It's Confirmed: These 15 Classic Outfits Are Compliment Magnets
Raise your hand if you've felt fatigued by how quickly fashion trends go out of style. You're not alone in your sentiment. Don't get it twisted—stalking the runways or searching for the best new arrivals can bring a sense of unbridled joy to any fashion person. But there's no denying that there's something incredibly appealing and, dare we say, liberating about adopting a more classic style. One could argue that the collective fatigue surrounding fast fashion is why we've recently seen so specific minimal aesthetics take off in the cultural zeitgeist, like the rise of quiet-luxury style or the obsession with "old money" fashion. But let us be clear: this movement isn't necessarily about being anti-trend per se, but shifting one's approach to personal style.
Classic style is all about centering wardrobe essentials that will always be in fashion—think clean silhouettes, minimal accessories, neutral color palettes. That doesn't mean you have to be predictive or old-fashioned with how you dress each day, but it's a call to balance wearing "simple" staples and the season's hottest trends. While that might seem impossible, we're here to tell you otherwise. It's incredibly easy to look timeless and trend-forward; you justneed a few tricks up your sleeve. In an effort to give you those hacks, we've done the research to show how to adopt a more streamlined approach to style. Ahead, you'll find 15 classic style outfit ideas with styling tips and shopping recommendations that are sure to solve your style woes. Plus, they're guaranteed to secure you a few compliments in the process.
What You'll Need: Sunglasses + trench coat + tank top + straight-leg jeans + ballet flats + crossbody bag
Style Notes: Styling staples together is the first step in adopting a more classic approach to personal style. But if you need a play-by-play, refer to the outfit above as the starting point for your journey. After all, what's more classic than a trench coat layered over a white tank top and straight-leg jeans? Not much. Although, we've got a few more ideas.
What You'll Need: Stretchy headband + sunglasses + sculptural jewelry + shaket + T-shirt + belt + wide-leg jeans + pointed pumps + handbag
Style Notes: Denim has become a cult classic because of its innate versatility. You can pretty much find a pair of jeans in any fit or wash for your taste. But if you're looking for more polished jeans, we recommend opting for a wide-leg pair. Bonus points if they're styled with other basics, such as a T-shirt, light jacket, and pumps.
Denim trends come and go, but wide-leg flares remain relevant.
What You'll Need: Sculptural earrings + sunglasses + leather jacket + T-shirt + belt + trousers + loafers
Style Notes: Beyond jeans, the next best bottom you can buy if you're trying to build a classic wardrobe is tailored trousers. These pants can be paired with just about anything for any occasion—although we're particularly fond of the approach taken above, which shows their versatility beyond the office.
It looks way more expensive than its price tag.
What You'll Need: Sunglasses + earrings + cardigan + button-down shirt + tailored trousers + pointed pumps
Style Notes: For more formal work settings, you don't have to sacrifice your personal style to adhere to dress codes. You can make "corporate" attire feel cooler through creative styling. Try pairing tailored trousers with a loose button-down shirt and throwing a cardigan over your shoulders.
Styling tip: throw this over your shoulders to add a preppy element to your ensemble.
What You'll Need: Frame bag + sunglasses + blazer + waistcoat + trousers + ballet flats
Style Notes: For those mornings when you're quickly trying to rush out of the house, it's essential to have effortless outfit formulas that still look elegant—the matching three-piece suit meets that criteria. Opting for a matching blazer, waistcoat, and trousers styled with statement accessories is the safest way to look good sans effort.
What You'll Need: Sunglasses + long coat + T-shirt + sweater + shorts + tights + slingbacks + shoulder bag
Style Notes: Just because you're trying to adopt a more classic approach to everyday dressing doesn't mean you can't take a few risks. The key to pulling off more "controversial" trends (such as short shorts) is styling them with layered staples like a long, double-breasted coat over a T-shirt, sweater, shorts, and stockings.
Tights are a must-have for fluctuating temperatures.
