5 Things I Wear in My 30s I Never Wore In My 20s

July 10, 2017



"Remember when you had long hair and wore jeans and contacts and we used to go outtttttttt?" a friend drunkenly asked me as we hung out in my kitchen late one night, recalling the heyday of our single girl times together. At the time it was the dead of winter in Vermont, my son was still less than a year old, and I was rarely changing out of hoodies and leggings. I could see why my friend would pine for more glamorous days, but what she was missing was that since those days as a flighty single girl, I had really come into my own and found a style that worked for me. No, I didn't feel the need to get fully dressed on days when I knew I wasn't going to leave the house with a child who couldn't walk yet, in 20°F weather, but when I did go out, I felt good about how I looked, and I was willing to try a lot of new things I wouldn't have dared in my twenties. We all receive so many signals, both subtle and overt, that many fashion choices are only for the thinnest, blondest, most able-bodied, youngest, perfectly tan (but not brown) skinned, most traditionally feminine bodies out there, but I am finding when you push past those messages, there are a lot of fun and awesome people and experiences on the other side. Here's the five things I am wearing in my 30s I never had the guts to wear in my 20s (also geeeeeez how emo am I in that old photo?):


1) Crop Tops: I started my thirties off with a bang, and bought my first ever crop top to wear to my 30th birthday dinner. There was something freeing about being out of my 20s that made me feel like I could try some trendier and more daring styles without feeling like I was wondering what everyone thought of the choice. I continued to love crop tops with high waisted skirts through my days breastfeeding my son, as they gave me an option that didn't require a lot of clothing adjustment. 

 2) Super Trendy Hair Styles: I dabbled with bright colors and short hair when I was younger, but never did I see a trend running wild and say to myself "I'm going to get in on that!" If anything, I picked styles that were specifically NOT stylish, in an effort to show how cool and detached I was from the masses. I thought I was too cool to join in with the crowd. Well you know what, the crowd is full of awesome stylish humans who are happy to have you join them! I am blessed to have healthy hair that grows quickly, so constantly changing my look with fun colors and bold cuts on the edge of fashion has been an incredibly fun form of self expression, and a great way to instantly bond with strangers when you meet someone with the same or similar look. My current mermaid colored side shave pixie is super trendy and comfortable for summer. I am really enjoying playing with less overtly feminine styles as I grow more confident in myself and no longer see people telling me I "look like a lesbian" as an insult. 

3) Bikinis: I bought a little black and neon strappy bikini six months postpartum, after many years of wearing a relatively modest J. Crew one piece. Why? Because I no longer felt the need to monitor how other people thought I looked in a bathing suit, and I thought it was darn cute. I only have a few stretch marks, but my belly button sure does look different than before I had a baby, and I wear both changes proudly. Also since I had a baby I have run way hotter and sweatier, so the less suit the better! 


4) A full face of make-up: When I was younger I had almost exclusively male friends, and I totally bought into the idea that being "not like other girls" was a good thing. By that logic, I really didn't wear any make up unless I was going to be on stage, because even deluded 20-something me knew that nobody looks good all washed out by stage lights.  It wasn't until I got into my late twenties and started actually making female friends that I learned that A) "not like other girls" is some misogynist bullsh*t, not actually a compliment, and B) makeup can be really fun and make me feel even more like myself. Now I love taking the time for myself to highlight my natural features, and bring some fun colors, glitter, or whatever else I feel like adding to the lovely canvas that is my face.


5) Shorts: I definitely did not wear shorts in my 20s, except as pajamas. I couldn't get over being self-conscious about my legs. Do I have "better" legs in my 30s? Hell no, but I love that they are strong from walking everywhere while carrying a 25lbs person, and I value my comfort over what other people my think of my very pale legs. Skirts don't offer the flexibility and coverage I need chasing a toddler, and pants are just too darn hot some days. Not only do I wear shorts now, I have even been known to wear that most daring of clothing items, a shorts romper.


If you find yourself reading this and thinking "that's all well and good for you, but you're a petite white chick, I could not wear these things" then check out these examples of how absolutely fabulous these kind of confident fashion choices can look on all shapes, sizes, and colors:
Latinas Celebrate Their Bodies by Rockin' Crop Tops
Five Black Body Positive Women Who Will Inspire You to Love Yourself Just as You Are
11 Plus Size Women In Crop Tops Who Prove You Don't Need A Six Pack To Look Hot

And last but not least this fantastic Queer/Trans Lingerie Shoot

How has your style evolved as you've gotten older and wiser? I would love to see before and afters if you want to share on Facebook! For more wisdom on this topic, check out this excellent article on 7 Things Women in Their 30s Should Stop Wearing. 




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Hey, I'm Jillian, and I'm creating an extraordinary life on an ordinary budget. 

I'm just an actual person, trying to make sh*t work. I'm doing pretty okay at it.  About Me.

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Hey Jillian features articles on self-care and mental health, budget beauty, parenting, recipes and meal planning, DIY home improvement projects, and product reviews relevant to people who are interested in those things. xoxo Jillian
Jillian Kirby | Burlington, Vermont | Email me at hi@heyJilliankirby.com