Best Big & Tall Outfits for a Summer Getaway

Best Big & Tall Outfits for a Summer Getaway

You’re going on a summer getaway? Yay, you for carving out some time for yourself! Let’s look at the best big and tall outfits to keep you looking sharp and feeling great.

First, the Fit

If big and tall clothes are your go-to sizes, you know the importance of fit. The great news is that Lands’ End fits every body, so you know we’ll have your back for everything from big and tall outerwear to big and tall tops and bottoms to big and tall pajamas, and more. Even if you think you know your current sizes, however, it’s a great idea to get out a measuring tape and double-check. Check your current neck, chest, arm length, waist, and hip measurements. Keeping this information on your smartphone with the date that you took the measurements is a great idea. If you shop online, make sure to choose a retailer that has a great return policy (like ours) in case you need to move on to a different candidate to get the look and feel that you crave.


Summer getaways almost always mean swimming! Make sure to have a comfy pair of big and tall men’s swim trunks and a T-shirt handy. It’s a great idea to stash this combination in your carry-on bag so even if your luggage gets lost or delayed you will be ready to relax at the pool or on the beach.

It may seem obvious but bring your go-to sunscreen, too. Many guys like the added sun protection of a rash guard. This will give you an instant outfit when paired with swim trunks as well as ensure that you will return from your getaway rested and not sunburned.

Shorts and a Polo Shirt

Big and tall men’s shorts will pair perfectly with either a polo shirt or T-shirt—pack both for added flexibility. Your shorts will probably be just fine to wear a second day if you have chosen a neutral color like black, classic chinos, or denim. Neutral bottoms make for the easiest mix and match outfits. You can pair them with everything from a white top to the brightest of brights.

Consider wrinkle-free shorts for added crispness. If you throw on wrinkle-free chino shorts, a polo shirt, and add a men’s belt and deck shoes, you can go almost anywhere short of a white tablecloth-styled restaurant. It’s amazing the power that a polo collar and banded sleeves together with a belt have to take an outfit from beach casual to cool, crisp, and ready for anything. When in doubt, a white polo is a great choice.

Jeans and T-Shirt

For a casual feel and classic look worthy of GQ, consider dark or medium wash jeans and a white big and tall T-shirt with shoes and a belt. Add a great pair of sunglasses, and you can increase your cool factor even more!

Jeans and a T-shirt are a great combination for travel itself. By wearing long pants, you will be comfy if you run into aggressive air conditioning in airport waiting areas, yet a T-shirt (especially if you choose 100% cotton) is just about the comfiest top around. In our father’s days perhaps everyone dressed up for air travel, but as long as you're neat and comfy you'll be just fine.

Jeans and Long-Sleeved Shirt

If you want to take your jeans up a notch, consider pairing them with a long-sleeved button-down shirt or a big and tall dress shirt. This combination can take you straight from the plane to almost anywhere you want to go—and be a great business casual combination for when you get back to the office.

If you want to go for a smart casual look with this one, make sure to wear dress shoes and a men’s belt. You could even stash a tie in your carry-on if you're likely to end up with a dress code at an event.

Step Out in Style and Comfort

When planning your summer getaway, make sure to think about what men’s shoes you will want to wear and pack. You’ll want to include at least one pair of great walking shoes. A pair of men’s sandals or slides for the beach or the pool is also a great idea. If water sports are on the agenda, keep your feet comfy with a pair of water shoes. Last, but not least make sure that you have a pair of shoes that are neat enough to look good when going out in the evening.

Most guys can get by just fine with one pair of super comfy shoes, one neater pair and then throw some slides in with their swimsuit. Make footwear part of planning those great mix-and-match outfits.

Have a great time on your summer getaway!


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