Tall Mens Fashion Advice

How to Dress up Sweatpants: The Men’s Guide

If you are looking to show up to your next big event and wow the crowd, this article on how to dress up sweatpants is for you.

How to Dress up Sweatpants

Men's Fashion

The first step in dressing up sweatpants is to stop thinking about them as sweats and start thinking of them as a nice pair of jeans or dress pants. Adding dress shoes, a well-tailored long coat and finishing it off with jewelry is a good place to start.

This is How to Dress up Sweatpants: The Men’s Guide.

So, there is dressing up your sweatpants, and then there is DRESSING UP your sweatpants.

With sweatpants and joggers being sold by every brand and TikTok influencer, the cuts and looks have evolved. Now you have pants that can be worn in more situations than your regular Sunday NFL marathon on your couch. 

If you’re looking to take your sweatpants up a notch for a day out, then you will want to read this article on what to wear with sweatpants.

If you’re here to dress up your sweatpants for a work event, party, or any other social event that needs some swag, keep reading.

If you are taller guy looking to find the perfect fitting  sweatpants, I created these guides of the top brands just for you.

How do you Dress up your Sweatpants, Men?

The number one way to dress up sweatpants is to change your mindset and start thinking of them like jeans or even a pair of slacks. Pull out your dress shoes, find your long jackets and bring out your jewelry and other complementary pieces. 

Is it Acceptable to Wear Sweatpants in Public?

It is acceptable to wear sweatpants in public; If you wear them with the same respect and mindset, you would like a pair of jeans.

If you throw on a baggy pair of sweatpants with dirty old shoes and a baggy t-shirt, you most likely will not feel comfortable in your choice of clothing. However, if you put on a fitted cut of sweats, a clean pair of Nike trainers and layer them with a t-shirt, open flannel shirt and a sweater underneath, then you’re feeling good!

Make your sweatpants acceptable by washing them properly, not having them shrink in the process. Drying them with care by line drying, drying flat or drying them other ways without the use of a dryer. Finally putting them away with care by folding your sweatpants or rolling them.

Learn how to use a dryer properly with this article.

How to Dress up Sweatpants for Work

Before you take your sweatpants to work, read the room of the company you work for to see what general work ‘uniform’ is. Take that knowledge when going to your closet to piece together your outfit. It is always better to switch your trainers for dress shoes and a long t-shirt for a well-cut sweater.

How to Dress up Sweatpants Men

A few hundred thousand women bloggers are giving their styling tips on dressing up sweatpants, and I thought it was time we men had our say and a better understanding of how to look good while feeling comfortable.

I have another article on how to style your sweatpants if you’re looking for a daily look to boost your confidence, but below is your guide to finding the right pieces to add to your sweatpants to look good at any high-class occasion.

Also, if your looking to use another piece of your wardrobe as your pillar, then read our other guides.

1. Fitted not Baggy

Unlike your last Friday night fit, out with your boys at the hottest lounge in town, your sweatpants need to be a fitted cut. The baggy look works for a fresh lifestyle look, paired with a new pair of Yeezy’s and a long tee shirt to use as your base layer of multiple layers.

We have put together these guides to making sure you have the perfect fitting sweatpants.

When dressing up, your sweats must be fitted, almost mimicking a pair of joggers. If you are unsure of the difference between joggers vs sweatpants, let me help you.

2. Trendy Coat or Blazer

Add a coat depending on the season or where you live (this might not be an option in the middle of Summer in Florida). The finishing touches on your look can come by a long coat that can tie the look altogether. Look for single-colour pieces that can work buttoned-up and open up and flared out, showing the layers below.

3. Wear Dress Shoes, not Sneakers

Pull out your not-so-often worn dress shoes and let them get more wear. A white pair of clean trainers can only go so far, and it can get played out. All types of dress shoes work here; you need to pair them with the colour of your sweats just like you would do with your dress pants. Black, brown, wingtip or cap toed, it doesn’t matter. Let your confidence soar. 

If you don’t own a pair of dress shoes then the sneakers will have do to! Follow our guides on how to make your sneakers presentable.

Don’t forget to give your shoelaces their own separate care.

4. Boots are Another Option

If you do not own a pair of dress shoes, you can always replace them with leather boots. It is better to go with an ankle height or higher boot (let the tongue be long), and the more personality the boots have, the better. Let your boots themselves be a fashion statement on their own, backing up your choice to make this bold but fashionable move.

5. Keep your Colours Simple

It’s safest to match the colour scheme from shoe to cap (if you choose to wear one.) This look will allow your outfit to work together and tie in the sweatpants with everything you have put together. However, if you are a maverick and always want to push the envelope, I would love to see a brown leather shoe, dark red sweatpants, and a navy blue blazer!

6. Style your Hair and Trim your Beard

As you would do for any other big event, spend a few extra minutes in the washroom and do a little extra grooming. Put some product into your hair and give it a slight shape. And if you have a beard, edge the lines up and trim back the lumberjack bush if you can. 

7. Add some Jewelry 

As you would do with any outfit, put it together using your jeans, slacks or dress pants, put the finishing touches on with some subtle jewelry. A watch, necklace, bracelets and rings are all excellent choices to finish dressing up your sweatpants.

How to Dress up Sweatpants FAQ

To make sweatpants stylish for a man you will want to make sure your sweatpants are not too baggy. Baggy sweatpants will make any look you go for to be sloppy and give the feeling of you just got off your couch.

To wear sweatpants to look good as a man you want to wear your sweatpants so they sit properly on your hips, not sagging below them. Also, you will want to have the cuff of you leg sit at the right height to match the type of shoes you are wearing (high top, low top or sneakers.)

Men you should wear underwear under your sweatpants, either boxers or briefs.

Written and reviewed by
Tall Paul
Tall Paul
Paul Marlow, standing at an impressive 6'7 (201cm) and weighing 225lb (102kg), is a mental health speaker, fashion expert, and ex-athlete who excels at helping tall men find well-fitting clothing and teaching them how to style it effectively. As a model in the fashion and film industries, Paul shares his expertise in tall men's fashion, offering valuable advice on measurements, tailoring, and alterations. In addition, he founded Never Alone, an organization that provides mental health and therapy inspiration, and started the Mental Growth Newsletter to support those facing mental health challenges, drawing from his own experiences.

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