5 Smart Style Tips When You’re Losing Weight

You're looking and feeling great – but what do you do about all your clothes that are too big?

5 Smart Style Tips When You're Losing Weight

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What is this?

Shedding pounds and hitting your goal weight is amazing for your body and your confidence, but it can present a challenge for your style. This is especially true if you’re in the process of quickly losing a significant amount of weight.

After all, you’ve probably spent a few years assembling a wardrobe that works for the body you used to have. You’re thrilled to be looking and feeling better underneath that XL button-down, but you want your style to reflect all your hard work.

Sure, the clothes can make the man. But you want the man and the clothes to be on roughly the same page.

Updating your style after (or during) weight loss can run into serious cash, and lead to some tricky questions: do you update all at once, or in stages? How permanent are the changes? Are you at your new, stable weight? Will you continue to shed kilos, or gain some of it back?

While the answers to these questions vary widely person to person, we’ve put together a few simple, budget-friendly hacks for the period while you’re losing weight to look good and save cash.

old belt vs anson belt

1. Microadjustable, Holeless Belt

Surprisingly, regular belts can only see you through a weight transition if they were pretty new when you started losing weight. Why?

As you’ve probably noticed, leather belts quickly develop creases and indentations from the buckle, especially when under a higher load. So by the time you're at your lower weight your belt will have all kinds of unsightly marks and notches.

Anson belts don’t have this problem because they don’t rely on a buckle to create a secure, easily-adjustable hold.

Anson belts use a ratchet style track system that eliminates holes – and the creasing and stress on the leather belt face.

anson ratchet system

The ratchet system on the back of an Anson belt

Instead of five holes an inch apart (who came up with that, anyway?) the Anson buckling mechanism allows for 30 options spaced a quarter of an inch apart – a must if you’re losing between five and ten pounds a month.

The Anson system allows for micro adjustments perfect for when weight fluctuates, or even when different items are made from thinner or thicker fabrics. It’s even more versatile when you consider that all Anson belts and buckles within the same width are 100% interchangeable.

In addition to being a smart buy, Anson belts come in a variety of colors and materials. Of note is that all of their leather belts are crafted from full grain leather for a premium look and feel, and long-lasting durability.

anson belt

An Anson belt paired with a stretch shirt from Mizzen & Main and stretch denim from Gap, which leads us to…

2. Stretch-Fit Jeans

Here at Primer we’ve closely examined selvedge denim as a style choice, and even shown you a DIY hack for achieving a perfectly-fitting pair of raw denim jeans.

The thing is, if you’re going through a period of intensive weight loss you probably don’t want to drop several hundred bucks on the perfect pair of raw or selvedge denim if they’re going to be too big in three months. On the other hand, they’ll be so far from broken in you can probably return ‘em and claim they were never worn!

We love the selvedge look. But sometimes jeans with the right amount of give have a role to play.

What does stretch-fit mean? In practice, stretch-fit jeans incorporate anywhere from 1-20% stretchable fibers into the jeans blend, with 1% providing a little give and 20% allowing you to kick people in the face with ease.

The major style bonus to stretch fit jeans when you’re losing weight is you can buy a size down and let your body catch up to the fit. They also re-tighten their fit after washing far more than non-stretch, 100% cotton sanforized jeans.

At the top end of stretch and the low end of price check out American Eagle’s Extreme Flex. Levi’s offers their own high-stretch model, the 511 Performance Stretch Jean.

For less flex and a more traditional jean, check out the 1% Levi’s 511 Slim Fit Jean.

3. When to Pay the Tailor Tax

Old joke: gym gains that make you bigger (or smaller), a diet that shrinks your waistline, a lifestyle change helps you achieve your target weight… time to pay the tailor tax.

The straight good news when it comes to tailoring clothes after weight loss is that the fabric is in your favor: you already have bigger pieces that can be brought in. From there, it gets more complicated.

There are two schools of thought on what clothes you should tailor and which you should buy again. On one hand it makes sense to tailor the items you wear all the time so you can keep wearing them.

On the other, you could argue it's better to buy new versions of the items you love to wear so they'll last longer and you can tailor the pieces you don't wear quite as often, allowing you to keep wearing them without paying full price for something you don't wear a lot.

tailor tax

Regardless of which strategy you decide on, it’s important to keep costs in mind. If you already have some nicer items, such as blazers, it can be cheaper to tailor them as you go rather than buying all new items.

