My personal style can be hard to pin down at times, but I know I’m doing something right whenever I put together a combination of clothes from my closet that feels like inverted armor — an aesthetic manifestation of all the things I like about myself, extracted from the core of what makes me me. Every time I hit upon one of these sartorial mishmashes and subsequently walk around all day feeling like the best version of myself, I’ve found that I always experience a number of interesting revelations about the overarching relationship between what I’m wearing and how I’m feeling.
I asked some of Man Repeller’s contributors what their “best self” outfits are, as well as how that relationship has played out in their lives. Read their answers below, as well as Leandra’s and my own, and deposit your thoughts on this topic in the comments.
1. Harling Ross (Me)
Tell me about your outfit and why it makes you feel like your best self.
Summer is my favorite season to get dressed because it allows me to wear my favorite garment: caftans (or really, any kind of colorful, loose cotton dress). I’ve actually noticed that winter can be emotionally challenging in that sense because I have to wear pants all the time, and most pants make me feel constricted/self-conscious. I crave clothes that I can move and breathe comfortably in, and this caftan from SZ Blockprints definitely fits the bill. Speaking of things that bring me both comfort and joy, these Maryam Nassir Zadeh sandals are the best summer walking shoes I own. The bag is also one of my favorites, thanks to its unique netting that somehow exudes the feeling of salt spray and sea glass — or at least it does to me. I felt really relaxed and really sartorially sated in this outfit, which is how I knew it worked.
What do you want this outfit to say about you?
That there is a secret extrovert inside me, waiting to emerge after a few heart-to-hearts or a few Aperol spritzes — whichever comes first.
At what point in your life did you really start to come into your own in terms of your style and why/what shaped that process?
This is hard to answer because I feel like my style is constantly evolving. I’ve always had fun with clothes, though, so that’s been a constant. I will say that since transitioning to the role of fashion editor at Man Repeller, I think I have a more informed relationship with style. I write about it all the time, I talk about it all the time, I do loads of market work (both browsing online and attending appointments) so I have a good sense of what’s out there, and that shapes what I want to wear. I’ve definitely become more decisive about what I like and don’t like.
2. Leandra Medine
Tell me about your outfit and why it makes you feel like your best self.
What do you want this outfit to say about you?
At what point in your life did you really start to come into your own in terms of your style and why/what shaped that process?
3. Tahirah Hairston
Tell me about your outfit and why it makes you feel like your best self.
It’s this vintage dress that I got in Paris over a long denim skirt from Zara. I’m going to be honest: I tried microdosing for a month, and the best part of it was that, for some reason, it helped me come up with some of my best outfit combination with clothes I already had in my closet. This outfit makes me feel like my best self because it works in many different scenarios — plus it’s fun.
What do you want this outfit to say about you?
That I have fun with clothes and in life, and “damn, that girl is good at layering.” Also, that I’m chill. So clearly a lot of things.
At what point in your life did you really start to come into your own in terms of your style and why/what shaped that process?
Developing my style has always been something I’ve been obsessed with. I had my own salesperson at Nordstrom when I was in middle school, and I’d talk to her about my look for the season (I’m talking glitter tees and leopard pants). I picked out the fabric and patterns for all of my homecoming and prom dresses in high school. I got really into thrifting and vintage in college. I definitely think I have had different levels of coming into my own style, and each stage has helped me refine my taste more. I’m still refining and figuring out what’s me, but I definitely know what I hate.
4. Juliana Salazar
Tell me about your outfit and why it makes you feel like your best self.
What do you want this outfit to say about you?
This is a hard question! I don’t know that I want this outfit to say anything in particular, but I never want my outfit to say I’m a mess.
At what point in your life did you really start to come into your own in terms of your style and why/what shaped that process?
I have never thought about my personal style as something I came into, nor have I related it to a specific point in time. As soon as I was able to dress myself, I did. I was super opinionated (read: annoying) about my clothing as a child. My mom says I was about five when I started refusing to wear the outfits she picked out for me. I vividly remember being so anal about my butterfly clips (they had to match my outfit) and rolling down my socks so they looked like doughnuts. I was the same way with my Barbies and American Girl dolls. I can remember so many instances as a child when I was obsessed with something super specific. I can still remember my favorite shirt and how I needed Old Navy flip flops in every color. I think I correlate my style to a strong sense of self, which I owe to my mama and papa.
For me, clothes/style is almost always an extension of whatever I am feeling and what mood I’m in. I would say 85 percent of the time, you can tell what’s going on with me by looking at what I’m wearing, but that connection can be really empowering. There have been countless times when I’ve used an outfit to fake a good mood. If I’m having a terrible day or really upset about something, I’ll wear clothes that are super bright or put extra effort into assembling an outfit — something I know I will like if I catch a glimpse of my reflection, or something that might solicit a positive comment from someone else. The latter example may sound silly, but sometimes you need a compliment or validation, and that’s okay. It always helps improve my mood.
