Buying Clothes While Losing Weight: 8 Easy-To-Follow Tips

by   |  in Style Tips

So you’re losing weight and need new clothes… but you’re still working towards your goal weight and physique, so you want to shop strategically? I’ll outline a few tips here to make shopping while losing weight much easier.

Look, you’ve basically stayed indoors for all of 2020.

You may have gained a bit of quarantine weight that never quite went away on its own, and now as the country opens back up, you’re interested in shedding those extra pounds you put on.

Photo by Andrea Piacquadio

Or maybe you were more proactive during quarantine.

You decided it was finally time to lose the weight you’ve gained over the past few years, and with a ton of hard work, you made significant progress.

That’s great!

Whatever your situation may be, you’re trying to figure out how to buy clothes while losing weight, and you probably have some questions:

  • Should you wait to buy new clothes until you lose more?
  • At what point does it make sense to buy a smaller size?
  • How do you achieve the perfect fit as you shed the pounds?
  • Should you get your clothes tailored, or buy new clothes?
  • How can I shop online when I don’t know my size?

As a former fat guy who vividly remembers his weight loss journey and transformation, I have 8 tips for you when it comes to buying clothes while losing weight.

Trust me on this, because I’ve wasted a good amount of money during those years. Hopefully this article will help you learn from and avoid the mistakes I already made!

Buy Belts That Shrink With You

As you lose weight, the accessory you’ll depend on most is your belt. Your pants will start to get looser, but not loose enough to warrant buying an entirely new size… yet.

The problem with normal belts is that there are only 5 holes, all 1″ apart. But your body weight and size doesn’t fluctuate in 1″ increments! Which means there’s a good chance your belt can be too loose or too tight at any given time.

Not to mention, during the day, your waist size fluctuates as you eat and drink, the amount of water in your skin and organs changes, and so on. This means you often expand as the day wears on, and you contract again during the hours you’re asleep.

That’s why I’ve been a huge fan of Anson Belts since I started wearing them 5 years ago.

They’re perfect for guys who experience any size fluctuation during the day (ever feel the uncomfortable snugness of post-lunch pants?) or for those consistently losing weight and needing a slightly tighter belt (without jumping to the next hole).

These belts didn’t exist back in 2005 when I finally decided to get fit. I wish they did. It would’ve saved me from buying many different belts over the years.

So Anson Belts work like this: Instead of 5 holes like a traditional belt, their track system has 30 different sizes, all 1/4″ apart… on ONE belt.

This means that as you slim down, your belt can slim down along with you, 1/4″ at a time.

camo belt with black watch shirt and dark jeans
My camo print anson belt with antiqued buckle 😉

I’ve written about Anson many times and it’s one of the few products I’ve consistently recommended for years. They’re the only belt I wear, even though I have plenty of traditional belts. When I go into my closet, I always reach for these guys first.

Not to mention, they provide a lifetime guarantee, amazing customer service, and are family owned (I’ve met the guys personally and have known them for years).

Check out the special deal to get the box set of 3 straps and 2 buckles (or 3 buckles and 2 straps), and for a limited time, they’re offering a third strap or buckle free. This gives you 9 potential belt combos, all for under $100. 

Incredible deal with just the 3/2 option, so having the bonus belt or strap is a no-brainer.

Buy the Clothes That Fit You Now

…not the clothes you hope to fit into someday.

Buying smaller clothes you want to eventually fit into doesn’t make sense because:

  1. You can’t wear them comfortably, 
  2. They have the sausage casing effect if you DO try to squeeze into them, and 
  3. They can actually be discouraging and make you feel bad about yourself

Buy clothes that fit well and look great on your body as it is right now, not as you hope it will become.

Speaking from experience, it’s tough to predict how clothes will fit your goal body when you get there, because your sizing guesses may be off, and also, every brand’s sizing differs slightly. 

Case in point: Sometimes I fit best in a 32” waist, other times I have to buy a 31” waist, or even a 30”! 

So avoid buying “goal size” clothing until you actually get your goal physique. Focus instead on what makes you look and feel good right now.

Focus on Fit First, Quality Later (And Don’t Worry About Being Perfect)

When you’re in the process of losing weight, brand or quality doesn’t matter as much, so it isn’t worth worrying about until later. 

Your body will be changing and most likely, you’ll need to buy a smaller size or fit later, so going with the more affordable option is totally understandable.

At the same time, go easy on yourself if you can’t achieve “the perfect fit”, or if clothes don’t look as great on you as you expect them to… yet.

Speaking of, depending on how your body is changing, you may need to consider trying other fit styles, not necessarily just sizing up and down. For example, a 34×30 slim or tapered pair of denim will fit much differently than a 34×30 traditional cut… even though the waist and inseam are the same.

Right now, in 2021 as I write this, the current style has swung towards looser and more forgiving silhouettes. During the 10-15 years prior, it was the opposite, everything had to be slim slim slim.

This swing is good news for most of us. Looser, relaxed cuts are waaay more comfortable.

grid of photos of asian man taking photo in a mirror
You can see examples of looser (but not oversized) fit examples on EG’s instagram

And the options available in 2021 (and probably for the next 10 years after this is published) will be looser but at the same time, fit correctly where it counts (e.g. the waist and length of pants, the shoulders on tops).

  • For shirts, choose a looser, traditional cut, but don’t simply size up. This isn’t the same thing as buying a tee in your actual size that’s designed to fit more loosely.
  • For pants, avoid the skinny and slim stuff. Those cuts only look good on tall and skinny guys. Go for straight leg or athletic tapered, which is a more flattering silhouette for bigger guys.

