Although what triggers embarrassment differs from person to person, some universal staples remain ever controversial—ahem, skinny jeans, for instance. No shade intended to those who love their slim-fitting denim, but we know for a fact there are quite a few people who wish they could scrub the internet clean of any evidence that they wore super-snug skinnies every single day. Yes, they were the denim silhouette that defined the mid-00s, but did any of us actually look good wearing skinny jeans back then? Jury's still out on that one. Few other denim styles have remained as "controversial" in the court of public opinion, so the denim style's recent return to the fashion world has struck many by surprise (or absolute terror, for some).
Now, we're entering a whole new era of tight-fitted jeans, as a succession of brands began releasing slim-fitting denim. Unlike previous versions of this "scary" denim trend, we've seen designers make the style more approachable through slightly looser fits, minimalist washes, and elongated hemlines—resulting in skinny jeans that are, dare we say, so much more flattering. Beyond the runway, we've seen this denim style surface in the real world too, as the style set has slowly incorporated slim-fit denim back into their closets. It's proof that this particular denim is back, whether we like it or not.
While we doubt everyone will ardently adopt this denim trend again, some styling rules could make skinny jeans more appealing (at least for some). Dubious? Ahead, we've made a case for skinny jeans by curating a few outfit ideas and some shopping recommendations. Consider this your rule book for wearing skinny jeans sans regret.
#1. Opt for a Monochrome Look
WEAR: Simple Earrings + Cropped Gray Jacket + Gray Skinny Jeans + Gray Handbag + Slingback Flats
Styling Notes: One of the simplest ways to make any pair of skinny jeans look far more sophisticated is to stick to a singular or super-minimal color palette. Whether you opt for a pair of jeans in a slate-gray wash (as shown above) or another denim wash, you can make them look elegant by styling them with elevated staples in matching shades—e.g., pair them with a tailored jacket, a small handbag, and slingback flats. It's a simple formula that works every single time.
#2. Go for Jeans With a Dark Wash
WEAR: Black Sunglasses + Black Blazer + White T-Shirt + Black Skinny Jeans + Black Shoulder Bag + Black Ballet Flats
Styling Notes: If you can't picture yourself slipping into a pair of white skinny jeans in the foreseeable future, consider going for a darker denim wash instead. By opting for skinny jeans in black, you'll make this controversial denim silhouette easier to style without overthinking it. In fact, we'd argue that you can treat wearing black skinny jeans like an old pair of trousers by styling them with your tried-and-true staples: a black blazer, a white T-shirt, a black shoulder bag, and black ballet flats.
#3. Shop Skinny Jeans With a Split-Hem
WEAR: Black Sunglasses + Gold Hoops + Red Blazer + Red Belt + Red Suede Shoulder Bag + Split-Hem Skinny Jeans + Black Ankle Boots
Styling Notes: In addition to considering the shade of your skinny jeans, another way to make this silhouette feel contemporary is to focus on your jeans' hemline. Part of the reason so many of us cringe when we look back at this denim shape is the cut was often, well, unflattering. But if you look for a pair that elongates your legs with a split hem, you'll find that you love the way your legs look in this denim. You can make this denim even more flattering by pairing it with a tailored blazer in a trendy color, a suede shoulder bag, oversize sunglasses, and pointed-toe ankle booties (like above).
#4. Pay Attention to Your Shoes
WEAR: Black Sunglasses + Navy Cardigan + Tan Boxy Blazer + Camel Crewneck Sweater + Camel Belt + Black Bowler Bag + Skinny Jeans + Brown Suede Knee High Boots
Styling Notes: By now, you've hopefully got a better idea of how to wear skinny jeans without resembling the infamous mid-'00s imagery. But if you're still unsure whether you can pull off this denim trend, you'll want to pay extra attention to your shoe choice. While some might find the idea of the "wrong shoe" theory endearing, there are, in fact, certain styles that pair better with skinny jeans—e.g., pointed-toe heels, round-toe flats, and knee-high boots. The latter is arguably the best option of all, as tucking your skinny jeans into knee-high boots is the perfect way to try them out in secret. After all, you might want plausible deniability that you're wearing this denim trend again! Re-creating the look above will give you that chance.
#5. Look for a Hybrid Silhouettes
WEAR: Aviator Sunglasses + Black Pony-Hair Coat + White T-Shirt + Black Skinny Jeans + Black Pointed Ankle Boots + Brown Bowler Bag
Styling Notes: While paying attention to where the cuff on your jeans lands can make your skinny jeans chicer, it's not the only trick in your arsenal. Another way you can make this "dated" denim feel contemporary is by looking for jeans that are a hybrid of skinny and straight-leg shapes—bonus points if they teeter into the territory of looking like cigarette trousers. It's one of the simplest ways to elevate your skinny jeans besides styling them with interesting statement pieces (as shown above).
#6. Consider a Low-Rise Waist or a Looser Shape
WEAR: Black Sunglasses + White Wrap Knit Top + Low-Rise Skinny Jeans + Pointed Heeled Mules
Styling Notes: If we're being honest, one of the main reasons so many of us still loathe skinny jeans is that early versions of this denim trend were far too tight, making them uncomfortable all-around. But rather than follow that tradition, it's worth considering a pair of skinny jeans with a low-rise waist or sizing up to create a slouchier silhouette, so your body can, well, breathe. It's such a minor tweak, but it can make you feel so much more comfortable wearing this style again. Additionally, you can dial up the comfort factor of this denim by pairing your skinny jeans with a knit top and pointed heeled mules.
#7. Keep Your Styling Simple
WEAR: Black Sunglasses + Black Leather Bomber Jacket + Black V-Neck Sweater + White T-Shirt + Black Belt + Light-Wash Skinny Jeans + Black Pumps + Black Handbag
Styling Notes: Paying attention to the fit of your denim isn't the only way to ensure maximum comfort; in fact, styling can do most of the heavy lifting in making this "controversial" denim comfortable to wear. When in doubt, you can't go wrong with keeping your styling simple by wearing your skinny jeans with your everyday staples—e.g., an oversize leather bomber jacket, a comfy T-shirt, a cashmere V-neck sweater, and classic pumps. It's a foolproof way to ensure you feel good in your denim.
#8. Embrace Double Denim
WEAR: Trench Coat + Denim Button-Down Shirt + Matching Skinny Jeans + Black Ankle Boots + Brown Suede Handbag
Styling Notes: It can feel somewhat risky to wear skinny jeans again, which is why you'll want simple outfit formulas to fall back on when you're in dire stress over what to wear—enter the ensemble above into the chat. When you're unsure what to pair with your skinny jeans, there's no safer styling option than embracing a "suiting" moment, or in layman's terms, a double-denim outfit. It doesn't get safer, or more stylish, frankly, than skinny jeans paired with a denim button-down shirt, a tailored trench coat, a suede handbag, and simple ankle boots.
