Member Tips: Dress Well While Losing Weight

Many men struggle to dress well while losing weight – especially if it’s a large amount of weight. It can be difficult to know what, if anything, to buy while your body is changing. However, many Styleforum members have gone through the same transformation, and if you find yourself in a similar position it may reassure you to know that you’re not alone.

Here, we’ve compiled some of the best member-submitted tips about how to handle a wardrobe while dropping pounds, and how to look forward to building a new closet. We’ve also included a handful of inspiration photos to help you hone in on your style throughout the process.

The following responses were originally posted in this thread, while the following inspiration photos have been taken from Styleforum’s various WAYWT threads.

“If you don’t have a job that requires suits, no need to invest there. Go to a local store and try on some dress shirts that fit you well…Try and get a spread collar in a white, blue, striped, and pattern to carry you through any interviews/weddings/events, etc. Invest in flat front pants, standard rise, no more than 8.5″ at cuffs. Get blue, grey, and one black.

For casual fits, get a few pairs of well fitting Levis and som

e crisp new polo shirts in new colors. Shoes – plenty of other shoe posters more knowledgeable than me to offer help there, but find the basics and get them.”

– Spoopoker


“Don’t spend a lot of money now. Buy interim clothes until your weight stabilizes. I wouldn’t drop big bucks until I hit my goal weight and managed to stay there. If you’re like most people, you’ll go up and down, especially at first.

In the meantime, look around and decide what you like. Check out WAYW and flip through Esquire and the like. Then think about how you could incorporate the styles you like into your own wardrobe.”

– DocHolliday


“Finding a good tailor should be your first goal, then go for a progressive move towards better quality and fitting clothes. Do not underestimate the effect of a good tailor. Looks for sales of quality stuff and good shoes.”

– Eight


” Look at your situation right now as research, research, research while you move towards your end goals. Sure, you want cool better looking stuff now – and it’s hard to argue when you’ve already lost 30lbs, I’d want to reward myself too. But if you’re not done yet, don’t bother. You’ll end up junking everything again or tailoring the heck out of it…Go crush it in the gym and think about the Partenopea you’re going to score in a couple more months.

Seriously, keep your powder dry for now – stockpile cash for once you get rid of your self described gut and use that as a motivator (“I’m not getting that 42 blazer until I can fit in it,proper!”). Once you get there, or near there, you’ll be ready to go big.

That said, maybe a couple of better items in the meantime, but think of them as a bridge from where you’re at to where you’re going – ie. disposable. Otherwise you’re going to waste a lot of money, time and effort – trust me (us!).”

– razl


“Been there, doing that. I still have 30 pounds to go, so I can speak from first hand experience of how frustrating it has been. I’ve dropped 145 pounds in the last 2 years, but have gained and lost the same 15 pounds repetitively over the last year.

But more to the point, I have also held off having any major suits or coats added to my wardrobe at this point, till I reach and maintain my goal for at least 6 months. But in the meantime, you can do what I do, and pay more attention to the smaller details, i.e., shoes, socks, ties, belts ( which can be shortened very easily by a cobbler) and if they suit you, even the smaller things like cufflinks and wallets, etc.

While most of these things aren’t wardrobe staples, it is fun to pick up things like these as a reward for the progress you make. Even things like dress shirts can be bought now, since your neckline wont likely shrink much more, but at least not enough to affect casual fitting shirts like a classic oxford cloth button down.
And these can be tapered in at the sides and sleeves if necessary by any competent tailor.

But save the suits, sports coats and dress pants, even the casual chinos and such till after you settle out. A pair or two of jeans would be fine, but just keep in mind you’ll likely replace them in about 3 more months.”

– Chips


“Just finished the same journey – lost 70 pounds over the past 15 months. Advice:

  1. Spend as little as you can until you hit goal weight. All you really need is one pair of jeans (levi’s are fine for now), one pair of khakis, grey wool trousers, a pair of khaki shorts (since you live in Florida), and maybe some other light-weight semi-nice pair of slacks (I went for seersucker). For shirts, a nice white tee shirt (I liked Alternative Apparel) a couple of polos (two of your favorite / most complimentary colors), a short sleeve linen or cotton shirt, a long sleeve cotton or linen shirt (white and blue), and maybe a rugby shirt. Be disciplined and try not to buy anything else. But as you loose weight, keep buying new items to replace the old. This is your way of rewarding yourself and staying good looking during your slide down the weight scale.
  2. If you want to spend, spend on ties. But since you don’t wear suits every day, you don’t really need to do that unless you just love ties.
  3. As you lose weight, your feet will narrow. Buying shoes now will mean that, when you’ve lost all the weight you plan on losing, your shoes will be too wide. Wait on this … trust me.
  4. Use your weight-loss time to keep reading about clothes and keep your eyes open. You think you like X now, but a couple of months from now, you might start migrating to look Z. A lot of people get the bug and discover how to dress well with a bunch of patterns and colors only to discover down the road that a more pared-down, monochromatic look is their preferred style. No need to rush anything during your weight loss though.
  5. Plan your purchases in advance. Make a budget for what you’re going to do when you hit goal weight and research what you will want. Try to resist the temptation to buy a lot – better to keep a smaller wardrobe that is high on quality than a larger wardrobe that is somewhat lower on quality. Replacing a wardrobe is very expensive, so you need to be disciplined about what you really need versus what you might want. A secondary benefit of this is that your “dream” wardrobe (that is, your planned purchases) will be a wonderful incentive to keep going – a big psychological reward at the end of the tunnel. That helped me a lot. A tertiary benefit of a high-quality wardrobe when it’s all done is that it increases the marginal cost of subsequent weight gain. You just invested a ton on some really great clothes – if you start going up the scales again, they will all have to go. That should provide some degree of deterrence.”

– J. Cogburn

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