The city is ALIVE with people, music, events, culture and activity. Make sure your clothing follows suit and has that same energy flow. Are you spending a day in town? Your city chic attire needs to feel fresh, lively and filled with playful details that make you feel fabulous when you catch sight of your reflection while window shopping. As day turns to night, your transition to rooftop party attire means adding more drama, something sexier--clothing that embraces an anything goes attitude. Want inspiration on city outfits? We’ve dreamed up looks for the day and night for men and women but must warn you--you could get mistaken for a local. 

City Chic for Her

Ladies, let’s do that season switch up the right way. Walk the streets and know everyone’s looking at you. We’re celebrating transitions here so while we say goodbye to warmer weather and embrace cool, comfortable temps, layering well means we can add or subtract items when needed. Besides, a layered look always gives the impression that you spent a lot of time on your look (even if you didn’t). 

What to wear to the city means different things to different people, but it should always be filled with color, texture and bring a big mood. You’re in the center of it all in the city. Act like you belong in the scene with looks loaded with confidence. 

Our outfit offers flattering silhouettes that still retain a strong sense of femininity. Show off your denim knowledge with Mother Denim. These jeans offer a lived-in look and proudly display some hardware in the exposed button fly. 

A graphic tee is always a win. RE/DONE’s New York city tee is beyond appropriate and brings that big city appeal. If you’re out of the sun and need more coverage, a blazer or jacket adds instant sophistication (a city necessity). This style from Indress is a mix of royal purple and beige/gold highlights that grab the light and have that hint of couture that you desire. 

Our sneaker pick from Valentino is the low-top comfort that’ll make it hard to stop touring the city. That slick negative and positive color combination of white and black packs a powerful visual but that’s the rule with city kicks--they should look wild, bold and never standard-issue. 

Styling tip: Add a belt bag to the look so you’re hands-free. Mini bags are all the rage and you don’t want to feel saddled down with a large tote. Free and unencumbered, you can pop in and out of shops and museums with everything in one spot. Plus, they have that cooler-than-you allure. 

Rooftop Party Attire for Her

So you’ve spent the day sightseeing, inspired and visiting every bookstore, café and food truck that you pass. Prepare for a night out among the stars. What to wear to a rooftop party translates to how many bomb photo opportunities you can squeeze in at dusk (chase that golden light). 

Do glam. Do sexy. Do it all with a large amount of modernity. You’ll be the skyline sweetheart in this rainbow plunge dress from Zimmermann. It shows off some skin (sultry) and when you add gold jewelry you’re ignore-proof. 

A dress with that much attitude means accessories should have subtle charm. Our new line of Wandler bags have elegant silhouettes in rich and warm leathers that are completely upmarket. When it comes to footwear, depending on your dress, you may add signature heels or trainers for that laid-back and luxe mix. We went with casual Valentino slide sandals to temper the look yet still speak to the logo-crazy crowd. 

Styling tip: Your clutch can set the mood. You might even style your whole outfit around an accessory (it’s not unheard of). Sequins, animal print--anything that’s festive and easy to carry around with a signature cocktail.  

City Chic for Him

Men, transitional looks will serve you well when late summer weather turns from warm to cold throughout the day (and back again). Layers are where it’s at so go all in. Your look should be way easy and steeped in the basics. If you’re staying in town you want to be able to breeze through that hotel in vibrant, trendy and comfortable pieces that say you own this city (even if just for the day). 

The Mother Denim California tee gives us a little bit of wanderlust, perfect for your mini day of traveling around the city. It’s got major street cred and is evocative of concert merch appeal (totally rad). Because you never know the situation or exact weather, having a shirt/jacket on hand is a smart choice. Tees are good for those stuffy subway rides but if you have a breezy day, add a layer! This Maison Kitsuné piece has a little bit of a utilitarian vibe and everyone’s digging on the overshirt trend so you look like you know what’s up. 

Denim is king in the city. The thing about it is it’s old-school, modern day and of the future. We live in and love our denim and Mother Denim has a rebellious streak we dig. The style we chose is faded with slashed knees and almost-broke through distressing that looks like it’s well-traveled. The double cuff hits at the ankle so it showcases your favorite footwear. 

Speaking of your choice in shoes, never worry about grime on the streets with the pre-scuffed and distressed Golden Goose sneakers. They have a retro feel and the marked up appearance is everything we love about gritty street looks. Besides, the city was meant for walking and shoes that are ready for the task are key. 

Have fun with accessories. They’ll help you stand out among the crowd. This linen baseball cap is youthful, sporty and is a pretty well-groomed option so you still look fly. It can be just the thing to hide under or give coverage from the sun. 

Style tip: Bring a pair of sunnies for your trip. Designer shades bring attention to your face but also provide anonymity. Take in all the sights but do it on your own terms. 

Rooftop Party Attire for Him

Day tripping around town to art galleries, neighborhood marketplaces and the breweries has you ready for a more chill evening. Head to the city’s highest point, to a rooftop fête where you’re literally above it all. What to wear to a rooftop party is all about effortless elegance. You are a walking mood board for smooth and dapper style.  

Start with a white v-neck with a flattering drape. It shows a little skin and is that bright pop of white you may need when working in your layers. We went with the brand Goodlife (so appropriately named). Because there might be a slight chill, opt for a dress shirt that you can unbutton and wear loose. It frames the white tee perfectly. The Eton brand is known for quality construction and you can feel it. This style is crease-resistant and offers a whimsical micro floral print that’s subtle if you’re hesitant about prints (don’t be, this is the place to wear them). 

The rule for rooftop looks is to ABWI: Always Be Working It. You can’t go wrong with these navy chino pants that can be casual and dressy so they are a great investment that stretches your wardrobe and wearing opportunities. These PT Forward pants feature a charming feather keychain at the back pocket that adds the wink of quirkiness we love about city styling. 

Guys, we can’t stress it enough. The ladies look at your shoes. It’s where you can shine so never miss an opportunity to stun them. This chunky dark brown brogue style is a step in the right direction for the fall season. This is the Archie style from Grenson and once those chinos are rolled, all eyes are on these dandy boys. 

Style tip: Add personality--everything you’ve got to offer. An air of luxury is achieved with a signature cologne. Your wrist looks less naked with a masculine, braided bracelet in leather. Make small adjustments to show your personality. It’s always worth it.  

The city’s pace is fast. It’s constantly moving and changing and when you’re a part of that, well, it’s a feeling that lights up the day and night. City chic is where you find a fascinating array of style diversity. It demands attention and drives conversation. Fashion tells a story. You can communicate a lot just with your choice of clothing!