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Miami Men's Fashion 2019 Trends & Style Tips

Hey, I’m Michael Checkers, a men’s fashion influencer and stylist creating looks inspired by my endless summer digital nomad lifestyle. On this men’s style blog you’ll find outfit ideas, fashion trends, and tips for street style, what to wear to the beach, and smart casual workwear. Since I’m based in Miami Beach,  I can show you some great ideas for what to wear in Miami and the latest Miami men’s fashion trends for 2020.  When I’m not living the beach life in Miami, I’m traveling around the world. So you can also explore this blog and see street style trends and outfits from my travels to places like Portugal, Spain, Italy, and New York City.

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      It’s starting to feel like Spring in Miami Beach

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      Getting ready for sunny days and warmer weather with my favorite pair of ripped jean shorts from Express Men. I can wear these with men’s slim fit short sleeve butting down shirts for striking balance between casual, trendy, and professional. I just put together a collection of my favorite Spring 2020 men’s sunglasses perfect for […]

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        Key West Casual Preppy Outfit at Sunset Pier

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        Checking out the waterfront in Key West. Sunset Pier is a great place to… you guess it! Watch sunset 😎
        Smart casual men’s outfit ideas from Express Men, on sale now! Perfect for Spring 2020. Miami, New York, Boston. Preppy men’s outfit ideas. Casual men’s outfit inspiration. Slim fit polo shirts and stretch chino pants.

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          Le Tigre Drops New Streetwear Collection for Spring 2020

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          American based heritage streetwear label, Le Tigre, just started dropping a new collection of dope knits, sweatshirts, track jackets and joggers. SS2020 is in full effect and the streetwear scene is heating up. Here’s an exclusive look at their Retro New knit varsity sweater that’s set to hit the stores Spring 2020. I wore this on a cool afternoon to go on a strawberry picking date south of Miami. The vintage firetruck made for the perfect backdrop invoking the sense of heritage that the Le Tigre brand now stands for.

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          Michael Checkers Miami Beach street style photo white pants and light khaki jacket

            Street Style Look 072 Miami Beach Neutral Smart Casual

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            My work days in Miami call for smart casual, on-trend outfits. I styled this look with the theme of neutrals in mind, one of my favorite SS2020 fashion trends. Read more about how to wear neutrals and the latest trends from New York Fashion Week on my blog https://mikecheck.co link in bio. @liketoknow.it http://liketk.it/2K1WJ

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            Michael Checkers Miami sitting model poses

              Street Style Look 069 Miami Beach White x Neutral

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              It’s heating up in Miami Beach. I’m enjoying the last few days of peace before Super Bowl weekend kicks off. Who’s coming down?
              ⚡️
              More men’s Spring 2020 outfit ideas with that white and neutral style on @liketoknow.it http://liketk.it/2JFZo

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              Michael Checkers wearing jeans and a leather jacket walking fast with city skyline in the background at night in Miami

              Streetwear Look 071 Miami Beach x Gotham

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              Hoppin out the bat cave in my black leather band collar jacket from John Varvatos. The dark tiger print shirt is from Express Men. It’s more of that stretch performance material I’m obsessed with. The jeans are from Express too, hyper skinny fit. Read more about my tips and opinions on how these jeans fit in this post.

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              Michael Checkers wearing gray jeans and a black shirt on his way to work standing next to a black cat

              Street Style Look 070 Miami Beach Grey Scale

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              New day. Let’s get it. Bagheera (my cat) thinks he’s coming to meetings with me today lol. Performance moister wicking shirts from Express Men are my secret to creating that smart casual look for workdays Miami. They give me balance when I’m walking in and out of warm weather and A/C‘d offices. Plus they really don’t show wrinkles the way most shirts do. Everything is 40% off right now so pick some up before they sell out. Now I’ve got to run, time to close some deals.

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                Streetwear Look 064 South Beach

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                Just another day in South Beach. Joggers, an athletic tee, and some dope sneakers. Perfect for walking the streets for a little post-Xmas shopping on a cool day. ✌🏼
                Shirt: @lululemonmen
                Joggers: @ExpressMen
                Sneakers: @Adidas
                Watch: @nixon
                Shop the look @liketoknow.it http://liketk.it/2IxiS 📸 @tinesays

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                Streetwear Look 065 White & Oatmeal Yeezy Miami

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                Walking along the harbor in Miami Beach wearing white ripped jeans, stone Yeezy 500’s, and a matching t-shirt. Check out this collection to white jeans, joggers, hoodies, sweatshirts, and dope sneakers. I picked some of my favorite Streetwear sneakers from Adidas Originals, some winter weekend outfits from East Dane, and men’s skinny jeans from Nordstrom he needs this Spring.

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                  Street Style Look 063 Miami Beach

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                  My Christmas tradition in Miami Beach is to always take a walk on the beach. You’ve got to enjoy what’s around you in this life. What your favorite holiday tradition?
                  Menswear look from Express preppy stretch slim fit polo and slim fit white pants, chinos. @liketoknow.it http://liketk.it/2Ivmu

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                    Streetwear Look 062 Minimalist Military

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                    Street Style Look 060 Winter in South Beach.
                    For this streetwear look, I tried going for that minimalist military trend. But I’m mixing it up with the school mock neck long sleeve shirt with the animal print detail on the sleeves. What do you think? Big thanks to Express Men for hooking me up with all the clothes. Check out the full photo collection in this post.

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                    Michael Checkers wearing all black in Miami doing a streetwear pose at an art show

                      Street Style Look 060 Miami Beach Black Sheep

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                      Thinking about what to wear going out at night in Miami Beach to Art Basel events, trendy bars and lounge? Here’s my Miami Street Style look from a night out during Art Basel in Miami Beach. Black ripped jeans, monk strap dress shoes, black t-shirt with a velvet tuxedo jacket. Black snap back hat. Sliver minimalist watch. Felt like a black sheep in this photo but not once I got to the event.

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                        Street Style Look 061 Faena Miami Beach

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                        Miami Beach Style 💦
                        The street style fashion trend alert is neutral and white outfit combos. I threw in theses Arizona Ice Tea print slides from Adidas originals to give the look a little pop.
                        You can pick up this shirt for $20 right now from Express Men. Shop my short sleeve shirt collection on here MikeCheck.co and @liketoknow.it.

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                          SCOPE Art Show Street Style

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                          ✖️Streetwear Look 058 SCOPE Miami Beach
                          This is what I wore to the SCOPE art show in Miami Beach.
                          🎤✔️ It’s the real hip hop hip hop.

                          I’m obsessed with slim fit t-shirts. But it’s hard to find good ones. Here are a few picks from H&M and Nordstrom. Plus some pants from Express, sneakers from Adidas, and a dapper minimal men’s watch to complete the look.

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