If you’re in doubt about your suits or blazers, check out Primer’s guide to how your suit should fit.

But if you’re dropping serious weight you can't tailor forever, and tailoring bills add up. Consider this example:

You have a favorite pair of pants. Pant waists can be adjusted about 2 sizes, but not much more. Along with the waist, the crotch will likely also need brought in. Should you do it?

Adjusting the waist and crotch on $50 pants probably isn't worth it. You'll be paying about half that in tailor costs. If they originally ran you $100+ the tradeoff starts to look more appealing, but keep in mind – alterations to the waist will also bring the back pockets closer together.

move dress shirt collar button

4. Collar Hack

Button-up shirts offer a lot of flexibility when it comes to weight gain. As long as the fit isn’t too baggy, you can hide some of the extra fabric by rolling up billowy sleeves and using the military tuck to hide the excess, with a well-fitting blazer on top.

military tuck

The Military Tuck – Check out our full guide to How a Shirt Should Fit

One area that’s truly difficult to hide, however, is the collar. If your neck has shrunk, you don’t want a too-big collar to make you look like a kid in his dad’s suit.

In the intermediate stage before replacement or major tailoring is called for, you can hack this issue by simply moving the top button to the right (i.e., away from the centerline of the body) by up to a half inch.

Simple to do yourself or very cheap to hand off to a tailor, this trick can help extend the life of a shirt you’ve under-grown.

feet shrink when you lose weight

5. Superfeet Insoles

Lesser-known fact: when you lose weight, you lose weight all over your body (well, nearly all over). This includes face, arms, neck, even your wrists. And definitely your feet.

One friend of the magazine who lost nearly 100 pounds went from needing a 12 to a 10 in most shoes. While we’re super proud of him, that’s a serious hit to your wallet if you need to replace every single workhorse shoe, boot, and sneaker in your lineup.

Chances are your target weight isn’t so dramatic. Most guys report more slip in their usual footwear after weight loss. At most you might go down a half size.

In these situations, there’s an alternative to replacing your shoe rack: pick up a quality insole.

For a few years now Superfeet have been at the top of the game, making quality insoles in a variety of styles and rigidities.

Generally, insoles are meant to replace the flimsy piece of foam that came with your footwear but if you really need to fill space simply place the additional material on top of the existing insole.

Have you had to change up your style because of weight loss or gym gains? Share your story below!

Special thanks to Anson Belt & Buckle for partnering with us on this post! Thank you for supporting the brands that support Primer!

Stillman Brown is a writer and TV producer who has created prime time content for National Geographic, Discovery, Travel Channel and many others. His interests span science & the natural world, personal growth, and food. He lives in Tulsa, Oklahoma.

  • Modern Connoisseur

    Yes I’ve had this situation, losing weight has been awesome but replacing literally everything in my wardrobe did create a high bill until I realized I could simply have most of my shirts and pants altered and when possible I’d wear a Blazer to hide any puffiness of my shirts

  • Toro

    also note that some clothing items cannot/should not be tailored beyond a certain extent – see: denim. trying to bring in the waste on a pair of jeans beyond 1 inch creates an odd, pleated “mom jeans” effect.

    I would also recommend that you hang on to a few favorite go-to clothing items, just in case – it sucks, but sometimes progress can be lost

    • http://www.primermagazine.com/ Andrew

      Do or die, never going back! Just kidding

      • Toro

        yeah, lol, i always told myself that!

        then I was pissed I got rid of those expensive slacks that would have fit after I put some weight back on 🙁

        it happens, so best prepare for the possibility than be left high and dry with pants that are too tight.

        not a big effort to throw some stuff in a plastic tub under the bed as a back up measure

  • Matt Christians

    https://uploads.disquscdn.com/images/4f7ae61ea303ea7b4314862ef08c12e99b43a367abd1d59155f15dc033bf96d1.png Yeah, to this point I’ve lost 160 lbs and my goal is still about 90 lbs off, so I’ve had to adjust most things as i continually change. I resisted making any wardrobe changes for the longest time because of the expense and then it just became too much to overlook. Now i find a new article or 2 every couple of weeks or so to slowly and continually change my wardrobe as my body continues to change and as my style and comfort change.

    • http://www.primermagazine.com/ Andrew

      Wow! Congrats!!! What’s been your keys to success??

