Skip to content Skip to sidebar Skip to footer

10 Stylish Men’s Boots and Watches for Any Occasion

10 Stylish Men’s Boots and Watches for Any Occasion

As seasons change, so do our fashion choices. But some staples stay the same no matter what the season. In today’s list of great fashion buys, we’re checking out 10 stylish men’s boots and watches for day to night looks. These pairs can take you from meetings with bosses to dinners with your significant other or playdates with your neighbors’ kids. These boots-and-watches combinations make for a stylish look that will take your outfit from bland to sharp-dressed. Check out the list below.


For Weekends with the Family

10 Stylish Men's Boots and Watches for Any Occasion

1. Steve Madden Men’s Harken Chukka Boot

Crafted with 100% leather and featuring a synthetic sole, this Chukka boot from Steve Madden features a 1″ inch heel and a blind-eyelet lacing and slightly distressed finish. It is inspired from rock and roll and the brand’s unique city roots, with collections featuring suede loafers and leather Derbies to sporty sneakers and chukka boots. Whether for formal or casual outings, this chukka boot, which features widely spaced stitches around the outsole that truly pops, is great for day to night ensembles. Founded in 1990, Steve Madden’s brand has long been providing men and women with smart fashion staples that you can take anywhere with you. Shop at Amazon.

2. Timex Weekender Chronograph 40mm Watch

Pair that Chukka boot with this Timex Weekender Chronograph watch which chronograph measures to the 1/20th second. It features a leather NATO style slip thru strap and an additional navy nylon strap that you can mix and match with any weekend outfit. It features analog-quartz movement and a crystal/lens and mineral case. The best part? It’s water resistant up to 100 feet so you need not worry about backyard swimming pool parties or lunches and picnics on the beach. This Timex watch is part of the brand’s Weekender collection, which is all about versatility, letting you switch it up with interchangeable slip-thru and quick-release straps in both leather and fabric. Rated 4.0 out of 5 stars with over 1,100 customer reviews on Amazon.


For Travels and Adventures

10 Stylish Men's Boots and Watches for Any Occasion

3. ECCO Men’s Jeremy Hybrid Boot Oxford

Crafted from leather and featuring a rubber sole, this contemporary Derby boot from ECCO features a hybrid sport dress sole and part leather lining that’s soft and comfortable, ensuring a perfect inner climate. Its leather covered insoles feature ECCO Comfort Fiber System for increased air circulation. Also features a direct-injected one-component PU outsole with welt creates a modern, lightweight wedge sole. It has a removable insole for easy cleaning and maintenance and smooth soft leather that provides a youthful look. It’s great for everyday adventures and also for smart casual ensembles. Shop at Amazon.

4. Citizen Men’s Eco-Drive Stainless Steel Watch with Brown Leather Strap

Bravely navigate through your next adventure with the Citizen Eco-Drive Watch, a stylish piece that is reminiscent of mid-century aviator style that is sure to turn heads. The Avion watch is a vintage-inspired timepiece reminiscent of transatlantic flights from the 1950’s and features design that takes its cues from the golden age of travel. Features a  rich brown leather strap with contrast stitching, luminous markers and classic day/date function, as well as a stainless steel case with charcoal grey dial. This timepiece features a cool vintage vibe that will turn any smart casual outfit into something others will admire. It features a stainless steel case, large luminous numerals and a leather strap with contrast stitching, all of which perfectly complement your jeans or khakis as you travel through the world in style. Shop at Amazon.


For Meeting the Parents

10 Stylish Men's Boots and Watches for Any Occasion

5. Calvin Klein Men’s Alixander Chelsea Boot in Dark Navy Suede

From the Calvin Klein Collection comes this versatile boot that features an elastic gore detail. It is crafted from leather and polyurethane and features a polyurethane trip and a round toe. Its slip on style makes it easy to wear and take off, while its fabric and polyurethane lining and EVA sole makes it truly comfortable even in the most stressful occasions, like meeting her parents! Rated 4.7 out of 5 stars on Amazon.