What You'll Need: Hoop earrings + long coat + T-shirt + belt + miniskirt + socks + ballet flats
Style Notes: Short shorts aren't necessarily everyone's cup of tea. Luckily, miniskirts exist. While you can't go wrong with this silhouette in general, if you're looking for a more classic style, we recommend opting for a pleated mini, as it's the most polished option.
What You'll Need: Sunglasses + sculptural earrings + moto jacket + tank top + pencil skirt + tights + slingback heels
Style Notes: If you prefer a longer hemline on your skirts, it's potentially worth embracing a pencil skirt. Although the silhouette is perennially relevant, it's popular again because of runway collections (like Saint Laurent's F/W 23 show) that have paired it with unexpected items such as moto jackets, low-scoop neck tanks, sheer tights, and slingback heels.
What You'll Need: Sunglasses + oversize blazer + tank top + belt + maxi skirt + pumps + handbag
Style Notes: While recent styling trends are a great way to spice up your staples, there's no harm in keeping it simple, too. Nothing will ever compare to the enduring elegance of a blazer styled with a matching maxi skirt, tank top, and pointed pumps.
What You'll Need: Sunglasses + oversize blazer + tank dress + tights + pointed kitten heels + handbag
Style Notes: Lean into the versatility of the classic tank by embracing it in the form of a dress. You can make the item feel a bit more elegant by styling it with an oversize blazer, tights, and pointed kitten heels.
Although we're impartial to the white version of these pumps, they do come in 10 other colors.
What You'll Need: Sunglasses + tweed coat + linen dress + socks + loafers + handbag
Style Notes: Although tank dresses are timeless, they're not always the best option for more formal settings—enter the linen dress. A more formal frock fit for the office, this style can be dressed up or down for any setting. Plus, it's the perfect item to wear with a light tweed jacket in colder weather or as is during a heatwave.
What You'll Need: Sunglasses + button-down shirt + denim miniskirt + heeled mules + shoulder bag
Style Notes: Choosing what to wear when it's warmer outside can be challenging, but let us tell you a little secret: Navigating the shift into late spring is easier if you stick to the classics. Try pairing a button-down shirt with a denim miniskirt and mules for a failproof 'fit.
What You'll Need: Earrings + cardigan + slip dress + thong sandals + raffia handbag
Style Notes: What's a simple solution you can turn to when it's too hot to try to look cute? Opt for a classic slip dress. When styled with statement jewelry, sandals, and simple layers, it's a low-lift way to look stylish without breaking a sweat.
What You'll Need: Sunglasses + button-down shirt + tank top + belt + pleated shorts + mesh ballet flats
Style Notes: Another way to look stylish when it's sweltering hot outside? Opt for pleated shorts. Just be sure to pair them with other staples to have them air on the classic side.
Investing in a quality button-down shirt will basically pay for itself.
What You'll Need: Matching plissé set + slide sandals + dainty jewelry + hobo bag
Style Notes: By now, we've hopefully provided you with ample inspiration on how to adopt a more classic sense of style. But if you still need one last dose of inspiration, let the outfit above be your guidepost. Simplicity is the secret sauce, so don't be afraid to lean on staples such as a matching plissé set, slide sandals, and a shoulder hobo bag.
Matching sets for the win.
Pair with the matching crinkle gauze wide-leg pants ($63).
Jasmine Fox-Suliaman is a fashion editor living in New York City. What began as a hobby (blogging on Tumblr) transformed into a career dedicated to storytelling through various forms of digital media. She started her career at the print publication 303 Magazine, where she wrote stories, helped produce photo shoots, and planned Denver Fashion Week. After moving to Los Angeles, she worked as MyDomaine's social media editor until she was promoted to work across all of Clique's publications (MyDomaine, Byrdie, and Who What Wear) as the community manager. Over the past few years, Jasmine has worked on Who What Wear's editorial team, using her extensive background to champion rising BIPOC designers, weigh in on viral trends, and profile stars such as Janet Mock and Victoria Monét. She is especially interested in exploring how art, fashion, and pop culture intersect online and IRL.
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