Arlene Matthews is a Filipino-American fashion stylist, over 50 style influencer and content creator based in Chicago.
Arlene has spent thirty+ years inside Chicago’s fashion world — building, styling, curating, and shaping a point of view that comes from…simply, doing the work. For over two decades, she’s run her own creative practice, moving fluidly between retail, styling, and content in a way that mirrors the city itself: resourceful, scrappy, and quietly original.
8 years into creating as an entrepreneur, a milestone came with cofounding twentythirtyforty.net, one of the earliest lookbook-driven e-commerce sites. As the site gained momentum, so did the commercial styling work — and that shift became Kit This, a small, independent styling studio that worked across campaigns, billboards, and brand imagery. The work found its way into Vogue.it, Refinery29, Time Out Chicago, Lucky, Paper, Chicago Woman, Rue, Interior Design Magazine, Huf, Austere, Ugly Magazine — plus on-air contributor spots for Good Day Chicago and stories for Glossed & Found, Fete Lifestyle Magazine, and Bullett. It was a chapter defined by experimentation, strong visuals, and a deep connection to the people making things in this city.
Arlene’s perspective has always been shaped by the cities she studies when she travels as well as the city she lives in. At the same time, her Filipino heritage and the local makers she loves to support anchor her style, giving it a personal, lived-in resonance. That mix shows up in everything she makes now — her blog, her Pinterest boards, and her YouTube channel Yeah Older Yeah Cooler — offering a different, much-needed perspective on (life)style over 50 and inspiring her community to see their wardrobes with fresh eyes and more joy.
style content | youtube pinterest blog | gen X POV
Expertise
Authentic Style
Influence with Purpose Inspiring 50+
Commercial Styling
Creative direction
Brand collaborations
Cross-platform storytelling
Audience
40-65+ age range
95% female
core interests : style over 50, lifestyle inspiration, gen X POV, beauty, wellness
▶️ 2.8K subscribers, 8.3% lifetime engagement rate
📍22.1K followers, 20K monthly views
🌐 234 views, 192 unique visitors, 581 pageviews/month
Most memorable fashion moment
Walking into middle school, early 80's, in a small town in Wisconsin, wearing a full tuxedo. That day, I discovered my love of menswear 🖤 — and that people will always notice (and judge) by what you wear.
Spirit Icons…
Lalah Delia, author…”I pray you entered 2022 with more self-appreciation and self-worth. Your are worth it on all levels.”
Deepak Chopra, author & alternative medicine advocate…”breath in for four, hold for two, breath out for six.”
Style Icons…
Angela Dimayuga, chef, writer, activist.. First off, Filipina??!! Never have I ever. And second, her NYTimes article, that’s all.
Naomi Osaka, tennis pro, luminary, social change advocate …the color combos, the patterns, the shapes & silhouettes, the shoes, everything!
JiaJia Fei, digital strategist in art, culture & technology…her 2pc lewks tho
My Asian name is Sirikit
A non-exhaustive list of anti-Asian racism and AAPI organizations to support
AAPI - gives you the latest news and reports and a place to report a hate incident
CAAAV - this organization works to help build the power of low income asian immigrants & refugees in NYC
Apex For Youth - delivers possibilities to underserved Asian & immigrant youth
APIenc.org - increasing the visibility on the non-binary, queer and transgender AAPI community
Reduce, Recycle, Reuse please for Mother Earth
The Consistency Project - Those reworked Stan Ray painter pants! I’ll be traveling in those, for sure
Friendly Neighbourhood Flea - what a great unique collective of vendors and tight (only 25 total) so you can really spend time and shop each one
Black Market Vintage - curators of black curiosities, heirlooms and collectibles. Aaaand If your space needs a refresh, they work interior spaces…projects on their insta feed!
Beacon’s Closet - FOUR locations in NY, OK??
The Real Real - this one’s no secret…I have scored designer pieces for a fraction of the (resale) price.