6. Fossil Men’s Grant Sport Quartz Stainless Steel and Leather Dress Watch Color

Dress to impress with this watch from Fossil, the brand that is inspired by creativity and ingenuity. This piece features round rose gold tone plated stainless steel case with navy blue dial and Roman numerals, a gorgeous 44mm case, quartz movement with luminous 3-hand analog display, and a mineral crystal case. It also features genuine blue leather band with buckle closure that’s interchangeable with all Fossil 22mm watch straps for versatility. The brand’s high quality leather is known for its softness and ability to look good over time. This multifunction watch features a stopwatch functionality, three separate dials to track hours, minutes and seconds, and a timer. It’s water resistant up to 165 feet and is perfect for spontaneous swimming because after all, you never know what life throws at you. Shop at Amazon.


For Galas and Formal Nights Out

10 Stylish Men's Boots and Watches for Any Occasion

7. Deer Stags Men’s Bangor Memory Foam Dress Casual Comfort Chukka Boot

Dressy need not be expensive. In fact, you can dress well and dress smart with the classic Deer Stags Bangor chukka boot, which features a simulated leather upper, lace-up enclosure, and round toe that will make you look like a true gentleman. It features a microsuede lining that provides a cozy feeling and EVA with memory foam insoles that provides optimal comfort. It also features a cement construction and durable TPR outsole for long lasting style and function. Shop at Amazon.

8. Michael Kors Men’s MK8606 Slim Runway

Be runway ready with this Michael Kors Slim Runway watch for men. It features mesh stainless steel bracelet with hook-clasp closure and round face for that classic, chic look. It features a three-hand analog display with quartz movement, while its dial features silver-tone hands, hour markers, and Michael Kors detailing. The case measures 42mm and the band measures 22mm. It is water resistant up to 5 ATM. Shop at Amazon.


For Weekends with Friends

10 Stylish Men's Boots and Watches for Any Occasion

9. Lacoste Men’s Ampthill Chukka Boot

Chill with friends and a bottle of beer with this casual boot from Lacoste, which features an eternally-popular chukka silhouette presented in smart core colourways. It features soft suede uppers that are enhanced by touches of gray marl canvas, tan elements, and debossed leather patch branding on tongue. Its rubber outsole ensures grip so you can go on weekend adventures in style. Its crocodile branding and brass eyelet completes its stylish look. Get some awesome weekend warrior vibes with this cool boot from Lacoste. Shop at Amazon.

10. SEIKO 5 Automatic Watch SNZG09J1

Strength and style combine in this automatic Seiko 5 watch that’s stylish enough for casual evenings around town or meeting new friends by the docks. It features a stainless steel case, nylon strap, automatic movement, Hardlex crystal case, dark green dial, black with Lumibrite hands and markers, and day and date display at the 3 o’clock position. It’s also water resistant up to 100 meters. With this automatic watch, your stylish weekends will look like days sitting by the beach with a bottle of beer in hand. Shop at Amazon.


The Teelie Blog archive is filled with great fashion ideas for men. We’ve curated more stories for you in the links below. Don’t forget to bookmark our page for more daily inspiration for how to dress and live well. From great fashion finds to bargains, the Teelie Blog is all you need to look chic.

Get Fit This 2019 With Zac Efron’s Favorite Workout Essentials

Top Must-Have Accessories that Men Need this Summer Season

Men’s Activewear that Gym Rats Will Absolutely Love

Father’s Day Gift Ideas: Fashion Accessories that Your Dads Will Definitely Use

Men’s Fashion: Five Ways to Wear a Suit

Just a disclaimer – We have partnered with these companies because we use their products and/or proudly trust and endorse them – so we do receive a commission if you make a purchase or sign up for services. Often, we are able to negotiate special discounts and/or bonuses, which we will pass on to you via our links. We often get short notice on sale items available for 24-48 hours as we will pass these savings onto you.

Show CommentsClose Comments

Leave a comment

Keep Updated With The Latest Trends
Subscribe to Newsletter

Subscribe to our Newsletter for new blog
posts, tips & photos.

The Teelie Blog

With the mission to become the ultimate trend destination whether in fashion or home, The Teelie Blog is committed to bringing the freshest news on your favorite celebrities’ favorite things and engaging content on the latest in fashion, lifestyle, home improvement, DIY projects, and more.