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The Best Menswear Looks for Fall 2019

by habituallychic

09 . 20 . 19

I’ve had such a nice response to my shopping and fashion posts that I decided to ask my Instagram followers if they had any fashion conundrums or questions that I could address in future posts. My dear friend Andrew Brown asked for a fall menswear post which I hadn’t thought of even though I know I have a large male audience. Women also tend to shop for the men in their life so hopefully it will be helpful for everyone.

This first outfit could be for a man who works in a casual tech office or for a weekend in the city or country.

This first outfit could be for a man who works in a casual tech office or could work for a weekend or travel. The mornings have been in the 50’s this week in New York so it’s time to start thinking about jackets and layering. Barbour is the perfect brand for autumn and I especially love this Regular Fit Weatherproof Waxed Cotton Jacket.

I’ve professed my love of zip up sweaters in the past and I love the leather trim on this Quarter Zip Merino Wool Blend Pullover. It’s available in three colors and it’s on sale.

Buttondowns like this Regular Fit Check Button-Down Sport Shirt are best for casual outfits. Don’t wear a buttondown with a formal suit.

Every time I think that men have it easy in the wardrobe department, I walk through Midtown where men are wearing blue shirts, ill fitting khakis, and black square toed shoes. If this sounds like it could be you, update your pants with these Slim Fit Stretch Chino Pants. You could also swap the chinos for jeans.

I love these Alton Chukka Boots in stone suede but they are also available in brown and black leather for rainy days.

Nothing elevates a man’s outfit better than a nice watch. This Orvis Big Crown Pointer Date Automatic 40mm Bronze and Leather Watch is the perfect office to weekend watch.

Bags for men can be tricky. This Filson Original Leather-Trimmed Twill Briefcase is a classic that looks good with jeans or a suit.

This Murdock London Great Bearded Expectations Travel Kit is great for a guy with a beard on the go.

This look is for the man who doesn’t need to wear a full suit to work but who does need to wear a blazer on occasion and wants to look professional.

I prefer men’s raincoats that don’t have a belt so they can be worn over a jacket or suit like this Lightweight Raincoat. A less expensive option is the Mac Long Car Coat.

I love the colors in this Classic Fit Plaid Wool Sport Coat. It could be paired with blue, grey, or even brown.

If you want a bolder option for a shirt, I like this Trim Fit Check Dress Shirt. For a more subtle shirt, try the Microcheck Performance Shirt.

Wear this navy Cashmere V-Neck Sweater under the sport coat on colder days or just over a dress shirt on more casual days. It’s available in four other colors.

These Luxury Flat Front Wool Dress Pants are so nice that you should buy them in multiple colors and wear them every day of the week.

A few of the men in my inspiration collage are wearing brown suede loafers. These brown Stubbs & Wootton Suede Loafers are the perfect shoe for fall. They could be paired with jeans and almost any color pant.

Just another PSA that you should not wear your sporty sunglasses with work clothes. These Ray Ban Classic Wayfarer Polarized Sunglasses are the perfect chic pair to wear during the week and on the weekend.

When you need to impress at work, try carrying this Mark Cross Parker Saffiano Leather Briefcase. I also like this Shinola Guardian Leather Briefcase for a slightly more casual option.

This Elemis Luxury Travel Collection Essentials for Him Set looks perfect for throwing in your gym bag.

This is another great outfit for casual offices, weekends, and traveling.

You can’t go wrong with a green jacket and this All Saints Baynes Jacket is the perfect option for autumn weather. I also really love this Slim Fit Wool Jacket.

I don’t think I’ve seen a chicer sweater for men than this Billy Reid Shawl Collar Pullover. I love the quilting and buttoned collar but the brown suede elbow patches take it to the next level. It’s also available in black and grey.

Cooler weather is the perfect time to wear this Regular Fit Plaid Button-Up Flannel Shirt. It could be worn on weekends with jeans but you could also wear it to work with grey flannel pants or a pair of khakis. It could also be layered under the sweater or jacket or both on colder days.

