How to Start on Your Own Style Journey!

Hey everyone! I had a reader ask me how did I begin my transition to my current style. You can read about why I started here but she wanted to know the first steps. She felt she was in a style rut and what she was wearing didn’t reflect on the outside who she was on the inside. Her usual go-to stores and go-to styles were starting to look matronly on her and frumpy. So, if you’re in a style rut or just haven’t given style a thought in years, I’ll explain how I started. With fall clothing out in the stores, now is a good time to start because most places put their best styles and largest selections out in the fall.

Before you start though, please read this post here about shopping tips so you won’t be frustrated. Also, you have to be in the right frame of mind to do this. Think of it as an adventure or as looking for treasure. It’s not going to happen as you run out to the store on your lunch hour. Ok, let’s do this.

First, and easiest, shoes.

I was convinced I couldn’t wear heels anymore. I refused to put my feet in any pain whatsoever so I didn’t even look at the heels. I kept buying flats or tennis shoes or clogs. I saw a group of women my age at an art event and they all had on tall boots with heels and they looked so stylish. I thought I’ll just give it a try and see if I can find some low-heeled tall boots. They had been in style for the last 10 years and didn’t look like they were on their way out and gosh, they looked cute.

style for apple shapes and big bust

Read original post for this outfit here.

I went to Famous Footwear (a staple in any mall) and tried on a pair that were $75, not cheap but not outrageous. I have a 17 ” calf, which is considered wide-calf, so I had to look for boots that had some stretch in the calf, usually stretchy fabric near the zipper, or were labeled wide-calf. I found a pair that I loved and were so comfortable. The heels on the boots are about 2″ high which I would never wear in a pump, but because the structure of the boot stabilizes your ankle, you don’t feel like you’re teetering in them. In fact, these are incredibly comfortable, even more comfortable than my flat pair of boots and I am able to walk long distances in them because my feet feel secure and don’t slip around. Now that the weather is getting cooler, you will be able to wear these boots for months.

best looks for big bust

Read original post for this outfit here.

If you’re definitely not interested in any heel at all there are cute options for tall boots with no heel like these. Either way, tall boots will up your style game immediately and show no sign of going out of style any time soon.

office wear for apple shapes and big bust

Read original post for this outfit here.

Second tip: get a jacket you love.

I don’t mean outerwear or something you wear from the car into the building. I mean a “third piece” jacket. An outfit looks more put together when it has a third piece. Usually the top is the first piece and bottoms are the second piece and the third piece can be a scarf, vest or sweater. I would recommend starting with a jacket. They usually have more structure and are less clingy than a sweater, which works for us apple shapes. Now, if you’re busty like me, or carry your weight in your stomach like I do, do not insist that the jacket buttons up or zips up. This jacket is meant to be worn open anyhow, and if your shape is like mine, to find a jacket that will zip usually means it’s huge in the shoulders and arms and looks like you’re wearing a box.

Make sure you find a style you like. And by that I mean when you put it on you say “Hey! Foxy lady!” and maybe do some dance moves in front of the mirror.  I’m at the point in my life where I want to look a little bit “bad-ass”. I want clothes that have some sass and go against the typical aging woman stereotype. The black faux leather jacket you see below was my first clothes purchase after the boots. I found it at Dress Barn (stores all over the U.S.) for around $50 in 2014. I wear it all the time and even though it doesn’t zip, no one will ever know! I just knew when I tried it on that this was totally my style and I was going to wear the heck out of it.

style for apple shapes and big bust

Read original post for this outfit here.

Last tip.

My guess is you wear lots of black pants. Don’t be embarrassed. I see tons of women wearing them every day no matter the season. I know. They’re easy to wear. They hide everything. They go with everything. All you have to worry about is dog or cat hair on them. I know. I’ve been there. My last tip is to buy a black skirt. Don’t freak out! Trust me, it won’t be that different from wearing black pants. There are many to choose from in many shapes. I prefer a pencil shape or straight shape and find the A-line shapes or skirts that flare out look terrible on me. Find a shape you like and pair it with your new tall boots. Now, I know you may be self-conscious about showing your legs, but a pair of black tights will completely cover your legs or you could get a longer skirt. If you have purchased the tall boots and a pair of black tights and are wearing the black skirt you should still be able to wear the tops you already own under your new jacket. You will be able to ease into this new style without looking like you’ve changed your personality.

best looks for apple shapes

Read original post for this outfit here.

So, that’s how I started this style journey. First the boots, then the jacket, then the skirt. It was enough of a difference to give me style without shocking my co-workers and family. It was just a bit of a change to get the ball rolling and helping me define my style. It made me realize I could do this. It gave me that confidence boost that a good outfit can give you, something I hadn’t felt about clothing in 20 years. And then I’ve been on a roll ever since…!

 This post contains affiliate links for products I love and own or love and would like to own!

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  1. This is a GREAT post, thank you! I went back and re-read all the posts you linked to and now feel motivated to find black boots and actually wear them. Yay!

  2. Good tips for easing into change. It’s amazing how we feel our clothing defines us…and how sensitive we are to how other people will perceive us based on our clothing and GOD FORBID the tiniest of changes! But it’s true. We do…and we are.

    So yeah, unless you’re a balls out serious bad ass MAMA, baby steps do just fine 🙂

  3. I love how you keep fashion so simple! I love how I can bargain shop for clothing wardrobe staples that you recommend! Hey, let’s face it – some of the outfits and clothing that I see other fashion bloggers wear and tell about are so outrageous in price, that there is no way I could afford any of it! I swear it was meant for me to accidentally find your blog! Thank you for the ideas and keeping it real for us normal people!

  4. I have the exact opposite problem. I’m a AAA so I have to figure out how to dress without looking like a lopsided Christmas tree! Love your style, especially your statement necklaces.

  5. This is such good advice! I live in boots during the winter but haven’t gotten new ones in forever. I’m looking forward to shopping. I ride a motorcycle so I have plenty of leather jackets. I’ll have to start incorporating them, into my everyday wardrobe.

  6. Great tips, it really is about trial and error until we find what works . I totally agree about the ability of a jacket to always add a little something
    Thankyou for your kind comments on my blog.

  7. Really great tips, Julia! It is amazing how a nice completer piece can so transform a look. I enjoyed seeing the many different styles you featured here, especially the black sweater and patterned skirt.

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