How to Style 1 Shirt 7 Ways – OOTW

Happy Friday, friends! We made it through another week.

As part of a new series, I thought it’d be fun to post the outfits that I wore this week. I don’t often feel like I’m a terribly creative person, but I really like putting outfits together and I would say that is definitely the one area where I do feel a little creative.

I had a little more focus when I put my outfits together this week. After wearing a navy flannel shirt to walk the dog last Saturday, I decided to style it and wear it for the rest of the week.

It’s a shirt that I bought secondhand at a consignment shop last fall for my husband. And although I picked it up in his size, it didn’t fit him. I really liked it so I decided to keep it for myself. But I didn’t reach for it much.

After wearing it this past week, I don’t know why I ignored it. It was really easy to style and I felt really comfortable all week. The outfits that I was able to create felt like “me”.

The shirt has a masculine vibe and I think I paired it with a good mix of items for some versatile outfits. But I’d love to hear your opinion at the end.

All of the items that I wore this week are old favorites. Of the items that I wore, 11 were secondhand, 3 were made by me and 9 were new. If you see something that you like, I encourage you to search for it in the secondhand market first 🙂

So, that’s enough blabbering from me. Let’s get to the outfits.

Outfit 1 – 10.11.2020

My main goal when I get dressed is to look put together but to still be really comfortable. This goal has definitely become more of a priority this year, and even more this fall. I’m sure many of you can relate.

A white woman with blonde wavy hair is wearing a navy blue shirt unbuttoned over a black top and rust colored pants. She is also wearing black combat boots.

I really like the look of an oversized shirt with a pair of casual pants. There’s a level of effortless chic to it. I paired the shirt with an old black bodysuit and a pair of pants that I made.

A closeup of the shirt, top and pants. The necktie and necklace are also very visible.

I added my black combat boots because they are my favorite cold weather boots and I think they complete the outfit perfectly.

For accessories, I tied a grey silk hankie around my neck and added my very old gold necklace and pendant. And of course, my watch and forever present scrunchie.

\\ Outfit //

Vintage Freedom Foundry Flannel Shirt

Old Bodysuit

Arnite Pants (pattern)

Dr. Marten’s Leona Boots

Ozma of California Silk Hankie

Outfit 2 – 10.12.2020

When I had planned to wear this shirt for the week, I had immediately thought of a couple of outfits that I wanted to try. Wearing it with this dress, which was my very first item that I ever made, was at the top of the list.

A white woman with blonde wavy hair is wearing a navy blue shirt unbuttoned over a cream colored dress. She has the shirt and dress belted at the waist with a black belt with a silver buckle. She is wearing black moto boots with silver arrow detailing.

Since the previous day’s outfit had a more casual vibe, I decided to dress this outfit up a little while still keeping it relaxed. I added a vintage belt and a pair of moto boots. The silver detailing of the belt paired perfectly with the silver detailing of the boots.

I hadn’t used my old black backpack in a while, so I grabbed it off the shelf and it think it was the perfect finisher piece. It’s been important to me to use items that aren’t too fussy right now and a backpack that I can sling over my shoulders has been great!

\\ Outfit //

Vintage Freedom Foundry Flannel Shirt

Wilder Gown (pattern)

Vintage Belt

Frye Moto boots

Old Backpack

Outfit 3 – 10.13.2020

I love the simplicity of a matching set. It’s kinda like a dress in that “one and done” aspect of dressing. And I have been loving the combo of navy and tan lately.

This vintage set is made from a tencel/rayon blend, so I’m trying to get a little more wear out of it before it gets too cold and I have to (a) layer underneath it so that I don’t freeze, or (b) put it away until spring.

A white woman with blonde hair tied up into a knot is wearing a navy blue shirt unbuttoned over a matching tan tunic and pant set. She is wearing Leopard print socks and brown Oxford shoes. She is using a grey hankie as a headband.

I added some cool blue earrings, fun leopard print socks and my old brown oxfords. My hair was a hot mess and I was too lazy to do anything about it so I pulled it up into a knot and added my sill hankie as a headband. I actually think it really adds to the outfit so that was a win-win 🙂

\\ Outfit //

Vintage Freedom Foundry Flannel Shirt

Vintage Timbuktu matching set

Old Børn Oxfords

Matatraders Earrings

Ozma of California Silk Hankie

Outfit 4 – 10.14.2020

I have been counting down the days until it was cold enough to start wearing this sweater dress again. It’s a vintage dress that I found last fall. I had been looking for a sweater dress for a while and the initial plan was to look for a wool sweater dress. But when I came across this cotton mock neck dress, it felt like the perfect item!

A white woman with blonde wavy hair is wearing a navy blue shirt unbuttoned over a long black mock neck dress. She is also wearing a black circle waist belt under the shirt and black combat boots.