5. Kellie Brown
Tell me about your outfit and why it makes you feel like your best self.
I feel like the best version of myself in a great dress. I feel powerful, attractive and feminine.
What do you want this outfit to say about you?
I want this outfit to say I’m really sweet — but also don’t mess with me.
At what point in your life did you really start to come into your own in terms of your style and why/what shaped that process?
I’ve always been into fashion, but for most of my teenage years, I felt really excluded from it. I think after moving to New York after college and landing my first fashion PR gig, I started to see how I could carve out my own path and make fashion work for me. Now, my clothes are usually an expression of how I feel at any given moment. Today a dress, tomorrow track pants and a head wrap, who can say?
6. Claire Beerman
Tell me about your outfit and why it makes you feel like your best self.
To me, this outfit is the perfect balance of dressy and playful. I’m a control freak who feels the most at ease when her apartment is cleaned and her pencils are sharpened. On the other hand, I hate routine, love to be thrown out of my comfort zone and really need my freedom. I’m also a bon vivant; I love to dress up as if I’m going to a cocktail party even though it’s a normal Tuesday and I need to see the dentist. I guess this outfit pretty much reflects that: the ironed shirt (stolen from my dad), ’60s Prada skirt and white Neous mules represent my love of orderliness. But the shirt is tied the other way round, the mules have globe-shaped heels and my earrings look like grapes — they supply the requisite dose of fun I long for not only when I get dressed, but also generally in life.
What do you want this outfit to say about you?
“I’m a disco ball who loves writing to-do lists.”
At what point in your life did you really start to come into your own in terms of your style and why/what shaped that process?
I’ve always had a penchant for elegant and glamorous clothes. I understood early on, probably mostly from watching my mother get dressed, that fashion has the power to counter the mundanity of everyday life — it’s a form of escape. I’ve had some confused phases (like after the movie Juno came out in 2008 and for three days all I wanted to wear were hoodies and ill-fitting jeans), but recently, maybe over the last two years, I’ve really come to understand what kind of clothes are “me.” I think that transition had a lot to do with accepting the feminine body I live in instead of trying to hide it. I realized I feel much better in a beautiful skirt that suits my shape than I do in a pair of heroin-chic ripped jeans.
7. Katie Sturino
Tell me about your outfit and why it makes you feel like your best self.
The print of the skirt, sunglasses and bag all make me so happy. They definitely give off a vacation vibe. I’m also obsessed with these Reebok pumps. Not only are they on trend, but they are also really supportive for my messed-up feet. Plus, you can’t go wrong with a Nudes sweatshirt.
What do you want this outfit to say about you?
That I’m fun … and maybe that I hail from Italy.
At what point in your life did you really start to come into your own in terms of your style and why/what shaped that process?
8. Yaminah Mayo
Tell me about your outfit and why it makes you feel like your best self.
This outfit is special because it cost me less than $40 to put it together. It also combines my two favorite things: thrifty prices and special pieces. The sweater is Forever 21, the skirt is thrifted, earrings are Machete and the Rachel Comey shoes were thrifted for $17.50!
What do you want this outfit to say about you?
This outfit (hopefully) says that I love to play with silhouette, color and texture, and that I’m put-together yet fun.
At what point in your life did you really start to come into your own in terms of your style and why/what shaped that process?
I used to fiend for designer clothes until I got them and realized designer clothes are nice but are not everything. I buy what makes me feel special. People seem to gravitate towards my style because they can sense that I’m comfortable. I’m not trying to one-up anyone else. Style can be great and low-key at the same time.
9. Stella von Senger
Tell me about your outfit and why it makes you feel like your best self.
I took this mirror selfie after dropping my kid off at kindergarten. I hadn’t showered or put on any makeup, which is very typical for a weekday morning as I prefer using my time to cuddle with my kid and make him food and convince him that it’s a really cool idea to brush his teeth and put clothes on instead of going to school naked. After all that I barely have a minute to get ready, so I literally wear whatever I see first, which is usually something lying on the floor from the night before. Ironically, getting dressed under these circumstances is always when I feel my absolute best. I didn’t waste a second on my outfit, so it’s comfortable and not overly styled. I felt like a good mum and ready to hustle for work.
What do you want this outfit to say about you?
That I don’t give too many fucks (I didn’t necessarily want it to say that, but I think it did just because I really didn’t give any). I can be wearing something not at all fancy and still feel 100 percent awesome, though.
At what point in your life did you really start to come into your own in terms of your style and why/what shaped that process?
When I became a mother, for sure. I just have so much less time to overthink things, and I also like my body much more. I have come to embrace how it feels to be a woman, which makes wearing clothes so much easier. I have a lot of fun with my style. I dress up like the character I want to feel like that day. Sometimes it’s a conservative WASP-y mom, but more often than not it’s just Stella — a.k.a. the sum of 25 different personas all wrapped in Jacquemus.
