My friend, Jake, is really into fashion. Not so much thrift shopping like me, but fashion nevertheless. Sunday during choir practice, he leaned over and told me how he read my last post on the five dollar bag and was really curious how I would put together outfits, especially with the pants and the “hobo jacket”. He presented it as a dare, or a challenge.

At first I was like, “I’ll show him!” But a challenge it really was.

I started by shortening the pants using pins along each of the side seams.

I didn’t quite know where I was going with this idea when I started. I just began putting outfits together. Eventually I found a workplace style, a more casual ensemble, and a night-on-the town look. Tell me what you think!

I’ll start with workplace, because that was the toughest.

In case you forgot the pants in question. .

To begin with though, if you have baggy something, top/bottom, the other half of you should be form fitting. This, for example, is baggy pants, so form-fitting top. You don’t want to look like a sack of potatoes.

 

Look #1

Obviously solid colors are key so I started with this basic brown sweater. The sleeves are rolled for a more “let’s get to work” look. This one is a very safe, not too crazy or daring look.

Look #2

This is a somewhat causal but professional ensemble. I pulled my hair back also.

 

Look #3

#3 is my favorite, because of the plain yet elegant way of the black, which holds back and lets the pants speak for themselves.

Next, for cute and casual.

#1

As you may know, I love orange and fall colors. So I was excited that this put-together is actually in season.

I changed the shoes and added a knitted sweater to look cozy.

#2

I’m not totally sure how I feel about this one, so I had to share it. I was going more for modern, but I can’t decide if it’s the shoes or maybe the fact the green is a little off. Or maybe you like it? I don’t know.

 

Look #3

Finally I had to do a more sweet/cute look, because the other ones can be a little feisty looking. I wanted to prove you could pull “sweet” off too. The pants are floral after all. Just a solid tee and some pearls did the trick. Even a cardigan could work.

And finally for the conversion outfit. One that can go from work appropriate. . .

Pulled back hair and collared tops seem to scream “professional”

To, ready for a night out. .

 

Tell me what you think in the comments below! And what your favorite look is. =-) I hope you enjoyed this!