The “perfect” fit doesn’t matter much at this stage since you’re still losing weight. Just do the best you can and move on.

Replace the Things You Wear Most Often, First

Are you a jeans and button-up kinda guy, but now as you’ve lost the weight, your jeans and button-ups are baggy? Buy new ones!

The reason you want to buy replacements for the clothes you wear most is because you want to feel good every day! The clothes you wear every day should fit you well, because after all, they’re what you wear most.

Stuff that you only wear occasionally, or hardly at all, you can delay replacing until you get closer to your goal weight.

Like if you don’t wear suits that often, delay shopping for a new suit as long as possible. If you have an event coming up, take it to a tailor and see if he can work any magic for you.

Unless you’ve dropped significant weight (50 lbs+) there’s a good chance a tailor can alter the suit to fit you better.

Like I’ve mentioned a few tips above, you want to dress for the body you have right now, and you want your clothes to fit the body you have now (not your bigger body from a few months ago, and not this dream physique you hope to achieve in a year… the body you have now).

So start by taking a long hard look at your closet and identifying the 5-6 things you wear most, and start by replacing those. Worry about everything else later.

Measure Your Clothing for an Easier Online Shopping Experience

So let’s say you follow my tip about replacing a few of your favorite items that are now too big. You have a good pair of jeans, a great T-shirt, and a mid-layer or jacket that all fit well.

Your next task? Take measurements of these things and write those measurements down!

Looking for a guide? Here’s our article on how to measure your body and clothing. Since you are measuring garments that fit well right now, you just need to read the clothing measurement section.

Bonus points if you can also take your body measurements.

These will be useful, just know that since you’re still losing weight, you’ll have to update these periodically until you hit your goal.

So, how exactly does this help you?

garment measurement chart
garment measurement chart on a T-shirt from Aime Leon Dore

Most brands list garment measurements on their website. So if you’re unsure if you’re a Large or XL, for example, all you have to do is check out the garment measurement chart and compare those to the numbers you wrote down. 

garment measurement chart listing different sizes and their measurements
Measurement chart on J.Crew’s Site (with instructions for how to measure your actual body to compare)

Then, simply choose the size that’s closest to your own garment measurements. 

Taking this extra step will highly increase the chances of you buying the correct size, as well as having to avoid buying multiple sizes and returning the ones that don’t work.

Menswear Neutrals and Subtle Patterns Are Your BFFLs

(BFFL = Best Friendz 4 Lyfe)

Subtle, smaller patterns don’t highlight every curve of your body like bolder, more vibrant patterns can.

With larger prints, it’s much easier to spot any breaks or shifts in the pattern.

So if you have a love handle or two, or man boobs you want to hide, this is best achieved with a solid color, or a smaller, more subtle print.

Smaller prints read as solid colors from a distance, so the pattern shifts (read: the parts of your body you don’t want to highlight) aren’t as obvious.

photo of larger man wearing white shirt with blue dots, full body and close up
The small dot print reads as a solid color from afar. Photo via Bonobos

When it comes to solid colors, darker hues are obviously better at hiding, but I don’t think you should only wear dark colors… especially if that’s your main reason for wearing them!

It’s important to love and get used to your body; you’re taking the steps you need to in order to lose weight so be proud of that!

Stick with mostly menswear neutrals and you’ll have a variety of flattering colors to choose from, colors that will keep you looking handsome. Menswear neutrals go well with all colors so it’s easier to match, and they just happen to be very complementary to all body types.

A Tailor Can Only Do So Much To Your Clothing

As a rule of thumb, for every 10-15 lbs you lose, you go down one size (e.g. from a 38” to a 36” waist, or from an XL to an L shirt, etc.)

If you lose more than 20-25 lbs, it becomes more difficult to alter bigger clothing to fit your new size. That’s because as you alter them down, the original garment’s proportions change.

Technically, it can be done, but it would require major garment surgery and oftentimes it’s more cost effective to just buy something new.

Speak with a knowledgeable tailor about your specific situation and if they’re experienced, they should be able to give you advice. Most garments can be altered within reason, but if you’ve lost 25, 30, 50 lbs… you’re probably better off buying new stuff.

Celebrate The Little Wins

While this isn’t clothing specific, I do believe this tip will help keep you motivated to continue on the journey and stay on top of your regimen:

Celebrate the little wins when you can, and reward yourself for reaching those milestones.

Back when I was at my heaviest, I wore a size 40×30 in pants and an XL in shirts. I remember after 3 months of consistently putting in the work 6 days a week, I managed to fit into waist size 36, sometimes even 34.

That was huge for me! So I bought a few new pairs of jeans.

This (among other things, like getting leaner, seeing the changes with my own eyes, and generally feeling better) was a big motivation for me to keep going, and I made sure to celebrate that small win by rewarding myself with a few new things.

Taking the time to appreciate those wins is really important if you want to stay consistent and motivated.

Keep it up! You’re doing great.

Making great progress losing weight?

I hope you buy yourself a few new items of clothing using these tips I’ve laid out above. If you do, make sure to email me a before and after photo with your story! I’d love to hear it.

Thanks to Anson Belts for partnering with me on this article. As I mentioned, I’ve been a customer for years so I can fully vouch for the quality and usefulness of their belts.

Don’t forget to grab a box set; it really is the best deal. Plus, this offer of an extra belt or strap (9 belt combos total, insane) is running for a limited time and can end at any time.