How to Style the Cheugy Clothes Still in Your Closet


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Source: @lifew.erin
Source: @lifew.erin

“If wearing skinny jeans is wrong, then I don’t want to be right,” I say to myself as I fall upon yet another TikTok of a Gen Z-er scrolling through items, behaviors, and fashion choices that she deems to be “cheugy.” There are some aspects of Club Cheug that I can happily part with (“Live, Laugh, Love” home decor, the word girl boss, and fitted denim jackets, mostly because I find them restrictive), but if you come for my love for The Office, graphic tees, or charcuterie boards, I’ll double down and watch The Office while wearing my favorite Budweiser graphic tee while snacking on a charcuterie board. Let me live my life.

They can tell me that some of my favorite fashion choices are “out,” but quite frankly, they can’t make me care. With an ever-evolving fashion scene and trends that come and go comes the pressure to toss what’s labeled “out-of-style” and buy the next best thing, only to have it return slightly rebranded by a younger generation years later. The best part about being older is being wiser, so we’re not giving in to generational pressure this time around. Here are five ways to restyle those “cheugy” pieces in your closet that you refuse to part with:


1. Skinny jeans

shirt jacket / plus size shirt jacket / white tee / plus size white tee / black skinny jeans / shoulder bag / pointed-toe booties / gold hoops

I may be a bit dramatic. but give me skinny jeans or give me death. I’m all for a little playful banter between generations (cue me lovingly muttering, “OK, boomer” to my mother on a bi-weekly basis), but when Gen Z suggested that skinny jeans were a thing of the past, I about lost my mind. As someone who houses a plethora of skinny jeans in a far-too-small closet, I will fight for my right to wear skinny jeans, and I’ll make it my life’s mission to look good while doing it. 

Pairing skinny jeans with pointed-toe booties that just barely cover the hem and balancing a fitted lower half with an oversized tee and shacket is a foolproof way to update your basic skinny jeans. Pair the look with a shoulder bag and a simple pair of gold hoops to help elevate the ensemble.


2. Velvet headbands

button-down shirt / plus size button-down shirt / sweater vest / plus size sweater vest / straight-leg jeans / leather mules / leather tote / velvet headband

The Blair Waldorf stan in me is not giving up on big, velvet headbands anytime soon, and if you like them, there’s no reason that you should give up on them. Not only are large headbands a gift from the heavens on bad hair days, but they also serve as the perfect way to pull together a preppy outfit that’ll help you live out your wildest Gossip Girl dreams. Couple your velvet headband with a collared shirt, an oversized sweater vest, and leather mules for the perfect in-office look that will make you look polished in no time flat.


3. Block heel sandals

mock-neck undershirt / pullover sweatshirt / plus size pullover sweatshirt / leather trousers / plus size leather trousers / leather tote / block heel sandal / chain necklace

Whoever said that block heel sandals were out of style was seriously wrong. I’m not parting ways with my block-heeled sandals today, tomorrow, or ever for the simple fact that they’re the perfect summer shoe that transitions easily into fall. In early autumn, when temps are still lingering too high to be living our full-out fall dreams, block-heeled sandals let our feet breathe and keep us looking chic while doing it.

This crewneck sweater, mock-neck undershirt, and leather trousers combo doubles as an elevated office look that can transition beautifully into a date night out in downtown Chicago. Pair with a leather tote and a gold chain necklace for a fall outfit you’ll return to again and again.


4. Graphic tees

black pinstripe blazer / plus size black pinstripe blazer / graphic tee / high-rise jeans / baguette bag / Chelsea boot

Give up my go-to, oversized Budweiser tee because someone called it “cheugy?” Never. I have a thing for vintage graphic tees, and dressing them up for a night out happens to be one of my favorite hobbies (what can I say? I don’t get out much). I always have this particular outfit formula in the back of my mind for the times that I find myself spiraling out of control, 13 feet deep into my every-other-day outfit crisis. I love pairing my oversized graphic tees with slouchy jeans and combat boots and will add a structured blazer, a baguette bag, and simple gold jewelry to elevate the look.


5. Crossbody bags

trench coat / plus size trench coat / cropped hoodie / plus size crop hoodie / faux leather leggings / baseball cap / crossbody bag / white sneakers

As much as I flirt with the use of a good shoulder bag, my one true love is my go-to leather crossbody purse. Fashion aside, I have the memory of a fish, and I simply cannot be trusted with a bag that isn’t glued to my bodice. Crossbody bags are truly the only way that I can fashionably achieve this, and if you ask me, it still helps to elevate an outfit if it’s done right. For the most sophisticated Trader Joe’s run you’ve ever experienced, throw on a cropped hoodie, leather leggings, and a trench coat that is made more functional with comfy white sneakers, a hat to hide from the haters, and a crossbody bag that won’t leave your side.


and five that have to go