Fashion: It’s Autumn and Time to Dress Like a Grownup

Put your big boy pants on, son. Summer is over.

A man can get away with more boyish dress in the summer months as the ladies forgive shorts, t-shirts, sandals and such due to the heat. But, we’re post Labor Day now. Not only can you traditionally no longer wear white until Memorial Day, you can’t dress like a grammar school kid or shipwreck survivor anymore.

Autumn and winter offer an opportunity to show off some personal style. The seasons demand you grow your wardrobe up some. As always, the bottom line with men’s fashion — and the women we’re dressing up to attract in the first place — is to show up seeming as though you give a damn what you look like. Consider autumn an opportunity. Rather than weep and moan over the throwback 80s Jams, Crocs and tie dye wife beater you have to pack away burn because the leaves are falling, imagine the looks you can put together from smart to sophisticated to rugged in the Fall.

Related: Men’s Fashion Tips for Summer Wear

We’ll go over some autumn fashion tips from head to toe (literally) with ideas on how to evolve your style.

Head: Get yourself a proper hat — a great accessory to show off a little and distinguish yourself from the crowd. If you think I’m talking baseball cap, you’re just not getting it. A knit golf cap always fits the autumn mood, but you can also opt for a short brim Fedora or (if you’ve bold) a short cut Alpine.

Neck: Every fashion expert I talk to urges every man to invest in some scarves. They lend a little rugged rogue to a look and offers an opportunity to add color. 

Torso: Dress in layers, staying away from bright colors. When in doubt, look at a damn tree. You see browns. You see umbers. Maybe deep orange. Maybe reds inching to the rusty side. Wear solid colors as a base and patterns on the outer level for sweaters or sport coats. Obviously, wear the heavier fabrics (wool, fleece, flannel) on the outside. 

Legs: Shorts disappear as temperatures drop. That’s especially nice to see on airplanes because it’s a zero class look to fly in shorts, t-shirt and sneakers. You’re not in grammar school. Dress for business.

Jeans should fade out come autumn. In fact, for the most style conscious outfits should forego jeans any time of year if you’re dressing to impress. Even the best pair seems too casual in most circles. Pants should stay in the wool, blend or even khaki realm, offering solid base colors to build the rest of look on up high. 

Forgive a quick diversion here to discuss skinny jeans. Whether they’re the dreaded Levi 511s or another brand, these emasculating estrogen fests may very well be in style. They may very well stay in fashion. However, they will never — never — look masculine or remotely serve a grown man well. They are, by their nature, boyish and not remotely how a style-conscious adult man of purpose, authority and style looks to make an impact as he enters a room. They might as well be Elizabethan tights with their ass hugging angles and tapered legs. Perhaps that worked somehow for William Shakespeare and Sir Francis Drake in Queen Elizabeth’s court. But, these days, they’re strictly for prancing Little Lord Fauntleroy. 

Feet: Obviously, you’ll have to dump sandals because of the temperatures, and a man who wears flip-flops isn’t a man. Period. They should never touch your feet unless you’re in a gym locker room shower. As for sandals, they should be reserved for the 12 Apostles or hippies camped outside a Denver dispensary.

Calling back to the airplane environment, if you get on a plane in open toed foot ware, you should be sat in an exit row and ejected at 35,000 feet. You didn’t stumble out of a Third World Country, Mowgli. Get some shoes on over there. A couple personal favorites for Fall footwear include Cole Hahn (for modern, canvas-based looks) and Allen Edmonds (for classic, leather-based casual and dress shoes and boots).

Finally, make socks a secret fashion weapon. It’s the one clothing item that a guy can experiment with while getting away with quite a bit. Make sure the socks’ base color match the pants. But, beyond that, you can go with patterns, stripes, shapes, etc. Women notice shoes, and a little peacocking when their eyes are down there can only help distinguish you from the pack.


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