      • Matt Christians

        Thank you! My biggest keys have been to have a very specific and powerful “why”, to make changes that were livable so that they could be maintainable and to be realistic with my progress. So instead of saying I’m going to have salad for lunch every day I started with just having fruit with my lunch every day. So small and specific would be my 3 keys Thanks again.

        • Kenneth Brill

          Congratulations on your weight loss. I admire your willpower and commitment to change. It must be an amazing feeling. It’s surprising how much of a difference small decisions and changes can make in your life.

          Reading “The Power of Habit,” by Charles Duhigg made a tangible difference for me in losing weight. Trying to maintain an awareness of the ingrained trigger and reward cycles we’re all irreversibly tangled up in and reprogramming them bit by bit has been difficult, but rewarding.

          • http://www.primermagazine.com/ Andrew

            That’s awesome! Thanks for sharing your journey!

  • Ze-evmagen

    I actually, started improving my fashion, because muscle weight fluctuations.
    When I first started hitting the gym, I gained a total of 15lbs in a single year and it continued to grow from there (now 5 years later I’m 50lbs heavier and proud of it).
    Though I look better, I was still way behind in fashion, and felt it was time to wrap those new muscles in something that look as good as they made me feel. So I started studying which lead me an adventure that got me to this site.
    Always a good read!

    • http://www.primermagazine.com/ Andrew

      That’s so awesome, congrats! Glad you found us! 🙂

    • http://www.primermagazine.com/ Andrew

      What’s your success been for the gain in muscle weight? Emphasis on protein/calorie intake?

      • Ze-evmagen

        About 2700-3000 calories daily. 50% carbs/30% protein/20%fats ratios. Mass Gainer mixed with powder peanut butter is a big help, as well as Ezekiel bread, rice, potatoes, and those boiled eggs that you find in shopping markets. Admittedly I dirty up the calories often but who doesn’t?

        Mostly in training i just alternated between Stronglifts and 5/3/1 programs adding curls/triceps pulldowns where ever I felt I needed them. Linear progression was a key component for me.
        Started as a slim 135lbs and now I maintain a decently cut 185lbs now.

  • Zac Silk

    Stretch denim has been fantastic for me. As well as that stretch selvedge is a complete revolution for me. It doesn’t take as much time to break in as regular raw denim but has the same selvedge cuffs.

    Gap do a great range of jeans as you both pointed out and their selvedge line is really good quality for the price. Hopefully they will continue on this vein in the fall.

  • Kenneth Brill

    I’ve lost about 40 pounds in the past year and a half. Having been a bit of a denimhead, finally make the decision to retire and sell my jeans (and the fades that went along with them) was an emotional and financial nightmare. A good option I found while looking for a balance between quality and affordability in raw denim in smaller sizes has been the Unbranded Brand. Their jeans have a clean, minimal design, quality construction, and their denim is respectable. The photos of fades speak for themselves.

    I feel more confident and comfortable. While my chest and stomach shrink, my shoulder measurement stays roughly the same. The cost of alterations on shirts reached a point that was unsustainable with my limited budget, but this opened the door to a new hobby.

    I picked up a heavy duty Singer sewing machine on sale for damaged packaging and discovered that taking in the body and sleeves of shirts is relatively easy and forgiving to beginners. As my skill improves, I’ve even started hemming lengths and shortening sleeves. As a result, my clothes fit better than ever and I feel a personal, creative connection to my clothing that I never had before. I just bought heavier needles and I’m getting ready to start messing with jeans and chinos, though admittedly I wouldn’t trust myself with anything except workwear and very casual clothes at this point.

  • Jim Avila

    Great article. 3 years ago I went on the quick weight loss center diet and dropped like 40 lbs. I had to buy all new clothes and smaller shoes. Wish I read this article then. Lol! https://uploads.disquscdn.com/images/c7fea3b718d3b9d8bd7dc36984c5186a0e142edff8dca811a33c74eea94345a6.jpg

  • Jack Daggett

    I gained 30lbs last year in the gym in Baghdad, something I’d meant to do for years. It’s been frustrating to outgrow most of my favorite clothes, including all of my suits and most of my nicer pants. On one of my later breaks from Baghdad I visited a tailor in Vietnam and had some business casual staples made.

    Fortunately my new assignment isn’t especially suity, giving me time to rebuild my wardrobe. But unfortunately, I am in place where clothes shopping is difficult and expensive. I am still trying to find an affordable tailor here to fix what we can.