I know that I’m not the only 30-something millennial woman who has struggled to figure what they should be wearing. It’s like one day I woke up, looked around, and didn’t recognize anything. My body was different, my lifestyle was different, but more importantly, so was my personality. In my 20’s I dressed like a college student, very casual most days and then scantily on occasion. Then after college, I dressed for work. I was in an office setting so most of my wardrobe suited that environment. On the weekends I only wore basic things or tried to make my work attire more casual. At the time, this didn’t feel strange. As a millennial of a certain age, at one point in time, business casual 24/7 was the norm. In retrospect, I see the tragedy that was my past fashion choices.

I turned 30, I also became a mom, moved to a different climate, and started working from home. As far as my wardrobe went, I pretty much had to start from scratch. I had to figure out what clothes made me feel confident but also fit my new life and body. This is pretty much the same experience many of the women I am in community with have. I, however, think I am temporarily out of that lost and confused state. Luckily for you, I came out on the other side with tips and tricks! If you need help finding your personal style, keep reading.
Set realistic expectations
The first step is to realize that you need to let go of a few things, physically and mentally. Due to weight gain/ loss, and body composition changes from pregnancy and breastfeeding, for over 6 years of my life it felt like I had a new body every few months. These constant fluctuations in the look and feel of my body made me self-conscious about almost everything I wore. The worst of this came from wearing the clothes I had before becoming a mom. Don’t be like me and take this as an opportunity to give in to self-pity, shame, and unhealthy eating practices.
Instead, get rid of those old tattered rags and the internalized-patriarchal-urge to “get back into your pre-pregnancy clothes!”. Focus your energy on your overall health and work with your body’s changes instead of against them. This work will health on your internal self-talk and show through your outward confidence! Remember, you deserve clothing that fits well and looks good at any stage of life you’re in. Realize that you will need to try new styles and silhouettes for your body. Stepping out of your comfort zone is where you will find the gold!
Do your research
Before you start buying things, you need to get very clear about what it is that you are looking for. The last thing you want to do is buy a bunch of Brunch outfits when you can never get a sitter or a brunch partner. Doing that will only make you feel more hopeless when you need to go to a doctor’s appointment and your only options are a tight dress and 4-inch heels or sweats. I mainly stay home to work and occasionally step out to run errands or to do family activities. The majority of the clothing I buy can be dressed up and worn to a restaurant with friends or dressed down for back-to-school night. It’s a cool-young-mom vibe.
After you decide the overall vibe you want to go for, you’ll need to know how to flatter your body shape. I will admit, this is a lot harder than any other step. But there are lots of articles to read and quizzes online you can take. The Kibble body type test is a popular self-assessment that will help you figure out your body type. If you want to take a shortcut, you can always google body types and see which ones best resemble your body. After that, search for outfit ideas that fit in that category to pick what you like.
Going through this process helps you study yourself and learn your body. Through this process, I have gained a better understanding of what structures of fabric look better on me. I have paid attention to those details, as well as what fabrics hug my body the best, and this has made shopping both in-store and online much easier. For example, I learned that stiff, high-rise denim with a button fly is great at holding in the mom-pooch. Before having kids, I hated a button fly and never wore anything besides stretchy skinny jeans. But now those same pants make me feel like an over-stuffed tube of toothpaste. This is why it pays to keep twirling, twirling towards the future.

Look in the right places for inspiration
A major part of my self-love/personal style journey included unfollowing most celebrities and style influencers who have a completely different body type than me. I think most of us have had this experience. You watch someone try on a great outfit in a haul video, and excitedly place your order. Then suddenly you’re shocked and disgusted that the mirror tells an ugly truth. Unfortunately, the body does NOT come with the clothes. Honestly, we can add this to the set realistic expectations section.
I try to only follow people who are in my age range and have a similar body type, lifestyle, and sense of style as me. Consuming this content validates my personal experience through representation, and gives me a non-toxic place to find practical outfit ideas. This also helps me save money when it comes to trend cycles. I am one of those people who has learned to approach trends with caution. There’s nothing wrong with trying trends but, you need to have an understanding of your body and sense of style first. This will save you time when it comes to trying out certain trends. For instance, low-rise jeans are allegedly coming back into fashion. I do not live the lifestyle, nor do I have the body type to successfully pull that off. So, I will be sticking to the high-rise, straight-leg jeans that I’m used to (yes that was a TLC reference). Everything, aint for everybody!
Do the work
I think a lot of people underestimate how labor-intensive achieving personal style can be. Unless you have a personal stylist, you will have to get out there and find what works for you. The hardest part about this is that you soon realize there is no “Forever 35” store or “Cools Mom’s R’Us”. I think I can speak for all of us when I say we took the ease of shopping for granted when we were in our early twenties. My divorce from Forever 21 was UGLY. I kept trying to come back and make things work but in the end, we had to part ways. (sigh!)
But I did say I have a good sense of style now, so where did I land? Unfortunately, the answer is, everywhere which is both freeing and terrifying. I cobble together my wardrobe by mixing pieces from Target, Old Navy, and the thrift store. Picking up things from stores like TJ Maxx and Marshalls is another favorite of mine. I also find great unique pieces at boutiques.
I figured out that I liked these stores by constantly, and by that I mean on a weekly basis for a while, searching through those racks and trying on everything. Sorry to break it to you, but you gotta try that stuff on sister. Before you leave the house to shop, make sure you eat a light meal. Put on your best nude bra & panty set, a little makeup, and do your hair. Set aside at least 1-2 hours and dedicate that time to trying on the clothes you like. In the dressing room, take photos and videos of yourself and save them for later.
Don’t feel pressured to buy anything on each trip! No matter how desperate you are for clothes. When you get home, study those videos, and make note of the pros & cons. Think about how the pieces made you feel and use that information to optimize your next shopping trip. If you don’t like the way the maxi body-con sun dress hugged your mid-section, you either need a new size, proper under garments or to style a different style of dress.
Bonus tips
Hopefully these tips and guidelines have helped you get started on your personal style discovery journey! Here are a few bonus tips that are just as helpful!
Get a tailor: It’s not as expensive as you think! Spending an extra $15-$20 to have straps adjusted, a waist band brought in or your pants hemmed can really elevate inexpensive clothes. But most importantly, they make your inexpensive clothes look more expensive by making them fit for your body!
Beef up your accessories game: The right shoes, jewelry and purses can really elevate any look. When you are on the go and busy, simple outfits like jeans and a white bodysuit can fit any occasion. Adding statement pieces and accessorizing well makes that basic outfit more chic and adds in personality.
Play dress up often. Any time I buy a new piece I try it to mix and match it with things I already have. This increases wearablity but it also weeds out those impulse purchases. If I can’t wear a piece 2-3 different ways, it goes back to the store!
Your dedication to quality is evident.
Thank you so much for saying that! I appreciate you 🙂