There is a phase you enter as a woman – typically in your 40s – that no one really talks about. You aren’t 25 anymore, but you’re not ready to adopt the ‘all elastic-waist’ wardrobe. You are raising children while also dealing with aging parents. You have lived several decades of life; your body has changed- slightly or significantly- and your tolerance for discomfort has waned. What hasn’t waned? Your desire to feel confident and put-together.
In this stage of life, your identity is more defined, priorities more clear; but your closet hasn’t quite caught up yet. You don’t relate to every trend you see and you don’t want to look like you’re trying too hard. At the same time, you also aren’t ready to give up on style.
This shopping guide is personal to me as I have recently hit a stage where it feels like nothing fits and I find myself having a “nothing to wear” moment almost everyday. I made a decision recently to start asking myself- What would actually feel good to wear? instead of What’s up with my body? This is the beginning of my journey to find items that fit, feel good and look good.
Finding My New Fit
If I am being completely honest, the biggest challenge I face at the moment comes down to one very specific area: my waistline. No matter how many crunches I do, my once-perfect ‘skinny’ jeans get tighter every year. The constant adjusting and sucking in is getting old. So instead of trying to force my body into what used to work, I have realized it’s time to find clothes that actually fit, and most importantly, I feel good in.
I started my new style journey from the comfort of my own couch (aka online). The only downside to this is the potential for endless returns when things don’t fit or look the way I thought they would. There is a lot of trial and error when shopping this way which is why I’m hoping what I have rounded up will save you some of that hassle. Here are the online finds that checked all of my boxes: comfortable, flattering around the waistline, and under $100.

The Key Pieces
- Straight Leg Jeans, $41.99, Amazon
- Cotton Modal Maxi Dress (Black), $82.00, Skivys
- Cotton Modal Midi Dress (Leopard), $68.00, Skivys
- Flutter Sleeve Maxi Dress, $35.69, Amazon
- Stripe Cap Sleeve Top, $12.99, Amazon
- Cap Sleeve Maxi Dress (Navy), $69.90 Quince
- Organic Poplin Button-Down Shirt, $69.95, Gap
- “Booty Boost” Leggings (Nightshade), $49.00, Spanx
- Linen Maxi Dress, $74.00, Quince
- Gauze Maxi Pool Cover-Up, $61.60, Anthropologie


The Accessories
Accessories do a lot of the ‘heavy lifting’ when your outfit leans neutral and also adds instant polish. A great pair of earrings or a bright shoe can add warmth and personality while also staying current and on-trend. The best part? You don’t need to spend a fortune here either. There are so many great outfit completers out there for under $100 and I have rounded up a few of my favorites below.
- Mesh Mary Jane Flats, $24.97, Nordstrom Rack
- Peak Burn Blue Sneaker, $59.97, Nordstrom Rack
- Leopard Star Sneakers, $62.00, Adelyn’s Boutique
- Gold Chain Hera Necklace, $48.00, Baublebar
- Gold Evil Eye Pendant, $28.00, Shop Fête
- Basic Sun Hat, $75.00, Carter & Co Hatworks

Some New Truths
During my search I have learned some new truths: Low-rise skinny jeans have become high-waist straight leg jeans. Minis are now midis and maxis (which honestly feel much more chic). Shoes do not have to be designer or name brand- there are some great dupes out there. A hat can cover a lot of hair sins and is great for protecting your skin. The best part? Looking put-together does not have to cost a fortune- everything featured here is under $100.
Since it’s Rodeo season, I must mention that many of these pieces would be great for a trip to the Houston Rodeo. Pair any of the maxi dresses back with a pair of boots and you are good to go! If you haven’t already, check out the Houston Mom’s Rodeo Guide for everything you need to know before heading out.













