Should I Shop For Clothes While Losing Weight?

Should I Shop For Clothes While Losing Weight?

Today’s question comes from Andrew, he asks:

“What do you think about buying aspirational sizes to motivate me to lose weight? Or should I just wait until I hit my goal weight before investing in nice clothes?”

I understand that thinking behind buying aspirational sizes to motivate you.

You imagine this ripped version of you fitting into that suit that’s 2 sizes too small for you, looking like Ryan Gosling in Crazy Stupid Love. 

But as someone who’s lost over 50lbs himself, and worked with dozens of clients who’ve lost as much as 200lbs, here’s the reality about buying aspirational sizes as fitness motivation:

They don’t work.

One of the most eye opening things I learned getting into shape for my wedding: how much bodyweight you actually need to lose to look how you want to look. 

I thought I needed to get down to 150 to hit my aesthetic goal. I was totally shocked when I got there at 170lbs.

We’re REALLY bad at guessing how our body’s going to change as we get into shape. 

The last thing you want to do is spend your hard earn money on clothes you can’t even wear. 

Plus, a closet full of clothes in a size or two too small doesn’t really motivate me.


My recommendation to all my clients is to focus on now. 

You don’t have to wait until future date 3 months down the line to look good, you can actually start today. 

In fact, this can be extremely motivating in continuing your fitness goals. I’ve worked with tons of clients who found themselves thinking “Man I look this good now, I can’t imagine what I’m going to look when I hit my fitness goals.”


A client of mine getting measured at Bonobos

Longtime readers of The Essential Man know how much I stress the importance of fit. 

Dialing in your fit will solve 90% of your style problems. 

This can be challenging, especially if you’re working on your fitness to improve how clothes fit you. Whether your goal is to gain mass because you’re lanky or want to lose that dad bod gut, you can still find a great fit off the rack.

It starts with shopping at brands that offer more fit options so you can nail without having to resort to getting something tailored.

The brand with the widest selection of size and cut combinations I’ve found is Bonobos. It’s replaced J.Crew as my go-to place to stock my client’s closets with essentials (and then some). It’s also the first place we go when we start working together (see pic of my client getting measured at Bonobos above)

I’ve worked with enough guys to experience every type of body type combination over the last few years.

Below are the more common fit challenges I’ve run into, and what I recommend you try out if any of these fit issues resonate with you:


Problem: Your shirts have baggy sleeve and body.

Solution: Regular-sized shirts can be cut a little too generously for a slim guy. Baggy sleeves and bodies give me flashbacks of bad high school prom suits. The solution: Opt for a slim or tailored cut shirts, which slim down the sleeve and body for a much closer, flattering fit.

Recommended products: My clients are big fans of Bonobos’ Daily Grind shirts and Jetsetter shirts, which have a hint of stretch to make them more comfortable. Note about Bonobos’ cuts – their tailored is their slimmest fit, while slim is in-between regular and tailored. I recommend trying both slim and tailored to see what works best for you.


Problem: Pants are too tight in the butt and thighs. When you size up, the legs get too baggy and look like you’re wearing bell bottoms.

Solution: Guys that don’t skip leg day know the struggle. Pants are too tight in the thighs, so you size up. But now you have that dreaded bell bottom effect from pants that are too big. Go for pants with an athletic cut, which give you more room in the butt and thigh, but taper down past your knees to avoid the bell bottom look.

Recommended product: Bonobos’ stretch washed chinos in the athletic cut


Problem: Suits that “fit” feel too tight and uncomfortable. When you sit or move, you feel like you might pop a button or rip your pants. Bigger suits are comfortable but make you look sloppy.

Solution: Just like the athletic guys advice, we’re going to go for an athletic cut suit but also pay attention to the fabric. Look for suits made with a bit of stretch, which will make sitting and moving a lot more comfortable as the fabric will have a bit of give. All my bigger clients end up wondering how they lived without stretch.

Recommended product: Bonobos’ Jetsetter Suiting, which has a hint of stretch, in the Athletic Cut


Problem: T-shirts and tops are too long, making you look like you’re wearing a dress.

Solution: Go for tees and tops that offer a “short” length option, which shave off an inch or two from the length.

Recommended product: Many of Bonobos’ tops come in a short length. For a good starting point, every guy needs a classic white tee, and Bonobos’ super soft Peruvian cotton yarn spun tee comes in a short length.


Problem: Jacket sleeves are too short, making it look like your jacket shrunk in the wash.

Solution: Make sure you pick up tops (dress shirt, blazers, and jackets) in “long” instead of “regular”, which just means they add a bit of length to the sleeves and body to keep things proportional.

Recommended product: I’m a big fan of Bonobos’ denim chore jacket, which comes in a long length for all you tall guys out there.



My friends at Bonobos wanted me to let you all know that they’re having a huge sale from July 12th to July 16th – 30% off every product in every category. 

You guys know I’m a big fan of Bonobos for not just my styling clients but myself! I highly recommend you take advantage of this sale and stock up on your wardrobe essentials before it ends.

Click here to shop Bonobos’ Biggest Fit Sale

This post was in partnership with our my friends over at Bonobos, who’ve been my go-to shop for my 1-on-1 client work. Thank you for working with me on this featured story!

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