10 Things I've Learned Shopping With Men

We're coming up on the third anniversary of Pivot. It’s been such a blessing to work as both a personal shopper and personal stylist for the men I've worked with. In this time, I’ve learned a few things about the male psyche. Even things I haven't noticed as a man myself. Particularly, I've learned a lot about our approach to shopping and buying clothing.

During a consultation, my job is not only to walk you through and educate you on your style but also to get you out of your own way to get you what you need. This means changing your relationship with your image and how you think about clothing. 

This list is only a generalization of things I've noticed. But, Hopefully, some of these thoughts can help you out on your next shopping trip.

Here are ten things I’ve learned exclusively styling men for the last few years...
 

 Ryan Gosling In " Crazy Stupid Love".

Ryan Gosling In "Crazy Stupid Love".

1. Just because you don’t understand something, doesn’t mean that you should hate it.

The default emotion to something we don’t understand is rejection. When we’re not sure what to make of something, we push back against it.

At least once during every consultation, there comes a moment when I know an item will work perfectly for a guy. However, he’s hesitant because of some preconceived notion. I never force anything on a client, but if I know it works, I’ll push. 9 times out of 10, they’ll message me telling me how much they love the item once it grows on them.

What I’m getting at here is that just because you don’t understand something, doesn’t mean that it doesn’t work for you. You just haven’t seen it in practice yet.
 

2. You need to try on every piece of clothing.

Shopping in-store will always be preferable to shopping online. You get your items immediately, you can get a feel for the quality of the garment, and most importantly, you can try it on. You’ll see how it sits on your body, how it feels against your skin, how it moves with you. This is something online shopping will never be able to compete with.

Another thing to note is that every garment is cut a bit differently. An item like jeans in the exact same brand, fit, and size, might fit a little differently than another pair that is exactly the same. You need to account for a bit of human error. Always try on everything.
 

3. Men are less likely to try something new.

Women love trying something new just for the sake of trying something new. Men are the opposite. If it doesn’t make complete sense at the moment, we’re not buying. This discernment can be a great tool in editing down your wardrobe, but it can leave you stuck in a rut. It’s good to try something new every once in a while to shake things up.

Buy those trendy sneakers you’ve had your eye on. Step away from your grays and navys. Wear something that has a fit tighter or looser than you usually go for. You might love it, you might hate it, but at least you tried.
 

4. There is not one way to wear something when it comes to fashion.

When I’m out working with a guy and pick something out for him, I usually get “ I like this, but what would I wear with it?”. There are some rules in classic menswear that state what you should and should not pair with certain items. However, the lines have been blurred considerably over the last few years.

Ask any stylish youngster and you’ll find out that we’re in a fashion free-for-all. There is no right fit or right pairing. The more outlandish the better it seems. This pertains more to fashion trends than good-looking style though. Just know that you will be forgiven more than ever for your “style mistakes” and people may even confuse you for a trend-setter.
 

5. You should stop relying solely on the style advice of a significant other or salesperson.

Just because your girlfriend things something looks good, doesn’t mean it actually does. Most men default to their partner's advice when it comes to clothing. Keep in mind, they are looking at you from the standpoint of what is attractive to them, not what looks best on you as a whole.

There are certain nuances of menswear that they won’t be familiar with, and even if you trust their opinion on what would make you look “hot”, you better be careful when they dress you for the boardroom.

The same goes for salespeople. They will often, be very knowledgeable about the item you’re looking to buy, but they don’t know your personal style, what’s in your wardrobe already, or the look you’re actually after. This can lead to some expensive purchases that you never end up wearing.

I say all this to warn you not to rely on their advice exclusively. But, if you have no idea what you're after and you’d otherwise be shopping alone, your partner and a helpful salesperson can be great resources. Make sure you retain enough of your own discernment though.


6. Comfort does not have to be sacrificed in order to look good.

Let’s start with a fact. It is not acceptable to wear athletic wear outside of the gym. It doesn’t make sense to do so. Your clothing should always be situationally appropriate. When I tell some men this, I usually hear back “but I want to be comfortable”. I get that. But the not-so-secret secret is that you can look good and be comfortable (gasp!).

You can buy good looking shoes with ridiculously comfortable rubber soles that go up to EEE (ridiculously wide). You can find nearly any garment in stretch fabric. There are more varying types of cuts than ever before. The options for comfort are nearly endless. But the most comforting feeling should come from the fact that you’re dressed well.
 

7. If you despise shopping, it’s because you don’t know how to do it correctly.

You know what I hate? Volleyball. I don’t understand how to play, the rotation, and I’m flat out terrible at it all. I turn down every invitation to play, although it looks fun. The only reason I don’t like the sport is that I’m no good at it. As men, we enjoy doing things we’re good at.

Shopping is no different. The reason most men hate shopping is that they don’t know what they’re doing. They don’t know the stores to hit, the brands to look for, the fits to try on, or how to interact with salespeople. So they put it off unless they absolutely need to replace something. The more you practice, the better you get. Hitting the mall once or twice a month to methodically add a piece or two into your wardrobe will give you a better familiarity with shopping in general.
 

8. Menswear is as classic as any other gentlemanly hobby or activity.

Most men want to be James Bond. Why wouldn’t we? The women, the cars, the gambling, the guns, and… the clothing? Having an appreciation for well-made menswear is as classic as having an appreciation for a well-made car or whiskey.

How can clothing be “feminine” while the rest of it is “masculine”? It doesn’t make sense. This all goes into the lifestyle of a well-rounded gentleman.
 

9. Don’t let price motivate you.

I used to make the mistake of hitting the clearance rack pretty hard. I would see something that I kind of liked, that kind of worked with the rest of my stuff, and then look at the price (a steal!), so of course, I would buy it. That stuff was never used much. I had no connection to it and neither did any other item in my closet.

The purchases that I love most now are items that I would set my sights on after doing some research and then save for. I knew what I needed and worked towards it like a goal. You build a great wardrobe slowly and methodically, not by hurriedly scanning the clearance rack.
 

10. Trust your gut more.

You know more about your personal style than anyone else in the world. You know your likes and dislikes. You know who you are and who you want to appear to be.

When I’m working with a guy, I’ll find that in their closet, there are plenty of items that work well for them. Usually, it's the colors of their items that are actually on point. Why? Because they wear this stuff every day. Of course, they’ll get a sense of what colors look good on them, even if it’s only through being complimented.

Look into your closet and I bet you’ll see more of a direction than you thought you had. When you’re out shopping, trust your instincts more and you’ll be pleasantly surprised where it leads you.

 

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