wear: Banana Republic, Loft, Ann Taylor, Gap, Old Navy, Target.

How about you, any tips for styles you’ve transitioned to? I still haven’t quite tackled statement necklaces!

1 Comment

  1. So true! I’ve always been a jeans, t-shirt and sandals girl, even in the winter (although I live in Phoenix, so it never really gets cold), but I’ve been wanting to dress a little more stylish on the weekends. I ended up buying a pair of boots, some leggings, and a couple cute tops and now I love how it looks. It’s more comfortable than I thought it would be and I definitely feel better when I look better. Now I just need to work on statement necklaces and scarves!

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