Cheating on Fit

With fit being the most important aspect of dressing well, most men who are just starting out are left in a tough spot. Either they pay for all new clothes, or they pay to have their existing clothing altered. Neither one is an especially cheap option.

My recommendation is to start off buying one new piece or having your tailor tweak with one existing piece at a time .

For most of us, our clothes don’t fit because they’re too large. Let’s say you have to wear a shirt and tie to the office every day like I do. That’s a lot of button-up shirts to replace. There’s a cheater option though, and this option is a lot easier now that the winter months are upon us.


Here’s a picture of an old shirt I have that doesn’t see much rotation in my closet. The sleeves are too billowy and the body of the shirt balloons out at my pants – not particularly flattering. I like the color of this shirt and it’s a good one to have around if the laundry hasn’t been done and I’m in a pinch.


Here’s my cheater solution. With a fitted sweater over the top, no one has any idea how poorly this fits. I still get the color on the cuffs and collar and I don’t have to have it altered. On top of that, the sweater will work with any shirt I have that doesn’t fit.

And here it is with my jacket on as well.


The sweater cost me ten bucks at H&M a couple of years ago. Cheaper than having a single shirt altered and now I can wear a few extras that hang out in my closet if I want to. Easy.

If you go the cheater route, get a neutral color. Things like grey, blue and brown go with almost everything. I personally avoid black because it’s too overplayed but if that’s your personal preference, run with it. The sweater isn’t a permanent solution but it’s a good cheater option while you’re building up your others.