Newly Divorced 40 to 50 Year Old Men Work With a Personal Stylist for Men’s Casual Wear

Are you a newly divorced man in your 40s and 50s? Need to revamp your style and get back out there? Work with a Personal Stylist to revive your men’s casual wear wardrobe.

It’s common for divorced men in their 40s and 50s to fall into a style rut.  Perhaps you’ve been married for 10, 20, or even 30 years, and all of sudden you’re experiencing a life change.  Your kids are getting older. Some are going off to college.  You want to start dating! And your ex used to shop for you. So, you have no idea what men’s casual wear over 40 looks like.

That’s when you enlist the help of a personal stylist.

You don’t want to wear that plaid shirt, khaki pants, and the same old brown shoes and belt.  You’d like to look smart — casually put together.

As personal stylists, crafting a look for men’s casual wear over 40 is not that cookie-cutter. Your look will vary upon location, ethnicity, and preferences.

So, we will suggest some men’s casual wear over 40 looks for a man who wants to look classy, casual, and affluent that lives in a metropolitan city.  UK and American men in their 40s and 50s who want to take their look one notch up would benefit from our shopping guide for the divorced guy.

Let’s start with the blazer. If you’re British or have worked in corporate America, chances are you have a blue blazer.  However, is it the same blazer you would like to wear on a date?  “Does it matter?” you wonder.  Yes, it does! Unless you are going on a date straight from the office, like meeting for happy hour, let’s change your look.

It can be as simple are wearing a blazer, button-down shirt, and jeans. Please don’t go to the extreme and wear a t-shirt, jeans, and sneakers for your first date unless you’re wearing a blazer over it.  Incidentally, this look is very Italian – the blazer with a relatively fitted t-shirt, jeans, and sneakers.

You’re probably used to wearing a loose t-shirt, relaxed jeans, and sneakers (running shoes) casually while hanging out with your ex-wife and kids. However, unless you’re taking your date to a dive bar or Starbucks (by the way, we don’t recommend this venue for first dates!), let’s dress it up a bit, please.

To look classy, casual, and affluent, we recommend the following below

Feel free to shop our selection of recommended items when you press on the image or press on the heart to get a sale alert.

1. A Blazer: Set aside one blazer that you wear for nights out. Let’s separate work from social. 

2. A Button-Down Shirt: Go for a crisp white shirt, perhaps with some texture or a small pattern to add interest. You can never go wrong with a crisp white shirt from work to social. If you’re not that physically fit, this is your go-to shirt from work to play. If you’re from the UK, get a pink button-down shirt.

3. The T-Shirt: If you insist on a t-shirt because you’re a relatively fit or lean guy, get a fitted one.  It will emphasize your physique.  Perhaps that’s the look you’re going for, sexy casual.

4.  Jeans: Dads, slim-fit jeans are usually reserved for men in their 20s and 30s. However, depending on how skinny your legs are, a relaxed cut might be too baggy for you – and also hard to find. Go for a jean that gives you some wiggle room but doesn’t look too loose.

5.  Shoes: Depending on the color of your hair, you may prefer brown over black shoes. Personal style is all about personal preference. Just know that women always look at men’s shoes and choice of wallet (visit the first row of images and scroll all the way right to see an example of a nice wallet) to determine their affluence. So please don’t wear Birkenstocks with this look or use a nylon/velcro wallet.  Here’s an assortment of shoes that would go well with this look.

Want a more personalized experience to revamp your personal style? We know this look is pretty basic, so work with a personal stylist for men’s casual wear. Our service is LIVE ONLINE. We can revise your look with just 8 – 16 pieces that translate into four to eight outfits.  That should cover your social life for a month or two.     

Upgrade your casual wear with these items – you’ll definitely make an impression

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Dating After Divorce

After a divorce, it can be difficult to adjust to dating again. You may have been out of the dating game for a while, and you want to ensure that you make a good impression when out on dates with someone new.

Sterling Personal Styling is here to help you look and feel your best for those first few dates or a whole new dating experience. Sterling can help you find clothes and accessories that express your true self and make you feel confident. We’ll create a wardrobe of stylish pieces that suit your lifestyle and individual tastes, so you can show up to each date looking sharp and feeling good about yourself.

Additionally, it is just as important to work on your inner self after a divorce. Working on yourself through counseling or activities such as yoga and meditation can help you to build self-esteem and reduce stress. At Sterling, we can help guide you to make the most out of this new time in your life, so that you can be emotionally healthy and ready for whatever experiences come next.

So don’t wait – take the steps to up your style after a divorce with Sterling Personal Styling and feel good about yourself out there in the dating game. You never know who you may meet! Contact us today to get started on a new journey of self-discovery and confidence. You deserve it!

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Michelle T. Sterling is an award-winning American, internationally renowned image consultant, personal stylist, and online personal shopper.  She’s available for virtual consultations if you’re not located in New York, DC, San Francisco, Miami, or Dubai. Her style advice has been featured in the Wall Street Journal, the Huff Post, Details, and Forbes, among others.

Your Online Personal Shopper + Stylist