When it comes to men’s denim, I think darker and slimmer are a little better. Styles like these Slim Leg Jeans can be worn in casual offices and on weekends but don’t look sloppy.

These GrandPro Tennis Sneakers could be worn with jeans, khakis, and even a suit. They also come in four other colors.

These brown Leather Over Ear Headphones are much chicer than Apple AirPods for the gym or traveling.

Upgrade or gym bag or carry on with this Herschel Supply Co. Duffle Bag. It’s also available in navy.

Give your beard the boot with this The Art of Shaving Travel Size Starter Kit & Bag.

This look is for the man who has to wear a suit to work and travels for business.

I’m always surprised how many men I see in New York who don’t wear overcoats. It’s not chic to freeze in colder temperatures. Find a coat like this Wool Twill Coat to wear over your suits and jackets.

This charcoal Classic Fit Plaid Wool Suit is chic enough to get you a new client or a raise. I prefer navy and grey suits for conservative offices. I think black is best for more fashion forward industries.

If everyone else in Midtown is wearing blue shirts, why not wear this pink Regular Fit Plaid Dress Shirt instead.

Pick your favorite animal and Ferragamo probably has a tie with a cute print of them like this Rhinoceros Print Silk Tie.

It’s always chicer to pair brown or cordovan shoes like these Cap Toe Oxfords with a grey suit rather than black.

I once read an article about feng shui that stated it was important to keep your money is a neat and tidy wallet. How about keeping it in this Bottega Veneta Two-Tone Intrecciato Leather Wallet with an orange interior.

I don’t care what color suitcase you buy but please don’t make it black. But if you want to upgrade your current carry on, I love this navy 22-Inch Domestic Expandable Spinner Wheeled Carry-On.

I’m not as familiar with the brand Baxter but this Travel Size Skin Care & Hair Care Set from them looks so chic that I want to buy one for myself.

I think every man should own a tux, even if you don’t think you need one. If you own a tux, you become the person who can be counted on for last minute invitations to black tie affairs. Just think of all the fun events you will get to attend and who you might meet.

If you are planning to attend black tie affairs and evening events, invest in a black overcoat like this Mohair Coat so you can keep warm. You can also be a gentleman and throw it over the shoulders of your date who probably didn’t want to wear a coat over her evening gown.

When you think about cost per wear, you will definitely get your money’s worth out of this New York Classic Fit Black Wool Tuxedo.

This Slim Fit Textured Tuxedo Shirt has a texture which elevates the look and it comes with studs and cuff links so you don’t have to worry about buying them separately or more importantly, you don’t have to worry about forgetting to buy them.

If you own your own tuxedo, you should also buy a Silk Cummerbund & Bow Tie Set. If you don’t need a cummerbund, you could buy this Satin Bow Tie alone. But whatever you do, just don’t buy a pre-tied bow tie. Watch a YouTube video on how to tie a real bow tie if you need a tutorial.

Technically, you are supposed to wear a pair of patent leather formal pumps with a tuxedo. I think you could also wear velvet slippers or loafers like these Gucci Velvet Loafers for a more modern look. Maybe just not at a very formal affair or a visit to a royal palace. Orlando Bloom just wore a tuxedo with Gucci loafers and no socks to Misha Nonoo’s wedding in Rome tonight.

This Wispy Polka Dot Scarf looks like silk but it’s actually cashmere that will keep you warm on your way to a black tie event.

Did you know that a gentleman should never wear a watch with a tuxedo? The evening is supposed to end on its own accord and not at a specific time. You should also not be peeking at your watch when someone has invited you to their black tie event or as their date. But of course, no one said anything about iPhones. It should stay tucked in your pocket but I’ll allow you to use it to take some photos especially if you upgrade to the iPhone 11 Pro with the new amazing camera.

I was thinking that Tom Ford Noir sounded like the perfect cologne to wear with a tuxedo and then I saw this advertisement. If Tom wears it with his tuxedo, you should too.

I hope this post helps my male readers and ladies with boyfriends, husbands, sons, and other men in their life dress for fall.

Bon week-end !