Waistcoat Dressy Fall Outfits After 50

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Black Sunglasses Navy Tie White Dress Shirt Silver Watch Brown Bracelet White Check Blazer White Check Waistcoat White Check Dress Pants

A waistcoat and white check dress pants are definitely worth adding to your list of true menswear must-haves. When it comes to dressing for transeasonal weather, nothing beats a knockout ensemble that transitions easily between seasons. A great example of how to dress fashionably as you move into your 50s.

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Black Sunglasses Dark Brown Leather Gloves Dark Green Wool Waistcoat Dark Brown Polka Dot Tie Light Blue Vertical Striped Dress Shirt Dark Green Polka Dot Pocket Square Silver Watch Olive Barn Jacket Navy Suit Dark Brown Leather Oxford Shoes

Rock a waistcoat with an olive barn jacket if you're going for a neat, smart look. If you wish to easily amp up your getup with a pair of shoes, complement this look with a pair of dark brown leather oxford shoes. When temps are falling and fall is settling in, you'll love this getup as your go-to for summer-to-fall weather. So if you're after outfit ideas on what to wear as you slip into your 50s, this outfit is an amazing example.

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Olive Barn Jacket Brown Cardigan Olive Wool Waistcoat Navy and Green Plaid Tie Light Blue Dress Shirt Charcoal Wool Hat Tobacco Leather Gloves Brown Gingham Scarf Navy Wool Dress Pants Dark Brown Leather Briefcase Dark Brown Suede Desert Boots Black Socks

For a look that's classy and wow-worthy, consider wearing a waistcoat and navy wool dress pants. Finishing with a pair of dark brown suede desert boots is a fail-safe way to bring a hint of stylish nonchalance to this outfit. When temps are starting to drop and autumn is setting in, you'll love this getup as your favorite for transeasonal weather. So if you're on a mission for a great yet age-appropriate combo, this is it.

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Dark Brown Sunglasses White Crew-neck T-shirt Blue Denim Waistcoat Navy Check Double Breasted Blazer Silver Watch Navy Check Dress Pants Dark Brown Leather Tassel Loafers

This polished pairing of a waistcoat and navy check dress pants will hallmark your sartorial chops. Go off the beaten path and jazz up your outfit by finishing off with dark brown leather tassel loafers. As you can see, it's extremely easy to look awesome and stay toasty when chillier weather hits, all thanks to combos like this. A no-brainer pairing proper for middle-aged gentlemen.

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White Dress Shirt Black Tie Green Pocket Square Pink Waistcoat Pink Blazer Pink Dress Pants Red Leather Brogues

Teaming a waistcoat with pink dress pants is an on-point option for a stylish and refined look. Throw red leather brogues in the mix to instantly amp up the wow factor of this getup. It's a viable choice if you're crafting a kick-ass ensemble for in-between weather. An amazing example of how to dress well and look age-appropriate.