What I Wear In My 30s: Stylish, Classic Clothing that Kills

Updated 10/02/19
Product Disclosure

Allyson Payer shares her experiences with, and advice on, shopping and outfit-planning as a 30-something fashion editor for our sister site, WhoWhatWear. Although Allyson's style has certainly changed since turning 30, she believes that age is just a number and people should wear whatever makes them feel the coolest and most confident.

Upon turning 30 I didn't exactly wake up and decide, "OK, I can't wear this anymore." I've just found that as time passes, there are certain clothes I simply don't want to wear anymore and that some things I wore in my twenties no longer mesh with my current wardrobe. I realize, though, that everyone's style is different: What I don't want to wear in my thirties might still work for you, which is perfectly fine.

Here, I've pinpointed 10 pieces of clothing I'll be skipping for the foreseeable future, alongside some post–age 30 alternates. See them on me (IRL!) and shop the pieces I'm presently wearing on repeat.

Ditched: Ultra-Skinny Skinny Jeans
Kept: Straight Skinny Jeans

Skintight jeans are something I left behind with my 20s, although I haven't ditched skinny jeans altogether. Instead, I opt for roomier styles that look cooler to me now.

A brown-haired girl with a long rust colored coat, white blouse, skinny jeans, and snakeskin cowboy boots.
@allypayer
A woman modeling a pair of slim fit, ankle length jeans.
Citizens of Humanity Olivia High Rise Slim Ankle Jeans $238
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Ditched: Cheesy Graphic Tees
Kept: Special Graphic Tees

No tees reading, Tres Chic! for me anymore. These days, I shop for more unique versions that are a bit more interesting. Clearly, this unicorn rainbow tee by Re/Done fits the bill. (It's sold out, but there's another one I also love, below.)

A brown haired girl wearing a white tee with a unicorn-and-rainbow print.
@allypayer
A black vintage looking Blondie tee with the singer singing on a microphone.
MadeWorn Blondie Distressed Printed-Cotton Jersey T-Shirt $160
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Ditched: Shorts With Less Than 3-Inch Inseams
Kept: Modest Shorts

In the summer, I used to practically live in short shorts, but I don't feel very comfortable in them anymore. Luckily, there are plenty of cool, longer styles as opposed to the Daisy Dukes of yore. And, for the record, I disagree with anyone who says denim cutoffs shouldn't be worn beyond age 30.

A woman wearing cutoff denim shorts and a floral long-sleeve blouse.
@allypayer
A woman modeling cutoff denim shorts with a white tee and white sneakers.
Agolde Dee Ultra High Rise Shorts $128
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Ditched: Trendy Sunglasses
Kept: Classic, Cool Ones That Flatter My Face

I'm always intrigued by the latest "It Sunglasses," and used to order them online without even trying them on. I then wore them even if they didn't suit me. These days, I invest in classic styles I'll wear for years—like this Krewe x Reformation Ward pair I'm wearing. Although the Wards are no longer available, I found similarly-shaped frames, below.

A brown-haired woman wearing sunglasses and a leopard-print shirt while sipping a cocktail.
@allypayer
A pair of green tortoiseshell sunglasses atop a table with a flower and striped blue and white tablecloth.
Krewe x Reformation Milan Sunglasses $215
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Ditched: Glittery Sneakers
Kept: Neutral Kicks

I went through a bit of a sparkly-sneaker phase at some point in my 20s, which, I'm relieved to say, I've outgrown. They were certainly fun but I've learned that versatile black sneakers suit me better in my day-to-day life.

A brown-haired girl wearing sunglasses, a black leather jacket, black jeans, and black sneakers.
@allypayer
A pair of black Nike M2K Tekno Sneakers with white outsoles.
Nike M2K Tekno Sneakers $100
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Ditched: Boho Gear
Kept: Two-Piece Sets

I was never much of a bohemian clothing-type girl, but there were times when I dabbled with it in my 20s. I eventually learned it doesn't suit me. When I want to wear something fun when the weather is warm, I gravitate toward chic two-piece sets.

A brown haired girl wearing a black and white two-piece set of a crop top and long pants.
@allypayer
A woman wearing a green polka dotted two-piece outfit with black leather sandals.
Reformation Liana Two Piece $248
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Ditched: Tulle
Kept: Silk and Satin

Although actress @sarahjessicaparker beautifully pulled off a seafoam tulle skirt off on Insta, I feel a little silly wearing it at this point. Among the clothes I'll never retire? Sophisticated silk and satin pieces, like this silk-crepe number.

A woman wearing a black and white polka dot dress with red shoes.
@allypayer
A black and white polka-dotted dress
Réalisation The Violette $225
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Ditched: Low-Rise Jeans & Leggings
Kept: High-Rise Styles

I don't find low-rise jeans and leggings to be all that flattering on anyone, but back when they were cool, I wore them anyway. Luckily, I think high risers are here to stay. And my outfits are so much better for it.

A brown haired girl wearing high-rise jeans, a zebra-printed jacket, sunglasses, and black leather boots
@allypayer
A woman modeling a pair of black, high-waisted, cropped jeans
Goldsign The Cropped A Jeans $325
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A woman modeling a pair of gray Alo High-Waist Lounge Leggings
Alo High-Waist Lounge Legging $98
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Ditched: Short & Tight Dresses, Skirts
Kept: Flowy Ones

Some of the tight dresses and skirts still lingering in my closet make me cringe. I'm much happier when I'm wearing something that skims—not hugs.

A woman modeling sunglasses, a jean jacket and a white and black polka dotted dress.
@allypayer
A woman modeling a long green floral dress
ASOS Design Midi Tea Dress $60
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Ditched: Flip-Flops
Kept: Rubber or Leather Slides

Despite the fact that designer (and heeled) flip-flops have reemerged, I'd much rather wear pool slides. They're more polished.

A long-haired woman wearing a striped tee with a jean skirt and black pool slides.
@allypayer
An Isabel Marant Hellea Leather pool slide.
Isabel Marant Hellea Leather Slides $430
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