I added my gold necklace, which I put outside of the mock neck (this always feels very 80s to me and I love it), along with my circle belt bag. The bag was perfect for carrying my stuff and also for adding a little shape to the dress.

A closeup of the shirt, dress and belt. The necklace is also very visible.

And of course I’m wearing my combat boots again because I think they are the perfect compliment to this dress!

I would 100% wear this outfit again! And probably soon.

\\ Outfit //

Vintage Freedom Foundry Flannel Shirt

Vintage L.L. Bean Sweater Dress

Cuyana Circle Belt Bag

Dr. Marten’s Leona Boots

Outfit 5 – 10.15.2020

I decided to dress this shirt up today while simultaneously dressing down this pant and blouse combo, or at least I think I did.

I found this vintage silk blouse at a consignment shop last fall and it has become one of my most favorite pieces. It’s funny how I used to feel so precious about silk clothing and now I treat it and wear it like any other piece. I no longer believe that the best stuff should be saved for special occasions. Even though I wore my best stuff for the everyday before the pandemic, it has definitely been driven home now!

A white woman with blonde wavy hair is wearing a navy blue shirt unbuttoned over a cream colored blouse with an equestrian print. She is wearing brown wide leg trousers and brown heeled boots.

This blouse has a great equestrian print of a jockey on a horse. I love the rich browns and greens. And I always think that it pairs perfectly with these wide leg trousers.

A closeup of the shirt, blouse and pants.

My secondhand brown suede boots are always a fall go-to and I also grabbed this vintage mini bowler bag that I purchased last year.

This bag smelled so badly of cigarette smoke when I bought it. So I soaked it in the sink and used some detergent to lightly wash the leather. After it air dried and I confirmed that the smell was gone, I used some leather conditioner to make it supple and shiny again. I also had to repair the shoulder strap as it was coming apart.

That little detour was just a friendly reminder that even the grossest secondhand items can usually be redeemed. Remember this post?

\\ Outfit //

Vintage Freedom Foundry Flannel Shirt

Vintage Chebella Silk Blouse

Secondhand Eileen Fisher Pants via Eileen Fisher Renew

Secondhand Free People Suede Boots

Vintage Chaco Mini Bowler Bag

Outfit 6 – 10.16.2020

I had totally planned to wear a different dress with this shirt. But then I saw this one hanging there and I realized that I hadn’t worn it yet this year.

This is a dress that I bought online secondhand last year. I had seen a friend wearing it about a year before and I searched high a low for it for a while before giving up on it. Then one evening, I was browsing online and I found it in my size.

My patience definitely paid off!

A white woman with blonde wavy hair is wearing a navy blue shirt unbuttoned over a red and pink floral midi length dress. She has her hair tied back at the base of her neck. She is also wearing a black belt under the shirt and black combat boots.

I really enjoy the juxtaposition of the soft floral print of the dress with the combat boots. This dress is a pretty dressy piece and I think the shirt and boots make it more suitable for everyday wear.

Because it has a heavy floral print, I like to wear a belt with it, just to break it up a little. And especially if I’m wearing a pair of heavy black boots. I think it gives it a little more balance.

There are little black flowers all over the belt which feels fitting with the dress.

And I love the little gold pins that hold them into place. I think they tie in nicely with the brass detailing on the boots.

\\ Outfit //

Vintage Freedom Foundry Flannel Shirt

Secondhand Burberry Brit via The Real Real

Secondhand Tory Burch Belt via The Real Real

Dr. Marten’s Leona Boots

Bonus Outfit

I ended up liking this more, like way more, than I thought I would when the combo crossed my mind. I’ll probably wear it all weekend!

I’m a pretty big fan of oversized silhouettes and have no issue wearing oversized pieces together. Sometimes it works out and sometimes it doesn’t but that’s the fun of experimenting with clothing.

A white woman with blonde wavy hair is wearing a navy blue shirt over a brown and white gingham maxi dress The shirt has the top 2 buttons closed and the rest is left open. She has her hair tied back at the base of her neck. She is also wearing a brown and black leopard print low heels boots.

This is a dress that I made back at the beginning of summer. It has a pretty open neckline so I would have to wear something under it or over it during the colder months. This shirt was perfect.

I simply did up the top 2 buttons and let the rest of the shirt hang open. This allows the rest of the dress to “peek” out from underneath. I think this helps the 2 oversized pieces to work well together.

For my feet, I chose my low heeled leopard print booties for a little pattern mixing. I’ve learned that if I keep differently printed items in the same color family, it typically works out.

\\ Outfit //

Vintage Freedom Foundry Flannel Shirt

Gingham dress made by me

Huma Blanco Ortencia Boots

Well that’s it for what I wore this week. This series is something that I’ve had on my mind for a while and I had fun planning it and putting it together this week.

I’d love to know what your favorite outfit was.

Do you have a similar shirt that you can style a number of different ways?

Until next time,